VP Jonathan Blackburn talks hyper-scaling in real time

You’ve heard how great Revenue Leaders hyper-scaled in the past few years. But, what does it take to do it now – at this moment in the market?

In the last 14 months, Jonathan Blackburn, VP of Sales turned a 6 person sales team with no scalable process into 40+ reps and is on his way to making Nooks the fastest growing startup of 2025. 

For everyone currently on their own rocketship and looking for contemporary wisdom, find out what Nooks is doing right now to hyper-scale: 

• Going against all good Sales advice and winning 72% of the deals that offer the controversial FREE trial! *gasp.
• Reversing the industry norm of pushing up market to instead be pulled up market by strategic processes that build trust.
• Capitalizing on their exceptional timing in the market by doubling down on outbound pipeline generation with the best SDR team in the game.

“Hyper-scale or die” is the battle cry for SaaS in 2025 and Nooks is set to win. Their VP of Sales, Jonathan Blackburn shares all the details of exactly how they’re doing it right now with Bravado CEO Sahil Mansuri.

Time-coded show notes:

00:00 — Introducing Jonathan Blackburn, VP of Sales @ Nooks
03:21 — Expanding the sales team and a 60 day internal evaluation
08:51 — Try before you buy
20:32 — Profile of rep to hire at Nooks
30:20 — Red Flags while hiring
35:32 — Setting up the team for success
47:07 — Managing up as a VP of Sales
54:03 — Pipeline and the resurgence of the SDR
01:01:54 — Sales as a Superpower
01:05:13 — Best advice early in your career

Full transcript:

00:00:00:03 - 00:00:08:11
Sahil Mansuri: Nooks gets, a lot of inbound applicants, coming in. How do you vet through that? Because obviously you have a limited amount of time.

00:00:08:11 - 00:00:26:06
Jonathan Blackburn: So the honest answer is I don't go through dates, I don't have time. But ultimately, we're hiring people who can break through the noise. And if someone can't break through the noise for themselves, I don't have a high level of confidence. I'll be able to do it for a product or tool.

00:00:26:08 - 00:00:43:16
Sahil Mansuri: Hello and welcome to another episode of the Bravado Pod. Today I've got my good friend, fellow East Bay resident Fremont for life, Jonathan Blackburn, the legendary VP of sales at nugs. Jonathan Easy Bay living. What's up sir, how are you doing?

00:00:43:16 - 00:00:45:00
Jonathan Blackburn: Good man. How are you?

00:00:45:02 - 00:00:59:02
Sahil Mansuri: I'm so happy. So excited to do this. Thank you for agreeing to come on the show and share some of your expertise, because there's a lot of people in the world that want to know how you've been cooking over at Nux over the last year. Plus, and, excited to get into it.

00:00:59:02 - 00:01:02:08
Jonathan Blackburn: Appreciate it man. Very kind introduction. Maybe to kind.

00:01:02:10 - 00:01:27:10
Sahil Mansuri: Well, you know, I guess is background, you know, you and I met, as most salespeople do, on the golf course, and had, had a great, Half Moon Bay experience a few years ago. At the time, you were at lattice, you know, selling, I guess mostly in air and OBS teams. How is the transition been for you to transition from selling into that department to selling into sales leaders and revenue leaders?

00:01:27:10 - 00:01:42:19
Jonathan Blackburn: It was easier because it was actually a bit of a difficult transition for me, moving into to a lot of selling an HR leaders for so long, I'd sold or lead team selling it to go to market. So selling it to HR leaders was a bit of a departure. I think. Learned a lot, had a lot of fun.

00:01:42:19 - 00:01:48:09
Jonathan Blackburn: But coming out of that, it's actually been really fun to be able to sell to salespeople and sales leaders.

00:01:48:11 - 00:01:58:09
Sahil Mansuri: So why don't you start by just giving us some context? So when did you join Nook's and when you joined about how big was the team, about what are about how many customers like what stage where you guys at?

00:01:58:10 - 00:02:25:12
Jonathan Blackburn: What? I joined the team. Let's see. We had three stars. We had three A's. I would say, all the s, the the A's were kind of just doing all the deals. There was a segmentation. There was nothing really in place. There. We had, low I'd say, let's say low hundreds of customers. And we were single digit RR so we were in many ways like we I think just what you mentioned earlier, we had strong signs of product market fit.

00:02:25:12 - 00:02:40:22
Jonathan Blackburn: We had some really happy customers. But it was still very early days and there was no, I'd say, clear, replicable motion or process that we were, operating off of, which is exciting, but also a lot of room for opportunity.

00:02:40:22 - 00:02:52:07
Sahil Mansuri: So three stars, three, eight years, low, hundreds of customers and low single digit, RR and when was that again? What was the was a month here.

00:02:52:07 - 00:02:56:07
Jonathan Blackburn: Although over a year ago, I think it was the first week of January that I joined Delta last year.

00:02:56:08 - 00:03:04:22
Sahil Mansuri: Okay. So Jan 2024 okay. So now we're we're fast forwarding 14 months. And roughly where are you today with all of those counts?

00:03:04:22 - 00:03:20:15
Jonathan Blackburn: Roughly, we're around 20 stars were around 28 years. We are double digit millions. We had a very good year last year. And we are closer to 1000 customers than we are to 500 customers.

00:03:20:15 - 00:03:42:10
Sahil Mansuri: Wow. So you've basically, you know, roughly six XT the the size of the team, seven x to the size of the team tripled more than tripled the number of customers, and, you know, more than three or 4 or 5 extra revenue, even more than that on the revenue side, that's a hell of a year. Congratulations.

00:03:42:10 - 00:03:46:06
Jonathan Blackburn: Thank you. Man. It was a very fun year. It was a very busy year to let's start.

00:03:46:06 - 00:03:54:15
Sahil Mansuri: I mean, the first thing that comes to mind is, is going from six people on the team to 40 people on the team. Is is crazy. How did you do that?

00:03:54:15 - 00:04:14:22
Jonathan Blackburn: A lot of interviews, a lot of conversations. You know, we actually don't have a go to market recruiter. And so, one of the first hires I made was actually our head of sales about, her name is Melanie. She's absolutely amazing. She has done a lot with the SDR. Org to really kind of, like, lead and grow that for the majority of the year.

00:04:15:00 - 00:04:34:19
Jonathan Blackburn: I've really been spearheading all of the go to market, like, sales revenue hiring. We've been doing on the a side rub up side, the into the ancillary pieces of the of the org. It's been a lot of interviews been it's been a lot of interviews, a lot of, I guess white knuckling, if you will. But we're at the point now where we're starting to peel out.

00:04:34:19 - 00:04:39:02
Jonathan Blackburn: We're building out the infrastructure around us to make it easier to scale this year.

00:04:39:05 - 00:04:50:08
Sahil Mansuri: Maybe talk me through your first, like 30, 60, 90 days as a VP of sales. You walk in, how do you think about your priorities? How do you think about your onboarding your own ramp, in order to get in seat?

00:04:50:08 - 00:05:24:12
Jonathan Blackburn: Yeah. I think, one thing that I actually did with our founders is we, we created a 60 day plan. You know, I was the first executive that I ever hired. There are three salespeople before me. The first leader, executive that I ever hired. And so I think, it took a little bit of, it took a little bit of time for us to get to know each other or for us to work well together, for us to be able to find find our groove on the 30 day mark, I'd say like early on, how I really approached it is, you know, we didn't get to where we were without being good

00:05:24:12 - 00:05:43:17
Jonathan Blackburn: at something, without being good or to quite a few things, actually. And so early on, I really wanted to figure out, like, what were we good at? Why did people love us? Why did they love the product? What made them excited? And what about our sales process? Our sales motion was working, and how do we do more of that?

00:05:43:19 - 00:06:02:21
Jonathan Blackburn: I think in that in that process, you're always going to be able to find, especially if you're a little bit more senior and coming into early stage company things that maybe don't really make sense, things that could be done better. But I actually think focusing on what the company does well early on is more valuable than fighting all the gaps.

00:06:02:21 - 00:06:08:19
Jonathan Blackburn: There's going to be a ton of gaps, especially at an early stage company. So that was really my focus of the first kind of 30 days.

00:06:08:19 - 00:06:11:02
Sahil Mansuri: And what did you find? What does the company do? Well, what.

00:06:11:02 - 00:06:34:02
Jonathan Blackburn: We did really well, and I think we still do really well, is we put our prospects and our customers first in our sales motion. We run trials as a part of our sales motion, and something coming from someone who's been in kind of like SaaS tech for almost 16 years now, mostly selling enterprise tech. The word trial and sales motion just didn't really jibe well with me, if I'm being honest with you.

00:06:34:02 - 00:06:58:18
Jonathan Blackburn: It makes me really nervous. Really scared. For many, many, many reasons. I spent a good deal of time learning our products, being on calls of the team, learning our trial motion. And what I found in our trial motion is we do about 50% of the implementation during trial, which sets people up for success during the trial.

00:06:58:18 - 00:07:25:15
Jonathan Blackburn: But it also makes it significantly easier for our customer success team to onboard, our customers during the trial or. Sorry, after the trial. Excuse me. Which is really, which is really helpful. We also then our trial process is like, it's the is the is the most in-depth trial process I've ever experienced. And and we've only gotten more in-depth.

00:07:25:15 - 00:07:29:09
Jonathan Blackburn: And what I mean by that is.

00:07:29:11 - 00:07:51:11
Jonathan Blackburn: Our team will our sales team, our our, our team, they'll set up our workspaces. They'll, they'll they'll, they'll pull numbers for for customers. They have to act as a bit of like an SC at the beginning part of the trial, they'll do implementations, and then they have to actually kind of transition to being like almost like SDR managers, because to use looks especially for our dialer.

00:07:51:13 - 00:08:10:00
Jonathan Blackburn: You need to call and you need to get the prospective team excited about calling. Not only do you need to get them to call, they need to be effective and efficient, because the one thing Knox does really well is connects you with more people. If you're connecting with more people and you're not doing anything that those connects, it's not a great experience.

00:08:10:00 - 00:08:30:14
Jonathan Blackburn: So we need to be able to coach them. We need to be able to answer supporter questions. We always act to support during trials as well. And what I kept hearing time and time again on trials from prospects and people that signed up with us is the trial experience was their favorite part about Knox and the team support that they got throughout that experience was amazing.

00:08:30:14 - 00:08:51:13
Jonathan Blackburn: Our founders set the tone really early when I came of like, nothing is above anyone, and the amount of trials that they would jump into to support was, was pretty insane, actually. And so like, I could go deeper on that, but essentially our trial motion was, one of the things that jumped out to me as being a differentiator for us as a company.

00:08:51:18 - 00:09:24:02
Sahil Mansuri: In the age of AI products. This has been, you know, hotly debated because you're used to SAS up front enterprise, 12 month, 24 month contracts. But AI products are generally like usage based pricing or come in and and pay per outcome. You know, you see a lot of that sort of thing coming into vogue. And so companies are even if they don't call them trials are effectively in trials because, you know, the person doesn't use a product for a long time, then you're going to have some fallout.

00:09:24:02 - 00:09:25:01
Sahil Mansuri: So how.

00:09:25:02 - 00:09:25:16
Jonathan Blackburn: Do you think.

00:09:25:16 - 00:09:40:16
Sahil Mansuri: About the, you know, what advice would you give to a company? And how do you see this kind of playing out at other organizations outside of Knox, you know, in terms of adopting a mentality of try before you buy? One of the.

00:09:40:16 - 00:10:08:00
Jonathan Blackburn: Reasons I had probably so much scar tissue coming up in SAS in the earlier days, my earlier days of SAS is you really couldn't try something before you buy it, especially with enterprise wide, like implementations, for a lot of tools and having the product, for lack of a better phrase, be trial, having like being able to actually try the product, and experience it has made the sales process significantly easier.

00:10:08:02 - 00:10:25:10
Jonathan Blackburn: Everything leading up to the sales process was a little bit tougher. We do a lot of security, a lot of legal, a lot of those things before we actually begin the process. But the amount of times that we did all of that set the team up for success, turn the trial on. And people said, I don't want you to turn this thing off.

00:10:25:12 - 00:10:48:03
Jonathan Blackburn: Like, how quickly can we get this wrapped up? Has actually made it a little bit, I'd say extended the process slightly to get to a trial, but our close rates on trials are insane. I think as of last quarter, we had a 72% win rate on every deal that went to a trial. And the majority of them don't want us to turn it off.

00:10:48:05 - 00:11:00:20
Jonathan Blackburn: And so they'll, they because we do most of the work up front, you don't have to we can actually move to commercials pretty quickly from that point on, which from a negotiating standpoint, makes our lives a little bit easier to for sure.

00:11:00:22 - 00:11:19:15
Sahil Mansuri: Are the trials paid? They're free trials. And so you're committing a lot of resources if you're doing super in-depth implementations, SDR coaching support, etc.. Without the guarantee of revenue. On the other side, in this, you said this was a process that was established prior to you getting there.

00:11:19:20 - 00:11:21:06
Jonathan Blackburn: Yes. Yeah.

00:11:21:08 - 00:11:32:10
Sahil Mansuri: Interesting. I you know, I wonder how many companies would have chosen to do something like that. You know, it feels like it's something that a lot of companies are allergic to trying to do up front. You know, this.

00:11:32:10 - 00:11:47:21
Jonathan Blackburn: Was the big part of our sales process coming in that like just I called it out with our founders who coming in of like, I don't know if that makes sense, but I'm going to keep an open mind when I saw the data, when I experience it for myself, I realize it was the right thing for us to do, but also to be transparent with you.

00:11:47:21 - 00:12:13:08
Jonathan Blackburn: If our win rates were 60 or 70%, we would probably it might have been a different conversation, I would say, or we might have had to adjust what we were doing there. But, it definitely made a big impact. And I, I will say to going back to like your original question of 36,000 ID, I kind of talk to some of the 30, the 60 DPS is really, I think, where like there was no 90 DPS, if I'm being really honest with you, it was 30, 60 days.

00:12:13:08 - 00:12:32:20
Jonathan Blackburn: It was like evaluate and fix and do and that 60 day, I think that, that second part of the 30 days or the 60 days was really me focused on, like up leveling the team and this skill set at the team. What are my early KPIs coming in was help us win more 40 K deals. I think we had 1 or 2 deals.

00:12:32:20 - 00:12:52:23
Jonathan Blackburn: Maybe our customers may be above 70 K when I joined, but there was this kind of glass ceiling. We had around 40 K deals. Our win rate just wasn't what it needed to be. If you fast forward to the end of the year, we were winning security deals at a much higher clip than we ever won 40 and it for quite a while actually, we've broken the record for largest deal closed in history.

00:12:52:23 - 00:13:19:17
Jonathan Blackburn: Feels like every month almost part of that is up living the skillset of the team, but a part of that is actually just making sure the companies able to actually have the conversations that it needs to and support those, those types of customers. And I felt like that's where early on we needed the biggest uplift, was making sure that we were able to support those large customers, but that that kind of 60 day period of like, okay, I've gone through this.

00:13:19:17 - 00:13:49:17
Jonathan Blackburn: I know what we do. Well, I want to double down on that. Where do I actually figure out, how do I implement or like, how do I spend time figuring out like the the bigger list for us to do or fix on the, on the go to market side? And that was a big that was a big part of it is like, how can we put ourselves in a position, in position as a company to be more successful with those up market deals by being able to support them and also help them understand that, like we, help us earn their business is maybe a better way to put it.

00:13:49:19 - 00:13:50:12
Jonathan Blackburn: What does it.

00:13:50:12 - 00:14:06:22
Sahil Mansuri: Take to support, 5070 500 K customer that you can get away with with like 20, 30 K deals? But you can't get away with, with larger. What do you mean by the company needed to learn to be able to have those conversations?

00:14:07:00 - 00:14:46:02
Jonathan Blackburn: A lot of things we were doing, we were we weren't building enough trust in and in our sales motions. We had, for example, like there was security, there was legal, there was implementations. It was like when we brought in our CSE team and like what that look like and what those conversations were like. And I think a big, a big part of it is early on getting ahead of some of these things, actually having, having an MSA, we felt comfortable with having a legal process, having a security process and not handling each of these items, was like a one off, like, we got an infosec questionnaire or we got red lines on our MSA. Like, how do we handle that? What do we do? One of the bigger things I did was actually just pulled more people into the sales process. I pulled in our founders a lot. We pulled in engineering support, security support. We pulled in a lot of people earlier in the process, and I think that gave customers more trust in us as a company that we would be able to support them.

00:15:06:03 - 00:15:29:22
Jonathan Blackburn: What actually really helped too, was leaning into customer references and investor advisor notes. Maybe something we can go to more if you want to a little bit later, but, I've never been at a company where we leverage our investors and advisors as much as we do here and our customers, as much to and building a replicable motion and process around how we pull them in when we pull them in.

00:15:29:22 - 00:15:49:05
Jonathan Blackburn: And it will be ask of them had was incredibly important in us building more trust with our customers to be able to close those larger deals.

00:15:49:07 - 00:16:09:08
Jonathan Blackburn: We are big on process. And so, there's a couple more. There's a couple, a couple of facets of that. We pushed back really hard. So in our MSA, like in, in our, in our terms, we have like logo rights and KSAT rights and a couple other things. 99% of the time those get redlined out by legal.

00:16:09:09 - 00:16:29:23
Jonathan Blackburn: Pretty early on, we actually pushed pretty hard. That actually has become one of our kind of sacred cows in our in our terms, it was such an important part of how we how we grew and just word of mouth people talking, talking about docs and being willing to share their experiences, that we actually lean pretty heavily into, that we don't just fold.

00:16:29:23 - 00:16:52:07
Jonathan Blackburn: I guess this is like the easiest way to phrase it when people push back on that. We do hold a pretty clear line there, especially if there's any kind of discounting or anything a tie to the deal. We have a list internally of, customers how we actually leverage them. We do give advisory shares to, a decent amount of customers that are willing to be references for us as well.

00:16:52:09 - 00:17:14:02
Jonathan Blackburn: So they have some skin in the game, and they're excited about referencing us and talking to potential customers, not just because they love books, which a lot of them are willing to do it simply because of that, but also because they're vested in us and our success as a company and a business. And our investors and our investors and our advisors are, are so excited to talk about us.

00:17:14:02 - 00:17:37:10
Jonathan Blackburn: We actually have, a couple of lists that I manage to keep internally where, we've gotten, our investors to basically send out weekly in some cases, if not monthly notes to customers where our sales team will actually go in, they'll put the customers. We have emails that we write that they send for us, to show competence in books.

00:17:37:10 - 00:17:57:23
Jonathan Blackburn: And we have all different spreadsheets. And this is all tracked not just in in Google Sheets, but also in, in HubSpot in other places, too, where we lean really heavily into, like, building processes and like building more repeatable motions around how we leverage them. What I found, what I found is that investors and advisors are generally excited and willing to help.

00:17:57:23 - 00:18:16:17
Jonathan Blackburn: Where it tends to kind of fall off the rails is if you don't leverage them enough, or if it's just kind of messy, like we're all busy people, they're busy people, they're happy to help. But if we make it too hard on them and we don't and we aren't consistent with our asks, they they they typically kind of lose focus with this pick up political priority.

00:18:16:19 - 00:18:26:21
Jonathan Blackburn: But by keeping it top of mind, by being, by making it really easy for them and by being very consistent with the asks, we have a number of investors that will send out notes for us every week and.

00:18:26:21 - 00:18:28:11
Sahil Mansuri: Or these notes for.

00:18:28:11 - 00:18:29:14
Jonathan Blackburn: Intros, or.

00:18:29:14 - 00:18:37:20
Sahil Mansuri: Are these people mid-flight in process or like where where do you find the greatest ROI with using investors?

00:18:37:22 - 00:18:59:19
Jonathan Blackburn: All of the above, I'd say, is my honest answer. We love them at every point in the sales cycle, the sales process. We leverage them to help us break in to companies. If there's connections, a non insignificant amount of our pipeline, especially our like SaaS tech pipeline is built around that. We leverage them early in the process, especially if we find out that it's a competitive deal.

00:18:59:21 - 00:19:36:14
Jonathan Blackburn: Typically we'll pull in, customer reference or to very early in the process if it's a competitive deal as well. And then we'll leverage them, throughout the process. And in the rare cases where, like, we're in a trial or we're coming out of a trial and like, we need to make a business case, or it's like it's not an immediate yes, we'll pull in advisors, we'll put investors to send notes to reach out to people, during the sales motion, the, the a lot of parts of it, the notes that we send, how we, how we, ask them to to share like what sentiments we ask them to share.

00:19:36:14 - 00:19:50:12
Jonathan Blackburn: Like, that's all unique to the part of the sales process and the mission. But our goal is to stay top of mind with prospects throughout the process. And, we, we leverage them at for unique parts of our sales motion.

00:19:50:13 - 00:20:02:06
Sahil Mansuri: Super interesting. I, do you use a tool or you said you use Google Sheets and your CRM to track it. You don't use like a specific tool to do this. Did you bring this to Nook's or was this there before you got there?

00:20:02:06 - 00:20:25:05
Jonathan Blackburn: This was there before I got there. We actually do use, we have two different ways we do it. Most of it is through spreadsheets and through that we do use high five, though, as a way to like, kind of partner with, with some of our advisors. But we have a separate process, like I mentioned, for our investors and another core group of people, but I kind of run all those motions simultaneously.

00:20:25:05 - 00:20:44:03
Sahil Mansuri: Got it. How do you find time to do that and to hire, you know, 40 people in a year? Maybe. Let's talk about the, the profile of rep that you bring on, maybe for the SDR role and for the role. What are you looking for? What makes someone excellent, an excellent seller at Nook's.

00:20:44:03 - 00:21:09:06
Jonathan Blackburn: We've gone through an evolution of this in my time here. Early on, when I first joined, I hired a couple people for my network. And people that I like, I knew were really good sellers. And I was excited to, to kind of bring them on with me. They worked really well. They were really fantastic sellers. And then we went through kind of like a, hiring class in the summer, and transparently like some of the people worked out and some of them didn't.

00:21:09:08 - 00:21:25:23
Jonathan Blackburn: And that was really the first time as a company where we had a cohort of people who did it, who who had it worked out. And we we kind of had some trial and error with that. We knew what types of sellers worked well for nooks. Typically, we had hired people who had sold into the sales tech landscape.

00:21:26:01 - 00:21:46:01
Jonathan Blackburn: We had hired people who had been either in a competitive like a come from a competitor or similar space. And the reason for that was they could bring some kind of Rolodex or some kind of deals with them. It helped them ramp a little bit faster. Selling to salespeople can be can be a little bit tough. I'm a sales leader.

00:21:46:02 - 00:22:09:21
Jonathan Blackburn: You've been a sales leader. You're a founder like we're busy. A lot of times. I just want people to get right to what they need of me or, like, what the value prop is. And we tend to be a little bit direct, and we do this for a living. So I think we're like, whether people want to admitted or not, there's always some bias coming into it of what I coach my team to sell like this, or do I think they're doing this right?

00:22:09:21 - 00:22:32:10
Jonathan Blackburn: They can be very honest, but also very direct. It's kind of a double edged sword there. And we have brought in people who we sold to our tag, who sold to more technical buyers. And they just haven't worked out quite as well as a, as a cohort, if I'm being honest here, I think having people who have experience helping you to sales tech or people who are excited or willing to to take that challenge on has been important.

00:22:32:12 - 00:22:35:20
Jonathan Blackburn: And we try to build that out in our sales, our sales motions.

00:22:35:20 - 00:22:56:11
Sahil Mansuri: I mean, it's something that obviously we spend a lot of time recruiting across many industries at Provato. And one of the things that I think many founders and sales leaders underestimate is the criticality of having sold into the same buyer persona. Now, in some cases, the same buyer persona can buy similarly, even if it's not the exactly the same persona.

00:22:56:13 - 00:23:10:19
Sahil Mansuri: But, you know, I think if you are used to selling to CISOs or CTOs and now you're going to sell to sales leaders, you're going to find that to be really difficult in the inverse of that as well. But, you know, if you sold martech and you sell sales tech, you probably can get get away with that.

00:23:10:19 - 00:23:29:01
Sahil Mansuri: You know, you can figure out how that works. But yeah, I think there's like different phenotypes and different emotions, different processes. And you need to be I think the competitive sell is a really important one too. Obviously nux has a couple really big, you know, main competitors and a bunch of other ankle biters that are coming. And this is a hot space to be in.

00:23:29:01 - 00:23:39:00
Sahil Mansuri: And so you've got to be, you know, able to speak with some domain expertise and some authority, build trust in the customer that you know, what you're talking about as a seller.

00:23:39:02 - 00:23:48:15
Jonathan Blackburn: Totally. And there are some traits that like we we interview for and that we hire for in the process that are important, to us as well. And I'm happy to tell me more if you want.

00:23:48:15 - 00:23:49:05
Sahil Mansuri: Yeah, tell me more.

00:23:49:09 - 00:24:08:13
Jonathan Blackburn: There's a couple of things that are important to me, and I think there's a couple of things that are important to us as a company. What's really important to me on the sales team is that we build a strong culture, specifically of culture, of people who want to be here, who are excited to learn, who want to work together.

00:24:08:19 - 00:24:26:10
Jonathan Blackburn: It's really important to me that we build a strong team. I want to work, with people, and I want people to come here that are excited to build something and do something not just for themselves, but for each other. I want people to, to to show up and be excited about the people working next to them. I have a wife and a daughter.

00:24:26:15 - 00:24:47:21
Jonathan Blackburn: I see this quite frequently in interviews. I love them to death. I would probably rather be with them than doing anything else. And if I'm not going to be with them, that I really I really want to fucking enjoy what I'm doing and who I'm doing it with. It's really important to me. And so working with people who have a similar mindset of like, yeah, I'm going to show up to work every day to do my best.

00:24:47:21 - 00:25:05:14
Jonathan Blackburn: But I also want to make sure that, like, I want to be a part of a team, I want to help people. This isn't me versus everyone else. This is us trying to accomplish something together and research that out to the interview process in various ways. But it's also important to me is people are coachable. None of us are perfect.

00:25:05:16 - 00:25:30:18
Jonathan Blackburn: I'm far from perfect to ask my wife. She'll probably say the same thing. And I think that's true of every person in the org. And I typically lean into that during interview processes, because I really want people to think, I want them to know that none of us are perfect. We're all trying to grow, we're all trying to improve, and I want to create that space so that when we do our sales interviews and our processes and our mocks, I've created that space for them to be open.

00:25:30:18 - 00:25:56:12
Jonathan Blackburn: We do, we do mock disco demos and the sales, as part of the interview process. And there's various things we test for their acumen and how they ask questions, what their what their sales process is like. At the end, we ask people for feedback. And honestly, man, if there's one thing that I get from these interviews, the look on someone's face when I say, is it okay if I give you some feedback?

00:25:56:14 - 00:26:18:10
Jonathan Blackburn: It's probably all that I need to know from that entire conversation nine times out of ten. Yeah, because no matter what someone says, you can't hide that look on your face. And typically what I'll do when I say that is, they'll they'll always say yes because it's an interview. Typically. And like, you know, they're likable. Like, but I can tell based on how they respond and what their, what their, you know, face tells me and everything like that, just kind of their general body language.

00:26:18:10 - 00:26:39:06
Jonathan Blackburn: I typically give them some feedback and I'll be pretty direct and pretty honest. And I'll say, hey, you did this really well, but there it is. You know, this thing in this thing you did incredibly well, that was, you know, very, very impressive. And then I'll be very direct about something they could have improved on. And again, I want to see how they respond, because a lot of times when we're selling to these salespeople and sales leaders, they get this direct feedback.

00:26:39:06 - 00:27:01:01
Jonathan Blackburn: And you would be surprised how many people in the interview process say they want feedback, don't actually want feedback, and then when they get some kind of like, feedback that constructive generally tend to disagree with it or have a lot of reasons as to why. It's like it's it's invalid feedback and that's completely fine. Like everyone you know, everyone has their own perspective and their own opinion.

00:27:01:01 - 00:27:15:03
Jonathan Blackburn: But that is so important to me, not just from the feedback perspective, but because you will be selling to people who will constantly be telling you in a very direct, a blunt way what they think you're doing well and what they think you're not. And that's a part of the process that we really leaned into. As you've continued hiring, we.

00:27:15:03 - 00:27:34:14
Sahil Mansuri: Want people who have expertise in selling to your domain. You want people who are coachable. You want people who are willing to grow and have kind of the, it's almost like an entrepreneurial mindset where you're you're always looking to get a little bit better. And you know that, like, today's the worst that this product's ever going to be.

00:27:34:14 - 00:27:54:02
Sahil Mansuri: Today's the worst. I'm going to show up to work. And every day I'll try to get better. Are there other kind of secrets that you've figured out as you've been scaling so quickly? Because I'll tell you, there's a lot of companies that I know that are facing a similar sort of growth plan in front of them, or they're trying to go from 5 to 20 or, you know, whatever, two to 2 to 15 and, and a year.

00:27:54:04 - 00:28:23:04
Sahil Mansuri: And it can be daunting, you know, like to successfully having gone from 3 to 20, there's very few companies that can do that in a, in a year, especially without, you know, having a large recruiting team, at your behest to be able to handle that, you know, gets, a lot of, gets a lot of inbound, applicants, coming in, gets a lot of attention and, LinkedIn, etc..

00:28:23:06 - 00:28:34:22
Sahil Mansuri: How do you vet through that? You know, what is your process to try to even figure out and filter how you can spend your time? Because obviously you have a limited amount of time, you've got those customer notes to get out to.

00:28:34:22 - 00:28:58:15
Jonathan Blackburn: So the honest answer is, I think for across our sales roles, we maybe had 12,000 applicants over the last like four months. I don't have any recruiting. I don't have the time or the space to actually go through the applicants, the ATS and and like and and track that because just like there's just not enough AI that is probably two for a full time job for two people.

00:28:58:17 - 00:29:25:03
Jonathan Blackburn: What I actually tend to rely on are people who are creative in the interview process, because to me, that's actually what we're really hiring for, is how do you break through the noise? And so I'll just share, like anecdotally, of those like 12,000, it's just a 12,000 ish people that have applied over X period of months. I maybe have gotten a thousand LinkedIn notes over the past three months, which feels like a lot sometimes.

00:29:25:05 - 00:29:27:06
Jonathan Blackburn: So I should try to manage my LinkedIn inbox.

00:29:27:08 - 00:29:29:01
Sahil Mansuri: But but it's only 8%.

00:29:29:03 - 00:29:48:02
Jonathan Blackburn: Yeah. And of those I've maybe gotten 100 emails and of those that maybe gotten 35 people who called me. Wow. So the honest answer is, again, I'm not saying this is right or wrong, but it's the truth. I don't go through dates. I don't have time. We are hiring recruiters, so we will. But ultimately we're hiring people who can break through the noise.

00:29:48:02 - 00:29:58:19
Jonathan Blackburn: And if someone can't break through the noise for themselves or for their own career, for the job that they want, I don't have a high level of confidence I'll be able to do it for a product or tool that's.

00:29:58:19 - 00:30:15:18
Sahil Mansuri: So, well, sad. I mean, that's going to turn into a great jam, that we're going to post on social media. That was really, really well stated. If you can't, even if you can't even sell yourself, get breakthrough of the. No. It's going to be hard to sell a product. Yeah, I think that's really well said.

00:30:15:20 - 00:30:38:17
Sahil Mansuri: Before we move on, because I want to talk a lot about enabling and onboarding those people. Are there any red flags that you've learned along the way of whether it's mis hires or people who seemed really promising in the interview process that kind of flopped at the end? Are there any are there any kind of red flags of qualities as you're assessing talent that you found to try to avoid?

00:30:38:19 - 00:30:41:08
Sahil Mansuri: That can help you avoid a mis hire?

00:30:41:08 - 00:30:56:20
Jonathan Blackburn: The one thing that we really look for in the process, I mentioned coach ability. I mentioned some of the softer things. There's more stuff that I can go to there, but like at the risk of getting too detailed in some of that, how people treat the interview process I found to be very similar to what their sales motion looks like as part of our mock disco demo.

00:30:56:22 - 00:31:15:19
Jonathan Blackburn: We imply we kind of actually we don't apply, we say. And in the prompt, feel free to set yourself up for success. Tell us who you want us to be. Tell us what you want us to talk about. I ask people to sell their products. I want to see them as comfortable as humanly possible and and also ask them in the feedback section.

00:31:15:21 - 00:31:31:12
Jonathan Blackburn: I'll ask them how we did because I, you know, I'll kind of want to get feedback there too. I find it really helpful when people actually do give us feedback and say, you did this really well, you could have done this better. This is different to my current customer because it shows me that there's some critical thinking there.

00:31:31:14 - 00:31:46:07
Jonathan Blackburn: When they send probes before, as if this is a sales call or sales motion, they say, hey, excited to meet with you later today. These are the things I want you to talk about, the things that I want you to, these are the problems. I want you to have, the pains. I want you to have.

00:31:46:09 - 00:32:04:07
Jonathan Blackburn: And then they send detailed follow ups when, like, when people treat the interview process like a good sales process, I found that to be a really good litmus test for just how they actually sell in general, which is really important. I also look for people who have been promoted internally I don't really like. I don't really care that much, truthfully.

00:32:04:09 - 00:32:18:06
Jonathan Blackburn: Like how like like job tenure, how long someone's been in the job, like, I've been doing this for a long time. I think a lot of us have been do this for a long time. Know that sometimes you just make mistakes. Sometimes you think you picked the right company, it wasn't the right company, or the company doesn't do right by you and it's hard.

00:32:18:12 - 00:32:38:23
Jonathan Blackburn: It's hard to, it it it feels wrong for me to put too much of an emphasis on something that some people don't have in their control. But what I do look for is how often people get promoted internally. As you probably know, as I know, it's way harder to get promoted internally than it is to get promoted externally.

00:32:39:01 - 00:33:09:08
Jonathan Blackburn: And I found that people who are really high slope, who get promoted internally often who run a really tight, interview process, tend to do really well. I think what you said earlier, when people who tend to have more of a founding kind of like, entrepreneur mindset tend to do really well. The last thing I'll say to this is at some point in the interview process, I, I will move away from selling for books and move into selling against nooks.

00:33:09:10 - 00:33:29:22
Jonathan Blackburn: And I think I'm in a very privileged position to be able to do this. Because to your point, in our little ecosphere, in our bubble nooks gets a lot of recognition online. I think we're number three or 4 or 5 on rep view or something. Something obscenely high. I think we're one of the top companies on, Glassdoor as well, for our size.

00:33:30:01 - 00:33:51:20
Jonathan Blackburn: I love both of those things, because it means that we've been able to build a winning culture and all the time and effort and work that I put into our culture really permeates and kind of shines, and people are excited about that. But I will lean into selling against nooks to tell people this will probably be the most rewarding, fun, fulfilling, and hardest job I've ever had.

00:33:51:22 - 00:34:09:17
Jonathan Blackburn: And then I'll usually kind of pause, let that set, and then I'll lean into, are you sure you're you're are you sure you're excited about that? Are you sure you got a point in your life, or a season in your life where you're able to commit to something like this and are really kind of leaned in to the like, this is fun, but like, don't get it twisted.

00:34:09:17 - 00:34:32:19
Jonathan Blackburn: Like, like Nook's isn't flying off the shelves per se. Like we have to sell it a gets a job. It it's a fun job and it's rewarding, but it's really hard. And I guarantee anyone that comes to Nook's will have more fun and work harder than they've ever done in their life in both of those aspects. And I really think that, like, it's my duty to lean into that early on with people and call that out.

00:34:32:21 - 00:34:42:21
Jonathan Blackburn: And I, I've had people self-select and say, that sounds amazing, but that's not right for me right now. And I love that because I want people to make that decision now as opposed to three months down the line.

00:34:42:23 - 00:35:03:09
Sahil Mansuri: That's so well said and such a great nugget. I think many companies, when they fall in love with a candidate, get into sell mode too quickly without being honest or earnest, with themselves and with the candidate about whether this is the right fit. I love what you said about is this a season in your life where you can do that?

00:35:03:11 - 00:35:14:00
Sahil Mansuri: That's a that's a really that's a really thoughtful way of putting it. Because we do all have those moments when it's not right for us to be doing that. And times when we can. Totally.

00:35:14:00 - 00:35:18:02
Jonathan Blackburn: I think those of us with, children or small children can probably attest to that, too.

00:35:18:04 - 00:35:38:20
Sahil Mansuri: Oh my God. Yeah. Having two kids under the age of, three while trying to run bravado was was me. Not at my peak, I would definitely say. But where we're coming out the other side. All right, let's shift to. All right. You've got all these people. Let's start talking about how you actually set them up for success.

00:35:39:01 - 00:35:54:00
Sahil Mansuri: Tell me about what you've done around sales ops, or on enablement, around tech or on management levels, around KPIs and ramps and like how do you think about getting your your class of people in such so that they're set up for success and productive as soon as possible?

00:35:54:00 - 00:36:19:07
Jonathan Blackburn: Is is an ongoing thing of us constantly trying to improve. I am really bullish that we hire incredibly talented salespeople. We have a really rigorous interview process. We have a high level of applicants to which we pass a few through. I go really deep on not just the sales, not just the interview process, but also we go deep on referrals, back channels, everything.

00:36:19:09 - 00:36:38:16
Jonathan Blackburn: Which is all to say that I know that when someone comes to X, there are talented sellers who has done very well at their job, and from there, it's kind of on me and us. If we're hiring incredibly talented people, it's on us to make sure they're successful. And if they're not, then that's our that's our fault essentially, in my opinion, not theirs.

00:36:38:16 - 00:36:58:13
Jonathan Blackburn: And so this is something that I take incredibly serious when we had our first like kind of like cohort of hiring and we've evolved this ever said. But we had our first big cohort of hiring. I sat down and I built out a really detailed spreadsheet of like, I'm a new rep coming into nooks. What do I need to be doing every day for the first 30 days?

00:36:58:15 - 00:37:21:08
Jonathan Blackburn: And so I built a really detailed sheet of like, what, what they needed to do on a daily, a weekly, and like kind of a monthly basis for their first, first couple days, first week, first month for first, first quarter, I'll go into the details of what that looks like. But the first thing I'll say is, I think ramp is how you structure Ramp is really important in this process.

00:37:21:10 - 00:37:52:15
Jonathan Blackburn: Some companies do draws, some companies don't. Some companies guarantee ramp, some companies don't. Some companies have ridiculous expectations for ramp and some have, almost laughable expectations when it comes to like, the ease of something, what I really try to focus on and building our, our ramp processes, how do I align with the business needs are to what the, the reps desires are.

00:37:52:17 - 00:38:24:04
Jonathan Blackburn: So what we actually do at Nook's is we don't do a guaranteed, draw or a guaranteed card. For your first couple months. We pay an incredibly high percentage of commission on every deal. Closed within your first couple of months. It's pretty obscenely high, especially for it's obscenely high for SaaS, for tech. But it's intentional, and I am so excited to pay it when people close deals, because what I want them to do is get ramped as quickly as possible and become as effective and efficient as quickly as possible, and close deals as fast as possible.

00:38:24:04 - 00:38:37:17
Jonathan Blackburn: And I will pay a very high amount of commission to achieve those things. And what we found is it's been incredibly helpful and helping us ramp reps and getting them motivated to go through the process as fast as possible.

00:38:37:17 - 00:38:38:21
Sahil Mansuri: What is obscenely.

00:38:38:21 - 00:38:44:15
Jonathan Blackburn: High? 25%. We pay 25% commission on every deal sold in your first four months.

00:38:44:17 - 00:38:51:02
Sahil Mansuri: Wow. That's, that that can be a big chunk of change. If you're knocking out a couple of 5000 K deals.

00:38:51:02 - 00:39:04:17
Jonathan Blackburn: It can be. And I'll tell you what, man, I'm very glad to pay it. Especially if that means that they're crushing grab quota in their first couple months. If you're not going to get 5000 K deals in your first four months, that's a win. That's, that's a huge win.

00:39:04:17 - 00:39:27:12
Sahil Mansuri: But it's so motivating, and so exciting to be able to do that. I, I, I glassdoor we had a thing which we called our Cadillac bonus and it was anybody who hit their annual quota in their first year in nine months. So if in nine months you hit your annual quota, you got an extra $10,000 in cash, from the VP of sales.

00:39:27:12 - 00:39:50:13
Sahil Mansuri: And I remember the amount of hard work that went into people just trying to get that, that, that bonus in. Yeah. You know, in ten grand was nothing to the business relative to how hard people worked for it. But but just to have the VP sales hands you a bad to a $10,000 in cash. I mean, you know, this maybe, maybe is like illegal from like a tax perspective or whatever, you know, these days.

00:39:50:13 - 00:39:59:04
Sahil Mansuri: But back in the good old days, you know, I could literally they would just come over, just drop a band of cash on your desk if you hit it. And it was just the coolest thing to be able to do. Yeah.

00:39:59:04 - 00:40:18:12
Jonathan Blackburn: That's awesome. Yeah. Might it be gift cards or something? Nowadays it is important and we have SMB, mid-market commercial enterprise. So like the ramp is a little bit different for each segment and each part of the business. But we still do 25% commission regardless of the segment. The time to ramp is a little bit different. Kind of working back into like what that looks like and what that looks like early on.

00:40:18:12 - 00:40:40:17
Jonathan Blackburn: We have a series of certifications that we had the team go through, so we do a disco certification and a demo certification, a trial certification. And then we actually circle back after we've done all of those to do like deeper levels of certifications on them, specifically as it relates to like competitive Intel and stuff like that. Like your first couple of weeks, your first month, you're not going to pick up all of that.

00:40:40:17 - 00:40:49:04
Jonathan Blackburn: Like, you need to be able to do the basics really well. And then once you've learned that, like we do, a second pass of like going a little bit deeper on more of the nuance of all of this and.

00:40:49:04 - 00:40:50:11
Sahil Mansuri: Who built all of that?

00:40:50:11 - 00:40:53:11
Jonathan Blackburn: I did the initial iteration of everything. I built it. Did you just.

00:40:53:11 - 00:41:06:09
Sahil Mansuri: Work like 27 hours a day in order to do this? I mean, I still haven't heard whether you sold any deals yourself while you were doing this. I guess I was. That's the other thing I was thinking is, as you're building all of this, like, were you actually selling at the same time?

00:41:06:10 - 00:41:24:18
Jonathan Blackburn: When I first joined, I, I certified myself on some of these and then I probably did like 10 to 15 deal cycles. What I will say is like when things got close to being, like ready to buy, I would just pass it to a rep like I would, I, I would want to make sure someone else got credit.

00:41:24:18 - 00:41:41:07
Jonathan Blackburn: But early on my first couple of weeks, I did, I did sell a note. I thought it was important for me to, especially that early on to learn the motion and to, like, really get to experience it and feel it. It is something that we have all of our new managers go through, though we do this, I I'll kind of share.

00:41:41:07 - 00:42:02:08
Jonathan Blackburn: This is a bit off topic, but I'll share with you anyway. At our offsite or onsite to do to a year, we do one and a half. We do one somewhere sunny during the summer. We have a cold call competition and the cold call competition involves every single person in the company, engineers, marketing products, no matter who you are.

00:42:02:08 - 00:42:24:22
Jonathan Blackburn: We're cold calling. And I remember we had our on site my first month at the company and it was up in S.F., which is where the first one always is. And I was like, oh, this seems like kind of a cool idea, I don't know. And then, we pull a bunch of list and then dude, seeing engineers and seeing these like technical product people call it book meetings, by the way, was like, so fucking mind blowing.

00:42:24:22 - 00:42:48:15
Jonathan Blackburn: I was like, this is amazing. But it also really set the context of like as a company, one of our big kind of like general ethos is like we all do the work and nothing is beneath any of us. And one of the things that I do, and why do you hire the leadership if I'm promoting leadership, obviously this a little bit less relevant, but if I'm, hiring someone externally for a leadership role, I'll set the context of like your first month you're going to sell.

00:42:48:17 - 00:43:06:15
Jonathan Blackburn: And it's important that you sell and it's important you're excited to do that too. So yes, I did I did sell I built all of this. But thankfully we hired people who were much smarter and much better at these things. And I had to kind of like, build the second and third versions of this to to make sure they're, constantly improving.

00:43:06:17 - 00:43:44:16
Sahil Mansuri: I can't let that point go, which is, I feel like so many VP's, the sales show up to a role and, you know, just focus on like the deals and the raps and stuff, but it seems like you were building so much. I mean, you're building all the training, you're building this process and references. As you're building the interview process, you're building, you know, like you're you've got your, yeah, I recall you told me that you're even, like, doing, like, financial modeling and stuff, like, you know, you're like, basically doing all of it at and and having that like ownership mentality across it, I think is really is really, a unique trait across

00:43:44:16 - 00:43:47:02
Sahil Mansuri: What I see many VP of sales do when they show up to a role.

00:43:47:02 - 00:44:08:13
Jonathan Blackburn: It's really easy. At a certain point in your career, especially if someone will let you to sit back and say, I've been doing this for a long time. I'm really good at this part of the process. I'm just going to focus on this. I think it's a mistake, though, and I think when I see people who take on these kinds of roles, maybe not even as early stage, to be honest with you, man, like, this is such an early stage role.

00:44:08:13 - 00:44:17:13
Jonathan Blackburn: Like, I knew coming in, I was going to have to do this, but also like, I enjoy this, like I'm good at it, I enjoy it. I think I'm good at it. People keep pay me to do it.

00:44:17:13 - 00:44:26:18
Sahil Mansuri: So that's right. That's how you got good at it. That's a good that's a good sign. As is when when the market supply demand equation seems to indicate that you're probably good at it. I think it's.

00:44:26:18 - 00:44:45:03
Jonathan Blackburn: A big mess when people don't do that. There are some things I can share too, if you want to get to them later around. Like, we kind of touched on my first couple of lines and like, how as a new VP of sales to set yourself up for success there, but I will just say kind of going back to the original, kind of like, spirit of the question around onboarding.

00:44:45:03 - 00:45:02:18
Jonathan Blackburn: We do all these certifications, we have scorecards built out for each of these, and we have sales acumen, trades, characteristics, things. And like we wait certain scores based off certain things that like give a percentage based on what's important to us and what we've seen people be successful with. And so there's like on some level it pass or fail.

00:45:02:18 - 00:45:27:08
Jonathan Blackburn: Yes. But we do give credit scores. Say, hey, is this a 92%. Is this an 87%. Like how how good is good on this. And depending on where someone is, we will, actually spend more time or maybe less time with them, depending on their needs. I recently brought in, a sales enablement leader who I'm so excited and so lucky to have been able to brought in.

00:45:27:10 - 00:45:49:23
Jonathan Blackburn: He was on my team at Lotus. He was, our team leader, mid-market team lead. I had the privilege of promoting into, manager, and I one point he was ahead of Mid-Market for Lotus. After I left, and he went on to become a VP for a short stint. And as he was thinking about what he wanted to do next, he really wanted to get into enablement.

00:45:50:00 - 00:46:22:20
Jonathan Blackburn: And he's he's so good at everything he's ever done that I said would do whatever he want to do, like, I would just be lucky to have you on the team. And I think he's been a tremendous addition to us being able to open up a lot of our skills and processes and will he'll actually do is we build a process where he will spend the first three days of a week with a new hire and teach them the nuance of, like how we do discovery, how we get to pain, how we progressed, the conversation forward, how we demo, how we close each section, all the nuance, which like, we have a pretty detailed process that I've kind of built out here, that we want to make sure people, that we feel bullish about. I want to make sure people follow, and it takes some of the pressure off managers of, of our management team of having to teach people how to sell and support their current team and teach them how to like the tool works and more of the nuance of that.

00:46:42:14 - 00:46:45:15
Jonathan Blackburn: And it's been really beneficial to us as we started to scale to.

00:46:45:16 - 00:46:57:01
Sahil Mansuri: Is this your first sales enablement hire, by the way, or did you have one before? He is. Yeah, he's a first. So what about for sales ops? Do you have people that are doing that now? Did you have that early on. Are you just doing all of it?

00:46:57:03 - 00:47:07:09
Jonathan Blackburn: I'm currently hiring somebody, for that at the moment, I think, it's a role we probably should have hired four months ago, but I'm currently hiring somebody for that right now.

00:47:07:09 - 00:47:31:00
Sahil Mansuri: Let's talk about managing up a little bit as a VP of sales. Walking in, to working with some, young founders, and, and you're the first kind of exact that they brought on a board that's obviously excited to see how fast this thing can grow. Tell me about, you know, early days and even today, like, how you set yourself up for success as a VP of sales.

00:47:31:00 - 00:47:31:13
Sahil Mansuri: Managing up.

00:47:31:13 - 00:48:03:10
Jonathan Blackburn: I'm sure if you ask our founders, they will say that we had a lot of fun conversations early on. I am a big believer in pushing back where I feel it's necessary and pushing back pretty often. I think you've I think where I've, I've gotten better at this and I think where, I, where I've been told I'm really good at this is pushing back on the right things and not just pushing back on everything, because that can be kind of tiresome to just always be the person who feels like you're slowing everything down and pushes back on everything.

00:48:03:10 - 00:48:16:02
Jonathan Blackburn: But pretty early on, when I came in, and we had talked about this before I joined, but there was a growth plan like we wanted to get from X million in revenue to X meter revenue for the beginning of the year. By the end of the year. And my comp plan, my target was built off of that.

00:48:16:02 - 00:48:34:00
Jonathan Blackburn: But I realized after being here for a couple weeks that we weren't in a position I didn't feel we were in a position to hit the revenue number that I had signed up for after having been here, after seeing where we were at as a business, what was working was what wasn't, what we had in place and what we didn't.

00:48:34:01 - 00:48:52:22
Jonathan Blackburn: And so what I actually did is I think you mentioned the, the, the modeling. I built a couple of models. I was given a model by our founders, and I didn't feel that it was accurately reflecting the state of the business, and I didn't feel that it accurately reflected the complexity of getting to where we needed to go.

00:48:53:00 - 00:49:10:19
Jonathan Blackburn: So I built two models and I worked with some people on the team. I try to I work with people on the team to help build these models. But I, we built two models in. The first was if we're going to get to this size revenue work, if we're going to get to this number, this is what this org is going to look like.

00:49:10:19 - 00:49:27:13
Jonathan Blackburn: This is how many salespeople we need to have. This is what ramp is going to look like. This is what leadership capacity. This is what rev ops enablement like. This is what the entire org is going to look like. And this is how much is going to cost to get there. And this is the complexity that it's going to take to get there.

00:49:27:15 - 00:49:46:17
Jonathan Blackburn: And then I laid out a plan of what we needed to do every single month to be able to hit that. And the conversation was, you said, do you want to get here? This is what this is going to look like in reality. Are we sure we can do that? And are you committed to giving us and me the resources to doing that?

00:49:46:19 - 00:49:59:22
Jonathan Blackburn: And that created a really interesting conversation. And I will say, like our founders are young, they are incredibly smart. They are first principle thinkers by necessity because this is the first time they've ever, you know, had a job or done anything.

00:50:00:02 - 00:50:01:09
Sahil Mansuri: It's the only principle they know.

00:50:01:13 - 00:50:31:07
Jonathan Blackburn: 100%. And then do I fucking love that? Do I let a lot of companies say their first principles, but they're not really first principles. But like we we live and breathe it every day because that is who we are. And that is who they are. And we had a couple of really honest conversations about that. And the second was I built a pipeline model where we basically went through, if you want me to do this, okay, now we're aligned on what the complexity of talks to look like, how much is going to cost, what budget is going to look like, what burden is going to look like?

00:50:31:09 - 00:50:52:07
Jonathan Blackburn: If you want me to do this, I need this from a pipeline perspective, and some of it is outbound. Obviously, that's on me at the team, some of it is inbound and some of it, comes from well, a yobo and rebounded inbound was kind of the three primary channels that we kind of walk through. And basically I said, I can do this part of it, but I need you to commit to this.

00:50:52:07 - 00:51:13:03
Jonathan Blackburn: And if you commit to this, I will. And we had a lot of really honest conversations around, can we commit to that? What does that look like? And the culmination of that was they said, yes, we will commit to, to, to to getting you this pipeline. You we will commit to getting you this budget and we will commit to do what we need to build this org.

00:51:13:05 - 00:51:32:16
Jonathan Blackburn: And they did it and we did it, but it it took a lot of conversations. It took a lot of back and forth. And it took a lot of I think, I don't say negotiating, but like being transparent and pushing back pretty hard on things and I felt were unreasonable and that I didn't feel like we're we're things that we should agree to.

00:51:32:16 - 00:51:51:15
Jonathan Blackburn: and I think I've gotten I've gotten this advice often in my career from people who are mentors of mine and a little bit more senior than me of like, if you get a number, agree to the number and just find a way to make it work, or some version of just take the number, the that's the least risky thing you can do and do your best.

00:51:51:17 - 00:52:10:14
Jonathan Blackburn: And I've always had the mentality of like, no, that's fucking stupid. I'm not going to do that. I'm not going to commit to something that I don't reasonably feel like we can do, or if we are going to do it, I think there needs to be better alignment around what the reality of that looks like. And I give our founders so much credit because they weren't on board with that.

00:52:10:19 - 00:52:38:05
nJonathan Blackburn: We had a lot of conversations. They quickly got on board. They got on my side, or I should say, we joined forces, and we executed off of that. And I feel really confidently like that is what led us there. And I will say, one of the things that like just to be very transparent about this, that I lead with was during this early phase, this like, you know, you know, getting to double digit millions is a lot of defining product market fit.

00:52:38:07 - 00:52:59:09
Jonathan Blackburn: Yeah. We've got some people that have bought books and they love it, but we really need to define like what our mission is across all these segments. And we really need to define product market fit. And it's a risky thing to sign up for a big number and just hire a bunch of people based off spreadsheet math that I think puts the company and us in a pretty irresponsible position.

00:52:59:11 - 00:53:20:07
Jonathan Blackburn: And what I agreed with them on was, we're going to we're going to let the pipeline define when we need to continue to hire. It was really important to me that pipeline come first salespeople come second. And I wanted our team to beg me to hire more people. I wanted them to say, we are so busy, we cannot do this anymore.

00:53:20:12 - 00:53:48:20
Jonathan Blackburn: That could be a pretty fun conversation. I'm using the word fun pretty loosely, but that can be a pretty fun conversation to have. With early founders who have just taken a lot of money from VCs and have really high expectations. And the compromise was like in our first year, as we're defining product market fit, we move slower, and I'd rather put the team in a position to overperform, than hire a bunch of people and have to lay them off, and like, be irresponsible with that.

00:53:48:22 - 00:53:58:17
Jonathan Blackburn: And that's how we executed. And I will say, we averaged 126% quota attainment throughout the, throughout last year. So we were slow to hire.

00:53:58:19 - 00:54:15:10
Sahil Mansuri: That's a that's a really, really great nugget. And, and I guess, you know, when you talk about pipeline, how do you think about what percentage of the pipeline should be created by those same. You said there is SDR outbound outbound and then inbound. Those are the three segments.

00:54:15:14 - 00:54:41:10
Jonathan Blackburn: Yes. I'll tell you how I approach it and how I think about this. And it's very similar to how I approach and think about going up market. I don't think authority up market when sets are very similar, but I don't think you can force your way up market. It is my strong belief after having done this a couple times and have having been hired, including a lot, is to build up market orgs that you can't force a way of market, you have to be pulled up market and I think very similar.

00:54:41:11 - 00:55:04:20
Jonathan Blackburn: When you think about pipeline structure, it was really important for me to look at the historical data. I mean, there wasn't a ton of historical data, but like, look at the historical data to say, how has pipeline been coming in and how were we actually executing on that pipeline? Because if we were, if we got to where we are by 60% inbound and we're saying, great, we're going to do 90% outbound, well, guess what?

00:55:04:22 - 00:55:27:06
Jonathan Blackburn: Our entire go to market motion is going to be different are when rates are going to be different. Our sales cycle links are going to be different. And so I think it's a I, I believe it's a combination of looking at historical data, looking at the reality of what pipeline looks like and how revenue is coming in currently and incrementally building off of that and then making strategic bets on.

00:55:27:08 - 00:55:49:09
Jonathan Blackburn: We've had 0% a year about because our A's have been so incredibly busy, but if we can get capacity right, we can reasonably expect 15%. I'm just using random numbers 15% to come to here, and this is how we're going to do it. So it's a combination of looking at historical data and being real and honest about the situation, and then making some strategic bets on where you think that the team in the company can improve.

00:55:49:11 - 00:56:15:17
Sahil Mansuri: I mean, obviously you have such a unique perspective on this because of the product set that you're building. But I've been having a bunch of conversations with sales leaders around, SDR and kind of the resurgence of the SDR role. Has that been your experience as well that stores are starting to perform better than they were over the last couple of years and have built in part because of tools, but in part maybe because so many companies stop cold calling that the airwaves got a little emptier or something.

00:56:15:17 - 00:56:16:17
Sahil Mansuri: I don't I don't really know.

00:56:16:17 - 00:56:39:00
Jonathan Blackburn: This isn't a controversial opinion by any means, but I think that, I think outbound and orders have gotten better because they've had to, you know, when I joined Nokes before I joined looks, I had a couple of months off, and I must have talked to 200 founders, investors, VCs, incredibly lucky and privileged to have had that opportunity.

00:56:39:02 - 00:57:02:16
Jonathan Blackburn: I still can't believe how many people actually wanted to talk to me. But to be able to have those conversations and looking back at the companies that I was at that were incredibly successful, thinking about, like lattice and SurveyMonkey, these companies, they had a really good product at at the right time in the market. And I think so many people dismiss timing in the market.

00:57:02:21 - 00:57:23:10
Jonathan Blackburn: I've worked at companies that had significant, more developed products and maybe even smarter people. I just were not successful. But when you get a really good product and a really good team at the right time in the market, magic can happen. I don't think I've ever admitted this, like publicly, but like when I was looking for my next role, what I was really trying to figure out is like, you know, what does culture look like?

00:57:23:10 - 00:57:38:14
Jonathan Blackburn: Am I excited about solving this problem and working with these people? But also, how can I time the market? And granted, if I could time the market, I'd be a much richer person. But like, how can I actually time the market and figure out what's what's the right product or the right space for me to be in right now?

00:57:38:16 - 00:57:58:04
Jonathan Blackburn: And of this 200, let's just say I'm doing around numbers 200 founders, investors, people I talked to, maybe 180, 190 of them ask me some version of how do you build out, how can you do that? And the reason they would ask me that is because before last I was at a company called reciprocity, where we were 90% outbound driven, bootstrapped.

00:57:58:04 - 00:58:19:10
Jonathan Blackburn: It hadn't taken any money. And and we went from, you know, 2 to $24 million in two years being completely outbound driven. I was shocked, and my honest answer was, that was, you know, six, seven, eight years ago, to be honest with you. Like, I'm not sure we can even run those same places that even works anymore. And then I talked to the guys at Nook's and had a couple conversations with them.

00:58:19:10 - 00:58:39:16
Jonathan Blackburn: They showed me the roadmap, and I remember thinking, okay, like I've had 180 people, give or take, ask me how to build outbound pipeline. And these guys showed me a product and a roadmap for the next couple of years that actually does this and automates it. And it's a long way of saying, to answer your question, kind of a little bit of why I joined.

00:58:39:16 - 00:59:06:12
Jonathan Blackburn: Okay, but also a long way of saying, I think we've gotten better at outbound because we've had to inbound has dried out and people have said, shit, I need to figure out a way to actually do this and make it more effective. And what we found at Nook's through our data. But I can also just share anecdotally in my career, having done this for a long time, people who pick up the phone, people who have real conversations, meaningful conversations with prospective clients tend to do better.

00:59:06:14 - 00:59:18:08
Jonathan Blackburn: On average. People that cold call tend to do. I think it's like 1.8 to to X better, than their, their, their colleagues and counterparts that don't.

00:59:18:08 - 00:59:37:16
Sahil Mansuri: There's probably some like selection bias and that generally I would imagine because the people who are willing to pick up the phone and cold call tend to have more confidence and tend to, you know, what I've heard. So there's probably some like, you know, there's there's some of that. But but but overall, it has also been my experience in my career.

00:59:37:16 - 01:00:05:13
Sahil Mansuri: You know, my I started my career at a company called meltwater that had a thousand employees and 950 were in sales. I mean, it was the most burner sales job of all time. And and the CEO had this philosophy of setting up these, like 15, 20 person sales offices all over the world. So meltwater ad, I think it was like 55 offices, each one with like 15 to 20, 22 to 29 year old, like folks that were doing $100 a day there.

01:00:05:15 - 01:00:38:11
Sahil Mansuri: I had I didn't even know there was a concept called inbound until my second job. I'd never heard of inbound. I didn't I was not aware that such a thing even existed. And I recall that, like, you just had to generate your own pipeline because there was no other way to get any pipeline. And in that process, the people who were the top performers at meltwater, like, if you look at the top 10 or 20 reps while I was there, it's like SVP of Sales at slack, VP of Sales at Salesforce, VP of Sales at Box, SVP Sales at Okta.

01:00:38:14 - 01:01:06:12
Sahil Mansuri: Like it's all of these people have gone on to have insanely successful careers, and I bet many of them were. Too many of them are CEOs of their own companies. Like, it's like an insane sales mafia network. And it all stems from the fact I deeply believe that if the first thing you learned is that nobody is ever going to hand you a deal, you got to earn your own deal, and to end it just teaches you the reality of how you have to operate in a sales, in a sales motion.

01:01:06:12 - 01:01:18:00
Sahil Mansuri: And so I find it. I find it to be, you know, a core differentiator between good and great salespeople is just their ability to generate their own pipe, which obviously starts by picking.

01:01:18:00 - 01:01:21:10
Jonathan Blackburn: Up the phone. I agree, and there probably are some. Yeah, probably some buyers too.

01:01:21:10 - 01:01:39:13
Sahil Mansuri: Yeah. I could literally talk to you for another like two hours. This is such a good conversation. I would, but, I want to be respectful of your time. Jonathan. And before I have you go, I really do, want you to play our lightning round. That we do at the end of our day. So let's, we'll we'll do that if you'll.

01:01:39:13 - 01:02:04:17
Sahil Mansuri: If you'll commit, to stopping by doing a, an episode two with me at some point later this year. Because because I've got a lot more that I want to ask you about that I think is really good. But let's, but let's get let's get to the lightning round. So first question I have is, you know, we talk a lot here, bravado about how sales is a superpower, where and how, you know, sales is something that isn't just a job, but it's a skill set.

01:02:04:17 - 01:02:17:00
Sahil Mansuri: And as a sales that you can wield, in both your professional and your personal life, what's an example of where you used your sales superpower in your personal life that you think, is a is a cool story to share?

01:02:17:03 - 01:02:36:13
Jonathan Blackburn: I tend to push back a lot. Like I mentioned earlier, that's just my personality. I find that to be really helpful. And things outside of work, like we did a remodel on our house. So working with jacks and, like, you know, thinking about things like, as it relates to, like, my daughter and like, stuff like that, which I think is really helpful.

01:02:36:15 - 01:02:43:10
Jonathan Blackburn: I don't know if this is a sales superpower, so maybe I'm going to kind of cheat here or not follow the rules and cheat a question a little bit.

01:02:43:12 - 01:02:45:11
Sahil Mansuri: Sounds like a salesperson.

01:02:45:12 - 01:03:06:06
Jonathan Blackburn: Probably. I'm just such a naturally curious person. And like in every aspect of my job, of my life, of everything, I'm always asking why. And I find that like when, when my wife and I are in situations outside of our comfort zone, maybe we're somewhere at our daughter's school or somewhere like, that, like we're outside of our comfort zone.

01:03:06:06 - 01:03:37:14
Jonathan Blackburn: Just in general. I really enjoy connecting with people and just asking people about them. What I've also find is when you ask people, when you spend the majority of your time asking people questions, they tend to, I think, generally enjoy you more and that interaction more. And I think my ability to be curious, ask questions has significantly helped, in social aspects outside of work, because I generally am curious when I hear something that someone that does something interesting or people that are interesting, I just want to talk to them all the time.

01:03:37:14 - 01:03:40:15
Jonathan Blackburn: So I think that that, that's been fun to experience.

01:03:40:16 - 01:04:14:18
Sahil Mansuri: It taps into the hubris of people that they want to talk about themselves. And yeah, having a captive audience of someone who finds that interesting leads them to overshare or, you know, in turn give you a benefit or whatnot. But I have found that to be the same. It's funny, my my daughter, I think similar age to yours goes to goes to preschool and, you know, after a month or so of drop offs and pickups, at the school, my wife and I kind of take turns are like, I'll do a month of of pickups and drop offs, and then she'll do the next month.

01:04:14:18 - 01:04:43:08
Sahil Mansuri: So that way both of us get time to like, occasionally exercise or something. You know, I was off for a month and then I was back on the next month that I showed up. And the first day I walked in there, like, you know, you were the friendliest parent, no one else says hi to us, etc., etc. like, like they were just like so excited, like the ladies at the front to to see me and the, the benefit of which has been transferred over to my daughter who has like built they like have built this really sweet relationship with her.

01:04:43:10 - 01:04:59:11
Sahil Mansuri: So none of the kids are allowed to go back into the office. But my daughter, as soon as she gets out of school, runs to the back office, into the principal's office, jumps in their desk, steals her candy like literally. She's like a little terror because. And they just they kind of they kind of like, broken the rules just for her.

01:04:59:16 - 01:05:23:14
Sahil Mansuri: And every time my wife goes, she's like, why? Why does everyone say hi all the time to me? And why is Mira friends with them? And it's just like this really interesting, like connection through sales. But in any case, it. Okay, next question I have for you is what is the best advice that someone gave you early in your career that if they were to give it to you today, you know, or you were to give it to someone might get you canceled.

01:05:23:14 - 01:05:30:10
Sahil Mansuri: But, you know, it's like the sage advice, the truisms that are lost in today's post to woke society.

01:05:30:12 - 01:05:46:20
Jonathan Blackburn: I don't know if this follows an exactly, but like something that's really stuck with me is like early out of my career. I remember talking to a prospect and I talked more than they did. Like we connected, I talked more than they did, and I remember a boss telling me, and this kind of has always stuck with me too.

01:05:46:20 - 01:06:04:19
Jonathan Blackburn: Don't give a shit about you. You're in sales. You're only job is to make them feel special and to buy like, don't talk about yourself. No one. And like I think like it's it's true in some aspects it's not true. And others like it is important. Like, you know, like we build meaningful relationships with people and that typically only happens to two people sharing.

01:06:04:19 - 01:06:20:05
Jonathan Blackburn: But I do find it to be true that if you find yourself talking more about yourself to a prospect than them talking to you about themselves or them opening up, you're probably searching for something that you shouldn't be searching for in a sales call.

01:06:20:07 - 01:06:36:22
Sahil Mansuri: You know, I had a third question, but that was so good that I don't I don't think we could beat it. So I'm going to I'm going to say that that was awesome. Don't search for your it's not eat pray love on the sales copy. Is Jonathan's advice totally. My friend, thank you so much for doing this.

01:06:37:00 - 01:07:02:08
Sahil Mansuri: Thanks for being so candid and sharing so many of the insights of what you've learned, both across your long sales career and as well as, building out books. Congratulations on all of the, the success. And let's check back in with you six months from now or whatever to see how things are going. And do episode two, because you have so many great insights to share, and I'm really grateful for you sharing it with the, the sales community.

01:07:02:08 - 01:07:04:20
Jonathan Blackburn: Because I appreciate it, man, I appreciate you. It's been a blast.