How AI is disrupting the SaaS sales playbook: CRO Sangeeta Chakraborty

From Scaling GTM at Okta, Checkr, and Miro to How AI is Disrupting the SaaS Sales Playbook: CRO Sangeeta Chakraborty.

Discover how the AI era is transforming Sales teams, Sales Leadership, and even CS. Drawing from her experience scaling revenue at top SaaS companies during major market disruptions, Sangeeta reveals:

• Why traditional SaaS Sales strategies are being upended by AI-driven pricing and customer expectation changes.
• Battle-tested tactics for breaking into new markets without brand recognition.
• The most important skills for reps to thrive in the AI era.
• Strategies for Sales Leaders to meet today’s aggressive revenue targets.

Bravado CEO, Sahil Mansuri asks the questions Founders, Sales VPs, and AEs need answered to crush quota in 2025.

Listen to the episode on Spotify or Apple Podcasts.

Time-coded show notes:

00:00 – Welcoming Sangeeta Chakraborty to the Podcast!
06:41 – The importance of hiring the right people for Sales
12:12 – The evolution of post-sales in usage based pricing models
15:00 – The new AE role
22:20 – Building a culture of learning
28:34 – Winners don’t shy away from big targets
37:05 – Outlier performance will always lead Sales
38:42 – The right way to plan for outliers
42:28 – TOFU for startups
47:17 – The next phase of brand growth
49:05 – The work most companies try to skip
52:02 – Quick fire round

Full transcript:

00:00:00:00 - 00:00:13:22
Sangeeta Chakraborty: Even if it's controversial and there's many people who will, you know, throw me out of the room for even saying this. To maintain this, I would say, is the center cannot leave their current because they closed a number. And I think the CSM is going to have to become very, very business focused, maybe even have an upset number.

00:00:13:22 - 00:00:23:09
Sangeeta Chakraborty: I don't think there's a single person in go to market that can have a role that is not directly tied to having a sales outcome. Everybody is a seller. Who once again.

00:00:29:13 - 00:00:54:18
Sahil Mansuri: Hi and welcome to another episode of The Bravado Pod. I'm your host, Sahil Mansuri, and today I am super excited to welcome my dear friend, wine aficionado, Indian tech sales leader extraordinaire there, Sangeeta Chakraborty, who is most recently was the CEO at Miro. Hi, Sangeeta, Welcome to the pod.

00:00:54:20 - 00:00:57:01
Sangeeta Chakraborty: Hi Sahil. Great to be here.

00:00:57:03 - 00:01:10:12
Sahil Mansuri: So happy to have you. I guess, you know, I want to start by letting you introduce yourself to our audience. You share a little bit about your background. I'll probably have a couple of follow up questions on that before we launch into today's topic.

00:01:10:15 - 00:01:38:08
Sangeeta Chakraborty: All right. Hey, everybody. Great to be here with Sahil. My name is Sangita, as I mentioned, and I am a go to market leader. I love working with customers and selling them amazing solutions of been in this space for way more years than I want to admit and have sold a lot of mostly to startups. And then I tend to get acquired by big companies and I try to get out of that and then I'm back in that cycle again.

00:01:38:10 - 00:01:48:18
Sangeeta Chakraborty: Sold and of RSS for a while. Consumptions as PLG as synergy. And just really I am a sales nerd and love being in the space.

00:01:48:20 - 00:02:15:08
Sahil Mansuri: Amazing. You've worked at some really blue chip companies in your career checker Octane, obviously. Miro I guess, you know, one one thing I have is and you've also spanned across working both on like the Post-sales customers CSM side as well as working on the presales. And then both as you look across your career, what have been the most fun and exciting moments that you've had and where have you found your like real sweet spot?

00:02:15:10 - 00:02:39:15
Sangeeta Chakraborty: So the thing to know about me is that I am extremely customer obsessed and I look at everything through the lens of the outside in perspective. And so the best moments in my life have been really when we were in dire straits and our business was in real trouble. The economy was tanking and we had we had almost no hope, like our pipeline was in there not progressing.

00:02:39:17 - 00:03:09:04
Sangeeta Chakraborty: Nobody was buying. And this happened to me at least a couple of times. But I the example I was thinking of is the housing crisis and nobody was buying. So and we had an ICP and a product that was selling really well until the situation happened. And then in that middle of the gloom when we were doing everything, I was doing cold calls, I was sitting next to the SDR being an SDR myself, because you got to do what you got to do.

00:03:09:06 - 00:03:37:02
Sangeeta Chakraborty: One of our customers said, Hey, we think you could do this one other thing with your product. And as a rule, I said No, because I don't want to do anything else. This is my product but a customer came in and actually showed us a far larger market that we could go after. And if you do that right and find that that trust and that customer who shows you the way that that led us to have the next stage of growth to be eventually sold into VMware, that was super exciting.

00:03:37:04 - 00:03:40:17
Sangeeta Chakraborty: So those are the highlights of my career innovation.

00:03:40:19 - 00:04:13:12
Sahil Mansuri: Being the mother of necessity or pressure making diamonds is a common theme in sales. You know, whether it's the last week of the quarter where everybody's pushing to get deals done or whether it's bad economic times leading us to make changes to our go to market and be willing to look outside for help instead of being so, so sure that we know what we're doing are really common themes that we see play out, especially today as there's been a lot of upheaval and change in go to market.

00:04:13:14 - 00:04:38:06
Sahil Mansuri: Super interesting. So you know, this thing I asked you on to this podcast because you have some incredible experience and insight that I think could be relevant to some common problems that we are seeing across go to market today. And so what I find really interesting about, you know, what's happened over the last couple of years is that we suddenly have had this massive disruption.

00:04:38:06 - 00:05:02:06
Sahil Mansuri: Obviously, we had the downturn and then things pick back up and now it looks like we're kind of back on a growth trajectory. But what I found to be really interesting as we've been talking to sales leaders and to CEOs and founders has been this idea of what is the new benchmarks, what are the new ways we should be thinking about go to market in a world in which pricing is no longer tethered to this like traditional SaaS model?

00:05:02:06 - 00:05:25:16
Sahil Mansuri: How do I think about quotas? How do I think about cost models? How do I think about success criteria? You know, if you if you're RR is suddenly not so recurring and is much more, you know, in this world, you know, your outcome based pricing or whatnot, I think the disruption in pricing has had some really interesting downstream effects into how companies think about their revenue and their sales team and whatnot.

00:05:25:22 - 00:05:50:08
Sahil Mansuri: So so we started this podcast because there were so many questions out there and I was basically getting the same question over and over again. And instead of trying to answer them on a one off, we thought, What if we invite some of the smartest sales leaders who have seen this type of transformation before, you know, whether it's PLG, whether it's, you know, thinking about shifting pricing across industries or new technologies that are coming out.

00:05:50:10 - 00:06:07:21
Sahil Mansuri: And I thought of you right away because obviously you've touched on a lot of these themes in your career and thought that you would bring a really welcome perspective on that. So that's that's really the purpose of this is for us to think through as we look towards 2025, how does a company think about its go to market, especially those that are startups?

00:06:07:21 - 00:06:41:12
Sahil Mansuri: How do they think about their go to market? How do they think about their sales teams? How do they think about the profile of people to hire? How do they think about compensation, quotas, etc.? So that's the main purpose of this, of this conversation. And, you know, is something that I know you've talked about a lot. So I would love to start by just getting your perspective on, you know, you obviously at Miro, you know, went through some really big exciting changes at the company as you look towards 25 and beyond, how do you see SaaS companies thinking about quotas, pricing, the people that they're bringing on board in this world of AI.

00:06:41:14 - 00:07:07:02
Sangeeta Chakraborty: Maybe you start with the people and and you to think about that being sort of outside in from everything is also the customer in the middle of all of this change as well and how are they thinking about buying? But that's changing and they're also trying to figure this out just as we are. Right? So the first thing that I would say is good news is that the fundamentals are not changing.

00:07:07:04 - 00:07:31:14
Sangeeta Chakraborty: The type of people you need to hire are still the type of people that you would have been hiring, because the profile that I think are profiles of reps that are deeply successful, regardless of what happens, are people who are owners, they're owners of the business and have this ultimate accountability. They're almost operating their own little mini business.

00:07:31:14 - 00:08:04:23
Sangeeta Chakraborty: They're not carrying a quota. They are running their business. And so the people that I found to be the most successful and that I would expect to continue hiring are reps who are deeply curious and have what John McMahon I think everybody knows I'm sorry, needs no introduction. You used to say it. It's persistence, heart and desire. If you have all those three things, then what I think is the winning combination is that in times of change they are learning as fast as possible and are going to make that business happen for you.

00:08:05:01 - 00:08:26:07
Sangeeta Chakraborty: So the thing that you're testing for when you're hiring people are to ensure that you're hiring owners and people that are not waiting for leads to come in. They are not waiting for customers to show up for the CSM to do certain activities, for their CEO to go and make a pitch on LinkedIn. They are going to do whatever it takes to go find that business and own everything.

00:08:26:13 - 00:08:44:06
Sangeeta Chakraborty: I mean, yeah, they need help. They do need the leads, they do need help in moving this business forward. But what you're looking for is mental mindset and usually the founder CEO has it in like massive degree or they wouldn't be doing what they're doing. But this has to be the zero. It has to be zero down all the way into the rep.

00:08:44:06 - 00:09:07:08
Sangeeta Chakraborty: So the good news is that doesn't change. I mean, you still have to hire that in the world where people are now paying on outcomes. So I think it's super early, by the way, I'm seeing a bit of it, but people are still testing and I'm like, Intercom is famous for this and 11 mics and some of them, but it's just it's evolution that I, I think we should be how we should have said it.

00:09:07:08 - 00:09:26:11
Sangeeta Chakraborty: We saw it coming. So it was, you know, 25 years ago perpetual software You sold an IBM mainframe. You never had to talk to the customer again. Then came Salesforce and said, Hold on a second, we're going to do SAS software is dead, we're going to sell SAS. So now every year you have to make sure the customer cares about what you do and the value.

00:09:26:11 - 00:09:44:18
Sangeeta Chakraborty: And then became so surprising that it wasn't seats and not enough. It's going to be consumption. I'm actually using the seats. So that was the growth of all these consumption models policy, whatever tested and buy it. And now the customer is saying, but I don't know if I got value. And so this is just part of the evolution we should have expected.

00:09:44:18 - 00:10:14:06
Sangeeta Chakraborty: And I think the future is here, but we're all strapped trying to figure this out. So in this changing of outcome based pricing, you could make huge mistakes in how you compensated and we do it the wrong way. You're going to spend all your money paying people that really haven't built a business for you. So the thing that I think we also have to now start to think about is what are the leading indicators are going to have to start being on and how do we actually look at the buying cycle and the lifecycle of the customer?

00:10:14:08 - 00:10:32:08
Sangeeta Chakraborty: Because I think we're still attached to the old mistakes of the past, which is the sale ends when the rep closes the deal and then the rep can go close the next fancy deal and they don't have to worry about the customer. That is changing. I think this is where a lot of our go to market models are going to be upended.

00:10:32:10 - 00:11:07:21
Sahil Mansuri: I want to hear more about that because I think you bring up two things that I think are really closely tied. The first is that which is in the best interest of the customer, that which is preferred by the customer is always going to win, you know, like the market is going to pull it out of companies. And the idea that it's a deal when the deal is closed is when we ring the gong, when we pay the commission check, we, we, we mark the logo as a as a closed one and there's a celebratory moment.

00:11:07:21 - 00:11:30:23
Sahil Mansuri: It only works in a world in which you have guaranteed upfront non refundable revenue. And even then, obviously, you know, there's been a lot of talk about it all. You know, we wanted to renew the customer and like our business model falls apart if our renewal rates aren't high end, like net dollar retention. And so like we've we've already started thinking beyond that, but at least you had that revenue guaranteed.

00:11:30:23 - 00:11:54:19
Sahil Mansuri: Now, you know, you brought up intercom the car now I think is doing this There's a bunch of companies that are starting to say, hey, instead of charging you $100,000 a year or $1,000,000 a year, we're going to charge you $2.50 per ticket or $200 per booked meeting, and that that revenue almost has to be earned every single day in a world in which that is true.

00:11:54:20 - 00:12:12:16
Sahil Mansuri: How do you think about building a go to market model or a go to market structure that can support a customer's basically a customer being able to churn any day of the week? Because if they stop getting value from the product that they've effectively turned in terms of revenue.

00:12:12:18 - 00:12:36:21
Sangeeta Chakraborty: Yeah, I think the one concept that I talk about as really needing to put to bed and buried forever is that concept that we have of sales and we still have it. I think if you look at any sales playbook, there's a straight line where the customer buys and the line ends there and then to see us and picks up and it's all called for sales and nobody even looks at it.

00:12:36:21 - 00:12:56:21
Sangeeta Chakraborty: So all these decks have 80% of a line that says, yes, I close the deal, and then the remaining 20%, some mythical thing happens and you know, you assume that the customer is going to not just renew sale. Most of us are doing land and expand businesses. So who's going to do the expansion in this current scenario where the customer is looking at your value?

00:12:56:23 - 00:13:18:12
Sangeeta Chakraborty: Every transaction? I think the seller has to think about it end to end. So things that I expect to see upending is the seller moving on because they close the deal and doing the next thing. I think the sellers will need to remain attached to the account. They will need to stay very, very focused on continuous outcome selling and ensuring that success happens.

00:13:18:14 - 00:13:36:04
Sangeeta Chakraborty: And the selling doesn't stop when the deal is closed, then the questions that are going to get raised is what about the CSM? Do now need a CSM to do what they did in the past? And I would say no. So what did CSM do do in the past? They took on the account. They if it's a technical product, they were technical how to set up.

00:13:36:06 - 00:13:52:03
Sangeeta Chakraborty: If it was not a technical product, then they tried their best to be useful by showing you how to use the product and doing queries from time to time. Now you use a lot of products which could be as usual, up to none. None. I don't know who shows up to Kubernetes anymore because it's a waste of time.

00:13:52:03 - 00:14:12:17
Sangeeta Chakraborty: It's a waste of time from everybody. So the question that really is going to start to be asked is what is the role of this continuous relationship person? And I think we have been making a mistake in this for the longest time where we felt that the CSM cannot be commercial. And if they are involved in helping you upsell, then there they have sort of gone against the religion.

00:14:12:19 - 00:14:45:16
Sangeeta Chakraborty: I truly believe that that's a mistake and I have tried it myself. Very have had CSM characters and they were phenomenally customer focused. Not a single customer came back to me and said, I can't trust this person because they haven't got a they in fact like this alignment of incentives. So to me, even if it's controversial and there's many people who will, you know, throw me out of the room for even saying this because church and state should not mix, I don't think there's a single person in this world in go to market that can have a role that is not directly tied to having a sales outcome.

00:14:45:18 - 00:15:00:13
Sangeeta Chakraborty: Everybody is a seller. So but the the main changes, I would say is the center cannot leave the account because they closed a number. And I think the CSM is going to have to become very, very business focused, outcome focused, maybe even have an upsell number.

00:15:00:15 - 00:15:23:01
Sahil Mansuri: First of all, I, I think that's super interesting and and unique as you share it as a as a perspective. And that's the reason I wanted to get your insights here, because you have seen transformative business models at some of the you know, most blue chip premiere SAS companies in the world. And so your perspective carries a lot of weight.

00:15:23:03 - 00:15:49:05
Sahil Mansuri: I'm curious about let's start with this with the aiy side first. So if you're saying that an API can can't leave an account because they need to be stated, they need to stay in touch and continue to deliver outcomes, how does that work in terms of capacity modeling? Because I guess the way that we think about capacity modeling is you're like, okay, 180 is going to generate $1,000,000 in new biz in year one, 1.2 in year two, 1.5 in year three.

00:15:49:06 - 00:16:04:05
Sahil Mansuri: And predicated within that is the fact that they are able to get accounts off their plate if they are still on those accounts. Does that mean that each needs to take a smaller number? Does that mean that you need more? Is how do you think about that?

00:16:04:08 - 00:16:26:11
Sangeeta Chakraborty: I think what's going to happen is that is will need to look at their business as a book of business that they continue to grow, not necessarily get new logos at the rate. And I think it's a nuanced answer. So I wouldn't say this is go blanket statement, apply this at every business. I think it depends on the accounts segment and the touring, the sales cycle, the type of deal closing.

00:16:26:16 - 00:16:50:09
Sangeeta Chakraborty: But if you generalize and I'm generalizing vastly, I would expect that these are going to have a book of business, have a fewer set of accounts, but with continuously trying to expand those accounts and get more revenue. And so the growth number doesn't change, the economics don't change, but I don't think that they're going to be asked to go keep closing large logos and moving off because I don't see how that would be successful.

00:16:50:11 - 00:17:16:23
Sangeeta Chakraborty: And even this seems very radical. It isn't really because look at the consumption based software they're doing. It already begun to for to have this is walk off if you're selling snowflake you need the aid to be there making sure the customer continues to consume. So we'll have to take the best of those worlds, look at what outcome based really means because this is still new even to the consumption based companies.

00:17:17:00 - 00:17:37:20
Sangeeta Chakraborty: Understand what are those leading indicators that the e e has to continue driving. And the reason I feel so convinced about this is because I put myself in the customer's shoes. And when I'm buying something from you, as I don't want you to sell it, celebrate, get a paycheck. And then the next morning Sangeetha shows up with this person I trusted.

00:17:37:20 - 00:17:57:11
Sangeeta Chakraborty: Zero. So they wanted to have you in the room and stay accountable for what you promised. Now, the challenges that we'll have to really figure out is how do you scale this effectively? And thus I will need to do everything that they can needs at this point, I don't think so. That's not where he is great, but he cannot get off the hook.

00:17:57:11 - 00:18:06:14
Sangeeta Chakraborty: I think he needs to stay involved in ensuring success happens and then we bring the right specialist for whatever else needs to happen for the customer to keep getting the outcomes.

00:18:06:16 - 00:18:46:22
Sahil Mansuri: How do you think about the protocol? Let's go back to the profile of REP. One of the things that I know you've managed much larger and more teams that I've managed over the course of my career, you know, but but something that I noticed is that if you were to tell me, build a team of 20 people that were excellent at getting the deal closed and then passing it off to CSM versus build a team of 20 people who were not only great at closing deals, but then would stay on with that customer, build a long term relationship and be able to continue to service them many years into the future, I think I would

00:18:46:22 - 00:19:12:18
Sahil Mansuri: look for slightly different people. Like when I think about that in my head, it's not. I mean that maybe the top five or the same on both sides because great sales is great sales and great ownership is great ownership. I agree with that. But when I think about some of the people I know who are incredible salespeople who have been at the very top of the leaderboard at many companies I've worked at, part of what they hated was getting stuck into the mire of the account.

00:19:12:18 - 00:19:27:00
Sahil Mansuri: You know, that was that was draining for them, you know, And when they were put in situations in which they had to do that, I didn't get the best out of them. Maybe that was my fault as a sales leader. Maybe I just didn't know how to do it. But I felt like that was just not their skill set.

00:19:27:00 - 00:19:52:20
Sahil Mansuri: That was not their superpower. They thrived on hunting, not not farming. And and it seems like what you're saying is, as companies start to gain more of this consumption model energy into their business, DNA into their business, that maybe that like pure hunter profile of sales person, I don't know if it changes, but I would love to hear your perspective on that.

00:19:53:00 - 00:20:26:12
Sangeeta Chakraborty: I think there's there's immense talent in the pure hunter mentality. And I do think that that used to be something that we celebrated. But, you know, many of us have been in companies and I've seen companies that had massive bookings, but not necessarily massive continuous success. And it's because I think we we overly celebrated the early part of landing the customer.

00:20:26:14 - 00:20:49:06
Sangeeta Chakraborty: And so the the hunting instinct doesn't go away. You still have to do all of those hard things you had to do to land the account. But where I would say these reps who are actually very intelligent owners of their business, are automatically going to start thinking is they need to understand how to leverage resources at their disposal to continue to stay effective in the next stage.

00:20:49:06 - 00:21:12:21
Sangeeta Chakraborty: So they may not want to do everything themselves. I don't expect them to, but I think they are going to have to become more effective in leveraging services systems experts to stay effective so they don't have to go solve the problem. Like you said, they're not good at it, but they can't afford to walk away. That is what I, I believe, is going to be the evolution of our far off our field.

00:21:12:23 - 00:21:42:22
Sangeeta Chakraborty: How do you think about screening for this in an interview process or across a resume? Because one of the challenges that I hear across from both hiring managers and from candidates is this idea that the profile of REP that they are looking for, they're finding a lot of difficulty is seeing in the market. And then on the candidate's side, they feel like, you know, I'm trying so hard to get a role, but I can't seem to get a sniff it.

00:21:42:22 - 00:22:03:23
Sangeeta Chakraborty:
And it's really difficult to even make it through that, Like even get a callback, even get a first conversation. You know, they get on with the recruiter and it seems like they're being filtered out just because they don't have the perfect background or the perfect experience, regardless of their skill set or their ownership mentality or whatnot. You know, sales hiring has been a challenge for so many companies for such a long time.

00:22:03:23 - 00:22:20:01
Sahil Mansuri: You've built so many large, successful sales teams. What has been your secret sauce to getting that alignment? How have you managed to get a kind of escape through those waters and build world class sales teams giving people a shot? You know, How do you think about that problem?

00:22:20:03 - 00:22:40:00
Sangeeta Chakraborty: Oh, so there's a number of questions in that, Right? So the first thing let's talk about what what is the sales culture that I have found the most effective and what is the outcome that I'm trying to drive? The outcome that I'm trying to drive. Sale is an organization that is the most efficient learning organization in the world.

00:22:40:02 - 00:22:55:13
Sangeeta Chakraborty: The reason I'm looking for that is what worked in the past in different companies may not work where I am, but I know that if you bring the core learning skill set, then you're going to learn faster than I can even enable you to come back and tell me this is how I could sell. This is what I learned.

00:22:55:13 - 00:23:18:05
Sangeeta Chakraborty: And so first of all, it's about building a culture of learning, which means if to build a culture of experimentation, of massive psychological safety, and let people go and have those tests come back and tell you I failed at this or this worked, let alone together. And so it's a job number one for us as leaders. You know, we need to do three things.

00:23:18:05 - 00:23:43:03
Sangeeta Chakraborty: We need to inspire, we need to inspect and we need to coach. Part of that inspiration are people who are coming here and saying, we are going to build this career together, this business together, the hiring reps that just want to, you know, make their quota, they are not going to be successful in the long run. But if we get a rep that says, I want to be the best ever in this and build my best of a career, that means I'm going to come and learn.

00:23:43:05 - 00:24:00:11
Sangeeta Chakraborty: Those are the people that I want to hire. So but where do they want to be? They want to be places where they are trusted, that they are given help and they're able to go and make independent voice to understand how they can sell the best. And then they come back and share that the best people come back and share that.

00:24:00:11 - 00:24:27:09
Sangeeta Chakraborty: So first is the culture that you build and this tactics on how you can build it. And we can share that if you want to, all of the toxic tactics there. The second thing is looking for reps and the interview questions. This is a hard one and I don't think there is this one sort of golden ticket question, but questions that have given me most insights about the person are tell me about the toughest problem you've ever had and how you got out of it.

00:24:27:09 - 00:24:48:00
Sangeeta Chakraborty: And it doesn't have to be sales. Think anything, anything in your life. And what I understand there is what do they think is actually tough? Because you'll be surprised. You know, some things are not as tough, but they think that is the toughest thing they ever came across. And then did they actually have an open mind and take accountability on their own to get out of it?

00:24:48:02 - 00:25:14:20
Sangeeta Chakraborty: Or are they blaming everybody else? The coach of the other team injuries is something else. It's usually a sports problem that I hear, but I learn a lot about resilience and grit and curiosity and that owner mindset. So that's my one of my questions. And then the other question that I learn a lot from is tell me about the deals you walked away from and why or tell me about the customers you walked away from and why.

00:25:14:20 - 00:25:42:20
Sangeeta Chakraborty: And here I'm trying to understand are the intelligent and what is the framework that they're making for qualifying and they're doing it in time. And are they thinking about the right customer as well? So, you know, like I said, there's no golden ticket to any of these, but these teach me a lot on in terms of job hunting, you're right, it's there is simply more supply than demand right now.

00:25:42:22 - 00:26:00:15
Sangeeta Chakraborty: And so you have to be super creative and think of yourself as the product is the old adage, what do you need to do? Get it to build your awareness? How can you position yourself uniquely in solving the pain that you're selling to? And if you are talking to a recruiter who doesn't care, it's the wrong ICP for you.

00:26:00:17 - 00:26:21:07
Sangeeta Chakraborty: So find the right customers, find the strength, find the right companies that are hiring, do everything in their power to network, to go and get to people that actually care about what you've got to offer. Dig the recruiter quotes. I wouldn't say rule them out. You take every one of them, but don't count on that being the only thing that's like expecting that all the leads from marketing is going to be helping across your number.

00:26:21:07 - 00:26:28:16
Sangeeta Chakraborty: You got to do, you know, make it on pipeline. So just use those skills that you're really, really good at in landing that next thing.

00:26:28:19 - 00:26:53:11
Sahil Mansuri: I love your call out of what it is that people think of as the hardest thing that they've ever faced. There's definitely a connection that I've seen, a correlation that I've seen between folks who have struggled a lot in their personal lives, being able to overcome mountainous challenges on their professional lives, and people who've had maybe an easier path of their personal life getting stopped.

00:26:53:11 - 00:27:21:07
Sahil Mansuri: We call it getting stopped. You know, like at what point do you get stopped versus your ability to just keep going? One quick thing I want to call it and then I want to move on from this topic is you mentioned you get a lot of sports analogies around this. And this is something that, you know, is a is a conversation that comes up a lot in sales hiring, which is there's a lot of hiring managers that say that they want former athletes and they feel like former athletes make the best salespeople or make great salespeople.

00:27:21:09 - 00:27:25:13
Sahil Mansuri: What's your perspective on that, do you think that's true? Do you how do you how do you think about that?

00:27:25:17 - 00:27:51:01
Sangeeta Chakraborty: Yeah, there's so much to talk about this topic saying, not to mention that this whole field of sales is obviously dominated by men and sports is a part of, you know, a lot of their lives. So a lot of the analogies you get are aren't sports related. And it's something that I had to actually learn actively because I personally didn't follow as much of the sports as this field does.

00:27:51:03 - 00:28:11:16
Sangeeta Chakraborty: I strongly believe a great athletes make great sense people. And I'll tell you why. I think the best athletes are the ones that listen to their coaches and effectively appreciated what the coaches so told to them and coach them on. And I haven't yet found a rep who is effective, who's not good at coaching. So that's one of the critical areas.

00:28:11:18 - 00:28:34:07
Sangeeta Chakraborty: So I do think that athletes, great athletes, tend to become salespeople effectively because of that. The second thing is great athletes are not lone players. They know how to leverage the team. They're part of the team, they drive the team. And that's the other skill, I think that, you know, successful reps, I think there's some lone wolves, but most of them really need to be strong team players and in building their businesses.

00:28:34:07 - 00:29:09:03
Sahil Mansuri: I want to I want to switch tracks and actually talk about something that I think is another common problem that we are seeing in today's market, which is a fear from well, inserting a fear. How about this? There seems to be some dissonance between the way that sales leaders, especially kind of this like new rising generation of sales leaders, want to think about setting quotas and taking on an annual number versus the way that I think it's been done historically.

00:29:09:05 - 00:29:36:02
Sahil Mansuri: And what I'm referencing is this post that our mutual friend Dini Mehta posted recently, which we will have up on the YouTube channel for people to see. But I will summarize for those of you who are just listening and effectively in this post on LinkedIn, she wrote about the fact that she gets calls from like new heads of sales at early stage companies that say something like the following.

00:29:36:02 - 00:30:01:12
Sahil Mansuri: So I'll read a read what she wrote. The company has crushed it. This year, and now we're going to have big targets next year. Everything I see tells me we do not have the pipeline or market to hit the big 2025 goals. What would you do? And she writes, My answer is you should share your POV on the pipeline and market study the financial plan, but ultimately get ready to take on the big targets.

00:30:01:14 - 00:30:22:06
Sahil Mansuri: And then she talks a lot about how you can try to do that. And she talks about, you know, a lot of a lot of steps you can take in order to find ways to take on a bigger number. But the thing I find interesting about this post and this like dissonance that I'm seeing is that five years ago there seemed to be a lack of fear of taking on a bigger number.

00:30:22:06 - 00:30:49:09
Sahil Mansuri: You know, like if you hit 20 million and there are people are excited to try to figure out how to get to 40 or 50 next year. But today, you know, especially after the last two years of turbulence and people feeling a little shell shocked by what happened, maybe like hangover a little bit still from COVID days, there seems to be this feeling of like if we got to 20 and my pipeline says we can get to 30, let's set the number at like 27 and make sure we really hit it or something like that.

00:30:49:11 - 00:31:08:19
Sahil Mansuri: And it wasn't something that I was familiar with when I when I was a sales leader, which, you know, again was kind of in the 2010 to 2017 timeframe, you know, I wanted the biggest possible number. I wanted to go and prove to the world that we could build something exceptional. Today it seems to be a little bit more playing defense.

00:31:08:19 - 00:31:18:15
Sahil Mansuri: I wonder what you see in that space and how you think about navigating that yourself as a sales leader, what advice you give to up and coming folks and how they should think through that?

00:31:18:17 - 00:31:43:22
Sangeeta Chakraborty: Yeah, it's a pretty deep question. And I think the the reactions that you're seeing is and it's understandable because it has been really hard. It's been it's been a hard setting environment. And so sales leaders and not just seeing sort of their compensation impacted, they are seeing morale impacted. And that's the worst thing. Like once sales reps have lost morale, then you're done.

00:31:44:00 - 00:32:08:09
Sangeeta Chakraborty: So I think the trepidation comes from how do we ensure we remain winners? And that is the question to answer. So first of all, I think. Denise Right. I don't think that the answer is you go negotiate the CFO down and say, hey, I think it should be 27 or 25. And that used to be part of the dance that you played during the planning season.

00:32:08:11 - 00:32:26:11
Sangeeta Chakraborty: And so there's two two people in this in this situation. There's the CFO, they manage risk. Their job is to manage risk. And so they may have multiple scenarios and they could have the upside scenario, the middle tier that let them do their job. Your job is to be the best representative of the business that you possibly can be.

00:32:26:11 - 00:32:53:15
Sangeeta Chakraborty: First of all, to your first team, which is the leadership team and then to the company and to job number one is to actually understand why the number is being given to you first. And so the reason could be, you know, assumptions that are being made by by the board, by the CEO, by somebody else in this business and so the first thing you do try to understand is what has brought us to this situation and have very deep understanding of the financial plan.

00:32:53:15 - 00:33:12:09
Sangeeta Chakraborty: To Denise point, that was just one of the assumptions. Don't let any mysteries in any part of that go by because those are the ones that are going to come back and bite you. Then I think you have to do two things. You have to have a responsive, all but still aggressive, optimistic outlook for the number you can hit.

00:33:12:11 - 00:33:28:20
Sangeeta Chakraborty: And it may or may not be the number you've been given, but you have to go and take put the belief that you can go stretch and make that business happen and that is why you're in the seat. If you're the one who's taking the least amount of risk, that's again, somebody else's job, that's the CFO job. That's not you.

00:33:28:22 - 00:33:48:14
Sangeeta Chakraborty: Your job is to take that team up the mountain and show them how to do it and go drive that biggest number possible. The only caveat I would say is you have to explain what the assumptions are that you are going to see throughout the year and measure very, very carefully through the year. That's the cockpit for you that you are measuring.

00:33:48:14 - 00:34:06:04
Sangeeta Chakraborty: These are the indicators that I'm going to drive that is going to get me to the number and make sure that you're executing many activity to that. But I don't think your job is to renegotiate the CFO down to a number that, you know, feels safe. That is not why you're in that seat. You're in that seat because you can make the promise happen that nobody else could see.

00:34:06:06 - 00:34:10:09
Sangeeta Chakraborty: And because you are the exceptional operational machine that's going to make it happen.

00:34:10:11 - 00:34:41:13
Sahil Mansuri: First of all, I love your perspective and there's like two things in there that strike the strongest chord with me, which is that if the business is at 20 today and can reasonably get to 30, the ROI of having you in that seat is to go beyond 30, you know, And that's that's, that's the job, right. If any sales leader with this pipeline and with these expectations and with these numbers can get from 20 to 30, then why are you the person that's in the seat?

00:34:41:13 - 00:35:13:23
Sahil Mansuri: And I think having to justify that to yourself, not not to anybody else, you don't need to justify to the CFO, you don't to justify to the board, need to justify to yourself, which is to say that like the sales leaders who people want to hire, the synergy tells the deeds, the SAM bonds, you know, the people, the Stevie cases of the world, the people who get sought after as as a world class sales leaders, they get sought out because there are people who can who can transform the expectations of what a great business and what a great go to market team can deliver.

00:35:14:00 - 00:35:37:07
Sahil Mansuri: And finding that a finding those channels, finding those, those those customer plays, finding finding those ways of of exceeding even the wildest expectations in the business, that's how you make a name for yourself and go to market. You know, nobody nobody ever made a name for themselves and go to market by, you know, getting to 105% of their number, you know, like that wasn't that wasn't how it was done.

00:35:37:09 - 00:36:02:11
Sahil Mansuri: And yet it feels like this this gun shyness. And what I really like is this idea of morale that you brought up are on the team. You know, I maybe something in go to market has changed and I really want your perspective on this because you have have such an important one. But I remember when I was at Glassdoor and when we were at like 30 or so reps, there were basically three reps myself.

00:36:02:11 - 00:36:22:17
Sahil Mansuri: This guy named Clay Batali in this guy named Jeremy Jackery. And the three of us would bring in somewhere like 75, 80% of the revenue of Glassdoor and like a 34, 50 person team. And I never saw that as unusual. You know, I was like, of course, that makes sense. You know, like we're the best. And and this product is easy to sell.

00:36:22:17 - 00:36:41:16
Sahil Mansuri: Anybody can sell this product. The other reps just don't know what they're doing, you know? And it felt like we were just playing a completely different game than what the rest of the company was playing. And and that and that was very common. I don't think that we had a sales team that was demotivated. I don't think we had a sales team that was feeling like we were losers or something.

00:36:41:16 - 00:37:06:00
Sahil Mansuri: It was just a it was a team that was being carried by a small number of outlier performers that were then raising the bar for what the rest of the company should be doing. And here today, I'm not sure that that culture is as well-represented any longer. Maybe it is, and maybe I'm missing it. But I'm curious how whether it mirror or in other places, like how you're seeing the culture of outlier performance being represented in a company.

00:37:06:02 - 00:37:26:03
Sangeeta Chakraborty: I'm still seeing the outliers. I still see there's those few that everybody knows. They show up to the all hands, to all the enablement sessions they are predated at RKO. I think that is going to continue. You're going to have the outliers, but this now, this democratization expectation, everybody needs to have that number. That's not true. It's never going to be true.

00:37:26:03 - 00:37:48:11
Sangeeta Chakraborty: And that's not how you set up sales trends anyways. But there is that expectation that you're going to have to pander to everyone. And maybe that's why there's this risk aversion as that is coming up. But I think the old adage of the top few that are carrying the number remains true and those are the people you want to increase in from top to the top ten.

00:37:48:12 - 00:37:54:06
Sahil Mansuri: Can you tell me more? You said that's not how sales plans should be set up. How should sales plans be set up?

00:37:54:07 - 00:38:11:09
Sangeeta Chakraborty: I think, you know, there's going to be some very clear winners that are going to hit it out of the park and they're going to people, they're going to be people that are not going to make that number. And I feel that in many cases, sales plans are trying to sort of come down to try and give everybody something.

00:38:11:11 - 00:38:36:15
Sangeeta Chakraborty: And I think it's fails because sellers I here because they are risk takers and they are winners and they don't want to make just something. They want to go buy enough to make enough to go buy the house. And so I think sales plans have to be enough that we want the top performers out of the party. Those are the people that are making incredible amounts of money and then just be prevent.

00:38:36:17 - 00:38:42:00
Sangeeta Chakraborty: There's a certain number of people that are not going to make it, and that's fine. And they may be in the wrong business.

00:38:42:02 - 00:39:08:11
Sahil Mansuri: I you know, it's really refreshing to talk to you in many ways because I feel like a lot of the content and and discussion that I see in sales doesn't doesn't speak candidly about things like this. You know, there's this whole like in the new world, you know, we need to drive towards 100% from every rep. And there's this like a sense of trying to artificially create equality.

00:39:08:16 - 00:39:34:10
Sahil Mansuri: It reminds me of something actually that I'm seeing in education in a very interesting way this this whole model. I started thinking more and more about it because I've got a daughter who is about to go into kindergarten, but she's been on advanced programing for a while and she could easily test into first grade. But the school district won't allow her to into first grade because they're like, No, we don't.

00:39:34:10 - 00:39:59:12
Sahil Mansuri: We don't offer advanced programing, whatnot. I had tested in the first grade as a as a kindergarten, so I was familiar with it. So, you know, in the school district that we that we that I used to go to was in the city of San Francisco, which today would never allow such things to happen. But you know, it's it's interesting to me when I was when I was in elementary school, we had a program called Gate, which was a gifted and talented education.

00:39:59:14 - 00:40:16:12
Sahil Mansuri: I heard that the program is de-funded now because they feel like they don't want to put additional resources towards the brightest students because they already have the most opportunity. They want to put additional resources towards the bottom students and try to bring them up. And like in principal, that sounds good, right? Of course, like no one is trying to leave anyone behind.

00:40:16:14 - 00:40:37:07
Sahil Mansuri: But even the very program no Student Left Behind probably created the most students who are left behind. And and so yeah. And so like, I wonder how much of this like you call it a democratization, you know, or almost like socialism type vibes that are coming into sales, which is maybe the most brutally capitalistic sport profession in the world.

00:40:37:09 - 00:41:06:15
Sahil Mansuri: Like, there just seems to be some real dissonance here. And I wonder if we're going to see some sort of a tipping point on this where companies have to kind of wake up and realize like, look, there are certain places in which, you know, and I guess, you know, and I want to end by saying I can see the connection to sports now really clearly, because athletics is one of those places where if for any reason you don't perform, you get replaced because the the team only cares about winning.

00:41:06:15 - 00:41:22:09
Sahil Mansuri: And if you're not the absolute best at your position, going to be out of a job really quickly. But it doesn't feel like we have that culture in at work as much anymore. I think it's still there and it's certainly there and great sales teams, but there's a lot of sales teams that I feel have gotten soft and I wonder what you think about that.

00:41:22:09 - 00:41:27:18
Sahil Mansuri: Our sales leaders have gotten a little soft over the last few years and I wonder what you think about that.

00:41:27:20 - 00:41:53:08
Sangeeta Chakraborty: I will not pass judgment on my fellow sales leaders, but I do see this The lack of interest in coaching is part of the problem because you could coach a rep to be an amazing rep. You're also coach somebody saying they're not in the right role. And that part, it just hasn't happened because people don't care about individuals as much as they, I think need to be.

00:41:53:08 - 00:42:11:13
Sangeeta Chakraborty: And some of the best advice I've been given in my in my career have been people that have been saying, look, you're not good at it. You should be doing something else. You'll be more successful doing something else. And I think while you're trying to pander to everybody and try to make them successful just because they're in the role, I don't think that growth is going to come.

00:42:11:15 - 00:42:28:01
Sangeeta Chakraborty: I'm all for the growth mindset. I think we need to give people a chance to learn. And then you know, some people are going to be amazing at it. Let's reward them. And maybe there's something else that the others are going to find out for themselves. If we, you know them there.

00:42:28:04 - 00:42:46:20
Sahil Mansuri: Yeah, that totally makes sense. Okay, the last topic I want to touch on before we we end our session today is the topic that you hinted at at the very beginning, which is being kind of customer obsessed and being customer focused. And I want to do that through the lens of how we build our sales process these days.

00:42:46:22 - 00:43:05:22
Sahil Mansuri: And so, you know, one of the things that I think most companies are challenged with these days is top of funnel. I think it's always been a problem, but it's really come to the fore in the last few years because of the decay of the mass email programs that so many companies were reliant upon. And I wonder how you think about top of funnel.

00:43:06:03 - 00:43:25:10
Sahil Mansuri: You know, for a startup that maybe doesn't have a great brand yet and is trying to claw their way to try to create, you know, get their first hundred, 500,000 customers, you know, what would you do if you were starting a fresh with a with a company or a brand that had, you know, five, ten, 15 clients and not big marketing budget.

00:43:25:16 - 00:43:29:20
Sahil Mansuri: How would you think about creating top of funnel for for an early stage startup?

00:43:29:22 - 00:43:56:14
Sangeeta Chakraborty: So I do advise many startups of this age and the stage of their growth and the advice that I've been giving them say is, first of all, you have to cast a shadow that is larger than your actual shadow. And the way to do that is you have massive thought leadership that stands out because what people are ultimately attracted by is learning something that they didn't know before.

00:43:56:16 - 00:44:21:18
Sangeeta Chakraborty: And so the question is how can you get people's attention by showing them something that they didn't realize existed? And this goes beyond just buying LinkedIn, that this goes to you getting out there, understanding the profile that you're selling into and becoming a really big part of that ecosystem by showing them something new. It's hard. If you're a meta product, you're going to find it extremely hard.

00:44:21:20 - 00:44:46:19
Sangeeta Chakraborty: But if you have something that's unique, you want to go bravely into that community and say, Hey, look, I may be a 22 year old startup founder and I have a very small company and just got by Wiki, but I'm going to show you something that you did not know while you were in the business. 25 years, the right people will pay attention and I think that's how you got to start to do something different than this.

00:44:46:19 - 00:45:00:13
Sangeeta Chakraborty: But now this doesn't scale forever. So you are talking about a very early stage startup. This is one of the things that I would recommend. And then as you get bigger and bigger, you have to find other ways that are more scalable than just doing founders setting and founder evangelizing.

00:45:00:13 - 00:45:22:04
Sahil Mansuri: Can you can you maybe talk about just the next stage beyond that? So I think thought leadership is something that, you know, I can speak to with my own personal journey and bravado. You know, we we when we launched our talent marketplace in 2021, 2022, it was you know, there's a million sales recruiting agencies and sales recruiting products that are in the market.

00:45:22:06 - 00:45:48:10
Sahil Mansuri: And our opinionated point of view at the time was, yes, that's all true, except the biggest difference is that, you know, none of you have any performance data on any of these reps. And we have performance data on sellers through bravado. And so we can give you a perspective you've never seen on a LinkedIn profile or a resume, and it captured a lot of attention and it actually allowed us to win competitive deals because we had folks who are like, Oh, but I've never seen something like this before.

00:45:48:12 - 00:46:09:00
Sahil Mansuri: Well, to be clear, we spent 18 months before we launched the product on this very idea of like when we launch this product, there's a thousand sales recruiting agencies out there. How will we be able to compete? And we kind of isolated what would be the one or two things that we could really compete against, worked really hard to make those show up and the product worked really hard on product marketing materials around it.

00:46:09:00 - 00:46:29:16
Sahil Mansuri: We trained our sales team to speak about them, trained our sales team to speak about them, and ultimately made, you know, I think it was Peter Thiel who once said, you know, like if you can't win the game the way it's played out, then change the rules of the game. And so, you know, instead of trying to say, hey, we can help you get the best reps or the fastest, you know, time to placement or whatever, which is what every other recruiting agency would say.

00:46:29:18 - 00:46:52:17
Sahil Mansuri: We would just say we are the first agency where you can trust that you'll get verified performance data on the rep. And, and in doing so, you know, kind of stacked the odds in our favor. And it works for a little while. You know, we got we got our first 100 200 300 customers through that and then yeah, you're right, it kind of started drying up, you know, like enough people had heard the pitch, enough people had seen it and we needed to unlock new ways in order to do that.

00:46:52:23 - 00:47:10:13
Sahil Mansuri: I wonder how you think about, like once you get to your first 51st hundred, maybe you're like a series B companies or C company. You have a little bit of a brand, you have a little bit of momentum, but not fully baked yet. What is that? That's kind of like the hardest part in some ways. You know, the trust, I think trying to get from like 2 to 20 or whatever, like how do you think about that?

00:47:10:13 - 00:47:17:12
Sahil Mansuri: What what are some of the things that you feel like work the best or maybe some of the things that don't work well that you see a lot of people wasting their time on?

00:47:17:14 - 00:47:39:14
Sangeeta Chakraborty: I think what happens at this stage. So unfortunately, this is the stage where there isn't any one quick answer. Yeah, and the thing that I feel I've seen these companies struggle with is qualification, because they're now somewhat somewhat blinded by that initial success. It feels like I've got a product everybody wants. How is it that somebody would not want it?

00:47:39:16 - 00:48:00:00
Sangeeta Chakraborty: And so then he goes pre and pre and it doesn't work. So the next hard job you really have to do is to be the best ever at understanding how to qualify the recipe. What is the company company size? Who was the buyer that would truly get what you're selling and differentiate differentiation compared to anybody else. This hard work more start ups don't do.

00:48:00:02 - 00:48:17:09
Sangeeta Chakraborty: They are now so interested in getting to that massive number that they've signed up for and now it's like, Well, we're just going to do everything we possibly can think of, but you actually have to slow down and be very, very regimented about figuring out your ICB, because once you figure that out, then you can start scaling again.

00:48:17:09 - 00:48:41:13
Sangeeta Chakraborty: So it's okay to slow down a little bit and know what they actually truly is. That can scale without the founder in the room, without the thought leadership impacted. Just have to be doing hardcore pain identification and showing the solutions. And this is back to, you know, all the fundamentals of selling. But the biggest mistake that see is that lack of qualification.

00:48:41:13 - 00:48:47:21
Sangeeta Chakraborty: It's just you're so much in love with the product, you don't realize that you're not doing that part of the work.

00:48:47:22 - 00:49:05:19
Sahil Mansuri: When you say qualification just, just, just so I make sure I understand. Are you saying that like you're asking the right questions upfront to disqualify companies that might other be otherwise seem to be a good fit, but for some common reasons don't seem to convert very well? Is that what you mean? Or do you mean something else?

00:49:05:21 - 00:49:28:23
Sangeeta Chakraborty: Yes, that's what I mean. The find the right companies, they may look like they need it, but there's a reason your product has a value and it would apply only to it could be the size of the company. It could be the industry could be the persona that is going to understand the value that you bring uniquely. And you just have to do that very, very fine tuned to work to get to the next stage.

00:49:29:01 - 00:49:44:18
Sangeeta Chakraborty: Eventually you're going to get to all the big companies, but that may not necessarily be the next thing that you're getting into. So it takes evolution and hard work to identify the ICP that you can now sell at somewhat of a scaled model. Not not you in the room everywhere.

00:49:44:23 - 00:50:07:04
Sahil Mansuri: Yeah, that totally makes sense. Well, this is so much fun. I honestly could do like two more hours of this with you, but I want to be respectful of your time and have our calendar. I will twist your arm to try to have you come back and do this with me again in a in a couple of months, because I want to actually spend so much more time diving into a bunch of the things that we talked about.

00:50:07:06 - 00:50:30:09
Sahil Mansuri: But before we go, we've got our final kind of lightning round, you know, and end with some end with some fun questions that I've got for you. So going to I'm going to go through these and get your instinctual answer. So maybe the first question I have is, you know, from the from pop culture, what fictional character do you think would make a great salesperson?

00:50:30:09 - 00:50:38:21
Sahil Mansuri: No, You can pick like, you know, someone from Glengarry Glen Ross or something. You got to pick a real fictional character. Who do you think would be an amazing salesperson and why?

00:50:38:23 - 00:51:02:21
Sangeeta Chakraborty: Okay, I'll give you my answer. And it's based because I am a book nerd. I love fantasy. And it would be an answer that you wouldn't expect to hear because I think most people would give you a male response. This is a female. This person has intelligence and persistence, heart and desire to win. And is Hermione Granger from Harry Potter.

00:51:02:21 - 00:51:08:06
Sangeeta Chakraborty: I think she is going to be an effing amazing salesperson. She wanted to be interesting.

00:51:08:06 - 00:51:32:01
Sahil Mansuri: Interesting. I you know, the thing I think about with her myeni, I mean, obviously she's like the smartest character in the in the in the book is that she seems to have a difficult time making friends. You know, she seems to like be socially off putting with her like, you know, specific ways, but but a channel that in the right way and I bet she can like impress the crap out of a lot of customers, huh?

00:51:32:03 - 00:51:33:07
Sahil Mansuri: Is that kind of what you're going after?

00:51:33:10 - 00:51:54:09
Sangeeta Chakraborty: So, I don't know. So here's another controversial topic. I don't know that the the sales reps that are most successful are just simply good at making friends. They're great at gaining trust because they know their stuff and they know how to help you. And I think her she knows the stuff. She figure out what she needs to know to gain your trust because you know she's the best at what she does.

00:51:54:09 - 00:52:03:01
Sangeeta Chakraborty: And then you'll trust her when you give her that. You know, that's in a sign on the dotted line that she's going to come through for you. That's the best sales rep and that's that.

00:52:03:02 - 00:52:19:21
Sahil Mansuri: I love that answer. Okay. So outside of the workplace or some professional context, what is one time that you've used your prodigious sales talent in order to score yourself a great benefit or get yourself out of a tricky situation?

00:52:19:23 - 00:52:33:22
Sangeeta Chakraborty: Oh man, I don't have great answers for you. I try my sales superpowers on my kids and completely fail. I've tried it in other places. My parents completely failed. No, I'm still learning that one time.

00:52:34:00 - 00:52:51:08
Sahil Mansuri: Oh, come on. You can't. You know, you're not getting off the hook. You got to you got to tell me. You're telling me that you have never been able to flex your sales muscle in any situation in which you were able to. Or maybe you're just doing it so well that you're like forgetting the moments in which it works.

00:52:51:08 - 00:52:54:18
Sahil Mansuri: And you only remember the failures. Like any good salesperson.

00:52:54:20 - 00:53:06:23
Sangeeta Chakraborty: I just I just don't want to admit it. I use it for I use it for stupid stuff like getting restaurant reservations and getting the best dream of the hotel. But it feels so terrible. I don't want to admit it.

00:53:06:23 - 00:53:26:13
Sahil Mansuri: Oh, come on. What do you mean you don't want to admit it? Sales is a superpower. And and, you know, we if we have to deal with all of the crap of, like, you know, being labeled as a salesperson and whatever, then at the very least, we should be able to speak freely about our ability to leverage the skill to personal benefit.

00:53:26:15 - 00:53:41:02
Sahil Mansuri: I would say my my favorite is I convinced the airline hostess for our honeymoon to give my wife and a free upgrade to first class on Emirates flying from SFO to Dubai.

00:53:41:04 - 00:53:42:07
Sangeeta Chakraborty: Wow. Tell me that.

00:53:42:07 - 00:54:03:18
Sahil Mansuri: Trick. It was. Well, it was. It was just, you know, showed up really eager beaver excited. Tell them this whole story. Asked if we could upgrade. They told us yes. They said it was, you know, $7,000 per seat. And then we looked crestfallen and said, we can't afford it, unfortunately. And then we walked away looking sad. And then when we got to the ticket counter and we scanned the ticket, they were like, Oh, can you come with us?

00:54:03:18 - 00:54:19:19
Sahil Mansuri: And they like pulled us to the side. And they had upgraded us to first class and the captain told us ever. So just look, I just gave them an offer. One of the things I've learned is that people really want to be a hero. You just have to give them a chance to do it. You know, everybody. Everybody wants to be Superman.

00:54:19:21 - 00:54:27:08
Sahil Mansuri: Okay, how about this one? Best advice that someone gave you in your career that you don't hear repeated much these days?

00:54:27:10 - 00:54:51:05
Sangeeta Chakraborty: Oh, best advice. I think the best advice it's probably repeated. The best advice I was given was if something seems really hard and nobody wants to do it, you should go sign up for it because that's got so much value attached it. And that's basically been my no straight line to a career outcome advice that I've been using, and I learned a lot from it.

00:54:51:05 - 00:55:00:00
Sangeeta Chakraborty: I know that people look for that anymore. They're looking for the easiest path out and it doesn't necessarily serve you in the long run.

00:55:00:02 - 00:55:03:22
Sahil Mansuri: Can I just double quick? Why do you think that's such important advice?

00:55:04:00 - 00:55:25:10
Sangeeta Chakraborty: Because it really challenges you to grow. There's a growth mindset coming into play and usually the things that are really hard have high value, and if it was easy to do and people would have done it, but they are hard and people don't want to sign up. But if you do, and because you are creative and curious and an owner of outcomes, you're going to figure out the answer.

00:55:25:12 - 00:55:29:14
Sangeeta Chakraborty: I think there's so much value you're creating, and I'm all about value creation.

00:55:29:16 - 00:55:47:13
Sahil Mansuri: I love that answer. That was such a good one. I absolutely love it. Sign up for the things that nobody else is willing to sign up for is is amazing. Jason Lemkin actually wrote about this recently. He said, you know, when you're the CEO and you ask someone, you know, you basically have a really hard project and you say, okay, who wants to own it?

00:55:47:13 - 00:56:04:22
Sahil Mansuri: And nobody raises their head. If you're the one person who raises your hand in that moment, it says much more about who you are as a person than it does anything else. You know, just like what? What what is it that compels someone to raise their hand when they know the project is hard and it's going to be annoying and whatever.

00:56:04:22 - 00:56:24:17
Sahil Mansuri: But but they are still willing to do it. It just speaks to your character and your mindset towards life. And I think it's a really it's a really, really powerful and I love that. And then the last and easiest question of all, which is I'm sure there's going to be a lot of people that have follow up questions that want to ping you, that would like to get some advice from you or ask you something.

00:56:24:23 - 00:56:26:17
Sahil Mansuri: What is the best way to get a hold of you.

00:56:26:18 - 00:56:31:15
Sangeeta Chakraborty: Know, it's usually LinkedIn is the best one. I'm fairly responsive on LinkedIn.

00:56:31:16 - 00:56:52:05
Sahil Mansuri: Okay. Amazing. We will drop a link to your LinkedIn profile then in the in the description and I'll have it populate here as well so that people can just copy it. So thanks to the magic of podcast editing. All right, Sanjay, thank you so much for your time. This was such a wonderful conversation. I really I really enjoyed it.

00:56:52:05 - 00:57:00:18
Sahil Mansuri: And I really hope that I get an opportunity to continue this with you in a few months because I feel like we just scratched the surface and there's so much to talk about with you.

00:57:00:20 - 00:57:04:19
Sangeeta Chakraborty: Thanks for having me. So I really, truly enjoyed it as well. I look forward to more.

00:57:04:19 - 00:57:05:18
Sahil Mansuri:
Awesome. Thank you.

00:57:05:22 - 00:57:19:06
Sangeeta Chakraborty: Thank you. Once again. Once again.