SgtAE

WR Officer

Politicker

OG Sales Savage

Selling alongside the founder as the first sales hire?

Hi team, keen to get some feedback from anyone who may have been in a similar situation.

So I'm the first hire for a small startup (7 people) and the sales process has been completely founder led in the past.

The product is quite technical and our sales process sees me getting on the calls with the founder.

He's technical in background and I find a lot of our calls end up deep diving into the technical realm with heavy ratio of around 80-20

Has anyone else sold alongside a technical founder and how have you ensured that sales conversations are balanced in commercial and technical discussion

👑 Sales Strategy

31 comment

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GDO

Politicker

BDM

People will take him more serious than you. Always plan ahead. Especially with technical founders, they sometimes do not know how the sales/negotiation game is played.

jefe

Arsonist

🍁

Very good point.
You'll have to manage upwards here. You want him to act as an SE more than anything.

CadenceCombat

Tycoon

Account Executive

This sounds like a nightmare for me personally. I feel like I know the type. They don’t understand selling as a craft and think it is akin to ‘order taking’ or not too far off from it. If he’s open to loosening the reigns on sales process, great. If he’s not, it’s going to be a pissing contest where he’ll be reluctant to take your feedback while simultaneously questioning why deals aren’t closing. The worst.

I find this is the biggest blind spot with technical founders. They feel like if only people could see the genius of the product, it will be compelling enough but product in isolation isn’t compelling. Maybe with highly sophisticated, technical buyers, the approach will resonate but likely to hit a wall when targeting a broader audience.

Sunbunny31

Politicker

Sr Sales Executive 🐰

Your last paragraph really resonated. It's also the same thing that leads to reps overselling on feature/functionality rather than what the product solves for and the value it brings.
The challenge will be to ensure you have a value discussion lined up and part of the time you spend. The "why this is important" phrase should be at the ready so you can bring it back.

Dolphin

Enterprise Account Executive

100% on target. My last gig (AE for Enterprise) was with a very small, 6-person startup where the first-time CEO wrote much of the initial code and came from managing sw dev teams. He couldn't understand why customers weren't just buying the AI SaaS product. His view: We demonstrated it and provided the price. Just need to negotiate the contract and get it closed! If we aren't getting sales then it is all the reps fault who can't sell. Got to the point where he was rewriting sales emails, requiring pre-approval before sending stuff out, questioning everything, etc. Drove the BDR crazy and he quit. Became a very toxic environment and ended when a large company decided they could do the same in-house for less than the $200k quote. So quit or be fired. So very, very happy to be out of that madhouse.

CadenceCombat

Tycoon

Account Executive

Sweet lord

hola

Valued Contributor

sales consultant

wow this almost sounds like my experience being a first sales hire

JBlazingBandido

Director

I had a very similar experience. Wild how common it is.

Pachacuti

Politicker

They call me Daddy, Sales Daddy

You're the quarterback and you need to set up the play. So understand what he needs in order to score - background, conversations, pains, and other factors you learned in discovery. From there learn how he wants to be teed up - short intro, long intro, jumping right into it, etc.

Then be ready to wrap things up with next steps, follow-ups, etc. Take it over after he's done with the propeller head stuff.

FoodForSales

Politicker

great points!

Director, Partnerships and Key Accounts

Spot on. Love the way to have defined the role: Quarterback.

Beans

Big Shot

Enterprise Account Executive

Been there, their expectations will be through the fucking roof and they'll expect the same commitment from you.

CuriousFox

WR Officer

🦊

Yup. It's like they learn nothing. Ever.

DirtyHarold

Consultant

I've worked at an organization for the past 10 years. The founder is an old school technical programmer, who leveraged his knowledge, experience, and local identity, into a very successful Technology business. However, when they wanted to pivot into the more lucrative SaaS / MSSP space, he found that while he had the tech stack and staffing to support his vision, client's just weren't biting. Which is where I came in. I realized very early on, that their Type A personality, combined with the data dump of information contained in the founder's sales pitch, always resonated with the potential client's tech staff, but NEVER resulted in an actual contract. No contract = no business = sad business owner. In my experience, technical staff never have the authority to sign off on deals, but you won't get a contract without their support. The ratio that you mentioned being 80% of the conversation being tech driven, and 20% being sales driven is your problem. You know it, but it's worth mentioning. You have to solve THAT problem. Here's a quick example of what I had to deal with: Our VP of technology was the WORST in appointments, but was a self proclaimed sales monSTAR. He would come into a meeting, telling the client about how their tech solutions were some of the worst that he's seen. Here is the only way that you should be solving these issues "filler technical discussion for 45 mins, while not letting the client or myself talk much at all". He would talk himself in circles and run out of steam. Then would come the fear mongering and dumb phrases that he would read online and fall in love with: "The dark web is like the abyss. When you stare into the abyss, the abyss stares back." We would then get back to the car and he was always proud of how he ran the appointment. 10% would result in closed deals. Here is how I solved that issue for both the VP of Technology, and our Founder: Stick with it if you believe in the company and the ownership staff. If not . . . leave. It won't be worth your time, I promise you. I had lengthy conversations with both owners. One went well, and the other . . not so well. The overbearing owner doubled down on his sales process. So, I stopped going on appointments with him. I would follow up with those clients 3 months after his last appointment, when he would lose interest and classify them as "idiots". I reviewed my closer rates on those the other day in prep for my November review: 82%. For the Founder's issues, he still believes that if he just talks enough, that he can sell better than anyone else. However, he has taken a backseat in my meetings due to the success rate that he has seen over the years. He found that it's more fun for him when he doesn't feel like the focal point of our meetings. He comes in, talks tech for 20 mins, thanks them for considering doing business with his company and he's out. You can't change people, you just have to find ways to work around them. Play to their strengths and make them feel like a valued part of the sales process. But step 1 . . . You have to have a conversation with the founder. Let him know your concerns, and just ask for a chance on the next 5 leads. And if you get it . . . bust your a$$ to make sure that you close them.

Retired Sales Professional

I agree with GDO. Perhaps for experience purposes you may ask him to allow you to take a call without his assistance which will allow you to show him indirectly (you dont want to fracture his ego) how to balance a sale call between tech and sales.

Director of Sales

I've been part of three different startups where I worked closely with the CEO/founder in sales. You have to accept that the CEO/founder will always be more knowledgeable about the product and company than you. Your role is to lead the flow of the call and the founder is there to answer any technical questions just like an SE. A few things worked well for me, game plan before the call, take 5-10 mins to discuss your findings, goals, key talking points, and roles with the founder. And also have the habit of debriefing after the call, talking about what went well and where you can improve for the future. It is hard in the beginning, you will feel bad that the founder is doing most of the work on the call, but with time, you should start picking up some of the technical answers and shifting that ratio towards you.

Manager- Strategic Alliances, Channels & Partners

Spot on advice Kristopher! Many times you can hold a first call on your own to qualify, qualify, qualify. Then bring in the CEO as the tech expert/SE. And VERY important to do a pre-call game plan and debrief. Debrief can help with accountability for next steps, esp. if some of them belong to the CEO.

kindagoodae

Executive

Account Executive

Find ways to compliment each other — with you leading the deal. His technical expertise might mean he isn’t as skilled in rapport building or negotiations as you are. The downside is that nobody cares more about the product than they do, so he may not be willing to compromise.

ThatNewAE

Big Shot

Account Executive - Mid enterprise

You'll have to be more in sync with the CEO first. The founder needs to know when to give the podium to you.

For that, you need to make suer you know when too much technical stuff have been spoken of. I tried selling with a technical founder.
All founders are too proud of their work. They will oversell their technology to the extent that you would have to undersell to compensate.

Let this not happen. Let the boundaries be clear. Let the pitch be clear. Let sales lead first.

ventox35

Politicker

Sales Leader

selling alongside a founder is TOUGH. their title gives credibility and it helps sure. but they often struggle with facing reality and can become a deterrent to winning deals. they know how to sell their vision for the company, but not always how to sell the product. give lots of suggestions and set an example for a good sales process. they will notice and hopefully apply some of the things you've taught them

wolfofmiami

Opinionated

🐺

Ive worked at a startup and the founder was on every sales call and get deep into the tech and so excited about it and wouldn't let the buyer talk and would piss the buyer off most of the time, so just make sure he knows how to sell and not just explain the tech. If thats how they are it might be good to ask him for a training and learn the technical side or try and get them to hire an SE that will allow you to do your job better, its a bold play, but you need to set some boundaries if youre losing deals bc the founder cant sell and gets too technical

Director

That doesn't sound like a sales call. That sounds like a technical/discovery call.

Jbeans

Opinionated

Director of Sales

In my experience- tech reps see a problem and a solution. But don't necessarily understand the art of the sale . It's a calculation to them, you said it was broken + we have a solution= the PO. I wish it was that simple. I've sold along side an owner who's also a tech consultant- interesting combo as I can appreciate his technical ability but it took him much longer to appreciate my skills of reading the room, setting the tone and the pace of the deal etc. The strategy of people want to buy, but not be sold too. My advice? You are the lead, prep with them for the call to avoid free consultation on their part and use the up front contract method to keep control of the process/timeline etc. They hired you for your skills, don't be shy to take the reigns 😎😎

Navigating

Old School Bravo

Head of Sales

If a founder with no previous sales title, or full-time sales experience, insists on being on every call in a sales cycle, run away quickly. They will never give you a chance to do what you do best, and they will take credit for every win.

Chief Revenue Officer

I have been in that position twice and can be quite challenging. I would ask you:- Has he been successful selling on his own? If he has, it could be an issue as he may think "he got it" and that you need to learn from him.
- Do you think you have product-market fit or are you in discovery mode? If the former may not be that bad, but if the latter (I assume this given the number of employees) he will try to push the product and might not understand why customers are not receptive. It may distract you from focusing on the problem (and will gravitate around the product) and ruin your opportunities.

The best way I got some progress was two-fold.
1. I got the CEO to take Kenan's training on GAP selling, so he got the crude "nobody cares about your product only on how it solves a customer problem" from him, not me. And as with the quarterback comment (from another contributor above),
2. I set the ground rules on how the calls would run (problem oriented not product oriented) and that I would drive them, giving him the company Intro (not product) and pass to him him to answer the technical questions for credibility, etc after we have discussed the problem and needs from the customer.

It wasn't perfect but made a huge progress. Hope it helps. We (that company) got acquired and I am taking some to recharge so if it would be helpful I would be glad to jump in a call and share more details. Good luck!!

themanwhosell

Member

BDM

I am currently doing the same.

First of all, it is twice as hard when you are selling for a new company with a very low number of employees and possibly 1-2 clients, in comparison to selling for a company that already has a decent online presence.

But, the opportunities to grow are also double.

AnchorPoint

Politicker

Business Coach

Planning will be even more important.

NiazMak

Executive

Director Sales

In light of this, it would be prudent to arrange a pre-sales call demonstration among our respective teams. During such meetings, I typically collaborate with our CTO, who handles technical inquiries, while I focus on commercial aspects and relationship-building. This division of roles has proven to be effective in maintaining a well-balanced and productive dialogue.

Kosta_Konfucius

Politicker

Sales Rep

I would say its setting a clear agenda, who talks about what

Redlinez

Executive

Principal

I'm a bit late to the party- but I'm up against the same challenge. The founder is an IT guy by trade second generation ownership. He clearly has the mentality that the "product sells itself" and doesn't really get or appreciates sales.
My advice would be- run the first call without the founder and a demo if you can- and do a really high quality discovery- positioning the demo as a proof of concept. Then during the demo- do your damnedest at keeping the founder on point- jumping in to reinforce the value the feature delivers based on the problem it'll solve the articulated to you. It'll probably be a challenge- but you have to own the conversation and room. May even have to jump in and ask him to move forward if he goes too deep into a feature... can do this by asking the prospect something like "does that look like it'll be a better experience/solve X challenge? Great should we move on to X?"
Anyways. I feel your pain!

bizdevwizard

Personal Narrative

Vice President, Business Development

I've been in your position before and what I found useful is to first, identify your sales process. It might mean that the initial discovery call/meeting is treated high-level to qualify the buyer.
Once all buying intent and successful qualification process has been completed, I would suggest that you invite your subject matter experts to the 2nd meeting/pitch-close call.
When you set-up the pitch-close meeting the stage should already be set to discuss specific technical questions or situations with the prospect and how your product/solution can solve their needs or if it requires a bespoke solution.
If it's the latter, I would suggest a paid discovery 'beta process' where both parties understand the exercise and collaborate to determine if the problem at hand can be solved.
In summary, it might be best to get the entire sales team and leadership involved and explore how the sales process is designed before it becomes more of an issue.
Sometimes we need to slow down, in order to speed up.
Hope this helps. Good luck and enjoy the journey. It can be quite rewarding to navigate this process for them and although it can be frustrating at times, the reflection on the process after is priceless!

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SgtAE

Selling alongside the founder as the first sales hire?

31 comment

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