Find your first seller
What you’ll learn
How to hire for your specific pain points and avoid the most common early-stage hiring mistakes.
Why it’s important
Get your first sales hire wrong and it can set you back months.
Keep reading if...
- You know balls are being dropped but you’re unsure which role to hire to fix it.
- You have a mental picture of who would make a good sales hire—and it looks a lot like a senior rep from Salesforce.
- You need a better idea of the soft skills and mindset required for a strong early sales hire.
It’s the evergreen founder question: “When should I make my first sales hire?”
What are you hiring for?
Before you hire anyone, make sure you've done enough customer calls yourself to clearly articulate the problem you need help with. If you're still figuring out your ICP or pitch, a salesperson won't fix that—they'll just expose those gaps faster. If you think this might be you, go back to step 6 and figure out how you can get more signal from customers.
You’re not learning quickly enough about customer needs.
Who you need to hire: Account Executive (AE) with startup experience—someone comfortable with the grind of multiple customer calls a day, who can translate what they're hearing into product insights.
“Hire a salesperson to help accelerate the learning velocity of the organization. So every week, our salesperson shares the top three things that he’s hearing from customers that are blocking adoption. Or, ‘These are the top three things I'm hearing from customers that are blocking them from converting to pay.’”
Patrick Thompson
Co-founder, Clarify
You need to build pipeline.
Who you need to hire: Sales Development Rep (SDR) or Business Development Rep (BDR) who can run campaigns across multiple channels to find and qualify leads and book meetings for the founder or Account Executives (AEs).
Sequence’s Riya Grover tested using AI SDRs for LinkedIn outreach but reverted to humans because "that human element, when there's so much noise, helps to drive really, really high-quality pipeline."
Riya Grover
Co-founder, Sequence
You need to close more deals.
Who you need to hire: Account Executive (AE). But only if you have already achieved product-market fit. If the product isn’t right, hiring AEs won’t fix that.
“The problem was not pipeline generation. If it was, we would have considered hiring an SDR. The problem was actually handling the pipeline we had. So we went directly for an AE.”
Marty Kausas
Co-founder, Pylon
You need to reduce churn.
Who you need to hire: Customer Success or account managers.
Equals’ Bobby Pinero saw registrations 4x after launching a free plan, but struggled to retain those customers. Reintroducing friction—requiring onboarding calls—fixed the problem. "We had to understand what you were trying to do with the product, why you wanted it. Who else on the team was going to use it? Is your manager on board with this?" For some companies, a high-touch post-sale process ensures more engaged customers.
Bobby Pinero
Co-founder, Equals
You need to manage and coach a growing sales team
Who you need to hire: Head of Sales or VP of Sales—but only after you have onboarded at least 2 salespeople who are succeeding. You are the sales leader until then.
When it comes to hiring a VP of Sales, Qwilr’s Mark Tanner warns that “good ones can be insanely expensive, bad ones will ruin your company.” He recommends waiting until you have at least two or three reps who are ramped and successful. “If you've hired reps and they're unsuccessful, therefore you’ve decided you need a sales leader—that is actually the incorrect diagnosis of the problem.”
Mark Tanner
Co-founder, Qwilr
The characteristics of a great early sales hire
Before you try to hire a seasoned salesperson with incredible logos on their resume (“Senior Sales Manager at Salesforce”), stop and think about it. Can they actually do well at a startup?
Somebody who was successful in selling Salesforce was likely doing less selling and more order-taking. With a massive brand like that, you're not selling so much as people are buying. It’s transactional rather than strategic.
At an early-stage startup, you don’t have a strong brand behind you. You don’t have case studies to reference. You don’t have the money for fancy steak dinners or field events. And the product is probably immature and a bit buggy.
(Don’t worry, you’ll get there.)
You need someone with a high-growth mindset, tenacity, and a great attitude. Who thinks, “Hey, I'm okay getting kicked in the teeth for the next 6 to 12 months as we figure this out.” They are joining because they want the experience. If they don’t have that mindset, they're going to fail.
1. Bias toward execution (not management)
In the early days, you don't want to hire a sales leader, and definitely not a VP of Sales, because you are the sales leader. It’s a mistake that Tofu’s Elaine Zelby has seen both as a founder and while working as a VC.
“I think so many founders hire somebody way, way, way too senior for almost every role, every first hire,” says Elaine. “You need somebody who has zero intention in the next 12 months of managing a team. If the first thing they wanna do is go hire a few people under them, they are not the right hire.”
In a lot of organizations, the playbook is set, and actually, AEs don't have to be that hungry, that tenacious; they're not reinventing a wheel. They might've hit great numbers in their previous companies, but actually, that doesn't translate over. The motivation, the hunger, the stretch challenge is really vital.
Riya Grover
Co-founder, Sequence
2. Relevant experience
While she might not want seniority, Elaine does look for experience. She wouldn’t hire an Account Executive (AE) who has never done it before, or give a first shot to a rockstar Sales Development Rep (SDR) who wants to become an AE. There’s simply too much hand-holding and training involved for a resource-limited startup. You’re already going to have enough work training up an experienced salesperson on your system, without having to teach them the fundamentals as well.
Two specific things that Elaine looks for are experience with similar-sized deals and similar-length sales cycles, which she thinks are more important than experience selling to your ICP.
“I do think it’s important to understand that a two-day versus 45-day versus eight-month sales cycle looks wildly different,” says Elaine. “And a $10K deal, $40K deal, and $300K deal looks wildly different. So, if your price point is around $40K, I would never bring in somebody who's never sold above $15K. They're not going to know how to run a sales cycle at that stage. I also wouldn't index on somebody who wants to go and sell mid-six-figure deals. That's just also not going to be the right fit.”
Other founders have found relevant experience in non-traditional places.
Steve Hind, co-founder of Lorikeet, a provider of AI-powered customer service concierges, says his first sales rep had “never closed an enterprise SaaS contract” before joining Lorikeet. Steve was tempted to hire traditional enterprise salespeople to complement his lack of sales background. He interviewed many people with great resumes, but the right fit turned out to be an agency founder. Selling professional services requires extensive customer education, which is exactly what Lorikeet has found it needs to sell enterprise AI.
“We’ve definitely seen a lot of people with what looked like the right sales experience on paper that doesn’t translate into the way we want to operate,” explains Steve.
“People don’t need someone who’s going to run them through a qualification checklist, do a demo, and send them a contract. They need someone who’s going to be a partner in helping them think about how to make that transition work in their unique circumstances. And it turns out if you can do that, then learning how to navigate a procurement conversation is the easy part, not the hard part.”
3. Intrinsic motivation
As a founder, your job is to find someone who thrives in ambiguity and doesn’t mind operating when their back is against the wall. They want that experience and are not purely motivated by compensation—they could probably earn more at an established company. They need to be motivated by helping a company grow from zero to $1 million in ARR—and all the learning, accolades, and, yes, equity that come with it. We’ll cover comp in more detail in the next tactic.
4. Curiosity
Qwilr’s Mark Tanner says that qualities like coachability, ambition, or just having done hard things, whether that’s having represented Australia in kayaking or managing a band on a tour of Europe, are clues that someone has the aptitude for sales. But there’s one quality he looks for over everything else.
“Salespeople need to be curious,” says Mark. “If they’re not curious, it's going to be a bad time. You just need to have people who are interested in other people and who ask lots of questions. They then turn this understanding of what the real situation is and flip it into, ‘Cool, I've understood all the things I need to understand. Let me now tell you what Qwilr is and why you should care.”
What great looks like in practice
Six months after hiring his first AE at Pylon, co-founder Marty Kausas had scaled to four AEs. On paper, things looked fine—deals were closing, pipeline was growing. But something was off.
"No one-on-ones, no team meetings, no forecasting meetings, no anything," says Marty. "I would basically just work with each of them individually as needed. It was basically totally unmanaged."
Then one of the AEs, Mana, came to him directly.
"She said, 'Hey, I think the team could be run a lot better. I think we're not operating in best-in-class fashion. We don't have this good, strong, established sales culture right now, and there's a lot more we should be doing. I think we're gonna hit walls if we don't start forecasting or thinking about some basic structure for the team.'"
Mana didn't just identify problems; she brought solutions. She pointed out that two different cultures were forming on the team, one productive and one not. She suggested which behaviors to reinforce and which team member might not be the right fit. She outlined exactly what the team needed to become world-class.
"She brought that to me as an AE," says Marty. "And over the course of the next month or two, I kind of realized that she would do the job better than me. She was already bringing up all the problems with the solutions to them. And at that point, I'm like, ‘Okay, you have great ideas for this, and you're bringing them up proactively, and these are hard things to bring up.’"
Six months after joining as an AE, Mana became Pylon's Head of Sales.
That’s what execution bias, curiosity, and intrinsic motivation look like in practice. Mana didn't wait to be promoted before acting like a leader. She saw what the team needed, diagnosed the problems, and proactively brought solutions to her founder. That's the person you're looking for.
Your job description is a sales tool
Think of your JD as an ad, not a requirements doc. Mark points out that it can be hard to attract good people to early-stage startup roles—especially in sales, where great candidates already have options. Your JD needs to sell the opportunity: the problem you're solving, the learning they'll get, the impact they'll have.
Don't just list qualifications. Paint a picture of what success looks like in the role and why someone would want this experience on their resume. The best early sales hires aren't looking for stability—they're looking for the chance to build something from scratch.
Realistically, you'll probably need to outbound to find the right hire. Post the JD, sure, but also identify 10–20 people who seem like the right fit and reach out to them directly. Yes, it's yet another sales process. Welcome to hiring.
What to actually ask them
Experienced sellers are…good at selling. And that extends to selling themselves. Don’t be wowed by polished candidates who can talk the talk but might not be able to walk the walk at your startup.
When you interview candidates, ask about their track record: "What was your quota? Tell me about the best quarter you’ve ever had. Tell me about the worst quarter you've ever had." You want to understand what their past roles looked like, how they performed, and how they handled adversity.
10 questions founders should ask potential sales hires
- What questions do you have for me?
- What was your quote over the last 2-3 years, and how consistently did you hit it?
- Walk me through your sales methodology. What’s your process from first contact to closer?
- Tell me about a time your usual sales process wasn’t working. What did you do?
- Describe a deal that went completely off the rails. How did you handle it?
- Tell me about a significant deal you walked away from because it wasn’t a good fit.
- What’s your approach when a qualified lead goes dark?
- Describe a successful tactic or approach you developed. How did you share it with your team?
- What do you do outside of work to stay competitive or challenge yourself?
- Tell me about the most complex sale you’ve managed and how you navigated it.
10 questions founders should ask potential sales hires.
Making your first hire is a big move for your startup. Consider de-risking it with a trial, something Steve has done successfully at Lorikeet. “We hire everyone on our team through paid work trials,” he says. “So people are spending a meaningful amount of time with us before we make the call.”
Reflect
Are you used to hiring on behalf of an established brand? You may be surprised how much your previous company’s brand halo effect did the hiring for you.
Would you buy from this person? Not at a polished enterprise, but at a scrappy startup with a buggy product and no case studies?
Does hiring feel like an emergency? Slow down. A bad hire is more expensive than a missed quarter.