How to hire your founding salesperson

If the founder’s job is to find product-market fit, the first salesperson’s job is to scale it. Your first sales hire is one of the most consequential hires you’ll make because they’re the first person entrusted to replicate your “founder sales magic.” Getting this right is a major milestone. It means you’ve successfully transferred your deep understanding of the problem your product solves, why your solution is uniquely positioned, who benefits most, and how to convert their pain into revenue.

So, who should you hire? Let’s break it down into two parts:

1. Attributes: what you’ll evaluate during your initial interview.
2. Experience: what you can gauge from their LinkedIn profile.

The attributes are the hardest but most important elements to screen for, so I'll address those first. A bad hire can cost you months, and most founders don’t have that. While you might intuitively understand the experience recommendations, I've shared them here anyways to help you avoid common pitfalls.

Now onto the attributes, which you’ll mostly screen through interviews and references, as the resume won’t necessarily reveal these traits.

The difference between a chef and a cook is that a chef prioritizes outcomes, while a cook optimizes for process. Chefs idealize making delicious food: recipes, ingredients, and techniques are fungible as long as the final dish is exceptional. Cooks, on the other hand, strictly follow recipes, emphasizing precision and efficiency, sometimes at the expense of asking, “Is this dish actually delicious?”

In an early-stage startup, the sales “recipe” is better thought of as a hypothesis, a working guess about your ICP, how to catalyze demand, and the best steps from first contact through closing. Salespeople with a cook mentality will follow the process rigidly, mistaking adherence for success, which becomes problematic when the process inevitably needs iteration. A salesperson with a chef mentality, however, continuously evaluates and refines the process based on what’s effective in the field. They prioritize closing new business, taking ownership of the sales process, and thoughtfully iterating until it consistently works.

At Northflank, our AEs are chefs. We’re selling a big product that solves many unique problems, depending on the size of the engineering team, maturity of the platform function, existing tech stack, and buyer personas involved. This means our AEs have had to experiment with messaging and sales process, thinking critically about what’s working, adapting, and sharing those learnings with the team.

Sales might be the most objectively measurable function in a company, with quota attainment providing a clear, relative indicator of performance. Don’t waste your time on reps who weren’t consistently in the top 10% or at least the top quartile of their team. I struggle to accept excuses like “I had a tough territory” or “a deal slipped” when peers around them were still successful. Clearly, success was achievable.

I emphasize “relative” intentionally: I’d much rather hire a rep who hit only 75% quota on a team where everyone else fell below 50% than someone who achieved 130% alongside peers who performed similarly. Assume it will be challenging for your rep to succeed given your imperfect or nonexistent sales playbook, and therefore, prioritize candidates who’ve demonstrated a consistent pattern of outperforming their peers.

Assessing individual impact, however, is trickier. When hiring from successful companies, you must determine if the company’s success occurred because of, regardless of, or in spite of the candidate’s contributions. It’s easy to confuse “wow, their previous company grew extremely fast” with “they must be great too.” I won’t spend time on how to weed out the obvious “in spite of” candidates, those tend to be easier to spot, but distinguishing between the other two is tougher.

A quick way to sanity-check this is to look at when they were there. If someone joined a company in 2020 that was founded in 2015 and already had 150+ employees, they likely walked into structure, not chaos. They were there when playbooks were in place, growth was steady, and inbound was plenty (yum).

This distinction boils down to their role in shaping the playbook that led to success, similar to the chef versus cook analogy. Was this candidate actively involved in discovering and iterating the sales playbook, attracting new talent, and helping leadership deeply understand the ICP and customer challenges? Or were they simply along for the ride, executing effectively without genuinely driving improvements?

When interviewing candidates, I typically ask about their current role, “What questions do you ask during a discovery call, and what typically takes place on a second call?” I follow-up that up with, “Did this change when you were there?” I don’t actually care about the first question. Instead, I’m focused on their involvement in whatever change might have occurred. A good answer looks something like this:

Yeah, it did change. I realized our discovery was broken, so I started asking about X and Y instead. That put us in a better position to do A and B on the second call and drove more urgency in the sales process.

You can also ask pointed questions about their involvement: Why did they choose their ICP? What mistakes did they make, and how did they adapt afterward? Which signals were they paying attention to, and how did they translate these observations into actionable changes in the sales process? That said, I’m a bigger fan of “questions behind the questions” as they’re harder to game on the spot.

Great salespeople are natural storytellers. This trait is invaluable in the sales process, as they help customers see themselves in the narrative of their current, broken processes that can be best remedied by adopting your product. However, this can make hiring tricky, since they're skilled at explaining away bad outcomes.

Watch out for reps who externalize their losses. I ask every candidate to describe the last deal they lost and why. Poor answers point to factors outside their control, like a delayed feature, lost budget, their champion leaving, or a prospect going dark.

Good answers place responsibility on themselves: I failed to properly multi-thread, misunderstood technical requirements, ran a poorly scoped POC, didn’t engage the budget owner effectively, mistook a “coach” for a “champion,” didn’t utilize internal resources well, etc.

The best salespeople understand that growth comes from being critical of what's within their control. Your startup environment will inevitably be chaotic and imperfect, giving them plenty of opportunities to place blame elsewhere. But truly self-critical reps rise above these circumstances and find ways to improve, regardless of the challenges around them.

While the phrase "immigrant mentality" may be controversial, it perfectly captures the spirit of reps who are driven to achieve more and are often fueled by their past challenges. They have something to prove and consistently push through walls to demonstrate their worth.

Succeeding at a startup demands exactly this level of motivation. Startups are messy but rewarding environments for those who can persevere and build something meaningful. During interviews, I seek to understand candidates' core motivations and look for examples where they've pushed themselves beyond conventional limits to achieve their goals.

I've found this quality in two types of people: those who've overcome genuine hardship and those who've excelled in highly competitive pursuits. The second group includes college athletes, military veterans, and academic competitors. The intense dedication required to succeed at these high levels mirrors the same irrational commitment needed in a startup.

Personal hardship should be explored with sensitivity through questions like: Where did you grow up? What did your parents do? The simple question "Why sales?" often reveals surprising depth. A superficial answer like "I like helping people with their problems" raises red flags. A more compelling response might be "I discovered I had a talent for it and could earn well, which helps me support my family."

I grew up in a small town in Oklahoma, which isn't exactly a launchpad for a tech career. I went to a state school for my undergrad (Boomer Sooner; IYKYK) before making my way to Silicon Valley, where I landed (somewhat serendipitously) at a startup filled with pedigreed people. I have a soft spot for candidates from lesser-known schools. They're consistently humble, deeply appreciative of opportunities, and the fact that they've made it to your interview? Well, that says something.

Curiosity is often described as table-stakes for success as a salesperson, as this attribute is essential for developing a strong business case. A great rep cares deeply about discovering their prospects' problems that their products could solve and understanding the negative impact of leaving those problems unaddressed.

But curiosity needs qualification. The research candidates have done before the interview and their corresponding questions provide the best "tell." Do they ask the deeper, second-level questions you'd hope they'd ask in a customer conversation, or are their questions generic and ignorant of your value proposition?

A great question might be:

Your documentation explains this set of capabilities, and online reviews suggest customers value them along these dimensions. What product investments might cause this value proposition to expand?"

A poor question would be:

What's the current valuation of the company?

Sure, valuation matters eventually, but it shouldn't be the first thing a rep asks.

The good news is that a lot of what you should screen for is observable on LinkedIn or a resume, meaning you can avoid unnecessary interviews.

Sales support structures vary significantly by company stage. Later-stage companies typically have robust resources like sales playbooks, engineers, marketing teams, and more, while early-stage companies rely mostly on founders and a repurposed fundraising deck. Hiring a salesperson from a more mature organization into your startup will likely cause friction, as they’re used to a higher level of support and structure. At < 10 employees, 70 % of the job is self‑enablement.

Prioritize candidates who have experience as one of the first five hires at a startup. This ensures they can thrive in the inevitably chaotic early-stage environment. I also recommend hiring someone trained in a high-performing sales organization. Unless you, as the founder, have a sales background, bringing in a salesperson without disciplined sales habits guarantees avoidable mistakes, such as insufficient discovery, weak qualification, mistaking enthusiasm for actual need, and investing time with people lacking influence.

Don’t expect a rep who’s succeeded selling to marketers to automatically replicate that success with engineers. Yes, good reps can learn, but as a founder, you probably won’t have the bandwidth to ramp them up on an entirely new buyer persona and category.

Your first salesperson needs to hit the ground running and immediately establish credibility with your customers, already understanding their problems, current solutions, tech stacks, and even how they advance in their careers.

When selling into an existing category, your buyer already knows how to purchase: there’s an established budget owner, allocated funds, designated stakeholders, and clearly defined buying criteria. In these cases, the salesperson’s job is to uncover this buying process, meet the customer’s criteria, handle objections, and close the deal.

Conversely, selling into an emerging category is entirely different: your customers may not even realize a solution exists to their problems. Selling here demands a missionary rather than a mercenary. While mercenaries excel at running a tight sales process and coordinating resources (sales engineers, executives, channel partners), missionaries help prospects imagine a better future state with your product at the center. They guide prospective buyers to see their problems more clearly and inspire them to champion their solutions internally.

We look for missionaries at Northflank, and, specifically, people who are good storytellers and share our vision for helping software teams focus on what truly matters: creating and running workloads, not managing infrastructure. Our AEs subscribe to a belief that the entire post-commit experience (building, deploying, running, scaling, observing) should feel like one system, not a bunch of tools wired together. We’re category creators with the aim of becoming the category definer.

You don’t need an account manager, but it’s easy to accidentally hire one.

Many account executives at mature companies function more like account managers, primarily managing existing business rather than generating new sales. While these reps might identify new business, it takes a completely different skill set to sell into companies who’ve never heard of your product. You need salespeople who’ve repeatedly shown they can prospect into entirely new accounts, source net new opportunities, and convert those opportunities into revenue.

However, simply knowing whether a candidate sold new business or expanded existing accounts isn’t enough. Many account executives rely heavily on BDRs, marketing-generated leads, or channel partners to build their pipeline.

Hiring your first salesperson is a pivotal decision, one that sets the tone for growth and shapes your early sales culture. Applying these filters will help you avoid costly early mishires. If you do hire the wrong person, trust your instincts and act decisively. You can always try again.