Hiring a first head of sales is a milestone moment in a company’s development. It signals that something is working — not perfectly, not at scale, but enough to warrant structure and investment. But this hire is one that many founders, particularly technical ones, find challenging. Unlike product or engineering, sales can feel opaque. If you’ve never done it yourself, you might even default to reengineering quotas, pipelines and rep compensation from first principles.

And while there’s nothing wrong with a founder wanting to understand how sales works, we’ve seen well-meaning technical leaders overcomplicate this process. They create elaborate comp plans, avoid words like “quota” or second-guess the on-target earnings (OTE) compensation numbers that good sellers expect. This approach can create friction with the very sales leader founders want to hire. A new head of sales might walk into this environment and think they’re being second-guessed at every turn.

This piece will guide founders — especially technical founders who focus on product, engineering and design — who are approaching the moment where it’s time to hire a sales leader to manage a burgeoning AE team. It expands upon our earlier piece on moving from founder-led to AE-led sales.

You’ve proven that you can sell the product. Now the job is to make sure others can too, at scale, with leadership, systems and support that don’t always involve you. Here’s how to know when the time is right, what to look for and how to make sure this hire helps you move forward.

Are you ready?

For most early-stage companies, the tipping point comes once a few account executives, usually two to four, are producing results. You’ve found customers beyond your immediate network, figured out the buyer persona and length of a deal, as well as how to overcome common objections. The sales process still has rough edges, but is repeating in ways that give you confidence.

At the same time, you’ve become the bottleneck, spending time on call reviews, sales enablement, proposal tweaks, CRM audits and late-stage deals. While important, they’re increasingly at odds with other responsibilities. Perhaps you’ve missed a few things lately, like getting behind on product roadmap discussions or declining intro calls with new prospects for lack of time.

This is the time to start thinking about hiring someone to lead the sales function. Simply put: It’s time to scale what’s working. But if sales still feel chaotic — no deals have closed without your personal involvement, or your ICP is still evolving dramatically — it’s probably not the right time. This hire isn’t meant to fix sales, but scale it.

How to hire an early-stage leader

A common mistake is reaching for someone who is too senior to be appropriate for your stage. Hiring a VP of Sales with a big company logo on their resume might sound great in theory, but they’re likely used to working inside a machine and may not want to build one again (or ever). They expect clean systems, clear territories, tight enablement and mature support from RevOps and product marketing. If they haven’t done early-stage work recently, or articulated clearly why they want to go back to it, they may not be energized by the messiness of your current environment.

The better fit is someone who sits one level down from that VP of sales on the org chart at a company that resembles yours but is maybe two or three years ahead in terms of progress and scale. This person has managed small teams, closed deals, built pipelines from scratch and had to justify headcount based on performance. In short, they’ve experienced some structure but aren’t dependent on it. And importantly, they’ve seen how slightly larger (though not greatly larger) companies operate when scaling and can bring the best of those approaches to grow your sales function in a smaller company.

Prioritize collaboration and compatibility

The person you want to hire should also be comfortable working with a technical founder — both in temperament and in substance. You want someone who can explain the reasoning behind their decisions, welcomes healthy pushback and won’t get defensive when asked to articulate a sales process. As a founder, you should recognize that while curiosity is good, micromanagement is corrosive. Your job is to support your hire, not shadow them; mutual trust is critical.

Intellectual compatibility matters as well. Your head of sales should easily engage in a conversation about product trade-offs, technical architecture or go-to-market sequencing. They should appreciate why you ask the questions you do, and you should appreciate that their answers reflect real-world experience.

Provide a flexible title, with clear expectations

Head of sales is a flexible title that communicates leadership without overcommitting to scope. It signals to candidates and your team that this role is hands-on and has potential to grow into something bigger — and that right now, the emphasis is on building, not hiring a huge team.

Compensation should reflect the hybrid nature of the role. You’re asking this person to manage, coach, forecast and occasionally sell. That’s high-leverage, high-responsibility work. Total compensation (base plus variable) will vary based on experience and geography, but ranges from $350K to $500K OTE, with meaningful equity — often between 0.5% and 1.5%, depending on seniority and stage.

How to find and close the right person

Like any important hire, your ideal head of sales isn’t browsing job boards, so you’ll need to go find them. Identify companies one or two sales cycles ahead of yours and see who helped them get there. Ask investors and current AEs who they’d work for again. Talk to customers, partners and advisors who’ve seen strong sales leadership up close.

Once you’ve identified a few promising candidates, work on your hiring pitch. That includes the message that you’re not offering a finely tuned sales machine, but the opportunity to help build one. That includes hiring, team design, process, metrics, reporting and culture — plus occasional chaos, limited infrastructure and a steep learning curve. They’ll help define how the company goes to market for years to come. That’s a rare opportunity, and the right candidates will see it as such.

Be candid about your strengths and gaps. If you’ve never built a sales comp plan before, say so. If you tend to push hard on strategy but defer on tactics, own that. A good sales leader doesn’t need perfection. They need transparency and the room to lead.

Should you work with a search firm?

If your network is tapped and you need to move fast, the right partner can be a huge asset. A good search partner brings more than just resumes. You’ll want someone whose judgment you trust and who can guide you, navigate curveballs and be in your corner.

Just as you would with interviewing candidates, calibrate. Ask fellow founders and leaders who they’ve used and get recs from investors, board members or advisors. Talk to at least three search partners. Look at their track record, how well they understand your market and company culture as well as how they define what great looks like for this role. We’ll dive deeper into this topic in an upcoming post on how to hire the right search partner.

Design a hiring process that reveals capability

Salespeople, especially sales leaders, are often strong interviewers. They can read a room, frame stories well and deliver confident answers. That means your process will need to delve beyond resume review and good vibes.

Design a loop that evaluates prospects’ thinking, and look for specificity in their answers. For example, ask them how they’ve coached a struggling AE, or designed a process from scratch that ended up working. Discuss how they’d evaluate when to open a new vertical or restructure the team.

Include a working session with prompts like “Design your 30-60-90 plan” or “Build a basic onboarding program for a new AE.” Then sit down and work through the prompt together. You’ll see how they approach problems, prioritize and consider communication. You’ll also get a sense of how it feels to collaborate, because you’ll be doing a lot of that.

This is also the moment to evaluate trust. Do you feel like they can challenge you without posturing? Do you respect the way they think?

Empower your new head of sales

The best sales hires don’t succeed by being perfect on day one. They succeed because the company creates conditions for them to thrive. That includes providing full context: access to calls, CRM data, AE 1:1s and product discussions. Let them see how decisions are made, and also to bring their own perspective to what’s in motion.

Even if part of the goal is freeing up your time, you’ll need to lean in heavily during the first few months. Check in often, ask for feedback and make space for their ideas, even when they challenge yours. And signal to the team that their voice matters.

Especially for technical founders, this is a test of both control and curiosity. You built your company by understanding the details, and you won early customers by being in every deal. But now you’re scaling. You’ll need to trust someone else to speak for your product, represent your team and chart the next stage of growth.

If you’re making this hire or thinking about it, feel free to reach out. Always happy to compare notes: jdimento@baincapital.com and mcornejo@baincapital.com.