Your product might be great — but if you can’t sell it, you won’t grow.
As a founder, you’ve probably led the earliest sales yourself — leaning on instinct, product knowledge, and sheer hustle. But at some point, founder-led sales hit a ceiling. To scale, you need someone who can build a process, lead a team, and close deals without you in the room.
That’s where your first Head of Sales comes in.
This guide is here to help you get that hire right — even if you’ve never worked with a sales leader before. Through real-world insights from experienced operators, we’ll break down what makes a great Head of Sales at the seed stage, and how to set them up for success.
By the end, you’ll know how to:
- Understand what a Head of Sales actually does in a seed-stage startup
- Spot what makes a candidate the right (or wrong) fit
- Avoid common hiring mistakes first-time founders make
- Transition from founder-led sales to a repeatable process
- Empower your sales leader without stepping on their toes
In this video mini-series, three experienced sales leaders from our community break down why this role is so unique early on, and what traits make someone successful in it. Featured guests include:
- Armen Zildjian, VP of Sales at Ankored and longtime early-stage sales leader with 28+ years of experience, including senior roles at Drift, LogMeIn, and GrabCAD.
- Michelle Pietsch, founding Partner at Beacon GTM and former GTM leader at Datadog, Drift, and Dooly, where she built early sales teams and scaled revenue from $200K to $55M+.
- Sean Marshall, Co-founder and COO at Copley, and former SVP of Global Sales at Klaviyo, where he scaled revenue from $25M to $450M ARR and grew the team from 15 to 300+.
Ready to get started? Let’s dive in.
Role Scoping
What’s Different About a Head of Sales at the Early Stage?
A Head of Sales at the seed stage isn’t just running a team — they’re building the entire revenue foundation from scratch. Unlike later-stage sales leaders who inherit structure, process, and resources, your first Head of Sales needs to be a Swiss Army knife: capable of closing deals, coaching reps, designing systems, analyzing data, and working directly with you on go-to-market strategy.
“You gotta focus on people that can ride the elevator up and down, can be really, really strategic and sit in a room with executives… but then get really detailed and get in the weeds with reps.” – Sean Marshall
If you hire someone too senior who can’t (or won’t) get their hands dirty, you’ll stall out. But if you hire someone too junior, they may not be able to see around corners or scale beyond the early stage.
Key takeaway: Your first Head of Sales needs to be part builder, part leader, and fully comfortable living in the chaos of early-stage growth.
Candidate Profile
What to Look for in a First Head of Sales
Hiring a Head of Sales isn’t just about finding someone who can close deals — it’s about finding someone who can build the system for other people to do it at scale. In this video, our operators break down how to spot a candidate who can lead strategically, execute tactically, and hire a world-class sales team around them.
One of the first things to consider is your go-to-market motion: Is your business driven by outbound sales? Inbound leads? Product-led growth? The right candidate should not only have experience in your specific motion, but also bring a playbook they can tailor and implement quickly — because building one from scratch will cost you time and traction.
Equally important: they must know how to hire, coach, and retain top sales talent. That’s the multiplier. In the early days, your sales leader will likely carry their own quota — but if they can’t scale themselves through others, you’ll quickly hit a ceiling.
“There’s a very big difference between somebody that is a manager and somebody that is more of an executive, and you’re trying to find the blend of those two.” – Sean Marshall
The best candidates bring a mix of executional and executive experience. Look for directors who’ve built teams, made strategic decisions, and worked cross-functionally with product and engineering. You’re not just hiring a manager — you’re hiring someone who can shape the go-to-market direction of the entire business.
Key takeaway: Look for a candidate who matches your GTM motion, has a track record of hiring strong talent, and can connect sales with the rest of the org — not just manage a pipeline.
Common Mistake
Common Mistakes to Avoid When Hiring Your First Head of Sales
Hiring someone with the wrong experience — or mindset — for your company’s current stage is one of the most expensive mistakes you can make as a founder.
It’s easy to be dazzled by flashy resumes and big titles: a candidate who scaled a sales org at a public company or led hundreds of reps might seem like the right pick. But those same credentials can be a red flag in the early days.
At the seed stage, you don’t need a CRO who leads from dashboards. You need a player-coach. Someone who’s not just designing a sales motion, but in it every day — running demos, listening to calls, and refining the pitch in real time.
“You can’t have your first-time Head of Sales be someone who likes to lead from spreadsheets and from a desk. They’ve gotta be out selling the product just as much as the salespeople they’re leading.” – Armen Zildjian
Founders often mistake “what’s impressive on paper” for “what’s effective in practice.” Here are a few common missteps to watch out for:
- Hiring for stage-inappropriate experience. Someone who led sales at a $50M company probably isn’t the best fit for your $2M startup.
- Over-prioritizing prestige. Titles like CRO or VP might be appealing, but they often come with the wrong expectations for early-stage execution.
- Avoiding the tough questions. Before you hire, ask directly: “Will you be on the phones? Running deals? Coaching the team hands-on?” If the answer is vague, that’s a signal.
This isn’t about hiring someone who will be perfect forever. It’s about hiring the right leader for this stage — someone who can build a strong foundation without getting ahead of your company’s needs.
Timing
When Should You Hire Your First Head of Sales?
Hiring too soon can waste precious resources. Hiring too late can stall your growth. So, when is the right time to bring on your first Head of Sales?
“Timing for hiring a head of sales is a very narrow window. Oftentimes, I’ve seen that folks hire too late more often than too early.” – Armen Zildjian
In this video, our sales experts unpack the signals founders should look for before making their first Head of Sales hire.
Here’s what to consider:
- You’re nearing $1M in ARR. That’s the ballpark where the need for scalable systems starts to outweigh founder-led hustle. If you’re still figuring out the basics, it might be too soon.
- You’ve got a rep or two in seat. Your Head of Sales should inherit a small team and turn chaos into clarity — not build from absolute zero. Ideally, you’ve hired a few reps to help you offload smaller deals and are seeing early traction.
- You’ve got some version of a playbook. Whether it’s a founder-led GTM process or something scribbled on a napkin, having early signals of what works helps your new sales leader refine and scale. If you don’t have a playbook, they should be ready to build one fast.
- Your funnel is getting repeatable. As seen in the Drift example, early signs of inbound traction were a green light to optimize and grow. A great sales leader can take that spark and turn it into a fire.
The bottom line? You don’t need to wait for the perfect process — but you do need early momentum and a willingness to hand over the reins. When done right, your Head of Sales will not only scale your sales motion, but also teach every new hire what “good” looks like from day one.
Repeatability
How to Transition Founder-Led Sales to a First Head of Sales
When you’re the one who built the product, no one sells it better than you. But if your company is going to scale, your sales process needs to extend beyond your personal expertise.
“Founders sell very differently than salespeople do, and you can’t build a repeatable sales process on how founders sell.” – Michelle Pietsch
This video explores how to shift from founder-led sales to a scalable sales motion — one your new Head of Sales can own, refine, and grow.
Here’s how to make the transition work:
- Translate founder instinct into a teachable narrative. Founders often lead with product features and domain expertise. But sales leaders need a story that’s strategic, repeatable, and rooted in customer pain points — not just passion.
- Hand off what works, not just what you do. Show your new Head of Sales what’s been resonating. Then trust them to turn it into a sales playbook that others can follow. Think patterns, not scripts.
- Reframe the pitch around the buyer. Your story shouldn’t hinge on insider knowledge. Instead, craft vignettes that speak directly to the prospect’s problems and get them saying, “That sounds like me.”
- Balance art and science. Effective storytelling is emotional and precise. A great Head of Sales knows how to combine founder vision with structure—and train others to do the same.
Key takeaways: Scaling sales starts by shifting from “only I can sell this” to “anyone on the team can.” And that begins with aligning on the story you’re telling—and why it matters.
Set The Foundation For Success
Setting Your First Sales Leader Up For Success
Hiring your first Head of Sales is a huge milestone — but the real work begins after they sign. To get the most out of this key hire, you need to let go without letting up.
“Most founders that are taking the sales calls and closing the deals themselves have a really hard time letting go… but that’s why you hired them.” – Michelle Pietsch
This video dives into how founders can empower their sales leader to thrive — while building a strong, lasting partnership.
Here’s what to keep in mind:
- Start with trust and patience. You’re handing over a high-stakes function, and that requires a real relationship. Set clear expectations, then give your sales leader the time and space to build the process.
- Recognize different communication styles. Sales leaders often have direct, fast-paced communication styles that may feel unfamiliar to product- or engineering-minded founders. Assume positive intent, and take time to understand each other’s working preferences.
- Let them lead. Founders often resist stepping out of the sales seat — but once you’ve made the hire, it’s time to shift your focus. Support your sales leader, but don’t hover. Let them run deals, build the playbook, and drive results.
- Refocus your time. Freeing yourself from day-to-day selling means you can invest in neglected areas — like product, marketing, or fundraising. That’s how your company levels up.
Key takeaways: Hiring is just the beginning. Great outcomes happen when founders set the tone, share ownership, and give their leaders room to win.
Summary
Hiring your first Head of Sales isn’t just about closing more deals — it’s about building the foundation for scalable, sustainable revenue. The right hire will free you up as a founder, accelerate your growth, and shape how your company goes to market.
We hope this series gave you the confidence to approach the process with clarity and intention.
