From Operators to Leaders: When It’s Time to Hire Your First Head of Sales
- Nissim Ohayon
- Sep 8
- 4 min read
Over the past few months, we’ve been breaking down the core sales roles that power a growing Israeli B2B SaaS startup selling to mid-market and enterprise clients. Each role is a building block in the GTM machine - and together, they form the backbone of a repeatable, scalable sales model.
Here’s the journey so far:
𝗠𝗮𝘀𝘁𝗲𝗿 𝗼𝗳 𝗦𝗮𝗹𝗲𝘀 𝗢𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝘀 -- the unsung hero keeping your data, process, and reporting tight.
𝗣𝗿𝗲-𝗦𝗮𝗹𝗲𝘀 𝗘𝗻𝗴𝗶𝗻𝗲𝗲𝗿 -- the bridge between product and sales, turning complex tech into buyer confidence.
𝗦𝗗𝗥 -- the specialized role focused on prospecting, not “junior sales.”
𝗔𝗰𝗰𝗼𝘂𝗻𝘁 𝗘𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 -- your first true closers, turning pipeline into revenue.
𝗔𝗰𝗰𝗼𝘂𝗻𝘁 𝗠𝗮𝗻𝗮𝗴𝗲𝗿 -- the relationship builder, growing accounts after the initial deal is won.
Now, it’s time to talk about the next evolution in your sales org: The first senior leader who won’t just sell, but will own, shape, and scale the entire sales GTM function.
Enter ➡ Head of Sales.
This role is a turning point for founders. Unlike SDRs, AEs, or AMs - who add capacity to an existing motion - the Head of Sales becomes a strategic leader. They take what’s been tested, add discipline, and build a team around it. But here’s where many founders get it wrong: they bring in this hire too early, or expect them to do the work of experimentation instead of scale.
In this post, we’ll cover the most common mistakes founders make when hiring their first Head of Sales - and how to avoid them.
Founder Mistakes to Avoid When Hiring Your First Head of Sales
Mistake #1: Hiring Too Early
Many founders think a Head of Sales is their first commercial hire. Wrong move.At the earliest stage, you don’t need a manager - you need doers. SDRs to prospect. AEs to close. AMs to grow accounts. A Head of Sales sitting in an empty org won’t magically create revenue. They’ll spin their wheels, frustrated by lack of traction and zero proof points.
✅ Better Path: Hire execution roles first, supported by a fractional CRO/VP Sales to design the GTM strategy. That way, when your Head of Sales arrives, they inherit real data, working motions, and a small team to lead.
Mistake #2: Expecting Them to “Figure It All Out”
Founders often assume that a Head of Sales will come in, define the ICP, build the playbook, and experiment from scratch. That’s not their job. A Head of Sales scales what’s already working - they don’t thrive in chaos.
✅ Better Path: Use fractional sales leadership (or an advisor) early to clarify ICPs, build messaging, and test sales motions. Document what’s working - then hand it over to your incoming Head of Sales to refine and scale.
Mistake #3: Confusing Leadership With Execution
A Head of Sales is not just a “super AE.” Yes, they should know how to sell, but their value lies in hiring, managing, forecasting, and building a repeatable engine. If you expect them to carry the full quota while also scaling the org, you’ll burn them out and stall growth.
✅ Better Path: Transition responsibility gradually. Keep your AEs selling, and empower the Head of Sales to coach, forecast, and build pipeline discipline. Over time, they shift from part-quota-carrying player/coach into a full leadership role.
Mistake #4: Skipping the Groundwork
Too many startups bring in a Head of Sales without laying the foundation - no CRM discipline, no lead flow, no consistent metrics. That’s like hiring a pilot before you’ve built the runway.
✅ Better Path: Put the basics in place first. Use early AEs and fractional leadership to enforce CRM hygiene, pipeline reviews, and feedback loops with marketing. That way, the Head of Sales can scale instead of starting from zero.
Mistake #5: Ignoring Fit With Stage & Culture
The “right” Head of Sales at $1M ARR is not the same person you need at $20M ARR. Hiring someone from a big corporate sales org who’s used to armies of SDRs and brand recognition will likely crash and burn in an early-stage environment.
✅ Better Path: Hire someone who’s scaled from slightly ahead of where you are today. If you’re at $1-2M ARR, look for someone who’s taken a company from $5M to $15M - not from $50M to $500M.
The Role of Fractional Leadership in Preparing the Ground
This is where founders can set themselves up for success. A fractional CRO or VP of Sales can help you:
Define and test your ICPs and personas
Build and document your GTM playbook
Set up CRM, reporting, and pipeline discipline
Guide your first hires (SDRs, AEs, AMs)
Coach you, the founder, on managing a sales org
By the time your first Head of Sales joins, they won’t be starting from scratch. Instead, they’ll step into a role with validated motions, early data, and a team that knows the basics. They’ll still make adjustments - but they won’t waste time on guesswork.
Bottom Line
Hiring your first Head of Sales is a milestone moment - but only if the timing is right. Jump too early, and you’ll waste precious cash and frustrate both sides. Wait too long, and you risk plateauing at founder-led sales.
The smartest founders prepare the ground first: execution hires + fractional leadership → then a full-time Head of Sales. Do this, and your new sales leader will actually be set up to lead - instead of firefighting.
Ready to Scale Your Sales?
At MarketFit Sales Partners, we help founders of Israeli B2B SaaS startups build repeatable, scalable sales models. From fractional CRO support to hands-on GTM execution, our mission is simple: give your team the playbook and foundations they need to win.
📅 Book a free initial Sales GTM Assessment and walk away with:
A clear view of where your current GTM motion stands today
Insights into gaps slowing down repeatable sales
Recommendations on your first (or next) sales hires
Practical next steps to start scaling revenue
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