The most expensive hiring mistake a founder can make is hiring a Head of Sales too early or hiring the wrong one.
I’ve seen it happen at every stage. A Series A founder finally has the budget to bring on a sales leader, hires someone impressive from a large company, and watches them fail within 90 days. Not because the person was incompetent. Because they’d never had to build anything from scratch.
Here’s the framework I use when advising founders on this hire.
The Two Types of Sales Leaders — And Why Most Founders Hire the Wrong One
There are two fundamentally different types of sales leaders:
Hunters — they build pipeline from nothing. They get on the phone, write their own sequences, knock on doors. They’re uncomfortable without a prospect to chase.
Farmers — they optimise existing revenue. They manage account relationships, expand contracts, protect churn. They’re excellent once you have customers to manage.
At seed and Series A, you need a Hunter. Almost every founder who has made this mistake hired a Farmer — someone who had managed large teams and large accounts but had never personally closed a deal in years.
The tell: ask them when they last personally closed a deal. If the answer is more than 2 years ago, they’re a Farmer.
What Good Looks Like in the First 90 Days
A strong Head of Sales hire at Series A should, without being told:
Days 1-30: Shadow every existing customer call. Read every won and lost deal. Map the sales process that currently exists — even if it’s just the founder selling. Identify the 3 biggest friction points in the current process.
Days 31-60: Run their own deals. Not manage someone else’s deals. Their own. You need to see them sell before you see them manage.
Days 61-90: Document the repeatable process. What’s the pitch? What’s the sequence? What objections come up and how do you handle them? This documentation is the foundation for everything that follows.
If your Head of Sales isn’t personally selling in month 2, something is wrong.
The Interview Questions That Actually Work
Don’t ask: “Tell me about your sales philosophy.”
Ask these instead:
“Walk me through the last deal you personally closed. What was the size, the sales cycle, and what almost stopped it from closing?”
This reveals whether they can actually sell and whether they understand the detail of their own deals.
“What’s the most creative thing you’ve done to get a meeting with someone who wasn’t responding?”
Hunters have specific stories. Farmers talk about process.
“Tell me about a time you built a sales process from scratch. What did you start with and what did you end up with?”
This separates builders from managers. Most people who claim to have built from scratch actually joined a team of 5 and optimised it.
“What’s your personal close rate on qualified opportunities and how have you tracked it?”
Strong sales people know their numbers. If they can’t answer this, they haven’t been paying attention.
Use this prompt to generate more tailored interview questions for your specific role:
“I am hiring a Head of Sales for a [stage] B2B SaaS startup. Our ACV is [amount], sales cycle is approximately [length], and we sell to [buyer persona]. I need someone who can build from scratch — currently it’s just me selling. Generate 6 interview questions that specifically test whether this person can operate in a zero-to-one sales environment vs a scale-and-optimise environment. Each question should reveal a specific capability I need.”
The Compensation Structure That Attracts the Right People
The right Head of Sales hire for a startup is not motivated primarily by base salary. They’re motivated by OTE — on-target earnings — and the equity upside.
A structure that works at Series A:
– Base: 60-70% of OTE
– Variable: 30-40% of OTE tied to quarterly quota
– Equity: 0.3-0.75% depending on stage and seniority
– Quota: Set at 3-4x OTE so the math works for the business
If a candidate negotiates heavily on base and shows little interest in the variable or equity, they’re not the right fit for a startup. The right person wants the upside.
The Red Flags to Walk Away From
They’ve never missed quota. Everyone misses quota at some point. If they claim a perfect record they’re either lying or they’ve only ever worked somewhere with sand-bagged targets.
They want to hire a team before they’ve proven the model. Any Head of Sales who asks about headcount in the first interview is not ready to be your first sales hire.
They can’t explain why deals were lost. People who understand sales know exactly why they lose. If their answer is “the timing wasn’t right” for every lost deal, they lack self-awareness.
They’ve only sold one type of product. Not disqualifying on its own, but if they’ve only ever sold enterprise software and you’re selling to SMBs, the muscle memory is different.
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