The Founder’s Guide to Senior Hires: When and Who to Bring Onboard

At Ascend dinners, I regularly gather founders of B2B and deep tech startups around a table for vulnerable, honest discussions. One recurring theme that generates intense conversation is the expensive mistake of hiring senior talent at the wrong time or for the wrong reasons.

Through these discussions and my direct work helping companies like PricingMonkey and Nourish Care build their leadership teams, I’ve seen first-hand how hiring decisions can either accelerate growth or burn precious runway. Here’s what we’ve uncovered together.

Don’t Hire Too Soon

Timing isn’t just important—it’s everything. Many founders hire their first product manager or VP of Sales too early, before they’ve personally validated product-market fit or built a working go-to-market motion.

“I hired a head of product when I should have been the head of product. Six months and £85,000 later, I was back to square one.”

The hard truth? Until you’ve nailed these fundamentals, these roles remain the founder’s responsibility. Delegating too soon creates a dangerous knowledge gap between you and your market.

Strong PMF and Proven GTM Before Your Hire

Before making senior hires, you need clear evidence you’ve achieved two critical milestones:

1. Strong product-market fit, evidenced by either:

Robust engagement metrics such as enterprise DAU/MAU ratios above industry benchmarks, retention curves that flatten, and positive NRR
Repeated sales of the same product to the same customer segment

2. Proven commercial viability:

For enterprise products with £50-100k price points, at least 5-10 completed sales within the same customer segment
Before hiring senior commercial leaders, approximately £1M in revenue or 15-20 customers

Interview for Specific Achievements Not General Skills

Sales professionals excel at one thing above all: selling themselves. This creates a unique challenge when hiring them.

The consensus among experienced founders was clear: specificity is your shield against a bad hire. Don’t look for “a good seller”—that’s dangerously vague. Instead, seek someone who has:

Taken a similar product (in complexity and price point)
To similar customers (in size, industry, and buying process)
Through the exact growth stage you’re targeting next (e.g. £1M - £5M)
Their playbook is still relevant, as it was created within the last 1-2 years

This stage-matching is crucial. If you’re scaling from $1M to $5M ARR, look for someone who’s successfully navigated precisely that transition. If you’re aiming from $10M to $50M, find someone with that specific experience. The challenges and required skills differ dramatically at each stage.

Then in interviews, dig deep. What exactly did they do day-to-day? What systems did they build? What failed? What did they learn? Look for concrete answers, not platitudes.

Be Very Wary of Brand Names

Hiring from Google, Nvidia, or other tech giants has an alluring safety. It feels like a shortcut to quality. But founder conversations revealed how misleading this can be.

What matters isn’t where they worked—it’s what they actually did there. Many candidates from prestigious companies operated in highly specialized roles with vast support systems that won’t exist at your startup.

One founder shared how their “ex-Google” hire struggled when faced with the scrappy, resource-constrained reality of startup life. Another countered with a success story—but only because they’d vetted the candidate’s specific accomplishments, not just the logo on their resume.

A Process That Works: The Pricing Monkey Case Study

Pricing Monkey’s search for a VP of Product became an impromptu case study for effective hiring.

Their approach was methodical:

They clearly defined what the founders would continue to own vs. what the new hire would own
This led to 3 must-have traits, 3 nice-to-haves, and 3 wish-list qualities
The resulting hiring brief narrowed the field to approximately 50 truly relevant candidates in the UK

This level of precision transformed their search from overwhelming to focused and actionable. It also provided a clear framework for evaluating candidates against what actually mattered for their specific context.

Use Workshops to See What the Candidate is Really Like

Traditional interviews reveal only so much, especially for senior roles. Several founders shared success with well-designed workshops where candidates tackle real business problems.

The key is authenticity. These shouldn’t feel like artificial exercises or stress tests. Instead, create scenarios that:

Feel genuinely connected to your current challenges
Allow the candidate to lead and present their thinking
Gently push them to the edge of their comfort zone to see how they actually think and communicate under pressure

One founder described how a seemingly strong VP Engineering candidate unraveled during a workshop when asked to explain technical tradeoffs to non-technical stakeholders. This revealed a critical skill gap that interviews had missed.

Your Candidate’s Little Black Book Doesn’t Count for Much

Senior hires often tout their networks as key assets—their “little black book” of industry contacts. But deeper examination exposed an important nuance: contacts are only valuable if they come with trust and credibility.

The question isn’t “Do they know people?” but rather:

Will those people actually take their calls?
Will they respond to emails?
Will they trust their recommendations?

Several founders suggested speaking with other founders to understand how much relationship capital actually transfers. Is it just names, or is it warmth and influence?

As a Founder Your Credibility is Helping You Sell

A pattern emerged among B2B founders: many hit a wall at around 10 customers or $1M ARR. Why? Their personal network runs out.

These initial customers buy because they trust the founder, not necessarily because the sales process is refined or the product messaging is perfect. When that network is exhausted, the real challenge emerges: can you sell to people who don’t already trust you?

This inflection point is critical when thinking about senior sales hires. The right leader needs to build systems that replicate what worked in founder-led sales, but scale beyond personal relationships.

Always Do Reference Calls

Perhaps the most enthusiastic agreement among founders centered on reference calls. Not the sanitized list provided by candidates, but thoughtful second and third-degree connections who can speak candidly.

References serve two crucial purposes when done well:

When you hear consistent positive patterns, they give you the confidence to make a hire
They give you clarity and conviction when you need to walk away

“The best hiring decision I never made was the VP of Sales I almost hired until a reference told me about their toxic management style. That call saved us six figures and months of cultural damage.”

Want to Join the Conversation?

Join our upcoming Ascend dinners to connect with other B2B and deep tech founders (Seed to Series B) for intimate, honest conversations about real company-building challenges:

Selling Before You’re Ready - June 3, 2025 in Shoreditch

These intimate dinners bring together small groups of founders to share the decisions, doubts, and discoveries that don’t make it into investor updates—like how to hand over control without losing your identity, how to spot signs of misalignment early, and what it really means to ‘let go.’

Browse all upcoming dinners to find the right conversation for your current challenges.

More Resources on Hiring Leaders

If you’re working on building out your leadership team, you might find these articles helpful:

Hiring PricingMonkey’s First Product Manager - A detailed case study of how we helped a fintech SaaS scale their product function
How to hire a product manager in a tight labour market - A guide to finding great PMs in competitive markets
How to interview your startup’s first product manager - Structured interview techniques for PM roles
What to look for in your first product manager - Key traits and experiences that matter
What product managers want from their jobs - Understanding PM motivations and needs
What’s the right amount of ownership for startup PMs to have - Balancing autonomy and alignment

Get the Complete Hiring Guide

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