I’ve been the first sales leader in a startup, so I know from personal experience that knowing when to hire you first sales leader – and knowing who to hire – can make or break a company’s trajectory
The brutal landscape of sales leadership
Let’s start with the stark reality. The average tenure for an early-stage VP of sales is a mere 15 months, with a jaw-dropping 70% not even making it to their first year. Why? Because most founders approach sales leadership like it’s a quick fix they can outsource to eliminate their revenue challenges.
This isn’t just a statistic – it’s a warning. Many founders believe hiring a sales leader is about finding a superhero who will miraculously solve all their sales problems. But the truth is far more nuanced.
The founder-led sales imperative
Before you even think about hiring a sales leader, you need to get into the trenches yourself. This isn’t just advice – it’s a fundamental strategy for sustainable growth. Your first mission is to prove the repeatability of your sales model.
Here’s a step-by-step breakdown of what this journey should look like:
1. Become your own sales champion
As a founder, you need to be the primary sales driver for your startup. This means:
- Understanding every aspect of your sales process
- Developing a deep knowledge of your customer’s pain points
- Crafting a compelling narrative around your product
- Personally engaging in sales conversations
2. Build a foundational sales team
Recruit two founding account executives who can:
- Manage their own prospecting
- Close business independently
- Demonstrate consistent quota achievement
3. Seek guidance
Consider bringing in a fractional sales coach to help you navigate this process. This isn’t about outsourcing – it’s about gaining strategic insights and avoiding common pitfalls.
This approach accomplishes two critical things: it proves your sales model’s viability and prepares you to effectively manage future sales talent.
Decoding Sales Leadership Levels
Not all sales leaders are created equal. Think of it like a career ladder with distinct rungs:
- Sales Directors: Hybrid player-managers who juggle team management and personal quota. They’re typically hustlers who are deeply embedded in the day-to-day sales activities.
- Head of Sales: Professionals who’ve managed a small team previously. They’ve got some leadership experience but aren’t yet operating at a strategic, cross-functional level.
- VP of Sales: Senior leaders with cross-functional collaboration experience and strategic vision. They understand how sales interacts with marketing, partnerships, and overall company strategy.
The cardinal sin? Hiring the wrong level for your startup’s specific stage.
When to hire?
Hiring a sales leader is all about timing. Do it too early, and you’ll have a frustrated individual contributor who feels misled. Wait too long, and you’ve essentially left money on the table through missed opportunities that could have accelerated your growth.
Critical signals you’re ready for a Sales Leader:
- Your calendar is drowning in sales activities
- You’ve consistently demonstrated sales repeatability
- You’re approaching a significant funding milestone
- You need more structured, methodical sales processes
Who to hire?
When looking for your ideal sales leader, you need to think about these three foundational criteria:
- Stage-specific experience Find someone who’s successfully navigated a similar growth stage. They don’t need to be from your exact industry, but they should understand your growth challenges intimately. If you’re moving from £1 million to £5 million in revenue, look for someone who’s made that journey before.
- Matching go-to-market motion Ensure their previous sales approach aligns with yours. An exclusively inbound sales background won’t translate perfectly to a 100% outbound strategy. The sales methodology matters as much as the industry experience.
- Comparable contract values Look for candidates with experience selling at similar average contract values (ACVs). Someone used to £250K contracts might struggle with £10K deals. The sales approach, negotiation tactics, and customer engagement strategies differ significantly across contract value ranges.
Pitfalls to Avoid
- Narrow hiring approach Posting on LinkedIn and calling it a day is not a search strategy. Cast a wide net. Headhunt. Use multiple channels. Your goal is to find the best talent, not just the most convenient.
- Big company poaching That sales leader from your massive competitor? Likely irrelevant to your startup’s specific needs. They’re used to big budgets, established brands, and completely different sales dynamics.
- Overlooking hands-on experience You need someone who’s recently done the granular, day-to-day sales work. Avoid candidates who’ve been several management layers removed from actual sales activities for years.
- Title inflation Prematurely giving VP or CRO titles creates misaligned expectations. This can set your new sales leader up for failure before they even start.
Sell the opportunity effectively
Top-tier sales leaders are discerning. I see lots of candidate disqualify themselves out of opportunities if the numbers don’t stack up or there isn’t enough transparency. To attract exceptional talent:
- Build a compelling, trustworthy brand story
- Develop a great product
- Prepare crystal-clear sales metrics
- Demonstrate a deep understanding of your sales funnel
- Set realistic, transparent expectations
The impact of getting it right
Getting this right will be a game-changer for you. A strategic sales leader doesn’t just drive revenue – they can fundamentally reshape your company’s valuation. Most SaaS businesses see a 10-12x valuation of annual recurring revenue.
So if you’re at £500K ARR – the right sales leader can help you build a multi-million pound team, potentially adding eight-figure valuation to your business in a remarkably short time.
But it won’t do this overnight.
Hiring a sales leader should be part of your strategic journey. It requires patience, self-awareness, and meticulous planning. Do the groundwork yourself. Prove your model’s repeatability. Be laser-focused in your search.
And the magic happens when you align the right talent with a proven, repeatable sales motion. Choose wisely, and then you’ll really see your startup’s potential unfold.
Author: Matthew Codd
I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.
I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.
I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.
