One of the most common mistakes early-stage founders and CEOs make is hiring the "big company sales gun" too early.
You know the profile.
They've worked at a well-known brand. They've got years of sales leadership experience behind them. Carried big numbers. Closed large deals. Managed teams. Presented beautifully to boards. On paper, they look like exactly the person who will transform your revenue.
And that is usually the trap.
The numbers here are brutal. A 2025 analysis from OpenView found that 68% of first sales hires leave within 18 months. Jason Lemkin, who's been close to hundreds of SaaS startups through SaaStr, puts it even more starkly for the top role: roughly 70% of first VP of Sales hires at SaaS companies don't make it to 12 months. These are not small misses. They are some of the most expensive mistakes a founder can make, and they keep happening for the same reason.
The logic is understandable. Early-stage companies are under pressure. Revenue is thin. Investors want proof. Boards want growth. Founders want to believe there's a shortcut. So they look for someone who has "done it before" and assume the experience can be transplanted into their business.
But sales experience does not automatically transfer across stages of company maturity.
A sales leader from a mature organisation is usually used to stepping into an existing machine. The brand is known, the CRM is running, sales ops already exists, and a whole cast of supporting functions surround the seller. Lead sources, sales enablement materials, case studies, pricing structures, product-market clarity, implementation teams, support teams, marketing assets, and established customer trust all exist before they arrive.
In an early-stage company, almost none of that exists.
The first sales hire may need to build the call list, write the sales deck, test the pitch, cold call prospects, clean the CRM, define the ideal customer profile, manage objections, chase proposals, create the pipeline, and close the deal. They may need to do all of this while the product is still evolving, the positioning is unclear, and the founder is changing the strategy every second Tuesday.
That is not a comfortable environment for many big-company sales leaders.
Becca Lindquist, now VP of Sales at dbt Labs and the second sales hire at Heap, captured it well in a 2025 First Round Review piece: "Hiring the enterprise rep who's been comfortable at a company for a long time may have forgotten the hustle it takes to be successful at a very early stage company." She's seen the pattern repeatedly. They come in with all sorts of preconceived notions, and often forget they also have to go and generate a lot of their own pipeline.
The founder of Branch, Mike Molinet, learned the same lesson the hard way. Speaking to First Round Review about his first VP of Sales hire, he said: "I went out and hired a VP of Sales and gave them 100 things to figure out. But there's no way a sales hire can be successful while figuring out the CRM, the ICP, the persona, building the team and figuring out sales development."
These leaders are not bad at sales. They're often built for a different stage of the sales function, used to leading a system rather than inventing one from scratch.
In the earliest phase, what you often need is not a polished sales executive. You need a builder.
Someone commercially sharp, resilient, self-starting, and comfortable with chaos. Someone who can sell without perfect materials, learn from rejection, create process where there is none, and stay motivated when nothing is obvious. The 2024 SaaStr playbook on this is blunt: "If you come from a large software company, don't implement their methodology. It isn't going to work in a startup. Literally 100% failure rate."
The right early hire has usually already done this work at a similar stage. They've closed deals worth $50K to $300K at companies under $10M in revenue. They've built a pipeline from nothing. They've written their own sales collateral. They know how to demo the product without a sales engineer standing behind them. They bring the skills your business actually needs, not the skills that worked in an environment that no longer applies.
But this creates a second problem.
The person who thrives in chaos may not thrive forever.
As the business grows, the sales function has to mature. You cannot run a company on heroics. You cannot scale revenue on hope, hustle, and founder energy. Eventually you need structure. A CRM that's actually used. A repeatable pipeline. Clear stages, conversion metrics, sales scripts, qualification rules, handover processes, forecasting discipline, accountability.
At this point, the early sales builder may start to feel constrained. The very things that made them valuable in the beginning (improvisation, independence, speed, flexibility) may become less useful as the company standardises.
That doesn't mean they're no longer valuable.
It means their role needs to evolve.
A great early-stage salesperson may again be better suited to now explore new markets to enter, test the company’s latest products, validate new ideal customer profiles, open new verticals, or run strategic growth experiments. They may remain incredibly valuable, but not necessarily in the same role they started in. Just like the business evolved, their role also needs to evolve.
Don't hire for the sales function you wish you had. Hire for the sales function you actually have.
Evolve individual sales roles as the business and sales function evolve.
In the beginning, you need someone who can build from nothing.
Later, you need someone who can turn that learning into a system.
Eventually, you need a team that can execute that system predictably.
The mistake is believing one person will always be perfect for every stage. They usually will not be.
The better question is not "who has the biggest sales CV?"
The better question is "what stage is our sales function at, and what kind of person is built for that stage?"
Get that question right, and you'll spend less on mis-hires, lose less momentum in those 12-to-18-month gaps, and keep the people you do hire in roles where they can actually win.
Justin Coutts is Head of Talent Solutions at Compono, an Australian people and culture platform that combines hiring, culture, and learning with people insight.