One of the most common mistakes I’ve seen founders make (and that I’ve made myself) is hiring staff that is too senior, too soon. While an experienced executive might seem like the perfect way to scale your startup, what early-stage companies actually need are builders: folks who can create something from nothing, who don’t just manage processes but invent them. Here’s what I learned the hard way…
The cautionary tale: Hiring staff that is too senior, too soon
Back in 2017, at monday.com, we were closing deals of between $1k and $10k and had just a handful of deals over $10k. Most reps were junior, well-trained in converting self-serve trials into paying customers, but lacked experience closing company-wide top-down deals.
Back then, very few well-known SaaS companies had enterprise motions and reps based in Israel, with reps experienced in closing $100k+ deals.
So, I hired one of the best sales managers from one of those companies, an experienced enterprise regional VP. He seemed perfect: great management experience, ran an enterprise team, and had a successful track record. On paper, he was exactly what we needed to get to the next stage.
But the truth was, we just weren’t ready.
When experience doesn’t fit the company
Despite our initial conversations about the role requiring flexibility and hands-on work, there was a fundamental misalignment of expectations on both sides. We needed someone who would primarily build and coach, while his past success came from leading teams in mature organizations with well established processes. Neither of us fully appreciated how different these contexts were until we were working together.
We lacked the basics he was accustomed to:
❌ We hadn’t yet established a top-down playbook.
❌ We didn’t have customer success, presales, or services org to support pre/post sales.
❌ The product wasn’t ready for hundreds or thousands of users.
❌ Marketing collateral was all feature-led/PLG oriented, without the relevant sales decks, messaging, or enablement materials.
❌ We had great, smart, and driven generalists, but they lacked enterprise experience.
We just weren’t ready as a company. Not just in terms of sales, but it was about the maturity of sales, product, and marketing together. All needed to evolve at the right pace.
It wasn’t about talent either. He could have been a rockstar in a scaled-up organization or enterprise-led GTM motion. But at our stage? We didn’t need someone to run the machine. We needed someone who could help us build it.
What early-stage startups actually need
Early-stage startups don’t need execs. They need builders.
They need the sales rep who do not require a full RevOps stack and a full team to close a deal. Someone who creates the sales deck when realizing it doesn’t exist, gathers feedback from the field and works with product and marketing to improve things.
They need the marketer who doesn’t just pitch a campaign – but writes the copy, builds the landing page, configures the email flows, and pulls together the analytics.
The truth is that life at a startup can be chaotic. Hiring people who thrive during that phase, who enjoy cracking the problem rather than just managing the process, is critical to your success.
Finding the right fit for your business model
This isn’t one-size-fits-all. The type of business you’re building matters.
If your Go-to-Market is enterprise-led, where relationships and credibility open doors, then someone with a strong network might be critical early on, assuming the entire company is geared toward that motion.
But if you’re running a high-volume, product-led, or transactional motion, where the goal is to land tens or hundreds of deals per month, then agility and iteration matter a lot more than title or network.
How to identify true builders
While it’s tempting to bring in an experienced VP of Sales or a CMO early on, that might not be what you really need.
Before you hire that big-name VP or seasoned exec, evaluate whether they are:
- True builders who love figuring things out from scratch and creating processes.
- Self-sufficient and able to thrive without an established team/processes/tools around them.
- Hands-on and willing to roll up their sleeves when things break (and they will).
- Growth-oriented which means eager to learn, resilient in adapting, and driven to keep pushing forward.
If the answer to these questions is truly yes, amazing. But if you’re hiring based solely on what they accomplished after things were already working, there’s a good chance you’re hiring too senior, too soon.
Remember: Your startup isn’t a machine yet. Don’t hire someone to run it. Hire someone who knows how to build it!
