Hiring your first salesperson as a cybersecurity startup founder is one of the most critical decisions you’ll make. Get it right, and you build a repeatable, scalable sales engine. Get it wrong, and you waste months (or years) of runway figuring out why deals aren’t closing. Even worse: Your company’s valuation plummets because you cannot demonstrate traction.
One story I hear a lot: The founder hires a salesperson—someone who crushed quota at a big-name IPO company but fails to deliver deals in an early-stage startup.
Here’s how to get it right.
1. Hire for the right stage, not for the big-name IPO past
Just because a salesperson was successful at an established cybersecurity giant doesn’t mean they’ll thrive in your startup. At a big company, they had a well-known brand, a marketing engine generating inbound leads, and a playbook for how to sell. In a startup, they have… none of that.
Instead, look for someone who has:
- Sold in an early-stage startup before (ideally as the first or second sales hire)
- Built their own pipeline (not just worked inbound leads)
- Closed complex enterprise deals from start to finish
- Worked without a fully developed product, messaging, or playbook
If they need everything to be structured for them, they’re not the right fit.
2. Avoid the “Rolodex Salesperson” trap
Some candidates will pitch their “Rolodex” of contacts as their biggest asset. This is a red flag.
Here’s why:
- Their existing relationships may not match your ideal customer profile (ICP).
- They’ll burn through their contacts in 12-18 months and have no repeatable process.
- If their strategy is “I’ll just call my friends,” they’re not the hunter you need.
Instead, ask: “How would you figure out who to sell this to?” A strong candidate will talk about ICP research, account mapping, and systematic prospecting—not just who they already know. Similiarly, if the just fall back on their previous sales process, they may not be experienced enough to understand the nuances of how your business may differ - another red flag.
3. Hire someone who understands your buyers
I’ve tried hiring sales people who have a solid track record and have sold technology before, but one thing that has set successful reps apart was whether they knew the buyer.
Selling to security analysts or CISOs is very different from selling to DevOps or IT teams. If they don’t already know how your buyer thinks, what their pain points are, and how they make purchasing decisions, they’ll struggle, especially if they still need to figure out the sales motion with you.
A great salesperson who deeply understands the buyer can learn your product. But a great seller who doesn’t understand the buyer will have a much harder time figuring out how to sell it.
4. Narrow the use case so they can sell
Founders can sell their product in a way that no one else can. They understand the technology deeply and can pivot on the fly to match any use case a prospect throws at them.
Your first salesperson? They can’t do that. And if they try, they’ll likely fail.
If your positioning is still too broad and unclear, you need to narrow it down before hiring sales. Define:
- The best-fit customers who convert easiest and pay the most.
- The use cases where your product delivers undeniable value.
- A repeatable sales motion they can follow.
Without that, they’ll struggle to close deals, and you’ll think they’re the problem—when really, it’s your lack of focus.
5. Keep a tight feedback loop
Your first salesperson isn’t just there to sell. They’re your front-line researcher, helping you refine positioning, pricing, and product-market fit.
But if you’re not checking in regularly, you’ll miss critical insights.
In the first few months, do daily or near-daily one-on-ones. As things stabilize, shift to weekly. These aren’t just pipeline reviews—they’re conversations about:
- Who they’re talking to and what they’re hearing.
- What objections they’re facing.
- What messaging is resonating (or not).
- What deals are moving and why.
The goal is to learn fast and adjust. And by learning I don’t just mean them - I mean you as well. As a seller, they have a lot more customer contact and feedback than you as a founder, who has more things on your plate than “just” talking to customers. A long feedback loop means you’ll possibly learn too late about how to adjust your product or GTM motion.
6. Structure comp to reward performance — without a cap
Early sales comp is tricky because sales cycles are unpredictable. Here’s a structure that I found works:
- 50/50 base-variable split: (e.g., $120K base, $120K variable compensation, $240 OTE)
- Compensation level: Make sure that you check benchmarks on how much a sales person makes for any given level. The above is an example but not necessarily the right level for your case.
- Quota: Keep the quota realistic and in line with what your company needs to achieve
- Equity: The founding sales person should get more equity than the second or third person because they’re taking on a lot more risk. Otherwise, you won’t be able to attract top talent. Carta has great compensation benchmarks that you can use to dial into the right percentage points.
- Uncapped commissions: Your sales rep needs to be rewarded big if they overachieve. If you cap their earning potential, you’re shooting yourself in the foot because they may push deals into the next year. Consider accelerators for over-achievement. If your company gets traction faster than expected, you’ll have more cash and more VC interest, so it’s well worth the expense.
7. Be realistic about sales leadership
Many first sales hires want to be a VP of Sales someday. But just because someone is a great rep doesn’t mean they’ll be a great leader. Selling and managing are two completely different skill sets.
The best-case scenario? Your first rep naturally steps up—leading team meetings, coaching others, and taking work off your plate. If they’re doing it well, it’s a good sign they’re ready for leadership. Make sure you coach them, either yourself or through someone with sales experience.
But if they don’t? That’s fine. Just be upfront: “This role isn’t a guaranteed leadership path—you’ll have to earn it.” Otherwise, you risk forcing someone into a VP role they’re not equipped for and losing a great seller in the process.
Final thought: Match the hire to your sales motion
One last thing: Hire the right rep for the right sales motion.
- If you’re selling enterprise deals, hire an enterprise salesperson.
- If you’re selling mid-market, hire a mid-market rep.
Trying to turn a high-volume mid-market rep into an enterprise seller is a gamble you don’t need to take. Get the right person for the job, and your startup will thank you.
Hiring your first salesperson is hard. But if you focus on the right experience, avoid common traps, and structure the role for success, you’ll set up your startup for repeatable, scalable growth.
Have more questions about building your cybersecurity startup? Let’s chat.