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Aug. 12, 2022

Who should be your first sales hire?

We are going to answer this question in today’s blog.

Any first hire in a department is important, but in cybersecurity sales, it’s critical. Get it right and you:

  • start bringing money in, rather than always watching money going out
  • start hitting milestones for the next funding round
  • accelerate feedback from prospects and from real, paying customers
  • reduce the time commitment from the founder for sales activities

Unfortunately, many get this wrong. Finding and attracting great sales people who deliver for you is hard. Especially if you have never done it before (like most founders).

Often founders have been selling their product, won the first few customers and have gotten their feet wet in the world of sales. But the mistakes they make are covered up because they have the clout of the “Founder” title. They are also very knowledgable about the product and market and they can do crazy things with deals that help get them over the line.

But they haven’t worked for a terrible sales leader or a great one to know what good or bad looks like. They are not sure how to prioritize the characteristics of a good seller. And unfortunately, they don’t have a network that allows them to tap an old sales teammate on the shoulder and say, “I need you, let’s go do this!”

There are many paths to start building the sales team in early stages. But these two tend to work better.


Path one: hire 2 or 3 junior sellers to sell with the Founders

These are people who have been selling less than 3 years and might even be recently promoted SDRs or BDRs. They know enough about selling to be dangerous and have been at a company (usually bigger) that has given them solid sales training.


  • They tend to be hungry, are willing and able to work hard, will aggressively go after getting meetings with prospects and will handle the minutiae for you.
  • With a year or three of sales experience, you can trust them to handle the day to day (with your supervision/monitoring) and you are just involved for critical sales calls.
  • Oh… and they will be a lot cheaper than hiring very experienced people

BTW - it’s best to hire 2 or 3 of them because you have some coverage if one of them doesn’t work out (very possible), so they can collaborate as a small team…and because they are cheap!


  • You will still be in the weed with cybersecurity sales
  • You will be on the critical calls (a lot them will seem like they are) and you will be the sales manager
  • As junior sellers, they probably won’t have the gravitas and credibility to work with CISOs and other senior leaders
  • they might struggle a bit if that is your common entry point
  • Crucially they might be in full sales mode (a good thing) but then not be aware of the learnings they should take from calls from prospect (bad thing)
  • What should have been a learning about why a prospect wasn’t interested or what we said that didn’t work, will often be a “they just didn’t get it.”
  • Prospecting is hard these days. Especially if they don’t have a network to use to get into their target accounts.
  • Execution may be spotty because they don’t know how to see around corners that more experienced sellers navigate better
  • They might not be able to, or want, to start creating the sales playbook for future hires

When is this the best path? If the founder is willing and able to still be selling and is good at it.


Path two: more experienced up and comer leader

This is the person who likely has been selling for 5+ years and has led a sales team for 3+ years. They are progressing in their career and are hungry to get a big win. They view this role as a chance to get a fancy title, build and grow their team with its own culture and make a difference in the world. They understand they will be wearing many hats and are OK with it.


  • More experienced people will have a network to use. They will know and have worked with great sales people, know security leaders, and know partners. Don’t undervalue this!
  • They will free up your time! They will take 80%+ of your sales responsibilities away from you. You may still be involved in (truly) critical meetings.
  • Execution will likely be higher because they’ve experienced what works and what doesn’t and will be able to see around corners
  • Will have the capacity to sell AND learn. They will understand that sales positioning and activities need to be constantly evolving as they learn more from prospect interactions.
  • They will have leadership experience so will be a natural fit to start bringing on more team members as you are ready


  • They might not have the true entrepreneurial instinct that is sometimes needed
  • Too often they could default to “this worked at my last role” rather than being able to think differently and run experiments
  • They might not be the CRO you will need in a year or two (even if they think they are!)
  • Having Board presence, scaling experience and strategic thinking often is not quite there for someone who is just used to running a small team
  • They might not be THAT willing to roll their sleeves up and do whatever needs to be done
  • They may lack entrepreneurial instincts (they could bring too much of a standard approach)

Your first sales hires are critical. Get them right and you will have confidence, positive momentum and wins! Get them wrong and you will be confused, feel stalled out and wonder if any salesperson is any good.

But, it can work great. Consider carefully what you really need and then commit.

Don’t half ass it. Don’t give it a try for 6 months to see if it works. Be ALL IN or ALL OUT with your sales team and any individual within it.


You might also like this blog: How to answer the "what do you do" question


Unstoppable’s sales operating system is designed for cybersecurity startups and removes the random guesswork, provides repeatable sales plays, and enables you to grow more consistently, and faster. Schedule a strategy call