5 common mistakes that founders make when hiring their first sales rep
And how to avoid them
As someone who has worked at and consulted for early-stage startups, I’ve seen founders misunderstand when, why, and how to hire their first sales rep. These mistakes don’t have irreprehensible consequences for the startup, but they can be avoided and used as a framework to hire effectively and successfully.
Here’s a list of common mistakes that founders of early-stage companies make when hiring their first salesperson, and some corresponding ways to avoid these early setbacks.
1. Hiring someone too senior
Early-stage startups get approached by senior sales leaders… all the time. Founders, how many times have you received a cold email or LinkedIn message from someone with 10, 15, 20+years of experience in your exact space?
In my experience though, hiring a veteran sales leader with deep product/market/industry knowledge rarely works out as well as one would expect. Take anyone with a “Golden Rolodex” — personal and professional connections to your target customers, partners, etc. — with a large grain of salt.
On top of high salary expectations, senior sales reps will be accustomed to having support from marketing, revenue operations, and BDRs. Underestimating the amount of meticulous work tied to sales at an early-stage startup — prospecting, making sales decks, etc. — will lead to disappointment and poor results.
As a rule of thumb, founders can avoid this common pitfall by not hiring anyone above the level of Director for their first sale hire. If a founder believes they’ve found a truly special VP or CRO, they should engage them as an advisor or consultant.
Wait to bring on your dream sales leader once you’ve found product/market fit and the company is ready to hire a full sales team. Everyone will be more effective and satisfied then.
2. Hiring someone too junior
As obvious as it sounds, early-stage startups should not hire someone with zero sales experience.
A junior sales rep (e.g. BDRs) can play a critical role in scaling sales teams and companies IF they are managed and mentored effectively and have a clear path to an upward trajectory within the organization. Founders of early-stage companies don’t have the time and skills to be hands-on with a junior sales rep and help them succeed.
So, founders, if you’ve never managed a BDR before, now is probably not the right time to try it. Instead, look for someone who already understands sales frameworks and tools.
Founders can avoid this mistake by hiring someone with a minimum of 1-year of prior sales experience. This person should be able to wear multiple hats within a revenue organization and has a strong desire to fast-track their professional growth.
If you think you’ve identified a talented and motivated person with little to no sales experience, give them a shot by hiring them as an intern or contractor. That’s actually how I got my first sales job at a startup!
3. Not communicating expectations and incentives
Founders have an obligation to set clear expectations for their first sales hire. The professional demands of early-stage startups are very different from Series B, C, and D startups. Not everyone you interview for this first sales role will fully appreciate this fact.
Founders should ask what their first sales hire is looking to get out of joining an early-stage startup and correspondingly adjust their expectations and incentives.
Sales reps need clear and attainable financial and professional incentives to be successful. No one likes missing quota. Make it a point to re-examine and adjust quotas and incentives on a quarterly basis to account for the natural fluctuations in an early-stage startup. This will help keep your first sales hire focused, engaged, and happy.
Founders should also guide their first sales hires to think in terms of long-term value, not short-term gain. If someone is looking to make a lot of money in a short period of time, an early-stage startup is almost certainly not the right place for them. Both founder and first sales hire should understand their compensation, professional expectations, and incentives upfront to avoid disappointment and resentment.
Founders, don’t skimp on company stock options and be transparent about how much equity you’re offering them as part of their compensation. Get your first sales hire excited about having a significant stake in a company they’re excited to help build over time.
4. Underestimating ramp
There’s some misconception in the early-stage startup world that sales is a plug-and-play, point solution. Au contraire, sales is a hard skill like engineering. Revenue doesn’t appear overnight.
Ramping your first sales rep takes time and effort from both the hire and their manager. Start by creating a mutually agreed upon week-by-week plan with your first sales hire. Write down weekly and monthly benchmarks and hold each other accountable to the plan.
Even assuming the first sales hire is a highly-motivated self-learner (which they absolutely should be), founders need to play an active role in onboarding and ramping. It’s imperative, for example, for founders to practice the sales pitch and demo with their first sales hire at least semi-weekly.
Founders, make sure your first sales hire understands the importance of a thorough ramp period (rather than starting to sell immediately). Ask them to provide regular feedback and take detailed notes that can be turned into a sales playbook or sales training guide for future hires.
One way to reduce the stress of ramping quickly and incentivize your first sales hire to become a knowledge expert is to offer draws in their sales commissions plan. Tie this compensation structure to the original, week-by-week ramp plan.
5. Not talking to customers anymore
When early-stage startups make the transition from founder-led sales to having a sales team, there’s a natural dropoff in how much founders talk to their customers and users.
At early-stage startups, founders need to constantly stay in front of their prospects, customers, and users to inform product development, corporate strategy, etc.
Founders should co-lead sales calls with important and large prospects, as well as promote a culture of good sales hygiene. Founders and early sales hires should agree to take meticulous call notes and log all activity in a CRM. You and your first sales hire should make it a point to ask for pointed feedback from your prospects, customers, and users. Write it all down.
Founders, don’t see your first sales hire as an excuse to stop being customer/user-facing, even though you’re stretched thin. Instead, think about your first sales hire as a means to gather more data by having more conversations with prospects and acquiring new customers and users.
BONUS: compromising on culture fit
Your first sales hire needs to be someone who fits the company's culture and reaffirms the startup’s values and vision.
Sales — especially at an early-stage startup — is a much more internal-facing role than many people appreciate. Yes, sales is the most external-facing organization in a company, but it will also have a huge strategic and cultural impact internally.
Your first sales hire will need to work closely with Product and Customer Success teams to succeed in their role. Avoid hiring someone who’s not the right culture fit and struggles to work with other departments by having them chat with different employees throughout the interview process.
Founders, ask yourself if you would be excited to eat lunch with the candidate this weekend. If not, you’re probably ok to pass on them, no matter how qualified or compelling they are.
Conclusion
Every startup is different so there’s no sure-fire way to avoid making a mistake when hiring your first sales rep. But founders can put their best foot forward when hiring their first sales rep by paying attention to the right balance of experience, as well as facilitating early conversations about expectations and incentives. Founders, give your hire time to ramp, and once they’re up and running, don’t forget to keep actively engaging with your customers and users. Good luck!
