Modern Logic collaborated with Lighter Capital on their latest webinar series, “Scaling and Accelerating SaaS startups”. This article is part of the series on the topic, “Accelerating Sales and Leveraging Technology to Build Engaged Communities.”

As a startup founder, it can be difficult to let go of the reins and put them in the hands of a sales team. Check out these tips to ease the transition – hard-won knowledge from Anna Talerico at Arthur Ventures, Derek Baird at Sensyne Health, Brian Loar at GoCheck Kids, and Dustin Bruzenak, our CEO.

Complement Your Strengths & Weaknesses

Anna tells us,

“Who you are looking for is really dependent on the founder and their natural inclinations. You have founders who love sales who want to be close to that, and others who begrudge sales. What involvement do they want to have? Get very real as a founder or small founding team about what the point of view is, and what strengths and gaps you have.”

Brian elaborates: “As a sales leader, I still love having the founder in the field with me. You can’t get more raw emotion and passion behind their solution and story. However, often, founders focus on the first sales hire thinking they need a VP – but you shouldn’t do this until you are ready to scale. Maybe as a founder, you’re great at closing. Maybe you need someone who creates more leads and then puts you in the place where your native genius can show. On the other hand, it could be that you have a strong network and you’re stuck in a certain sales stage, and you need to bring in a serious consultant.”

When You’re Doing Something New, Start With Two

Be sure to hire two sales people at one time. Even if you think it’s out of budget, find the budget – it will pay off in knowledge. If you just start with one sales expert, you won’t know if your success or failure is because of them or because of the product. Starting with two provides a good feedback mechanism.

Don’t Wait Too Long 

Derek tells us: “Most founders wait too long. It’s completely understandable – especially for those who like sales and  being in the field. But you’ll face the same issue that comes with only one sales rep. You may be closing deals based on the charm, passion, and charisma of being the founder. After that, you’ll see a huge dropoff.”

Don’t end up in a situation where only the CEO really knew how to sell his product. The team needs that institutional knowledge.

Be Willing to Change Your Focus 

“When I advise CEOs, part of that relationship is a quarterly assessment based on how they are spending their time,” says Derek. “Too often, what they are doing in different stages of the company looks way too similar. It’s natural. You have to be intentional about changing focus areas and where you are expending your talents. That’s easier said than done. The default is to do what you’ve always done, which people are good at.”

Find the Right Advisors

Advisors help you take an objective look and will help you see both the hard things and the obvious things you may be ignoring. The best leaders have a high degree of self awareness. Watching yourself and doing a sober assessment on a regular basis is much easier with a trusted advisor.

Find The Right First Hire

Brian shares,

“The problem starts when you realize that you haven’t had the knowledge transfer you needed. Hires who are not adaptable or coachable are a problem. It has to be a partnership with your first hire – this is like your work spouse. You have to be able to bounce things off each other. The first hire needs to match the founder’s energy and be that passionate.

That first hire requires a whole different set of skills – coachability, curiosity, durability. The last two commercial hires I made are recovering project managers. They’ve been very successful in ways that traditional sales people sometimes are not, because there isn’t a playbook. You need people who can roll with that – and it’s not for the faint of heart.

Anna elaborates,

“I talk about people who create the playbook and run the playbook. You need both – but you need to be clear about what you want. There isn’t as much crossover as you think. One of the most common mistakes is picking a builder when you need someone to just run it.”

Know When to Let Go: In sales, it’s easy to either fire too early, or not early enough.

Anna tells us, “It feels great when you’re living it and working with that person – but trust your gut. If the founder’s gut is saying it doesn’t work, this is important. I try to make activities and outcomes for 30, 60, and 90 days. Even if I don’t know how to set up a quota yet, I can set some expectations and have quantifiable conversations instead of nebulous conversations. Measure, measure, measure. That helps cut through the doubts about whether you need to let someone go early.”

Find the full webinar recording on our YouTube channel.