1/ One thing that was challenging as a 1st time founder was the transition from having built a product people loved to figuring out how to grow it beyond the word of mouth success it had become. Building a great sales & marketing org was frought w/ peril & I made many mistakes...
2/ First, I want you to know that you are not a failure as CEO just because you are bad at this skill. Many product/eng-focused founders screw this up. I thought I was particularly distinct at this until I reached out to CEOs who similarly went through waves of struggle.
3/ Should you think replacing yourself with a CEO who's great at S&M will fix the co, just know that it likely will create a gap in other areas (like prod). Divorcing prod & S&M strategy is perilous. There's no hard rule but the point is there's no CEO that's great at everything.
4/ Firing your first sales leader is really tough. The unspoken truth is that it happens often early on. Finding someone who will integrate with the co culture, can balance the short & long term incentives, & will keep in mind the future of the company's strategy is hard.
5/ Building the company's muscle around holding the spend of sales/marketing accountable, in a simple way, becomes incredibly important. Cost can easily get out of control. It's easy to hire more people than you need. It's the first area of a co that tends to become fat vs lean.
6/ So, how do manage your ignorance in sales/marketing as you scale? Counter intuitive: hire executives in functions that are going well first (like eng/finance/product). They will body check & help evaluate your future executives you're not strong at hiring along the journey.
7/ Hire a head of finance earlier (often hired later than they should be) so that they can create mechanisms to hold orgs spending accountable & be the check & balance to sales/marketing which will become huge areas of your opex. They will push them to become more efficient too.
8/ Hiring many sales people will culturally shift an org that's primarily product-based. I was scared but this was a trap. I should've embraced this. That said, I wish I had paused when we 2x'd the sales org & let the co grow into the new culture. The growth wasn't worth the cost
9/ Once you have a 10+ person sales/marketing org, it's worthy thinking through the unit economics of your business regularly (every 6 mo) to sharpen your understanding. The future of how you spend & hire will be strongly connected to this & you'll make much better decisions.
10/ Do not fall into the trap that sales people are primarily coin-operated. That generalization was a generation ago. Younger sales people do not optimize life this way anymore. They require a balance of pay & lifestyle. We should think differently now.
11/ If you're on your 3rd or 4th sales leader, you are not alone. It's much more common than you think. I was, unfortunately, part of this sad club. Some of it was my fault. Consider hiring a COO that can balance strategy with hiring executives who need to hit short-term results.
12/ If you're an engineer, you'll have to work twice as hard to love your sales & marketing orgs as equally as eng/prod/design. Perception = reality. I didn't adjust this perception fast enough & it was too late when I wanted to. Eric Schmidt famously had to change this @ Google.
13/ Sometimes hiring very exp ppl creates misaligned incentives between the executive's ambitions & the speed at which the co can meet those ambitions given its growth rate. This can create politics. Consider hiring high potentials instead: hard working folks getting passed over.
14/ Worst case scenario: I've constantly been surprised by how people, internally, who I thought couldn't do the top job rose to the occasion. Battle field promotions create stability, highly motivate those folks, & it shows people you can grow at the company.
15/ Like everyone else, you're learning how to be great @ your job. You're trying to do something that you wouldn't normally make your full-time job. Embrace your ignorance. Admit it to your team & have them help you. Find people that will lead those orgs. You'll figure this out!
In case you missed it, here's a thread on how I thought about acquiring our first 100 customers:
