My list is a bit quirky, but perhaps it will help a few others to accelerate — or drop — a few things:
- Doing international customer support myself. For months, I did European customer support myself rather than hire someone. This was just a terrible idea. I slept with my laptop next to me, and got up 4–5 times a night to deal with the top trouble tickets. I should have immediately hired a CSR or two in Europe, or at least to work the swing shift from the U.S.
- Having generalists do key account management / customer success for too long. I hired a very smart person to manage our top accounts, without traditional success background. This was a good strategy to start, but I should have quickly hired a true customer success team as soon as a I had Two Large Enterprise Customers.
- Waiting too long to hire a VP of Product. Don’t do this. My CTO and I hacked being the VP of Product together way too long. It’s OK in the early days, but then the product gets way too complicated to hack management of 100+ features and 500+ you could potentially build. More here: If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One – SaaStr
- Not building a dedicated QA team (or using RainforestQA if it existed then) on Day 1, or at least, very early. My engineering team wanted a dedicated QA team on Day 1, but I pushed back. I thought it was a bad use of scarce capital. I was very wrong. A good QA engineer or two, even in the early days, gives your dev team huge leverage. And decreases the odds critical bugs go into production that harm your relationship with your customers.
- Waiting too long to invest in dedicated DevOps and TechOps. Like QA, I made the core dev team manage DevOps and TechOps for too long. We did hire several great resources here fairly early, but I should have put in place 24×7 coverage at least by $2m in ARR. This was incredibly distracting.
- Waiting too long to invest in sales ops. We didn’t really build a sales ops function for a very long time. It helped that my VPM and VPS could hack it, but this was a mistake. Invest in a dedicated sales ops professional once you have 6–8 AEs, or 10+ sales professionals total. At a minimum, you can’t scale to a second level of sales management effectively without dedicated sales ops.
- CEO as VP of Business Development for way too long. This is a subtle one, but I should have hired a head of business development / partners as soon as I had a handful of important partners. Instead, I distributed ownership of biz dev across me (CEO), our VP of Product and our VP of Sales, with contributions from out VP of Marketing and VP of Customer Success. Like anything, not having a dedicated 100% owner means too many things fall through the cracks. And that even more importantly, biz dev stays reactive rather than proactive. Invest early in your ecosystem — as soon as you have even a small one.
- Lack of a sophisticated billing system. This is easier these days in the days of Stripe, NetSuite, Intacct, Zuora, etc. But not having a great way to manage 1000s of paying accounts led to hundreds of headaches down the road. Even if it wasn’t a big deal in the early days when we only added 1–2 paying customers a week.
I’ll add another 50–100 items to the list when I get a chance 🙂