8 things I’ve learned in 8 years running a software development firm

In honor of our eight anniversary, here are 8 things I've learned in 8 years of leading Red Squirrel.

1. Pay people the same, no matter where in the world they live.

It makes perfect sense to me for clients to find the best value per dollar spent on a vendor. I don’t have any objections to off-shoring, near-shoring, etc. But I do have an issue with running a business that depends on wages staying lower in certain geographies than others, especially when the owner of that business doesn’t live in that lower-wage geography.

2. Bring in great partner and get out of their way.

Heather Corallo is a brilliant strategist and business operator. As her business partner (and husband) I’ve learned to enjoy stepping aside and watching her shine. She’s left an indelible mark on Red Squirrel, arguably most visible in the next lesson…

3. Focusing deliberately on diversity and inclusion results in a more diverse team.

We tripled in size in 2021. As we saw that growth coming, I received some important advice about being intentional about the demographics of who we hired. Still clinging to the mythical ideal of meritocracy, I pushed back on Heather’s advice. She persisted and eventually won me over, under her leadership, we grew the delightfully diverse team that we have today.

4. Assembling multiple female-only engineering teams is entirely possible.

See previous two points! We’ve now staffed multiple female-only and female-majority engineering teams. For some female engineers it was the first time they had collaborated with another female engineer on the same project. It was an important lesson for all of us to see first-hand that this is possible.

5. Treat employees and subcontractors identically from a cultural standpoint.

Some of our most tenured and culturally impactful Squirrels have always been subcontractors. It would be a huge loss for us culturally to treat them as second-class citizens in deference to full-time employees.

6. Not having an office creates flexibility to grow and shrink smoothly.

We’ve been 100% remote since Day 1. There are plenty of operations that need to mature and evolve as a company grows, but it’s delightful to not have to worry about square footage or desk limitations. And when a company shrinks, it’s a blessing to not have the fixed cost of a lease to account for.

7. Change shirts to match the tone of the meeting.

I like wearing casual clothes to work, but that doesn’t always project the correct degree of respect with certain clients or in a sales context. Thankfully, I can just keep a nice shirt next to my desk and pop it on before opening Zoom.

8. My professional reputation was necessary to get us started, but is no longer sufficient.

Over the first 20 years of my career, I built up a good reputation with a community of clients and a bunch of software engineers. That reputation got us here, but it’s not going to get us there. Where is there? Our Big Hairy Audacious Goal: working exclusively on projects or with clients that unleash latent human potential.

I’d love to hear from you if you disagree with any of these lessons or want to share any lessons you’ve learned! Join the conversation on LinkedIn.

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