The Hard Truths of Startup Growth: Lessons in Communication, Silos, and Legos

I was the very first full-time employee at my first job, and honestly, it was like jumping on a rocket with zero safety instructions. We went from me, the founders, and a couple of IKEA desks in a tiny office to 25 people, six business units, and millions in revenue. Wild times, right?

I’ve been in startups from Seed to Series B ever since, and I like to think I’ve got a pretty good grip on the rollercoaster ride that is scaling. Whether you’re the first hire, the growth hire, or the “please help us make sense of this mess” hire, I’ve seen some stuff. So, let me take you through some of the organizational challenges that seem to pop up everywhere I go.

Communication (or the Lack Thereof)

Growth is hard. No matter how many celebratory Slack emojis you throw around, the road from 8 to 20 employees is a bumpy one. The number of communication channels grow exponentially with the number of people you add, and this phase of growth is usually the first where you’re hiring someone who doesn’t report to the founders. The reasons people join and the things that keep them motivated are different.

The Solve: Onboard intentionally, and mentor first-time managers. Keep the power dynamics in check, and over-communicate like it’s your job. My first boss was phenomenal at over-communicating without micromanaging, and modeled it incredibly well. We’d be in a 1:1, and he’d say things like, “You should talk to X because this affects their work.” On top of heading off miscommunications early, it taught all of us to think about how all the pieces of the organization interconnected, and it’s one of the most important skills I learned in that job.

Losing Customer Focus

Your job in Series A is to make your process repeatable, and it can be tempting to prioritize operationally efficiency over customer needs. It’s never one big decision that derails things—it’s a series of small, “it won’t be that big of a deal” moments. But those small choices pile up, and before you know it, you’ve got a system that’s more about keeping the trains on time than making your customers happy.

The Solve: Keep your team connected to your customers. You can’t just rely on customer empathy. You actually have to talk to your customers. And I mean, everybody on your team needs to talk to customers. As an introvert, you can bet your bottom dollar that I’m sweating as I write that sentence. But it’s necessary. I’ve heard of teams that keep cardboard cutouts of their ideal customer profile (ICP) in meeting rooms to remind them who they’re serving. And honestly, it’s not the worst idea—if a little creepy.

The LEGO Problem

This one’s personal, but I also can’t claim credit for it (h/t - Molly Graham). I remember being swamped with work at my first job, trying to keep all the plates spinning. So, when my boss hired someone to take some things off my plate, I completely freaked out. It felt like a signal that I wasn’t cutting it, and I fought the new hire like a kid not wanting to share their LEGOs. Spoiler: I was wrong. Startup growth always involves giving away pieces of your job, and that sacrifice of ego is what opens the door to more impactful growth.

The Solve: There’s no magic bullet here, but honest conversations help. When I was going through this, my CEO pulled me aside, assured me that this wasn’t a matter of me being inadequate, that the best thing I could do for the organization (and my own professional development) was to give away some of my LEGOs. And he was right. It wasn’t about losing power—it was about making room for bigger, more impactful work.

Departmental Silos

I once worked at an organization where marketing was given a goal to complete by the end of the month. The problem was, if marketing hit our goals, our operations team wasn’t prepared to deliver, through no fault of their own. Our VP of marketing charged forward anyway, put our operations department in a bind, and created a terrible customer experience.

The Solve: Your KPIs need to align across departments, or you’ll have teams working at cross-purposes. And when you can’t align them (which does happen), make sure to define them. For example, marketing might be incentivized to drive MQLs, while sales focuses on SQL Close Rate. Without alignment, marketing lowers the bar for MQLs, and sales raises it for SQLs, and the two teams start clashing. Department leaders need to agree on shared definitions and call balls and strikes in good faith.

Founder Personality Effects

Brace yourself, founders: the quirks and dysfunctions of your leadership will inevitably shape the organization. People watch and mirror what the founders do, even if it’s subconscious. And, let’s be real—founders are likely to shut down ideas that don’t fit with their instincts while praising those that do. It’s human nature, but it can lead to a narrow path if left unchecked.

The Solve: Your organization will be fighting this for the entirety of its existence, and that’s not a bad thing. Founders need self-awareness, mentors, and a balanced team that isn’t afraid to challenge them. Surround yourself with people who can speak hard truths to you—even when you have the power to overrule them.

Other Important Things to Keep in Mind

Celebrate your wins. In the rush to scale, it’s easy to keep pushing for the next milestone without taking a second to acknowledge what’s going right. Don’t move the goalposts so quickly that your team forgets they’re making progress. Recognizing wins, especially the ones happening behind the scenes, is crucial for morale. Those little deposits in the emotional bank account will be invaluable when the going gets tough.