Growing Pains Aren’t Just For Kids: Startup Inflection Points & Their Impact on Growth
- Robin Cohen
- 11 minutes ago
- 4 min read
Scaling a startup from 40 to 60 people sounds small, but it’s one of the most chaotic, high-pressure jumps a team can make. In this post, I share the behind-the-scenes story of building AllTrails’ first Year in Review campaign—an incredible win that nearly burnt our team out—and why projects like this tend to unravel as organizations grow. You’ll learn how to spot early signs of team dysfunction, why “growth edges” create friction across teams, and the alignment techniques every startup can use to keep their systems, communication, and culture from falling apart.
Back in the early days at AllTrails, a designer, engineer and I spun up a “Year in Review” brand campaign that was equal parts amazing and grueling. With a tiny team & minimal resources, we created one of the best brand campaigns the company had ever seen. We were so proud, and simultaneously so drained.
We manually pulled data. We drafted and re-drafted the copy. We revised layouts. We localized versions for the global audience. We tested what felt like 4000 variables. And truth be told, we almost burnt out.
But the work still got done, so what’s the problem?
The problem was, despite our best efforts to get ahead & prioritize, the work depended on multiple teams. Teams with competing priorities. Priorities that juggled & resulted in time-sensitive deadlines & impossible asks.
Did we put out an incredible product we were proud of? Yes.
Did we want to curl up like a present under the tree and cry? Also, yes.
So why did that happen?
We’ve all been there. The project that seems so far away that no one prioritizes it. Then you’re a month or two out and one little hiccup turns into a month-long request that’s stuck with another team because they’ve never had to try xyz before.
The exploration of something new–that’s the sticking point. The “growth edge” that so many founders talk about. It’s the inflection point when your team is pushed to try something new that things often fall apart.
For context, we were in a period of growth and the org had gone from ~40 people to 50-ish people in under one year. While 60-people is still small, that was a 50% increase in staff. Our old processes and ways of working couldn’t keep up.
Navigating Scale & Its Impact on Growth
There are inflection points when a company fundamentally changes. In my experience, the most painful one is when a company scales from ~40 - 60 people. At every startup I’ve worked with, regardless of budget or valuation, what worked then can’t work now.
It’s like a child growing out of shoes. At first, the shoe seems too big and like it’ll have room forever. Then, day by day, their foot grows and grows, until one day, their toes are curled up and the pain is unbearable. That pain is the same pain that happens when teams scale.
There are new faces asking new questions, new demands from the board, new requests for data, new expectations, new complications–the newness knows no bounds. The processes that worked for 20 people grind to a screeching halt. In other words, the organizational shoe no longer fits.
Identifying The Signs of Team Dysfunction
Like growth spurts, these breakdowns feel like they happen overnight. But the signs have been there: the missed deadlines, the snarky comment from a coworker, the stress coating every conversation. These are all signs of team dysfunction and that the current way of working no longer works for the team.
If a child outgrows a pair of shoes, the logical choice is to buy them a bigger pair.
The same is true for the way we work. When a system or process no longer fits, it’s time to try something bigger.
If you're a startup leader who finds their org in need of some new shoes, give these alignment methods a try:
Make the implicit explicit
State what you expect and what your goals are. It’s not enough to assume everyone knows the plan and what you stand for. In every meeting, project kickoff, and team all-hands, restate your purpose. It may feel repetitive, but it will ensure all of the players are coming to the game with the same rulebook.
Define roles & responsibilities
If you put 80 musicians in a room and just tell them to play, you’ll get a lot more noise than music. By providing guardrails of who will do what & when, you empower your team to excel in their respective lanes. By discussing roles & responsibilities up front with the team, it frees them up to focus and each do their part. Now, the orchestra can play together as one, all contributing meaningfully instead of chaotically.
Give it time to get more comfortable
Like a new shoe, you want a system that is pain-free & supportive. That said, it can take time to get used to change. Expect that there may be some discomfort as the team breaks in their new ways of working. By addressing this potential for discomfort head-on and acknowledging it with your team, you create space for open dialogue and feedback.
That said, if it’s been months and you’re still getting blisters, something needs to change.
Plan to keep growing
What works for you at 40 won’t work for you at 70 or 100. If growth is your goal, don’t be afraid to swap out a system or reassess your position as variables change. Adaptability is key to maintaining team productivity (and sanity).
It may take time to find the brand of process and strategy that works for your org, but like a good pair of shoes, it’s worth the investment.
Whether your startup is navigating change management or simply scaling in size to keep up, the team and the work will always benefit from discussions around organizational efficiency and ways of working. If you need help navigating process improvements or are looking for ongoing support as your grow, email robin@happieroffice.com. Robin is a fractional COO & the founder of Happier Office.