Scaling is a Human Challenge
People-specific patterns in growing startups
I’ve seen a lot of content focused on the mechanics of how to scale, but it often ignores the nuance of how to get there.
An IPO-ready company and a seed stage startup are like night and day. The skills needed to create something out of nothing are very different than the ones needed to interact with regulators and keep global operations running. The bridge from point A to point Z is where things get messy, and a big part of this centers around the human experience within your company.
After working in five startups, I’ve seen the same patterns play out over and over.
ICs in Manager Roles
The first point of scaling friction usually happens in your existing org chart.
My first startup experience was greatly impacted by my boss. I moved onto his team not long after joining, but barely featured on his radar. He was hyper-focused on his relationship with the founder, ditched 90% of 1:1s with his direct reports, and expressed little interest in our career goals. Needless to say, I didn’t get a lot of guidance from him. I understand now that I could have delivered much better results with a manager who, well, managed.
He pivoted into IC roles at a series of FAANG companies later, which I imagine is a much better fit. I moved on to more effective leaders, grew as an employee, and delivered better results.
Unfortunately, I’ve seen this play out many times in startups. Early team members are promoted into management roles not because they’re effective, but because of tenure, relationships, and ego. They stick around by managing up and producing decent results, but leave a lot on the table.
This is bad for people and bad for business. Lack of structure around leveling and people management can allow this to go unchecked for years.
The Fix: Respect for Craft
In the anecdote above, my manager wanted that role because it was seen as important. He was a fantastic product thinker, but had little interest in career development or effective delegation.
The solution here is to define high-level paths for IC roles so that folks can level up without taking on direct reports. At the same time, set expectations for what management entails: coaching, development, and a lot of meetings and process.
Respect the craft on both sides of the table. These are different skillsets, but both are critical to get the outcomes you need.
Role Anxiety
When I first joined that startup, I began as a 10-hour a week customer service contractor. I tracked patterns, created standard responses, and proactively relayed bugs to the engineering team—work beyond the scope of what they expected from this low-level temp role. This led to a full-time position managing customer service, behavior moderation, and data entry.
The company eventually scaled to the point that we needed someone more experienced in my role. I moved to a project management position with a much smaller scope. It was a better fit that ultimately led to roles vastly eclipsing the one I handed off, but I still felt like a failure.
Why? Because I was stuck in a fantasy idea of the company at the time I started. I was also invested in my own ego. In the long term, I got over it, embraced humility, and actively sought out positions that could help me level up.
However, that feeling stuck with me, and I’ve seen it over and over at the startups I’ve worked in since. Watching the startup you helped to build grow faster than you is hard.
The Fix: Create a Bridge
The best solutions to this problem typically involve creating intentional pathways for career evolution.
I later worked at a startup where Product and Customer Experience teamed up to create a pathway for frontline support agents to transition into Associate PM roles. At another, the newly established Policy function hired multiple founding team members from Trust & Safety. In each case, the transferred employees had valuable experience and knowledge that, combined with coaching, resulted in exceptional results.
BigCo Bias
The most jarring point of friction happens when a company tries to solve its scaling problems by hiring outside experience.
If you’re building a larger company, it makes sense to hire people who’ve worked in that type of environment, right? In theory, yes, but be selective.
Hiring employees from larger companies is not a magic solution. Folks who have only been at a Fortune 500 giant—even if it’s a similar industry—know what the end state looks like but not necessarily how to get there.
I’ve worked with many colleagues who were attracted to the idea of increased ownership and (potentially) valuable startup equity, only to discover the reality isn’t their cup of tea. This typically manifests as incredulity that basic operational processes don’t exist, a refusal to work on anything that isn’t “strategic,” or condescension toward colleagues who are willing to get scrappy.
The Fix: Screen Carefully
Your target profile should be a person who knows what a mature company looks like and is excited to figure out how to get there.
Startups change constantly, and this environment is not for everyone. Screen for resilience, curiosity, and creativity. Screen for the ability to see the future and sell the vision to skeptical stakeholders.
Later in my career, when I was hiring PMs at a hyper-scale startup, I had a stock question I would ask everyone:
Our headcount has grown from 700 to 4,000 and we’ve launched 20 markets in the last 18 months. What do you think would be unique about the day-to-day experience of working in an environment like this?
I was looking for two things:
The Emotional Signal: their reaction to the numbers. Were they excited? overwhelmed? curious? The folks best suited to the work, regardless of past experience, were inspired by the challenge. Their eyes lit up, while more dubious candidates had a deer in the headlights quality.
The Operational Signal: the ability to connect those numbers to a reasonable assessment of day-to-day reality. The hires I recommended correctly identified that the way the team worked was changing constantly, and that it was better to think in terms of goalposts than rigid game plans.
Exit Strategy
There’s a romanticism to startups, and I’ve seen many colleagues stay put for years while clinging to a past version of the company—just like I did at that first job. As I’ve leveled up my own career, I have a special empathy for others in this position.
Not everyone is cut out to work from the product-market fit phase to enterprise-readiness. Moving on isn’t a failure, it’s the end of a specific chapter.
As I moved forward in my career and on to new startups, I learned to constantly assess and reassess whether I’m a match to the company’s needs. Respecting what I have built while being honest about what the company needs next is better for everyone.
About Me
I spent 15+ years in five Silicon Valley startups ranging from entertainment to SaaS to CPG. I’ve built new functions, tackled budget crises, worked on a regulatory hearing, and created more processes than I can remember. I also have hundreds of hours of training and experience volunteering on crisis hotlines.
I’ve seen the highs and the lows of startup life: the feeling of printing money and impending world domination when your product is in demand… vs the time I pinched pennies by selling a plot of fake grass from the company’s office decor to a guy en route to Burning Man.
I work with startups on short-term, high-stakes engagements like rapid scale-ups, post-layoff chaos, and regulatory scrutiny.