v18 What I Learned Inside a Series A as Chief of Staff

One year ago, I had no idea what a Chief of Staff actually did. I was starting my first CoS role, armed with a few crash courses and a lot of curiosity, but most of the learning happened in real time, in the middle of the work.

Up until then, my career had been in late-stage startups, mid-sized enterprises, and Fortune 500 companies. I’d never been inside an early-stage Series A company, and certainly not in a role that touched every corner of the business.

This week marks my one-year anniversary. Looking back, it feels like a crash course compressed into twelve months. The lessons I learned fall into five areas:

• Strategy: how you steer the business.
• People: who you need around you.
• Execution: how you survive the day-to-day chaos.
• Leadership: how you create rhythm and clarity for the team.
• Personal growth: how the role changed me.

Some of these lessons surprised me, others stretched me, and all of them reshaped the way I think about building and running a company.

Here’s what I’ve learned in my one year as Chief of Staff.

Lesson 1 Strategy: Remove Dependencies to Unlock Speed

One of the biggest surprises for me this year was just how much being dependent on others slows a startup down. You think you’re moving fast, but the second your timeline is tied to someone else’s roadmap, you’re actually stuck waiting in line.

We lived this with hardware. We had a major panel manufacturer with clear demand on the table, yet we couldn’t get prioritized. The math made sense, but their pace didn’t match ours. So we made the call: instead of waiting, we’d build our own first-party hardware.

That one decision changed everything:

• We built hardware that was low-cost, beautifully simple, and installable in minutes with no truck roll.
• We made the setup intuitive: plug it in, download the app, and you’re live.
• We launched with our first national partner in June, while others in the space were still stuck in what I call “innovation theater.”

We saw the same thing in go-to-market. For every pilot, small or large, we made a conscious decision to keep things simple and run through our own app. One potential partner was building a “super app” and wanted us to be part of it. On paper, exciting. In reality, it would have meant months of extra work with no clear near-term outcome. So we passed, and focused on partners who already saw our value and were willing to move fast.

The pattern became clear. Removing dependencies isn’t just about controlling your tech stack, it’s about controlling your momentum. The more you rely on others, the more you trade your speed for their priorities.

👉 I wrote more about this shift in v13 Enter HomeAware, where I unpack the story behind our first-party hardware launch.

Lesson 2 People: The Right People Make or Break a Startup

Before I joined startups, I assumed the “best” startup people were the young ones: the fresh grads, the coders pulling late nights, the ones hungry to prove themselves. But I’ve learned it’s not about age. It’s about traits.

The people who thrive in early-stage startups tend to share three things:

1. High agency

Definition: They don’t wait to be told what to do, instead they step into the unknown, take ownership, and find ways to add value from day one. In short, someone makes an impact from day 1.

Example: We once had to let a new hire go just a month in. Smart person, but the fit wasn’t there. At this stage, we can’t afford to wait 90 days for someone to “get up to speed.” By contrast, other new hires have jumped in on day one: learning the business, working across functions, and immediately finding ways to contribute. That’s the difference between high agency and passively waiting.

2. Low ego

Definition: They prioritize progress over pride. They don’t let turf wars, personal credit, or being “right” slow down what the business needs.

Example: When I first joined the team, a teammate raised concerns about product performance but was dismissed as an “edge case.” Only later under new leadership, her feedback was taken seriously. The technical mess aside, what stood out was how ego had clouded the team’s ability to listen. In a startup, ego is a hidden tax on speed and truth.

3. Hat-wearer + Gap-filler mentality

Definition: They flex beyond their job description and step into the white space before anyone even asks. They don’t ask, “Is this my job?” They ask, “What does the business need right now?”

Example: Our UX designer came in to focus on app design. But she quickly expanded to packaging, marketing collateral, website visuals, even copywriting without hesitation. She became a one-person design team because that’s what the business needed.

These are the people who free up the founder to focus on vision and high-leverage decisions, instead of drowning in details. Without them, progress stalls. With them, the company compounds.

And when you meet someone like that in an interview? You don’t drag them through an endless process, you hit the golden buzzer. Recently, I did this with a CFO candidate. I saw how well he could fit our needs, and I immediately rallied the team to fast-track him. That’s how you hire for momentum.

👉 I wrote more about this in an earlier piece: v10 What I Learned Running a Startup for a Week.

Here is a case study that I did focus on the talent playbook. v7 DeepSeek’s Talent Playbook.

Lesson 3 Execution: Skip the Noise, Solve What Matters

Operating in a startup often feels less like following a playbook and more like being dropped into an escape room. You’re racing against the clock, juggling incomplete clues, and trying to figure out which puzzle actually matters. Progress doesn’t come from solving everything, it comes from knowing which things to focus on, which to skip, and when to regroup.

We recently changed our quarterly planning to a 45-day cycle. Shortening the clock forced us to do the opposite of what most teams do: instead of stuffing in more goals, we chose fewer, but the ones that matter most.

The shift has been refreshing. With less on the board, the team has sharper focus. We regroup more often, adjust more quickly, and know exactly which “puzzles” are worth solving. It’s given us clarity and urgency at the same time, which is rare in a startup.

This change also reinforced a bigger truth I’ve seen play out over and over:

• Priorities: You don’t need to solve everything to move forward. You just need to solve the right things.
• Alignment: Regrouping at the right moments is more important than constant alignment.
• Momentum: Celebrating the small wins gives the team energy to keep running toward the next one.

Takeaway: Execution in a startup rarely rewards perfection. It rewards focus, urgency, and the discipline to ignore the puzzles that don’t matter. For us, moving to 45-day plans made that lesson real.

👉 I wrote more about this in v11 Escape Room, Startup Edition, where I unpack why startups and escape rooms feel oddly similar. I also wrote about how strategy needs to match speed in different types of enterprise environment in v16 In Defense of Short-Term Thinking.

Lesson 4 Leadership: Create the Rhythm, Bring the Clarity.

Leadership in early-stage startups isn’t about delivering a perfect roadmap that never changes. It’s about creating enough rhythm and clarity for people to run, while staying open to adapt when the market demands it.

Clarity doesn’t mean stability forever. It means giving the team a clear direction today, and then being transparent when something needs to change tomorrow.

As Chief of Staff, one of the biggest things I worked on was building a business rhythm for how the leadership team operates. We introduced twice-a-week leadership syncs and quarterly offsite. In those spaces, we debated, reflected, and documented our decisions. That rhythm gave us a foundation.

But foundations don’t mean rigidity. Along the way, market signals forced us to adapt. Not every plan held up. That’s where leadership had to balance consistency with agility: we didn’t change direction for no reason, but when we did, it was thoughtful, debated, documented, and communicated clearly.

We also rethought how decisions flow to the broader team. From town halls to weekly Monday updates to timely Slack and email follow-ups, the goal was the same: make sure everyone knew what had shifted, why it mattered, and what was expected of them.

Takeaway: Startups aren’t cruise ships with fixed annual plans. They’re speedboats and jet-skis: moving fast, adapting constantly, and still steering toward a clear horizon. Leadership is about giving the team anchors: a shared direction, rhythms for alignment, and transparency when things change. That combination builds trust and keeps momentum, even in the fog.

👉 I wrote more about offsite in v5 Why ELT Offsites Are Worth It, a set of hacks I wish I knew ten years ago.

I also wrote about how strategy needs to match speed in different types of enterprise environment in v16 In Defense of Short-Term Thinking.

Lesson 5 Personal Lesson: Focus on What Matters, From a Higher Altitude

The Chief of Staff role stretched me more than I expected, not just in what I worked on but in how I work and think. The biggest shift was realizing that growth doesn’t come from doing more, it comes from doing the right things and seeing the business from a higher altitude.

Rock, Pebble, Sand

Every day as Chief of Staff my plate is overflowing. Early on, I tried to measure success by whether I could get through it all. Now, I use a different lens: did I move the big rock today? If I finish one meaningful thing that has the biggest impact on the business, that’s progress. The pebbles and sand can wait. I’ve had to train myself to stop defaulting to easy tasks that feel satisfying, and instead lean into the harder work that actually moves the needle.

From Senior Leadership to Executive Leadership

This was also my first real exposure to the C-level. I’d been senior leadership before, but the vantage point is different. As a function or business unit leader, you’re trained to advocate fiercely for your team. At the executive level, you learn that sometimes the best decision for the company won’t be the most convenient for your team. That doesn’t mean ignoring their concerns, but it does mean putting the business first, then working with the team to adapt. It’s a tougher balance, but one that makes you think differently about leadership.

Takeaway: The Chief of Staff role changed the way I measure progress and the way I view decisions. I’ve learned that:

• Moving one rock matters more than juggling all the sand.
• Seeing the company from the top means prioritizing what’s best for the business, even when it’s uncomfortable.

Growth doesn’t come from clarity, it comes from practicing these choices in the fogand realizing over time that the fog itself is the teacher. 

👉 I unpacked what does Chief of Staff do in v9 Chief of Staff, Explained (Finally).

Looking Back, Carrying Forward

Looking back on this year, I realize being a Chief of Staff at an early-stage startup isn’t something you ever fully “figure out.” It’s not a job you master, it’s a job that grows you in ways you don’t expect, and often in the middle of the chaos.

This year gave me more than just lessons on strategy, people, execution, and leadership. It gave me perspective on what really matters, patience when things don’t go to plan, and a higher vantage point on how decisions ripple across the company. It forced me to practice choosing impact over activity, to lean into the hard work instead of hiding in the easy, and to remember that moving one rock a day is enough.

It also taught me that clarity is never final. Plans change, markets shift, and startups will always feel like an escape room with the clock running down. The best you can do is set direction, stay transparent, and keep listening to your teammates, your customers, and the signals around you.

And maybe most importantly, this year reminded me that none of this happens alone. The people matter more than anything. The ones who show high agency and low ego, who wear the hats and fill the gaps, who keep saying “I’ve got this” before you even ask. I’m deeply grateful to have learned alongside them, debated with them, and celebrated the small wins that became big momentum.

So here’s what I carry forward: startups don’t reward doing it all, they reward doing the right things with the right people. Growth doesn’t come when the path is clear, it comes when you keep moving through the fog. And every day, progress is just one rock at a time.

🎧 P.S. Now My Newsletter Talks Back

Prefer to listen instead of read? I turned this exact newsletter into a podcast episode — so you can take it on a walk, a drive, or just hit play while hiding in your closet for ten minutes of peace. No judgment. Because sometimes hearing the words makes them land a little differently and you deserve to feel less alone, in whatever format works for you. Or if you want to share it with a friend who prefers podcast.

▶️ Listen to “Inside a Series A Startup: Lessons From the Chief of Staff Seat” on Spotify (Spotify link here).