A Day In the Life of a Chief of Staff

TL;DR: Not quite sure what a Chief of Staff really does? Join the club, there's no definitive answer. But here's my best contribution to answering that, with an authentic recount of one day as evidence.

"So what do you do for work?"

Cue a brief moment of panic as I decide whether to give the full long-winded answer or a generic catch-all.

Truthfully, there isn't a "typical" day but this post is intended to paint as thorough of a picture as I can. At a high level, I find my responsibilities involve some mix of:

1. Overseeing day-to-day general company operations –
   I refer to this as (internal) business operations or 'BizOps'. It's a combination of internal systems with a key goal to help unblock the team.
2. Driving and supporting company strategy and commercial efforts –
   Investor relations, business development, product strategy.
3. Leading our Humanitarian efforts –
   Building our technology with the lens to help those most vulnerable to climate risks.

Every Chief of Staff (CoS) position is unique because startups vary in size and team needs. From my experience at an early-stage startup (I joined WindBorne at a seed stage and now we're exploring early conversations for a Series B), the Chief of Staff role naturally becomes a catch-all.

That being said, I think if you speak to several CoS, the first two categories I highlighted above (Business Operations, Development, and Strategy) are common responsibilities if you're at an early-stage startup. The Humanitarian piece naturally fit at WindBorne given my previous work in philanthropy and a clear opportunity I saw – I'll speak more about this in the deep-dive.

A few disclaimers before I continue:

1. This post is not meant to be a guide to being a Chief of Staff (CoS), or an explainer on the role itself. Instead, I want to provide an authentic, inside peek at what the job is like, at least in my world.
2. What I do today as a CoS has evolved from my day-to-day when I first joined and will most likely differ from what I do in the future. The CoS role naturally grows with the company but in this post, I focus on where I am today.
3. This post is not meant to explore where a CoS role can lead in terms of career pathways. I'd love to dive deeper into this topic if helpful (expect an open ramble of thoughts) so let me know if this would be of interest!

If you're thinking about a CoS role, or just curious about what goes on behind the scenes, you're in the right place. Hopefully, at the end of this post, you'll find more clarity to the question of what a day in the life of a CoS could look like.

For a broader understanding of what a CoS does, expand the drop-down below to check out a few resources I'd highly recommend.

I chose to spotlight a day in April because I thought it captured a wide swath of topics. As I was driving home, I took a voice memo so I could remember the small tidbits that could add more colour to the day.

A Day at a Glance

Deep-dive

📞 8am – Strategy jam session
Started the work day at home by taking a call with a company advisor. While we have a few advisors, I work closest with our business advisor. This advisor boasts over 30+ years of experience in the commercial weather space and led the business strategy at one of the largest incumbents. I typically have monthly check-ins with him and in this call, we reviewed notes from our last board meeting, discussed the latest priorities, and our progress in our commercial products.

💬 9am – Zulip catchup & Kenya site strategy
Spent the next hour and a half catching up on discussions in Zulip, our internal company chat. Zulip is the nexus of WindBorne for communication – information is easily searchable and given the international nature of our operations, we rely heavily on chat given different time zones. I actually felt quite overwhelmed using Zulip when I first joined, but it's a core function of how we operate at WindBorne.

I jumped into our humanitarian thread as I had a few ideas for the Kenya launch site. For context, we set up a launch site in Nairobi, Kenya in partnership with the Kenya Meteorological Department last fall. This is work funded by the Gates Foundation, as a part of the goal to improve weather forecasts for smallholder farmers in East Africa. I made a trip out to Kenya last year to help kick things off but we've been working closely with local consultants to support the day-to-day.

I discussed with the team some considerations for our long-term strategy for Kenya and how to further leverage the balloon observations to improve forecast accuracy in the region. Our balloons out of Kenya are currently funded by the Gates Foundation – and while philanthropic partners like Gates are incredible in getting the technology up and running quickly in places with the biggest gaps, it's not a sustainable source. The tension for Kenya is that international governmental and local government funding is much more uncertain and limited – so we're actively exploring as many channels as we can to keep sites like Kenya permanently established.

Outside of our Kenya plans, I took a quick pivot to share some thoughts in our finance stream on another competitor in the space. Weather is a pretty small industry and so I passed on some latest insights I had come across. If I take a step back, the former consultant in me tends to seek external benchmarks often, but this is an old habit I'm learning to curb and be more thoughtful in how I manage. In truth, there's a fine line between trying to extrapolate learnings from competitors but then also not comparing ourselves to a benchmark that isn't accurate.

🚗10:30am – Commute
Drove into the office and avoided the morning traffic. At a startup, I definitely have a lot more flexibility in my day than in any of more previous roles. It so happens that WindBorne is a young team, mostly engineers, so it's not uncommon to see folks come into the office on the later end (you can correct my bias if you disagree that most engineers are nocturnal). In contrast to the regimented corporate schedule in consulting, WindBorne feels dynamic and quite chaotic. But I think of it more like "chaordic" – chaos + order – which was coined by Dee Hock, the Founder of Visa. One of our core company values is "Chaos and failure are features, not bugs".

🛠️11am – Walking into a Hardware Business
Settled into the office – most of our team is fully in-person, given we're a hardware business. After a few years of remote work during COVID and most of my career building solutions for other businesses, it feels electric to walk into our office and see a tangible product being built. We build our weather balloons at our "balloonfarm" (i.e. our manufacturing floor) and then you can later see float off into the atmosphere – keep an eye out for a clear balloon if you're ever driving on the 101...

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💸12:30pm – Finance & Project Management
Synced with our finance engineer and a third-party team where we reviewed account logistics. More logistics than strategy but necessary to keep a pulse check on our finances including the latest treasury rates to maximize on interest. In the same line of thought, I drafted up an internal project tracker for all of our latest finance action items. This is part of our ongoing effort to upgrade internal systems using new AI tools. At the risk of repeating "AI is changing the world", at WindBorne, we're starting with upgrades to internal system upgrades. Whereas once go-to enterprise solutions were off-the-shelf products provided by major SaaS companies, thanks to AI, we can explore more tailored solutions.

🤝1pm – Conversations in BD
Jumped into a call with the CEO & Founder of another weather-forecasting startup but their focus is on the insurance market. While WindBorne isn't prioritizing insurance products today, it was insightful to hear from another founder on what is working vs. not.

As a bit of background note: we get a number of inbound BD related conversations, an investor helped facilitate this one through their network.

Plenty of tidbits to noodle on but as we kept chatting, the CEO's background in energy trading came up and ended up being incredibly relevant to our existing commercial product (WindBorne Trader is currently our priority commercial product). It's always fun when discussions lead to unexpected follow-ons and I was shameless in asking if I could later connect him with our Head of Commercial Growth.

💰1:30pm – Tax discussion
Met with our tax consultants. Huge respect for the work they do but little insight to share in depth... I've yet to crack the code on enjoying tax-related work. I jokingly told our consultants that they reminded me of going to the dentist: you dread the topic but the people are always the kindest.

🌍 2:30pm – Synergies with Gates Foundation grantee
Hopped into a call with another grantee of the Gates Foundation. As a part of Gates' broader portfolio of solutions dedicated to agricultural development, we work closely with the other grantees. We discussed ways that her organization can help support the work we're doing in Kenya – she had recently returned from a visit to Nairobi and shared some observations from her trip.

🎈 3pm – Interview Wrap-up + Balloon Launch
Met with an interview candidate as the final discussion of their onsite. We bring all candidates to our HQ as part of their final interview stage. These chats are a chance to hear how the day went, answer lingering questions and offer a candid view of WindBorne. In these discussions, I get to sit at a unique intersection – supporting candidates as they assess their fit while also helping our team make informed decisions when we're ready to extend an offer.

We happened to have a balloon launch happening at the tail end of our conversation—always a fun moment to share a launch with first-timers and see the excitement as a balloon drifts off.

🧹4pm – Heads down working time
Thankfully, no more meetings today but hopped into some work including:

• Shared a draft of our upcoming All Hands to our CEO
• Picked up some action items from the afternoon tax meeting – and pulled in our Exec Admin to help find some of the key tax and financial docs to send
• Put a pin to revisit the build-out of a balloon launcher tracker for our various sites. As mentioned above, we now operate out of 4 continents and have 6 international sites (when I started in late 2023, we were at 1 international site). As such, with payments flowing to our contractors all around the world, I was supporting our Bookkeeper in setting up a system to track payments.
• Jotted down thoughts on managing our legal counsel as we reviewed our spend on immigration. WindBorne sponsors employees (and as an immigrant myself, I'm very grateful for this). This was a routine audit to check on our spend around the business.

🚗6pm – Wrap-up at office and some reflections overall

• This was a particularly meeting-heavy day. I have "working blocks" built into several days to try and create more productive heads-down time. Then there are other days – like this one – and I like to stack more back-to-back conversations.
• Also worth noting: how my calendar looks in the morning isn't often reflective of what was done during the day. It's common for unexpected things to come up. Putting out fires and keeping things running for the rest of the team is just a part of my role.
• Be available at odd hours. Although I don't love sticking around the office once it gets dark, the work doesn't end when the sun goes down. But it's also not about being always-on. WindBorne has an intense pace – and it should – but knowing how you work best (be it after an OrangeTheory workout at 6:30pm or heading into the office at 2am), and being thoughtful about how your team can rely on you is key.
• Context-switching is the job. A Chief of Staff role is a generalist position. You can carve out deep dives (as I have in the humanitarian work), but most days are defined by jumping between functions, teams and problems.
• There were more external than internal discussions on this day. On another day, I might just as easily find myself in internal meetings across different teams. It's worth noting, sometimes the best discussions happen in more casual settings – at a lunch get-together, while carpooling, or during a quick hallway chat.
• And yes, we talk about the weather, a lot. At WindBorne, we sit across the entire value chain of the weather solution: from data collector, to modeler and forecast producer, to insights generator. I have a copy of "Weather for Dummies" to help fill in some gaps but it doesn't quite do justice to hearing our Director of Meteorology walk through a weather event in real-time, or listening to our CTO recount his weekend trek to retrieve a sensor package from Angel Island.

Every day, I get to learn something new and seeing how the company has grown, the impact we can make as we continue to scale... that never gets old!