Q&A: Chief of Staff @ Series-B startup. Knowledge dump
Other details: Ex-consultant, and I'm very pro- joining a startup for those on the fence (even right now). I held a couple other roles at the same startup before becoming CoS (think: generalist roles, quick promotions).
I've gotten tons of useful information from WSO over the years, but there isn't a lot on this site about the consulting --> startups route. Feeling the holiday spirit so please ask away!
What are the challenges of joining a startup? Comps?
Compensation is a big one, if you're coming from a banking or consulting background. Your first comp package will almost certainly be lower TC than your current one, even when you assign a reasonable value to the equity component. That said, you can get promoted and level up from a comp standpoint very quickly (as little as 9-12 months for top performers). An analogy I use half-jokingly is professional athletes who are on a "rookie deal" to start and then get their "max contract" after they show how they valuable they are to the company (and if you're not into sports, I'm essentially saying you are paid below market to start, but then it catches up fairly quickly).
Another challenge is the lack of clear career model or promotion ladder. Most non-technical, non-sales teams (think: finance, bizops, strategy) will only have a couple people so this is understandable. This is especially pronounced for the Chief of Staff role -- as a CoS, if you are looking to stay at the company long-term, you will need to identify functional roles where you could see yourself leading the team OR identify potential "general manager" type roles if the business is launching a new product or entering new markets.
Obviously each company will have their own challenges, and they will almost always fundamentally come down to one of two things: culture and ambiguity. If you don't get along with the people and you don't see a path to product-market fit, you will probably not enjoy the startup experience.
Thanks for the thread. I have a few questions.
Do you mind sharing what kind of company? b2b saas? b2c?
Why are you pro-joining a startup?
What is the path to becoming Chief of Staff?
What does your day to day look like, and do you think it equips you with skills to start your own company?
B2B SaaS. We sell into insurance companies and large app developers, so we have long sales cycles and high ACVs. We have customers globally but 80-90% of the business is focused on the US.
In short, I love seeing the direct impact of my work in building something that's never been done before. Downstream of that, it's refreshing to work with people that are highly aligned -- ie, strong incentive alignment and minimal politicking. You are constantly pushed outside your comfort zone, which I think is healthy and makes it more fun overall than a job you get paid highly to do, but that you could do half-asleep.
There are two paths: external hire and internal hire. If you're an external hire you pretty much have to have 5-8 years of consulting, banking or PE/VC experience (you do NOT need startup experience). However, many startup CEOs will prefer to hire internally if there's a strong candidate with a proven track record at their startup. The unfortunate truth is that CEOs will usually look externally because not enough smart generalists work at startups, so the internal pool is often limited. If being a chief of staff is your goal and you don't have the traditional background, go work at a startup, crush it and let everyone (including the CEO) know that that is your goal.
Day to day varies depending on the time of the year or quarter, but on average, I will have 3-5 hours of meetings, 2-3 hours of heads down spreadsheet and slides work, and another 2-3 hours of informal catchups/brainstorming/admin/slacks/emails. There are some recurring projects like board presentations and company goal-setting that hit every quarter and take up a lot of time in short bursts. Then there's a whole bucket of work I'd consider "special projects" that might include fundraising, strategy, modeling and deep dives with specific functional teams to solve problems (eg, "our customer onboarding is too time-intensive...how can we streamline it?" or "prospective customers are confused by our pricing tiers...is there a better way to organize them?"). IMHO these are the really fun projects because they're usually ambiguous, cross-functional and high-impact.
To answer your last question -- yes. I have found the Chief of Staff role to be a great experience in building the skillset I need to be a successful founder. It's incredibly eye-opening to work directly with the CEO every day and appreciate the nuances of truly running a business.
Thanks for all the insight SB+
Few more questions came to mind if you don't mind. How did you go about looking for the start up you work at? And how do you judge if the start up is a winner?
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