If you’ve done any digging on the Chief of Staff role, you’ll know that it looks different at every company.
But for early stage startups, there’s two big buckets the role usually falls into — the role typically own some big swath of 1. internal operations (like Finance, People Ops, Investor Relations, Team Comms, and so on), and 2. support the Founders with GTM work (experiment on new growth channels, help with customer onboarding and support, wrangle product and marketing to talk more…). There are other buckets, but I find these two to be the most common for early teams.
While Chief of Staff happens to be the title that captures this work right now, every few years, there’s a new trendy title to represent the role: I’ve seen GM, Ops & GTM Lead, First Business Hire, even “Helper.” But the role has always been there, and the work has always been done by some mix of full-time, part-time, and contracted people.
This week, I speak with Hello Generalist member Whitney Smith on this topic. Whitney’s a familiar name in the early stage startup world: she’s been the first, or super early, GTM and Ops hire inside 6 YC-backed companies, including Elpha, Crowdbotics, and her current team at Factored Quality.
Structurally, her work’s been a true mix of full-time, part-time, and project contracts. Proof that smart people GSD — no matter how many hours they’re working for you.
These days, she’s Chief of Staff at Factored Quality, and also takes on Ops and GTM Advisory roles with early stage teams (you can hire her through HG). I loved Whitney’s energy, and she had me laughing out loud and nodding along during our recording time. I know you’ll enjoy learning from her!
Drop 1. GTM experiments? Start with the playbooks that have already worked.
“I don’t think there’s anything wrong with taking someone else’s playbook, especially if it’s tried and true. If you have read an article, listened to a podcast, where someone talked about a playbook they ran that worked for them — maybe you can duplicate that.
This early stage growth work doesn’t have to be expensive. I joke that it’s $free.99!”
Take it back to your team:
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Whitney references the famous Champagne Campaign that Sam Blond ran early on at Brex. Read about it here, and check out this great thread where Sam helps founders ideate their own versions of the campaign (make the idea yours!).
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Abstracting out the Champagne Campaign idea, Whitney names that people just love hand written notes — it’s basically free. When’s the last time you received a note from someone? It feels great. This, of course, is just an example. There are tons of other highly personalized ideas like this that will get you in front of your target customers.
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Another affordable idea her teams use early on: Content. At Factored Quality, they worked with an outsourced content agency to build case studies, expert pieces, and website writing. Content works 24/7 for you.
Drop 2. Build relationships with investors before you need to raise
“I’ve heard the argument many times that founders don’t think it’s a good use of their time to write investor updates. I could not disagree with that more! We do it monthly, I think that makes sense for a startup where things change quickly.
If you do it well from the onset, it can open up a tremendous amount of potential for you as a founder, for acquiring new talent, for lead generation as well.”
Take it back to your team:
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At Factored Quality, she built an “IRM,” an Inventor Relations Manager, just like your CRM, but for Investors instead of Customers. It wasn’t fancy — it held data on current and future investor information, comms history, cap table details, and more. It helped them get clear on and feel confident about their future investor pipeline.
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Whitney organizes her investor updates with sections called The Great, The Good, The Bad, and The Ugly. They add notes and metrics (using the same 4 - 5 key metrics every time) in each section.
Drop 3. Hire operations people who prioritize your customer’s experience
“There was a whole bunch of assumptions being made about our customer hand-off process. As they were scaling incredibly fast, it became a problem, not just internally for team process, but also for customer expectations.”
Take it back to your team:
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While it gets a dirty rep, building process isn’t a bad thing — process is a system that lets manage expectations for your customers, your internal team, and your product.
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When you’re hiring for early operations folks, there’s no doubt they’ll be process oriented, organized, great project and team wranglers. But Whitney advocates for another skill: consider interviewing on customer experience. The best early operations hires build process with the customer in mind — full stop.
Drop 4. Joining an early stage startup? Spend your first 30-60 days getting stuff done.
“It’s not glamorous, it’s not sexy, it’s not a secret sauce. It’s quite literally sitting down with the Founder/CEO to outline a list.”
Take it back to your team:
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Whitney’s come into 6 startups as an early or first GTM / Ops hire. She’s a pro at spinning up fast: sit down with the founders, make a list of what needs to be done, prioritize it, then start working. That’s it!
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Like she names, the simplest tasks (especially the ones that are lingering!) are often the right place to start: pick up a few, get them done fast, and you’ll see the team start to trust you.