Thinking Like An Owner As A Chief of Staff with Sarah Smith
Episode Summary:
Sarah Smith, Chief of Staff at Cubby, shares how her entrepreneurial mindset, forged through childhood micro-businesses and a COVID-era greeting card business, shapes the way she approaches her CoS role. From pulling reports to building AI-powered dashboards with Claude, Sarah reflects on why the best Chiefs of Staff don't wait to be told what to do, and how career moves and transitions can lead to the perfect eventual fit. Enjoy!
You can connect with Sarah on LinkedIn here!
FULL VIDEO
You can watch the full video of the episode here!
Episode Highlights:
0:00: How Sarah cofounded a Cards business during the pandemic
04:15: Sarah’s early entrepreneurial roots
05:45: How Sarah thinks about working in big corporate versus startups
07:30: How Sarah’s entrepreneurship efforts have supported her Chief of Staff efforts
09:30: Owner mentality and sending “zero-to-one” signals to other people
12:15: How we sometimes under-value our own projects
14:15: Nonlinear path to Cubby & trusting the process
20:30: Ops vs Chief of Staff; building & leading teams
24:45: Practical AI integration using Claude into startup ops
27:45: Productivity amplification via AI
28:45: Advice to Chiefs of Staff & career mindset
Episode Overview
Sarah Smith shares the story of her entrepreneurial journey and how it shapes her work as a Chief of Staff at early-stage startups. She and a college friend started a cards business during the pandemic, aiming to automate handwritten card sending for individuals and companies. Rooted in her family’s strong card culture and wanting to help support of her efforts and desire to remember important dates, the venture became a meaningful side project.
Sarah traces her entrepreneurial streak back to childhood: running a neighborhood plant- and pet-sitting business and operating a very casual “Bank of Sarah Smith.” Studying business at UNC Chapel Hill and interning at a large corporation clarified that slow, bureaucratic environments were not the best fit for her. Venture for America then launched her into early-stage startups, where she’s been ever since.
Now Chief of Staff at Cubby, a vertical SaaS platform for self-storage operators, Sarah explains how the CoS role at early-stage startups differs from big companies: it’s fluid, ambiguous, and focused on filling gaps, owning unclaimed problems, and convening the right people. Her side projects and side businesses, like the cards business, often come up in job interviews as evidence of her Founder-like ownership and zero-to-one initiative.
A major theme of the podcast episode is trusting a nonlinear career path. Leaving a venture-backed tech startup to become GM of a rentals business seemed risky, yet that role required managing 100+ storage units nationwide made her a uniquely strong fit for Cubby. Sarah also details how AI, particularly Claude, has transformed her work by automating data pulls and reporting, allowing one person to produce many times more output. She closes with advice to aspiring Chiefs of Staff: clarify expectations, lean into your strengths, do great work, and stay open to serendipity.
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Connect with Sarah
You can connect with Sarah on LinkedIn here!
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