Culture Uncovered

Ever wonder what it's like to work for the best companies in the world? Maybe you’re actively looking for a new job. Or maybe you’re thinking about your next strategic career move.

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Each week we meet with talent leaders at companies you’ve heard of - and many organizations you haven’t. Giving you a behind-the-scenes look at what it’s like to work there…before you even apply.

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Culture Uncovered

Stack Overflow

January 28, 2026 • Recruit the Employer • Season 1 • Episode 33

If “no surprise medical bills, ever” sounds like a dream perk, Stack Overflow might be your next favorite place to work.

In this episode, Jena chats with Stack Overflow’s Chief People & Culture Officer, Debbie Shotwell, about building an inclusive, mission-driven, fully remote culture where experimentation is encouraged and growth is real. They dig into how a beloved public Q&A platform for developers evolved into a global business with enterprise products, ads, and AI partnerships, plus how Stack Overflow navigates change with radical transparency.

What you’ll learn:

Stack Overflow’s public Q&A platform for developers, Stack Exchange network, enterprise tools, ads, and AI data deals with Microsoft, Google, AWS.
From 2008 garage startup to $200M business serving devs in 118 countries.
Fully remote for 320 Stackers across engineering, product, sales, marketing, and people teams.
Welcoming culture with buddies, ERGs, flexibility, and safe experimentation (no one’s an expert in AI).
Internal mobility via marketplace, Stack Overflow Academy, and 12-18% promotion rates.
Transparent leadership post-restructuring, with growth and selective hiring ahead.

Stack Overflow highlights:

Founded: 2008

Team size: 320 employees worldwide

Ownership: Acquired by Prosus in 2021; operates independently

Work model: Fully remote, global team

Culture: Mission-driven, welcoming, flexible, inclusive, experimental, transparent

Unique Perks & programs:

100% company-paid health benefits (medical, dental, vision) + HRA covering all deductibles
16 weeks paid parental leave for all; 4-week sabbaticals after 5/9 years
Monthly Learn, Share, Grow Days + $2,500 annual development budget
Nine ERGs, monthly AMAs, inclusion/engagement surveys with action
Internal “marketplace” for cross-team projects and boomerang opportunities

To learn more about The Stack Overflow: