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:

• Careers Page (They're hiring!)
• Linkedin Page
• Debbie's Profile