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