Jacob Stringfellow

Software Engineering Manager @Playlist

San Luis Obispo, CA, US

I lead the Developer Experience squad at Playlist, where we focus on removing friction, modernizing systems, and driving adoption of tools and practices that empower 400+ engineers to deliver high-quality software with speed and confidence. My role combines technical leadership, people development, and cross-organizational strategy; balancing near-term impact with long-term architectural direction.Highlighted Initiatives- AI-powered developer assistant: Conceived, developed, and scaled an internal AI application now used by 100+ engineers weekly, integrated across PR reviews and Slack. Described by leadership as “probably the strongest contribution to MB engineering in two years.”- AI Coding Assistants: Evaluated, negotiated, and implemented Cursor & GH Copilot adoption, growing active usage to 75% of developers. Optimized licensing and built a compliance and security framework around generative AI- GraphQL Standardization: Drove company-wide rollout with governance, training, and Apollo partnership, saving 2,300+ dev hours and eliminating legacy BFFs- Feature Flag Lifecycle Management: Designed and executed a phased strategy that removed 1,800+ stale references and 400+ abandoned switches, reducing technical debt and production risk- Engineering Rotation Program: Created a rotation model enabling engineers to explore new domains, contribute cross-team, and accelerate career growth.Leadership & Culture- Mentored engineers through promotions, role transitions, and performance challenges- Introduced growth frameworks, quarterly check-ins, and shield roles to boost engagement- Contributed to interview calibration, rubrics, onboarding, and Culture Council initiatives- Manage 10+ strategic vendor partnerships (Apollo, Cursor, GitHub, LaunchDarkly, OpenAI, etc.) and guide GQL/AI adoption- Trusted advisor leveraging 12 years at the company to guide leaders and squads through complex product and technical decisions.