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Chptr is a media-technology platform that automates the creation and distribution of content for local businesses and media organizations, including major partners like Hearst, Sinclair, Gray Television, and Paramount/CBS. The platform powers storytelling across obituaries, community spotlights, and business announcements, reaching millions while emphasizing dignity, authenticity, and transparency.
As Head of Engineering, you will lead Chptr's technical strategy and execution as the company scales from proven product-market fit in one vertical to a multi-sector marketplace. This is a hybrid hands-on and strategic role: approximately 30% hands-on technical contribution, 70% leadership, architecture, and organizational development.
Key responsibilities include:
- Architect and scale the core platform from MVP to production-grade infrastructure capable of supporting new verticals and marketplace expansion
- Lead and mentor a small, high-performing engineering team; recruit, onboard, and develop technical talent
- Balance hands-on coding with strategic planning—set standards for architecture, testing, and deployment
- Collaborate with VP of Product and Design to translate customer insights into scalable solutions
- Integrate AI capabilities into storytelling workflows, including intelligent content editing and creative-assistive tools
- Champion rapid prototyping and validation using existing APIs and tools before scaling
- Establish engineering best practices in CI/CD, observability, and documentation
- Foster a culture of craft, quality, empathy, and accountability
The role offers direct impact on how local stories are created and shared, equity ownership, and a voice in company direction. You'll work with a senior, mission-driven team that values trust, flexibility, and execution excellence.
Requirements:
- 8+ years of engineering experience, including 2+ years in a leadership or managerial role
- Proven success building or scaling a SaaS or marketplace product from early stage through growth
- Proficiency in Python, TypeScript, React, and AWS (or equivalent modern stack)
- Strong understanding of systems architecture, API design, and data integration
- Experience introducing AI-assisted or automation-driven workflows that improve creative or operational output
- Low-ego, high-ownership mindset; ability to balance velocity with thoughtfulness and empower teams
- Comfort operating in ambiguity and iterating fast while maintaining technical excellence
- Deep empathy for users and customers, especially in moments that matter most to them
