Head of Engineering

Head Of Engineering

Location: Remote (US-based) | Type: Full-time | Compensation: Competitive salary + equity

Chptr is a media-technology platform transforming how communities share life's biggest moments — from memorials to milestones.

We partner with local businesses and media organizations — including Hearst, Sinclair, Gray Television, Paramount/CBS, and hundreds of local affiliates — to automate the creation and distribution of media content.

Our fully automated storytelling pipeline powers everything from obituaries and community spotlights to brand and business announcements, helping millions reconnect with local stories told with dignity, authenticity, and transparency.

Our mission is simple: restore trust, transparency, and local connection to the way stories are told.

The Role

Chptr is seeking a Head of Engineering to help us scale from proven product–market fit in one vertical to a multi-sector marketplace.

This leader will be both hands-on (≈30%) and strategic, guiding architecture, process, and people as we grow from a small, senior technical team into an innovative, scalable organization.

You'll partner closely with the VP of Product and collaborate with executives to shape the technical vision, roadmap, and execution across product engineering, infrastructure, and emerging AI-assisted workflows.

What You'll Do

• Architect and scale Chptr's core platform from MVP to production-grade infrastructure supporting new verticals and marketplace expansion.
• Lead and mentor a small, high-performing team of engineers; help recruit, onboard, and develop future technical talent.
• Balance hands-on execution with strategic planning — contributing code while setting standards for architecture, testing, and deployment.
• Collaborate with Product and Design to translate customer insights into elegant, efficient, and scalable solutions.
• Integrate AI capabilities that enhance storytelling workflows — from intelligent content editing to creative-assistive tools.
• Champion agility and scrappiness: prototype quickly using existing APIs and tools to validate ideas before scaling.
• Establish engineering best practices in CI/CD, observability, and documentation to support long-term maintainability.
• Foster a culture of craft and care — where quality, empathy, and accountability drive every release.

What You Bring

• 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.
• A low-ego, high-ownership mindset — you balance velocity with thoughtfulness and empower teams to do their best work.
• 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.

Why Join Us

• Impact: Help shape the technology redefining how local stories are created and shared.
• Ownership: Lead engineering at a pivotal inflection point, with equity and a direct voice in company direction.
• Culture: Join a senior, family-friendly, mission-driven team that prizes trust, flexibility, and execution excellence.
• Innovation: Work at the intersection of media, AI, and local community, where creativity meets meaningful impact.

If you're excited to build systems that restore authenticity to local storytelling — and to lead a team that builds with both speed and care — we'd love to hear from you.

Please send your LinkedIn profile or résumé to View email address on click.appcast.io, along with a brief note on why Chptr's mission resonates with you.