About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model across our global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About the role

We’re looking for an operationally-savvy and passionate Head of Technical Program Management to be the strategic architect of technical execution for the Engineering, Product, & Design (EPD) organization. Reporting directly to the CTO and partnering closely with the CTO and the EPD leadership team, you’ll help ensure predictable delivery across teams, and build the Technical Program Management (TPM) function from the ground up.

In this role, you will focus on:

• Strategic Execution: You’ll partner with the CTO and senior EPD leaders to turn priorities into clear, measurable plans across teams. You’ll drive sequencing, milestones, and decisions while ensuring leadership has reliable visibility into progress and tradeoffs.

• TPM Org Architecture & Function Buildout: You’ll define the charter and operating model for TPM at Sentry and how the team partners across EPD. You’ll immediately start hiring and developing a high-performing TPM org with strong standards for ownership and execution, while also developing, implementing and continuously refining TPM processes, frameworks and tools.

• Data-Driven Delivery & Engineering Health: You’ll establish metrics and dashboards that reflect delivery health, risk, and roadmap confidence. You’ll keep planning and reporting high-signal and lightweight, focused on outcomes rather than activity.

• Capacity, Dependencies, and Risk Management: You’ll improve visibility into resourcing, constraints, and cross-team dependencies so leaders can align investment to the highest priorities. You’ll surface risks and bottlenecks early, drive tradeoffs when priorities compete, and keep execution focused as plans shift. The goal is fewer surprises and smoother delivery across complex initiatives.

You’ll love this job if you

• You’re energized by complex, cross-team work and get satisfaction from making execution smoother, more predictable, and easier to scale

• You enjoy turning ambiguity into clear plans, strong operating rhythms, and measurable outcomes

• You like working closely with senior leaders, bringing a thoughtful point of view, and helping teams move faster through clarity, coordination, and good decision-making

Qualifications

• 7-10+ years of progressive experience in Software Engineering/Technical Program Management within a high-growth, fast-paced technology company

• Strong organizational skills and an entrepreneurial drive with history of developing high-performing teams

• Strong ability to simplify complex problems and drive alignment among diverse stakeholders

• Strong written and verbal communication skills, with the ability to interact professionally, confidently, and empathetically with internal and external stakeholders

• Proven track record of managing and delivering multiple complex projects across matrix organizations and functional, geographic and cultural borders

The base salary range that Sentry reasonably expects to pay for this position is $280,000 to $320,000. A successful candidate’s actual base salary amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, ski