Staff Technical Program Manager
WFA Digital Insight
As the remote job market continues to evolve, demand for technical program managers with expertise in platform and infrastructure has grown significantly. With over 200,000 organizations relying on Sentry for application monitoring, this role offers a unique opportunity to work with a leader in the industry. Given the current market context, where companies are prioritizing digital transformation and reliability, skills like technical depth, strategic execution, and data-driven decision making are in high demand. Sentry's commitment to innovation and its AI-native future makes this an exciting time to join the team. Before applying, candidates should be aware that they will need to demonstrate a strong ability to lead complex, cross-functional programs and have a genuine appreciation for platform and infrastructure challenges.
Job Description
About the Role
The Staff Technical Program Manager role at Sentry is a critical position that operates at the intersection of technical depth and strategic execution. As a key member of the Platform organization, you will work closely with senior engineering leaders, the VP of Platform Engineering, and partner teams across Engineering, Product, and Design. Your primary focus will be on driving strategic execution, building data-driven delivery health, and managing capacity, dependencies, and risk. The Platform organization is the engine that everything else runs on, spanning developer platform, core infrastructure, SRE, security, and IT, making this a high-visibility role with real influence.The successful candidate will thrive in complexity, build trust with senior engineering leaders, and have a gift for turning ambiguity into clarity and momentum. You will report to the Head of Technical Program Management and work directly with the CTO and senior leaders, shaping how the Platform organization operates and helping Sentry scale through one of its most important chapters.
What You Will Do
- Drive strategic execution by partnering with the VP of Platform Engineering and senior EPD leaders to translate priorities into clear, measurable plans
- Own sequencing, milestones, and key decisions, and ensure leadership always has reliable visibility into progress and tradeoffs
- Build data-driven delivery health by establishing metrics and dashboards that reflect delivery confidence, risk, and engineering health across the Platform organization
- Manage capacity, dependencies, and risk by creating visibility into resourcing, cross-team dependencies, and constraints
- Surface risks early, drive tradeoffs when priorities compete, and keep complex initiatives on track
- Establish and maintain strong relationships with senior engineering leaders, the VP of Platform Engineering, and partner teams
- Develop and maintain a deep understanding of the Platform organization's technical capabilities and limitations
- Collaborate with cross-functional teams to drive alignment and ensure the successful execution of strategic initiatives
- Identify areas for process improvement and implement changes to increase efficiency and effectiveness
What We Are Looking For
- 8+ years of Technical Program Management experience at a high-growth technology company
- Direct exposure to platform, infrastructure, SRE, or security engineering organizations
- Proven ability to lead complex, cross-functional programs spanning engineering, product, and business functions
- Experience defining or improving incident management, on-call processes, or operational reliability programs
- Strong analytical instincts with the ability to build systems to track delivery health and use data to drive decisions
- Demonstrated ability to build structure and operating cadence in environments where neither existed
- Exceptional written and verbal communication skills with the ability to produce high-signal, low-overhead reporting artifacts
- Experience working in a matrixed organization with multiple stakeholders
- Strong understanding of platform and infrastructure challenges and their strategic implications
Nice to Have
- Experience with agile development methodologies and DevOps practices
- Familiarity with cloud-based infrastructure and security technologies
- Knowledge of data analytics and visualization tools
- Experience with incident management and crisis communications
- Certification in program management or a related field
Benefits and Perks
- Competitive salary and equity package
- Comprehensive health, dental, and vision insurance
- Generous PTO and holiday policy
- Remote work stipend and flexible working hours
- Professional development opportunities and conference sponsorships
- Access to cutting-edge technologies and tools
- Collaborative and dynamic work environment
- Recognition and reward programs for outstanding performance
How to Stand Out
- Develop a strong understanding of platform and infrastructure challenges and their strategic implications to stand out in the application process
- Be prepared to provide specific examples of your experience leading complex, cross-functional programs and driving strategic execution
- Familiarize yourself with Sentry's products and services to demonstrate your interest in the company and the role
- Highlight your ability to build strong relationships with senior engineering leaders and other stakeholders
- Prepare to discuss your experience with data-driven decision making and your ability to build systems to track delivery health
- Be ready to provide examples of your analytical instincts and problem-solving skills
- Research the company culture and values to ensure alignment with your own goals and expectations
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