Director of Technical Program Management

• As the Director of Technical Program Management, you will lead and scale a mature, high-performing team of Technical Program Managers responsible for driving execution across multiple product and engineering verticals
• Operating at a strategic level within OpenTable’s engineering organization, this role balances roughly 50% managing senior executives and 50% leading and mentoring individual contributor TPMs
• You will absorb ambiguity, translate complex business strategies into practical execution plans, and design robust operating rhythms and governance frameworks that impact hundreds of engineers across the organization
• This is a pivotal opportunity to act as a change leader and help rethink product development lifecycles and software delivery models as AI rapidly transforms the software development lifecycle. In an environment that values professional growth, trust, and a welcoming culture, you will establish execution standards that maintain visibility and accountability for executives while granting teams the flexibility to execute in smaller, faster, and more effective increments
• Executive Management & Collaboration: Serve as a strategic partner to senior leadership and cross-functional executives across Product, Engineering, Design, Data,
• Security, Infrastructure, and business teams to align priorities, manage dependencies, and establish high-stakes escalation paths
• Team Leadership & Mentorship: Direct, coach, and elevate a mature group of individual contributor TPMs, fostering an inclusive, high-performing culture anchored in trust, psychological safety, mutual accountability, and long-term career growth
• Operating Model Transformation: Design, iterate, and embed corporate operating rhythms, delivery mechanisms, planning frameworks, and risk management standards across large-scale technical portfolios to raise the organizational bar for execution quality
• Strategic Execution & De-escalation: Translate broad executive narratives into actionable program structures, timelines, and measurable outcomes while defusing complex, organization-wide conflicts through fact-based option analysis
• Process Optimization: Partner with engineering leadership to improve overall software delivery practices, technical planning, and developer productivity, utilizing modern tooling and data-driven metrics to mitigate hidden organizational drag

Benefits

• Generous parental leave
• Generous paid vacation + time off for your birthday
• Paid volunteer time
• Enriched learning and development opportunities - leadership development & access to thousands of on-demand e-learnings
• Work from (almost) anywhere - wherever you do your best work
• Mental health and well-being - company-paid therapy sessions through SpringHealth, company-paid subscription to HeadSpace, and company-wide weeks off a year so the whole team can recharge- 5+ years of experience formally leading, developing, and retaining engineering or program management teams within high-growth technology environments
• Demonstrated technical fluency and credibility, with the ability to engage deeply with engineering leaders on software architecture, dependencies, trade-offs, and release management
• Proven track record of managing technical program portfolios across complex, multi-entity organizations, including driving organizational transformation and designing cross-functional operating models
• 10+ years of technical program management experience spanning large-scale software development and cross-functional technical programs
• Exceptional executive presence and communication skills, with a verified ability to influence senior stakeholders and turn ambiguous priorities into concrete operational plans
• Prior software engineering background or deep, direct technical experience in software development lifecycles (SDLC) and developer productivity tooling
• Familiarity with or an active interest in automation, AI-enabled engineering workflows, and adapting product development lifecycles to emerging technology shifts
• Experience leading program management functions within two-sided marketplaces, high-scale consumer tech, SaaS, fintech, or hospitality engineering organizations
• Experience operating effectively within a globally distributed workforce across multiple international entities and time zones
• An entrepreneurial mindset with a high sense of ownership, comfortable building missing structures or running execution loops from scratch in fast-moving environments