Director, Technical Program Management (Hybrid)

New York, NY

With millions of diners, 60,000+ restaurant partners and 25+ years of experience, OpenTable, part of Booking Holdings, Inc. (NASDAQ: BKNG), is an industry leader with a passion for helping restaurants thrive. Our world-class technology empowers restaurants to focus on what matters most – their team, their guests, and their bottom line – while enabling diners to discover and book the perfect restaurant for every occasion.

Every employee at OpenTable has a tangible impact on what we do and how we do it. You’ll also be part of a global team and its portfolio of metasearch brands. Hospitality is all about taking care of others, and it defines our culture.

About the Job

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 acrossmultiple product and engineering verticals. Operating at a strategic level within OpenTable’sengineering organization, this role balances roughly 50% managing senior executives and 50%leading and mentoring individual contributor TPMs. You will absorb ambiguity, translate complexbusiness strategies into practical execution plans, and design robust operating rhythms andgovernance frameworks that impact hundreds of engineers across the organization.This is a pivotal chance to act as a change leader and help rethink product developmentlifecycles and software delivery models as AI rapidly transforms the software developmentlifecycle. In an environment that values professional growth, trust, and a welcoming culture,



youwill establish execution standards that maintain visibility and accountability for executives whilegranting teams the flexibility to execute in smaller, faster, and more effective increments

Responsibilities

- Executive Management & Collaboration: Serve as a strategic partner to seniorleadership 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 individualcontributor 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 operatingrhythms, delivery mechanisms, planning frameworks, and risk management standardsacross large-scale technical portfolios to raise the organizational bar for execution quality.
- Strategic Execution & De-escalation: Translate broad executive narratives intoactionable program structures, timelines, and measurable outcomes while defusingcomplex, organization-wide conflicts through fact-based option analysis.
- Process Optimization: Partner with engineering leadership to improve overall softwaredelivery practices, technical planning, and developer productivity, utilizing modern toolingand data-driven metrics to mitigate hidden organizational drag.





Minimum Qualifications

- 10+ years of technical program management experience spanning large-scale softwaredevelopment and cross-functional technical programs.
- 5+ years of experience formally leading, developing, and retaining engineering or programmanagement teams within high-growth technology environments.
- Proven track record of managing technical program portfolios across complex, multi-entityorganizations, including driving organizational transformation and designingcross-functional operating models.
- Demonstrated technical fluency and credibility, with the ability to engage deeply withengineering leaders on software architecture, dependencies, trade-offs, and releasemanagement.
- Exceptional executive presence and communication skills, with a verified ability toinfluence senior stakeholders and turn ambiguous priorities into concrete operationalplans.

Preferred Qualifications

- Prior software engineering background or deep, direct technical experience in softwaredevelopment lifecycles (SDLC) and developer productivity tooling.
- Experience leading program management functions within two-sided marketplaces,high-scale consumer tech, SaaS, fintech, or hospitality engineering organizations.
- Familiarity with or an active interest in automation, AI-enabled engineering workflows, andadapting product development lifecycles to emerging technology shifts.
- Experience operating effectively within a globally distributed workforce across multipleinternational entities and time zones.
- An entrepreneurial mindset with a high sense of ownership, comfortable building missingstructures or running execution loops from scratch in

📌 Director, Technical Program Management (Toronto)
🏢 OpenTable
📍 Toronto