Director, Technical Program Management (Hybrid) With millions of diners, 60,000+ restaurant partners and 25+ years of experience, OpenTable, part of Booking Holdings, Inc. (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. Hospitality is all about taking care of others, and it defines our culture.

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. This is a pivotal opportunity to act as a change leader and help rethink product developmentlifecycles and software delivery models as AI rapidly transforms the software developmentlifecycle.

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. Translate broad executive narratives intoactionable program structures, timelines,



and measurable outcomes while defusingcomplex, organization-wide conflicts through fact-based option analysis. 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. 10+ years of technical program management experience spanning large-scale softwaredevelopment and cross-functional technical programs. ~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.

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. An entrepreneurial mindset with a high sense of ownership,



comfortable building missingstructures or running execution loops from scratch in fast-moving environments.

Paid parental leave Generous paid vacation + time off for your birthday Travel Discounts Beautiful office in the Empire State Building with lots of building amenities, such as a gym, multi-purpose room, in-building Starbucks, and more. The best connections happen face-to-face, whether you’re sitting down to dinner or having coffee with a coworker. This role aligns with that approach, with an expectation of coming into the office two days a week—giving employees the best of both worlds: in-person collaboration and flexibility.

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required.

We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits. This role is eligible to be considered for an annual bonus and equity grant. At OpenTable, we pride ourselves on fostering a global and dynamic work environment.

While the majority of your responsibilities may align with conventional business hours, there will be instances where you are expected to manage communications - via calls, Slack messages, or emails - outside of regular working hours to effectively collaborate with international colleagues, respond to restaurant partners, and/or address urgent matters. OpenTable will always abide by and consider local laws and regulations.

Inclusion

We know the best ideas come when we bring different voices to the table, so we're building a team as agile as the diners and restaurants we serve—and fostering a culture where everyone feels welcome to be themselves.

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