Technical Program Manager Jobs in Milton, ON (NOW HIRING)

With millions of diners, 70,000+ 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 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. This posting is for an existing vacancy.

Responsibilities

• 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.

Minimum Qualifications

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

Preferred Qualifications

• Prior software engineering background or deep, direct technical experience in software development 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, and adapting product development lifecycles to emerging technology shifts.
• 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.

Benefits and Perks

• Generous paid vacation + time off for your birthday
• Work from (almost) anywhere for up to 20 days per year
• Focus on mental health and well-being:
  • Company-paid therapy sessions through SpringHealth
  • Company-paid subscription to Headspace
  • Annual company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)
• Paid parental leave
• Paid volunteer time
• Focus on your career growth:
  • Development Dollars
  • Leadership development
  • Access to thousands of on-demand e-learnings
• Travel Discounts
• Employee Resource Groups
• 20 days of paid time off
• Private health and dental insurance
• Life and Disability insurance

The best connections happen face-to-face, whether you're sitting down to dinner or having coffee with a coworker. That's why OpenTable has adopted a hybrid workplace model. 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.

Work Environment & Flexibility

At OpenTable, we pride ourselves on fostering a global and dynamic work environment. As a team member with us, you will benefit from a schedule tailored to accommodate a global workforce operating across multiple time zones. 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're committed to creating a workplace where everyone feels they belong and can thrive. We know the best ideas come when we bring different voices to the table, so we're building a team as dynamic as the diners and restaurants we serve-and fostering a culture where everyone feels welcome to be themselves.

If you need accommodations during the application or interview process, or on the job, we're here to support you. Please reach out to your recruiter to request any accommodations.

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