Technical Program Management Intern Jobs in Toronto, ON

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.

In this role, you will: 

As a Director of Technical Program Management, you will lead and scale a high-performing TPM team responsible for driving execution across multiple product and engineering verticals. You will define the TPM operating model, establish clear planning and delivery rhythms, and ensure teams can execute against company priorities with clarity, accountability, and speed.

You will partner closely with Product, Engineering, Design, Data, Security, Infrastructure, and executive leaders to translate business strategy into executable technical programs. You will create structure in ambiguous areas, identify risks early, manage dependencies across teams, and build the connective tissue needed for strong delivery across the organization.

This role requires strong technical judgment, executive communication, people leadership, and the ability to operate through ambiguity. You will coach TPMs, influence senior stakeholders, manage high-stakes escalations, and help shape how OpenTable plans, executes, and communicates large-scale technical initiatives.

Key Responsibilities:

• Lead, coach, and develop a team of Technical Program Managers, setting clear expectations for execution quality, stakeholder management, communication, and technical judgment.
• Define and scale the TPM operating model across multiple product and engineering areas, including planning rhythms, execution standards, risk management practices, and leadership reporting.
• Translate company and product priorities into clear TPM responsibilities, program structures, milestones, dependencies, and measurable outcomes.
• Partner with Product and Engineering executives to drive roadmap execution across complex, cross-functional initiatives.
• Oversee portfolios of high-impact technical programs, ensuring delivery health, risk visibility, dependency management, and timely executive escalation.
• Build strong operating mechanisms for planning, execution reviews, launch readiness, dependency tracking, and post-launch learning.
• Coach TPMs to influence across functions and levels, including engineering teams, product leaders, and senior executives.
• Represent the TPM function in senior leadership forums, helping shape decisions around prioritization, sequencing, tradeoffs, and execution strategy.
• Defuse complex org-wide escalations and help teams navigate high-stakes disagreements with clear facts, options, and decision paths.
• Partner with engineering leadership to improve software delivery practices, technical planning, developer productivity, and execution quality.
• Understand technical tradeoffs well enough to challenge assumptions, identify execution risks, and help raise the technical bar across teams.
• Develop executive narratives, leadership updates, and communication frameworks that create clarity across the organization.
• Build and retain a high-performing TPM team through hiring, coaching, performance feedback, succession planning, and career development.
• Create an environment where TPMs operate independently, make strong decisions, and are trusted partners to Product, Engineering, and business leadership.
• Champion team health, inclusion, and long-term career growth across the TPM organization.

What You'll Bring:

• Minimum Requirements:
• 10+ years of experience in software development program management across cross-functional projects.
• 5+ years in a program management role.
• Experience owning execution strategy across multiple product, platform, or engineering verticals.
• Strong background managing complex, cross-functional technical programs with dependencies across Product, Engineering, Design, Data, Infrastructure, Security, and business teams.
• Proven ability to build scalable operating models, planning processes, delivery mechanisms, and executive reporting structures.
• Strong executive communication skills, including the ability to create clear narratives, simplify complex topics, and drive decisions with senior leaders.
• Demonstrated ability to manage ambiguity, resolve competing priorities, and guide teams through tradeoffs under pressure.
• Strong technical judgment and ability to engage deeply with engineering teams on architecture, dependencies, delivery risks, quality, and operational readiness.
• Experience coaching teams through stakeholder management, escalation handling, risk management, and cross-functional influence.
• Strong understanding of Agile delivery practices, roadmap planning, dependency management, release coordination, and software development lifecycle processes.
• Experience hiring, developing, and retaining senior TPM talent.
• Hands-on experience with tools such as Jira, Confluence, Airtable, or similar planning and execution systems.
• Preferred Qualifications:
• Experience leading TPM teams in a marketplace, SaaS, consumer technology, travel, hospitality, or growth-stage technology environment.
• Experience building or transforming a TPM function, including defining role expectations, career frameworks, operating rhythms, and delivery standards.
• Experience partnering with VP/SVP-level leaders on multi-year technical strategy, organizational planning, and portfolio execution.
• Experience improving engineering productivity, software quality, platform reliability, or technical operations at scale.
• Ability to use data, dashboards, and execution metrics to identify delivery risks, improve predictability, and support better leadership decisions.
• Experience leading senior-level hiring loops and shaping the bar for TPM talent.
• Familiarity with automation, AI-enabled workflows, developer productivity tooling, or technical planning systems.
• Experience working in a global organization with distributed teams and cross-time-zone execution.

• 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
• Generous paid vacation + time off for your birthday
• 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.