- 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 setting 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

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