Director, Technical Program Management (Hybrid)

Remote Location - Ontariofull timeRemote

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senior

$220k–$240k

H1B: yes

Opentable Director of Technical Program Management at OpenTable leading a team of TPMs and collaborating with senior leadership to drive execution across product and engineering. This role focuses on strategic execution, operating model transformation, and team mentorship.

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.

Qualification

5+ years of experience formally leading

Required

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

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

PTO
Equity/RSU
Annual Bonus
Parental Leave
Life Insurance
Wellness

Company

Opentable

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Source: greenhouse

Active within the past hour

Remote-friendly

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