Platform Delivery Enablement Lead

This hybrid role requires working in the office two days per week. 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 The Platform Delivery Enablement Lead is a technical hybrid program leader who strengthens how Platform Delivery works across Infrastructure Engineering, Security, Enterprise Systems, Corporate IT, Tech Table, Product Engineering, and key vendors. Rather than owning a single project plan, this role designs and improves the operating mechanisms that turn strategy into coordinated execution: intake, prioritization, dependency management, decision forums, readiness reviews, communications, and escalation paths. The role will be central to enabling OpenTable’s AWS migration transformation and helping Platform Delivery adopt AI-assisted ways of working that increase visibility, reduce operational toil, and accelerate high-quality decisions. Success means smoother handoffs, clearer commitments, faster resolution of cross-team blockers, and a scalable delivery model that does not depend on heroic individual coordination. This posting is for an existing vacancy. Responsibilities - Build and continuously improve the Platform Delivery operating system, including planning rhythms, executive reviews, intake and prioritization, dependency tracking, risk escalation, readiness criteria, and decision records across Infrastructure Engineering, Security, Enterprise Systems, Corporate IT, and Tech Table. - Serve as the connective tissue across Platform Delivery and partner organizations, making handoffs explicit; clarify owners, commitments, capacity assumptions, sequencing, and acceptance criteria for work moving between platform teams, Product Engineering, business stakeholders, and vendors. - Enable the AWS migration transformation by establishing integrated delivery plans, migration readiness and sequencing mechanisms, cross-team capacity commitments, architecture and cost decision workflows, and change-management communications for a multi-year, large-scale migration. - Translate platform strategy, OKRs, security priorities, financial trade-offs, and transformation goals into actionable portfolios, decision points, communications, and leadership updates that help teams move with appropriate speed and governance. - Establish practical AI-assisted delivery workflows—such as automated status synthesis, risk and dependency detection, action follow-up, and communications drafting—while keeping human leaders accountable for judgment, approvals, and material decisions. - Identify recurring friction in Platform Delivery interactions, use data and stakeholder feedback to diagnose root causes, and implement playbooks, mechanisms, and continuous-improvement changes that improve predictability without adding unnecessary process. Minimum Qualifications - 8+ years of experience leading complex technical programs, portfolio operations, delivery enablement, technical operations, or a comparable cross-functional role in a technology organization. - Experience coordinating work across infrastructure, cloud, security, enterprise systems, developer platforms, or other foundational technology teams, including complex dependencies and shared capacity. - Demonstrated experience creating or improving operating mechanisms such as intake, prioritization, planning cadences, dependency and risk management, readiness reviews, executive reporting, and escalation forums. - Experience leading transformation enablement for a major technology change, such as cloud migration, platform modernization, security transformation, or an enterprise operating-model change. - Strong written and verbal communication skills, with the ability to turn complex technical and organizational issues into clear decisions, commitments, and messages for both technical and executive audiences. Preferred Qualifications - Experience enabling large-scale projects such as infrastructure migrations or similar cloud transformation involving many services, teams, architectural decisions, cost considerations, and change-management needs. - Experience working across Infrastructure Engineering, Security, Enterprise Systems, Corporate IT, and Product Engineering, with a practical understanding of how platform requests, dependencies, and handoffs move through those organizations. - Experience applying AI agents, automation, or workflow intelligence to delivery management, operational reporting, risk and dependency detection, or knowledge-work reduction—with appropriate human review and governance. - Familiarity with platform financial operations, budget planning, investment trade-offs, security and compliance programs, business continuity and disaster recovery, or executive portfolio governance. - Technical fluency sufficient to engage credibly with engineers and architects, understand delivery constraints and trade-offs, and challenge plans constructively without needing to be the primary implementer. Benefits and Perks - 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. The expected range of compensation for this position based in Toronto, Canada, including commission and/or bonuses, is $140,000-$155,000 CAD. There are a variety of factors that go into determining a compensation 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; 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. 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. #LI-SK1 #LI-Hybrid