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
At OpenTable, we are dedicated to helping our employees master the skills necessary to drive outstanding customer experiences. As a Senior Enablement Manager, you will act as a performance partner for our customer-facing teams, moving beyond traditional classroom instruction to ensure new hires are field-ready and outcomes-focused. You will design and deliver comprehensive programs that equip new Onboarding Specialists and other field teams with a strong foundation in restaurant workflows, system configurations, and consultative selling. Your work will directly impact our business by embedding yourself in the field, diagnosing performance barriers, and empowering employees to confidently guide restaurant partners through their OpenTable journey. By translating field realities into actionable learning experiences, you will drive tangible ramp-to-productivity and long-term success.
Responsibilities
Design and deliver high-impact enablement: Create scalable training programs that bridge the gap between curriculum and real-world execution, ensuring new hires are ready to drive business outcomes on day one.
Embed in the field to diagnose gaps: Proactively monitor live calls, conduct ride-alongs, and partner with frontline managers to diagnose performance barriers in real-time and iterate on training content accordingly.
Facilitate performance-focused learning: Lead engaging in-person and virtual sessions that prioritize practical application, coaching, and role-based scenarios over simple content delivery.
Own end-to-end readiness metrics: Partner with business leaders to track performance KPIs (e.g., time-to-first-deal, ramp speed) rather than just participant feedback, holding yourself accountable for the long-term success of your cohorts.
Translate field signal to enablement: Act as the feedback loop between the field and product teams, turning real-world objections, competitive pressure, and process friction into actionable talk tracks and practice scenarios.
Manage program execution: Drive the full lifecycle of training initiatives—from cross-functional planning and stakeholder alignment to delivery and post-training analysis—in a fast-paced environment.
Minimum Qualifications
5+ years of corporate learning experience in a mid-to-large organization, with a demonstrated ability to design training that drives measurable sales or operational results.
Demonstrated ability to use CRM (e.g., Salesforce) and call metrics to analyze performance trends, diagnose skills gaps, and adjust programming to improve outcomes.
Exceptional ability to lead high-impact sessions and influence stakeholders at all levels, adapting techniques for diverse learning styles and environments.
Preferred Qualifications
Experience in a field-facing or customer-success role; you’ve “walked the walk” and deeply understand the day-to-day opportunities new hires will face.
Proven track record of managing complex milestones, prioritizing conflicting deliverables, and collaborating effectively with cross-functional teams to keep programs on track.
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 $105,000 - $115,000 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; flexible spending account; 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.
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-Hybrid
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OpenTable Toronto, Ontario, CAN Office
Toronto, Canada
