Toronto, Canada

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.

About the job

The Lead, Sales & Revenue Enablement will lead a high-performing team of New Hire Trainers and drive the strategic vision for how OpenTable ramps go-to-market talent across the Restaurant Sales and Services organization. This role owns the end-to-end strategy for building scalable, role-specific onboarding architecture designed to accelerate time-to-value, instill high-performing sales behaviors, and drive repeatable revenue outcomes. As a key strategic partner to Revenue Operations and GTM leadership, you will define the intersection of enablement-led training, certification, and frontline manager coaching while leveraging data-driven insights and AI-enabled technologies to modernize sales enablement at scale.

Key Responsibilities

- People Leadership & Coaching: Direct, coach, and develop a team of New Hire Trainers, fostering a high-performance culture, setting clear priorities, and driving operational excellence across all onboarding programs.
- Program Strategy & Architecture: Own the multi-track onboarding strategy and end-to-end program design, establishing standardized graduation milestones, skill certifications, and readiness criteria aligned with GTM business priorities.
- Building Scalable Programs: Design and scale role‑specific ramp frameworks across sales, account management, and customer success, balancing central enablement delivery with structured frontline manager reinforcement and accountability.
- Data-Driven Enablement & Impact: Establish comprehensive enablement metrics—moving beyond completion rates to track ramp velocity, skill adoption, behavioral changes, quota attainment, and revenue impact.
- AI & Modern Enablement Modernization:



Evaluate and deploy AI-enabled tools and automated workflows to personalize learning paths, enhance role‑play coaching, optimize trainer efficiency, and provide just‑in‑time performance support.
- Cross-Functional Strategic Partnership: Collaborate with Revenue Operations, Sales Leadership, Product Marketing, and GTM teams to ensure ramp strategies continuously reflect evolving field realities and market conditions.

Minimum Qualifications

- 5+ years of experience in Sales/Revenue Enablement, GTM program management, or commercial learning and development.
- 2+ years of direct people management experience, leading team members such as trainers, enablement specialists, or program managers.
- Proven track record of designing, scaling, and executing role‑based onboarding programs tied to measurable revenue and performance milestones.
- Demonstrated capability in data‑driven enablement, using performance analytics to connect learning initiatives directly to pipeline generation and ramp metrics.
- Practical experience implementing AI tools or AI‑assisted workflows within learning, coaching, content generation, or sales execution tools.

Preferred Qualifications

- 7+ years of revenue enablement experience within a fast‑paced SaaS, B2B, or multi‑channel GTM organization.
- Hands‑on experience supporting multi‑track teams across field sales, inside sales, account management, and customer success.
- Expertise in defining the operating model between central Revenue Enablement and frontline sales leadership to drive co‑ownership of onboarding success.
- Strong cross‑functional leadership presence with experience partnering directly with VP- and C-level revenue executives.

Advantages 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
- Focus on your career growth:
- 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 $155,000 - $165,000 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.

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.

📌 Lead, Sales & Revenue Enablement (New Hire Programs) (Toronto)
🏢 OpenTable
📍 Toronto