Lead, Sales & Revenue Enablement (New Hire Programs)

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.

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

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.

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