Head of Revenue Enablement & Onboarding

OpenTable; Toronto (OH); Hybrid; USD 111,000 - 118,000; Full time

Benefits offered by this job

Work from (almost) anywhere for up to

Mental health support

Parental leave

Generous vacation

Volunteer time

Development Dollars

Leadership development

On-demand e-learnings

Travel discounts

Employee Resource Groups

Private health and dental insurance

Life and Disability insurance

Job summary

OpenTable, part of Booking Holdings, seeks a Lead, Sales & Revenue Enablement to guide a high-performing team of New Hire Trainers and build scalable onboarding for Restaurant Sales and Services.

You will drive end-to-end ramp strategy, define milestones, and leverage data-driven insights and AI-enabled tools to accelerate value and revenue. Collaboration with Revenue Operations and GTM leadership is essential for continuous alignment.

Qualifications

• 5+ years in Sales/Revenue Enablement, GTM program management, or commercial learning and development.
• 2+ years of direct people management experience.
• Proven track record of designing, scaling, and executing onboarding programs tied to revenue milestones.
• Data-driven enablement with performance analytics.
• Experience implementing AI tools or AI-assisted workflows in learning or sales tools.

Responsibilities

• Lead, coach, and develop New Hire Trainers to foster a high-performance onboarding culture.
• Own the multi-track onboarding strategy and end-to-end program design with standardized milestones.
• Design and scale ramp frameworks across sales, account management, and customer success.
• Establish enablement metrics to track ramp velocity, skill adoption, and revenue impact.
• Evaluate and deploy AI-enabled tools to personalize learning paths and optimize coaching.

Skills

People leadership

Coaching

Program strategy

Onboarding & ramp

Data-driven enablement

AI-enabled learning

Tools

AI-enabled tools

Job description

OpenTable, part of Booking Holdings, seeks a Lead, Sales & Revenue Enablement to guide a high-performing team of New Hire Trainers and build scalable onboarding for Restaurant Sales and Services.

You will drive end-to-end ramp strategy, define milestones, and leverage data-driven insights and AI-enabled tools to accelerate value and revenue. Collaboration with Revenue Operations and GTM leadership is essential for continuous alignment.