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 jobThe 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
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
Competitive retirement and health plans
Note for MA applicants: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this United States located role is $118,000 - $140,000.
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
#LI-CW2
Skills Required
- 5+ years of experience in enablement, onboarding, training, or learning program leadership
- 2+ years of people management experience, including direct leadership of trainers, facilitators, or program managers
- Experience designing or evolving role-based onboarding programs with clear milestones, readiness criteria, and performance expectations
- Experience using data to evaluate training effectiveness and connect onboarding programs to behavioral and business outcomes
- Experience applying AI tools or AI-enabled workflows to learning, coaching, content creation, or performance support
- 7+ years of experience in enablement, onboarding, training, or learning within a go-to-market organization
- Experience supporting sales, account management, onboarding, customer success, or other customer-facing teams
- Experience building onboarding programs across multiple role tracks, regions, or stages of the customer lifecycle
- Familiarity with balancing central enablement ownership and frontline manager accountability within ramp models
- Strong cross-functional leadership and stakeholder management skills, with familiarity using AI to improve enablement efficiency and personalization
OpenTable Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about OpenTable and has not been reviewed or approved by OpenTable.
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Leave & Time Off Breadth — Time off is positioned as generous, including ample PTO, company-wide recharge time, and additional one-off days such as a birthday/celebration day. Paid volunteer time is also included, reinforcing a broad time-off offering beyond standard vacation and holidays.
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Wellbeing & Lifestyle Benefits — Wellbeing support is positioned as a meaningful part of the package, including company-paid therapy sessions and a paid mindfulness subscription. Flexibility policies such as meeting-free Fridays and “work from (almost) anywhere” are also framed as lifestyle-supporting benefits.
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Strong & Reliable Incentives — Variable pay and upside are highlighted for some roles, especially sales positions where on-target earnings and accelerators can meaningfully raise take-home pay when goals are met. Some postings also indicate eligibility for annual bonuses in certain roles.
OpenTable Insights
What We Do
With millions of diners, tens of thousands of restaurants, and 20+ years of experience, OpenTable, part of Booking Holdings, Inc. (NASDAQ: BKNG), is an industry leader with a unique insight into the world of hospitality. We champion restaurants, bars, wineries, and other venues around the world, helping them attract guests, manage capacity, improve operations, and maximize revenue. 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 network that includes OpenTable and KAYAK's portfolio of travel brands including Swoodoo, checkfelix, momondo, Cheapflights, Mundi and HotelsCombined.
Why Work With Us
Hospitality is all about taking care of others, and it defines our culture. You’ll work in a welcoming and inclusive environment, and get the benefits, flexibility, and support you need to succeed.
