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Lead, Sales & Revenue Enablement (New Hire Programs)
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About this role
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
• 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 communic
Salary insight
The midpoint of this range ($129k) is about 11% below the median disclosed salary for Chicago roles listed on ForgeApply ($145k across 463 jobs).
See full Sales salary data for Chicago →
Based on live postings with disclosed pay on ForgeApply; refreshed daily. Not an estimate of this employer's offer.
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