Director, Operations & Enablement, Go-To-Market (GTM) (Chicago)

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 that includes and its portfolio of metasearch brands. Hospitality is all about taking care of others, and it defines our culture.About the RoleThe Director of GTM Enablement owns the strategy and execution of full-funnel enablement, ensuring our go-to-market organization is aligned and ready to execute effectively. You will translate company and product strategy into scalable enablement programs that improve productivity, accelerate ramp, and drive measurable revenue impact across acquisition, expansion, and retention motions.This role sits at the intersection of GTM teams, including Support, Onboarding, Sales, Product, Marketing, and Revenue Operations and is critical to ensuring strategy becomes consistent, repeatable execution in the field.Key ResponsibilitiesFull-Funnel GTM Enablement StrategyDefine and execute a comprehensive GTM enablement strategy that supports the entire customer lifecycle: demand generation, sales conversion, onboarding, adoption, expansion, and retentionAlign enablement priorities with company goals, marketplace dynamics, and GTM strategyAct as a strategic partner to GTM leaders to improve readiness, productivity, and execution Sales, CS & Partner EnablementDesign and deliver onboarding, ramp, and continuous enablement programs for Sales, Customer Success, Account Management, and Partner-facing teamsReduce time-to-productivity for new hires and drive performance improvement for tenured repsSupport multiple GTM motions (new business, expansion, renewals, cross-sell) across buyer and seller personas in a B2B2C marketplace model Messaging, Content & PlaybooksOwn the enablement content ecosystem including playbooks, messaging frameworks, pitch decks, battlecards, use cases, and talk tracksEnsure content reflects differentiated marketplace value propositions for all sides of the platformPartner with Product and Marketing to drive launch readiness for new products, features, pricing, and GTM motionsMarketplace & Cross-Functional EnablementEnable teams on the nuances of selling and supporting a two-sided marketplace, including value articulation, supply/demand dynamics, and customer outcomesPartner closely with Product, Marketing, and RevOps to ensure consistent messaging, processes, and tooling across the funnelProcess, Tools & ScalePartner with Revenue Operations & Sales to optimize GTM processes, workflows, and systems that support scalabilityEvaluate, implement, and manage enablement tools and platformsEnsure enablement programs are efficient, repeatable, and built to scale with growthMeasurement & ImpactDefine and track KPIs to measure enablement effectiveness (ramp time, quota attainment, pipeline conversion, win rates, expansion, retention, etc.)Use insights and data to iterate and continuously improve enablement programsCommunicate impact and outcomes to GTM and executive leadershipQualifications8–12 years of experience in GTM Enablement, Sales, Revenue Operations, or related rolesExperience supporting full-funnel enablement in a B2B SaaS environmentExperience working in or enabling a marketplace or multi-persona GTM model strongly preferredProven ability to influence and collaborate across Sales, Marketing, CS, Product, and OpsStrong program management, communication, and stakeholder management skillsData-driven mindset with a focus on measurable business outcomesWhat Success Looks LikeFaster ramp and improved productivity across customer-facing rolesClear, consistent execution of GTM strategy across the funnelHigh confidence and readiness during product launches and GTM changesDemonstrable revenue and retention impact tied to enablement effortsBenefits and PerksWork from (almost) anywhere for up to 20 days per yearFocus on mental health and well-being:Company-paid therapy sessions through SpringHealthCompany-paid subscription to HeadspaceAnnual company-wide week off a year – the whole team fully recharges (and returns without a pile-up of work!)Paid parental leaveGenerous paid vacation + time off for your birthdayPaid volunteer timeFocus on your career growth:Development DollarsLeadership developmentAccess to thousands of on-demand e-learningsTravel DiscountsEmployee Resource GroupsCompetitive retirement and health plansThere 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 based role is $170,000 -$193,000 USD.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 and equity grant.Work Environment & FlexibilityAt 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.InclusionWe’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.