Director, Operations - Chicago - OpenTable

Description

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

With millions of diners, 60,000+ restaurant partners and 25+ years of experience, OpenTable, part of Booking Holdings, Inc., 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 Role

The 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 Responsibilities

Full-Funnel GTM Enablement Strategy

• Define and execute a comprehensive GTM enablement strategy that supports the entire customer lifecycle: demand generation, sales conversion, onboarding, adoption, expansion, and retention
• Align enablement priorities with company goals, marketplace dynamics, and GTM strategy
• Act as a strategic partner to GTM leaders to improve readiness, productivity, and execution

Sales, CS & Partner Enablement

• Design and deliver onboarding, ramp, and continuous enablement programs for Sales, Customer Success, Account Management, and Partner-facing teams
• Reduce time-to-productivity for new hires and drive performance improvement for tenured reps
• Support multiple GTM motions (new business, expansion, renewals, cross-sell) across buyer and seller personas in a B2B2C marketplace model

Messaging, Content & Playbooks

• Own the enablement content ecosystem including playbooks, messaging frameworks, pitch decks, battlecards, use cases, and talk tracks
• Ensure content reflects differentiated marketplace value propositions for all sides of the platform
• Partner with Product and Marketing to drive launch readiness for new products, features, pricing, and GTM motions

Marketplace & Cross-Functional Enablement

• Enable teams on the nuances of selling and supporting a two-sided marketplace, including value articulation, supply/demand dynamics, and customer outcomes
• Partner closely with Product, Marketing, and RevOps to ensure consistent messaging, processes, and tooling across the funnel

Process, Tools & Scale

• Partner with Revenue Operations & Sales to optimize GTM processes, workflows, and systems that support scalability
• Evaluate, implement, and manage enablement tools and platforms
• Ensure enablement programs are efficient, repeatable, and built to scale with growth

Measurement & Impact

• Define 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 programs
• Communicate impact and outcomes to GTM and executive leadership

Qualifications

• 812 years of experience in GTM Enablement, Sales, Revenue Operations, or related roles
• Experience supporting full-funnel enablement in a B2B SaaS environment
• Experience working in or enabling a marketplace or multi-persona GTM model strongly preferred
• Proven ability to influence and collaborate across Sales, Marketing, CS, Product, and Ops
• Strong program management, communication, and stakeholder management skills
• Data-driven mindset with a focus on measurable business outcomes

What Success Looks Like

• Faster ramp and improved productivity across customer-facing roles
• Clear, consistent execution of GTM strategy across the funnel
• High confidence and readiness during product launches and GTM changes
• Demonstrable revenue and retention impact tied to enablement efforts

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

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 based role is $175,000 -$245,000 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 & 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 serveand 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.