Director, Operations & Enablement, Go-To-Market (GTM)
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- Toronto, ON
- Permanent
- Temps-plein
- 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
- 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
- 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
- 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
- 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
- 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
- 8-12 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
- 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
- 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
- 20 days of paid time off
- Private health and dental insurance
- Life and Disability insurance