Head of Commercial Operations and Enablement

Responsibilities

• Own the GTM data model — ensuring consistent definitions, clean data, and a single source of truth across Sales, Marketing, and Customer Success
• Design and maintain dashboards and reporting that give GTM leadership real-time visibility into pipeline, conversion, retention, expansion, and team performance
• Partner with Finance to align on revenue reporting and forecast methodology
• Establish and enforce data hygiene standards across all GTM systems, with accountability frameworks to sustain them
• Own the GTM tech stack — including CRM (Salesforce), marketing automation, customer success platforms, and any adjacent tooling
• Evaluate, implement, and optimize tools that improve team efficiency and data quality
• Serve as the primary liaison between GTM and IT/Engineering for system integrations and enhancements
• Define, document, and continuously improve core GTM processes — lead management, pipeline governance, handoff protocols, renewal workflows, and more
• Build the operating infrastructure that allows GTM teams to scale without adding proportional headcount
• Identify friction points across the customer journey and lead cross-functional efforts to resolve them
• Own deactivation processes — ensuring customer offboarding is handled with precision, proper documentation, and minimal revenue leakage
• Build and lead the enablement function for all GTM teams — Sales, Customer Success, Implementations, and Contact Center
• Develop onboarding programs, ongoing training, and role-specific playbooks that accelerate ramp and improve consistency
• Create a feedback loop between the field and Product/Marketing so customer and prospect insights inform roadmap and messaging
• Design the reporting cadence that powers weekly, monthly, and quarterly GTM leadership reviews
• Build and maintain the commitment log and accountability infrastructure for the GTM leadership team
• Provide the CCO and GTM leaders with the data and analysis needed to make confident, timely decisions
• Create board and executive-ready reporting on GTM performance across the full customer bowtie
• Own the end-to-end deactivation process for churned or offboarding customers
• Ensure all deactivations are executed accurately, on time, and with proper documentation
• Partner with CS, Finance, and Legal to minimize risk and protect data integrity through the offboarding process
• Identify patterns in deactivation data that surface retention risk signals for the broader CS team

Qualifications

• 7–12 years of progressive experience in Revenue Operations, Sales Operations, or GTM Enablement within a B2B SaaS environment
• Proven track record of building or significantly scaling an operations or enablement function
• Experience owning a GTM tech stack including Salesforce CRM; familiarity with marketing automation (HubSpot or Marketo), customer success platforms, and intent data tools (6sense, Demandbase) is strongly preferred
• Experience in a PE-backed or high-growth environment preferred
• Senior living, healthcare technology, or vertical SaaS experience a plus but not required
• Strong analytical skills — comfortable building models, interpreting data, and translating analysis into actionable recommendations
• Exceptional process design instincts — you see inefficiency and immediately start designing the fix
• Clear, confident communicator who can present data and recommendations to a CCO, CFO, or board audience
• Collaborative by nature — this role succeeds through influence, not authority
• High ownership mentality — you don't wait to be asked, you identify what needs to happen and make it happen