Cypress HCM · 1 day ago
Enablement Program Manager
San Francisco, CA
Contract
Onsite
Senior Level, Lead/Staff
$45.37/hr - $51.72/hr
8+ years expCypress HCM is seeking a seasoned Enablement Program Manager to own and scale their sales enablement systems, tools, and insights. The role will be critical in translating enablement strategy into execution, ensuring field teams are equipped and informed through data-driven insights.
Human ResourcesInformation TechnologyStaffing Agency
Responsibilities
Own the execution, operationalization, and continuous improvement of enablement systems and tools supporting central programs and go-to-market strategies
Serve as the subject-matter expert for enablement platforms (e.g., Gong, Highspot), driving adoption, best practices, and scalability
Translate enablement strategy into clear roadmaps, milestones, and execution plans
Drive actionable insights from enablement tools (e.g., Gong conversation intelligence, Highspot content usage) to inform sales effectiveness, coaching priorities, and program optimization
Partner with Sales, Enablement, and RevOps to surface trends, gaps, and opportunities that improve seller productivity and revenue outcomes
Establish and maintain metrics, dashboards, and reporting tied to enablement impact
Partner closely with Revenue Operations, Market Managers, Territory Leads, CRM, IT, and external vendors to define and deliver the enablement systems and processes required to support business growth
Act as a trusted advisor to field leaders, balancing strategic priorities with day-to-day operational needs
Proactively identify risks, dependencies, and tradeoffs—and escalate issues with clarity and recommendations
Prioritize and manage incoming enablement requests to align with company and field goals
Provide guidance, training, and troubleshooting support for enablement systems and workflows
Support rep onboarding and ongoing learning programs, ensuring tools and content are effectively integrated into the seller journey
Qualification
Required
8+ years of combined experience in sales operations, enablement, or related roles, with a proven track record of managing complex, cross-functional programs end to end
Deep hands-on experience with sales enablement tools, including Gong and Highspot
Demonstrated ability to analyze data and generate insights that influence sales behavior and outcomes
Experience working across the full customer lifecycle (pre-sales, sales, customer success)
Strong strategic and systems-thinking mindset—able to connect dots and translate strategy into execution
Excellent program management skills, with the ability to prioritize, communicate progress, and manage ambiguity
Exceptional verbal and written communication skills, including the ability to tailor messaging to executives and frontline teams
Strong business acumen and ability to build trusted relationships across a complex organization
Proven success operating both independently and collaboratively in fast-paced environments
High attention to detail, strong work ethic, and consistent follow-through
Proficiency in Salesforce, Highspot, Gong, Excel, and Google Workspace
Comfortable partnering with technical teams (CRM, IT) and external vendors
Company
Cypress HCM
Cypress HCM is a staffing and recruiting company providing technology and creative recruiting solutions.
51-200 employees
Funding
Current Stage
Growth StageLeadership Team
Mark Lillig
CEO
Philip Oommen
CFO
Company data provided by crunchbase