6+ years in customer success, with 3+ years in management
Experience in SaaS or AI technology
Proven track record with enterprise and Fortune 500 clients
Skilled in using AI and automation for efficiency
Experience in hiring and scaling customer success teams
Ability to manage customer escalations
Expertise in developing customer success playbooks
Data-driven decision-making approach
Responsibilities
Design the customer success operating model and segmentation
Own and report on net revenue retention and expansion outcomes
Define efficiency metrics and set improvement targets
Build relationships with senior leaders at key accounts
Automate routine tasks to enhance strategic engagement
Select and manage customer success tooling and workflows
Develop playbooks for onboarding, renewals, and risk management
Benefits
Medical, dental, and vision insurance
Paid time off and parental leave
Equity options
Company offsites
Continuous education opportunities
Commuter benefits
Flexible work environment
Full Job Description
The Role
As Director of Customer Success, you'll build and lead the team that helps Compa's enterprise customers get lasting value from our platform. You'll set the strategy for how we support, retain, and grow some of the world's largest companies, using data, AI, and automation to deliver a high-touch experience at scale. You'll work closely with Sales, Onboarding, Product, and our compensation experts. You will report to the Chief Revenue Officer (CRO).
What You'll Do
Design the CS operating mode: customer segmentation, coverage model, roles, and the handoffs between Sales, Onboarding, and CS
Own the net revenue retention, gross retention, adoption, and expansion outcomes, and report on them to executive leadership
Define how we measure efficiency (e.g., ARR per CSM, accounts per CSM, cost to serve) and set targets for improving it as we grow
Build relationships with senior leaders at key enterprise and Fortune 500 accounts
AI and automation
Design an AI first CS motion: automate routine work like health scoring, renewal prep, QBR prep, and customer communications, so CSMs spend their time on high-value strategic engagement
Select, implement, and own our CS tooling stack, and build or commission the workflows and agents that surface risk and opportunity early
Make "can this be automated or AI-assisted first?" the default question before any new hire request
Team
Hire, coach, and develop CSMs, and set the standard for what great looks like at Compa
Stay hands-on: act as a player-coach on escalations and key executive relationships, especially in the early stages
Customers and cross-functional partnership
Build playbooks for onboarding handoff, adoption, renewals, risk, and expansion, then keep refining them with data
Work with our compensation experts to deliver strategic guidance and value to customers
Turn customer feedback and usage data into clear Product roadmap input
What We're Looking For
6+ years of experience in customer success, including 3+ years in a management role
Experience in a SaaS or AI technology company
Experience working with enterprise and Fortune 500 customers
Experience using AI and automation to drive efficiency and improve customer success outcomes
Experience hiring, developing, and scaling a customer success team
Experience handling customer escalations
Experience building and implementing customer success playbooks
A data-informed approach to decision-making
As a Plus
Experience in a startup environment
Experience with compensation, HR tech, or data-driven products
Hands-on experience with customer success platforms and AI-enabled CS tooling
Compa offers a competitive and comprehensive benefits package including medical, dental, vision, PTO and parental leave, equity, company offsites, continuous education, commuter benefits and a flexible work environment.
