Director of Enterprise AI-Driven Customer Success

Compa; Denver (CO); On-site; USD 162,000 - 220,000; Full time

Job summary

Compa, a venture-backed AI startup redefining compensation data, seeks a Director of Customer Success to lead a global, enterprise-focused team. You will shape strategy for support, retention, and growth using AI, automation, and high-touch engagement at scale.

Collaborate with Sales, Onboarding, Product, and compensation experts to drive lasting value for Fortune 500 clients. You will report to the CRO and build an operating model that aligns with top accounts, while driving efficiency and

Qualifications

• 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

Responsibilities

• 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
• Design an AI first CS motion: automate routine work like health scoring, renewal prep, QBR prep, and customer communications
• 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
• 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
• 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

Job description

Compa, a venture-backed AI startup redefining compensation data, seeks a Director of Customer Success to lead a global, enterprise-focused team. You will shape strategy for support, retention, and growth using AI, automation, and high-touch engagement at scale.

Collaborate with Sales, Onboarding, Product, and compensation experts to drive lasting value for Fortune 500 clients. You will report to the CRO and build an operating model that aligns with top accounts, while driving efficiency and