Location: Remote (SF HQed)

Role Overview

StaffAI is on a mission to redefine how mid-market companies build their revenue teams.

We deploy commission-only AI employees that operate like human reps and are compensated solely on the outcomes they deliver, fully aligned with the revenue impact they generate.

This model lets companies scale their sales and marketing capacity instantly, without adding headcount, overhead, or ramp time.

Help coach our AI employees on how to be more empathetic with their human counterparts. We’re looking for a Head of Customer Success who can own customer relationships, surface business opportunities, document customer requirements, and help shape how we scale.

What You’ll Do

• Track adoption, confirm value creation, surface risks, and ensure value delivery
• Define and report on key metrics that demonstrate ROI of initiatives and ongoing projects.
• Act as the bridge between customers and our dev team, clearly communicating bugs, feedback, and iteration needs.
• Deliver weekly ROI reports of program to management and customers
• Define customer success criteria tied to measurable business outcomes (e.g., revenue growth, CLV, CSAT, cost reduction).
• Define the initial product and process requirements for customer engagements
• Shape our customer success playbook — bring ideas to improve how we support, engage, and scale with customers.
• Build and develop relationships with key customer business and technical leaders
• Utilize the StaffAI CRM to manage customer relationships through retention, growth, loyalty, and advocacy.