Head of Customer Success

SideShift•New York City, NY

17h•Onsite

About The Position

SideShift is hiring a Head of Customer Success to own adoption, retention, and expansion across its growing global customer base. This is not a traditional Customer Success leadership role: the company is looking for an AI-native leader who will build a lean, proactive CS function with agentic AI at its core. The role combines operating, building, and coaching: designing playbooks, implementing AI tooling, hiring and developing the team, and staying close to strategic customers to understand where value is being delivered or lost. The position owns the customer journey from onboarding through renewal and expansion, with a focus on helping customers realize meaningful, measurable value. The leader will develop the CS function’s processes, tools, metrics, and operating model; use AI to automate workflows and identify insights, risks, and opportunities; and translate customer goals and workflows into strategies that drive adoption, retention, and growth. The role also builds customer relationships, manages strategic accounts when needed, and creates feedback loops with Product, Sales, and Engineering so customer insights inform company priorities and product development. The position is based in New York City and requires in-person work five days per week. The stated OTE is $175,000–$225,000 plus equity, calibrated to experience and scope.

Requirements

5–10 years of experience, including significant Customer Success experience at a B2B SaaS company.
Demonstrated ability to build or materially improve a Customer Success function, playbook, or operating model from scratch.
Actively uses agentic AI in day-to-day work and is excited to rethink Customer Success workflows with AI agents.
First-principles approach focused on ensuring customers realize the value they purchased.
Strong commercial and analytical instincts, with experience driving adoption, retention, renewals, and expansion.
High ownership, exceptional communication, comfort with ambiguity, and ability to move between strategy, customer relationships, and hands-on execution.

Responsibilities

Own the customer journey from onboarding through renewal and expansion, delivering meaningful, measurable value to customers.
Develop the Customer Success function, including its playbooks, processes, tooling, metrics, and operating model.
Build an AI-native Customer Success organization using agentic AI to automate workflows, surface insights, proactively identify risks and opportunities, and increase team leverage.
Develop a deep understanding of customers’ businesses, goals, and workflows and use that understanding to drive adoption, retention, and growth.
Build strong relationships with key customers, proactively identify risks and opportunities, and personally manage strategic accounts when needed.
Create feedback loops across Product, Sales, and Engineering so customer insights inform company priorities and product development.
Hire and develop the Customer Success team.