Head of Customer Success

SideShift is building the operating system for the creator economy: brands run campaigns, creators make authentic product videos, and the platform handles matching, tracking, and payouts.

We’re ~20 people, ~2 years old, and growing fast: revenue roughly 3× last month and ~10× over the last 6 months. More than 1M creators and 3,000+ brands use SideShift; $100M+ has been paid out to creators. If you’ve seen social groundswell around brands like Cursor, Suno, or Dr. Melaxin, that content often started here.

This is not a traditional Head of Customer Success role. We’re looking for a leader who treats AI as the operating model for customer success – not a bolt-on. You’ll own adoption, retention, and expansion across our growing global customer base, and you’ll build a CS function that is AI-native from day one: leaner, faster, and more proactive than a headcount-heavy team could ever be.

You’ll be equal parts operator, builder, and coach. You’ll design the playbooks, wire up the AI tooling that runs behind them, hire and develop the team, and stay close enough to our most strategic customers to know exactly where value is being won or lost.

• Own the customer journey from onboarding through renewal and expansion, with a focus on delivering meaningful, measurable value to customers.

• Develop the Customer Success function, including creating playbooks, processes, tooling, metrics, and more.

• Build an AI-native CS organization, using agentic AI to automate workflows, surface insights, proactively identify risks and opportunities, and dramatically increase the leverage of the CS team.

• Develop a deep understanding of customers’ businesses, goals, and workflows and translate that understanding into strategies that drive adoption, retention, and growth.

• Build strong relationships with key customers, proactively identify risks and opportunities, and personally manage strategic accounts when needed.

• Create tight feedback loops across Product, Sales, and Engineering, ensuring customer insights inform company priorities and product development.

• 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.

• AI-native operator who actively uses agentic AI in their day-to-day work and is excited to rethink how Customer Success operates when AI agents can own meaningful parts of the workflow.

• First-principles thinker who focuses on the fundamental goal of Customer Success: ensuring customers realize the value they purchased.

• Strong commercial and analytical instincts, with experience driving adoption, retention, renewals, and expansion.

• High-ownership operator and exceptional communicator who thrives in ambiguity and can move fluidly between strategy, customer relationships, and hands-on execution.

1. Initial conversation with our recruiting team

2. Conversation with Chris Brantley, Head of Strategy and Operations

3. Conversation with Canyon Pergande, Co-founder and COO

4. Onsite interviews with Nick Lawton, CEO, Drew Levin, CTO, and more.

5. References + offer

Location: New York City, in person 5 days/week
OTE: 175,000–225,000 + equity, calibrated to your experience and scope.