Otterbrook

Enterprise Customer Success Manager

Full-Time · San Francisco, CA (On-site)

About the Company

A venture-backed startup building an agentic automation layer for a traditionally manual, document-heavy industry. The company is post-PMF, revenue-generating, and scaling fast — with enterprise customers that need dedicated strategic ownership

Why This Role Matters

This is the founding Enterprise CSM role. You're not inheriting a playbook — you're writing it. You'll define what enterprise success looks like at this company: the QBR framework, health scoring model, and expansion playbook. The urgency is real: accounts are growing fast and need a strategic owner who can deepen relationships, turn customers into advocates, and drive revenue growth proactively

What You'll Do

Own Your Book

• Serve as the strategic owner for a portfolio of enterprise accounts — the company's most complex, highest-value relationships
• Build multi-threaded relationships across each account: technical leads, champions, and executive sponsors
• Lead structured business reviews tied to measurable customer outcomes, not just usage metrics

Protect and Grow Revenue

• Own gross and net revenue retention; track health signals, forecast risk, and act early
• Identify and close expansion opportunities alongside sales — new use cases, integrations, seat growth
• Lead renewal negotiations with a commercial mindset; convert at-risk accounts by diagnosing root causes and owning the recovery plan

Define the Enterprise CS Motion

• Develop and maintain account plans: stakeholder maps, success metrics, expansion roadmaps, risk registers
• Test frameworks, document what works, and build the repeatable playbook the next enterprise CSM will inherit
• Synthesize customer feedback into prioritized, actionable input for product and engineering

Partner Cross-Functionally

• Own technical escalation communication alongside engineering and support
• Collaborate with sales on land-and-expand strategy and post-onboarding handoffs
• Maintain accurate CRM records — stakeholder maps, health status, open risks, renewal timelines

What Makes You a Great Fit

• 5+ years in enterprise customer success or account management at a B2B SaaS or fintech company, with real accountability for retention and expansion
• Owned a book of enterprise accounts ($100k+ ARR) and can speak to NRR performance year over year
• Experienced navigating complex, multi-stakeholder organizations and building executive-level relationships
• Commercially sharp — you understand contract structures, pricing dynamics, and renewal mechanics
• Technically fluent — able to grasp complex products, troubleshoot data flow issues conceptually, and bridge technical and non-technical stakeholders

Bonus Points

• Background in insurance, financial services, or compliance-heavy verticals
• Managed customers through complex technical integrations or significant product changes
• Startup experience