Otterbrook

Senior Manager, Customer Success

Full Time | San Francisco, CA (On-site 5x a week)

Base Salary Range: $165,000 to $180,000

Bonus: $30,000 to $40,000

Equity: 0.15% to 0.25%

Who We Are

• Our client is a venture backed startup building an AI powered workflow automation platform for the insurance industry. Insurance agencies still run on manual, error prone processes. Few systems communicate directly, which leads to endless copy pasting between emails, web portals, and desktop apps. Process by process, this company is bringing those workflows into a comprehensive automation layer.

Why This Role Matters

• Customers love the core product and new products are launching in waves. Keeping the customer base engaged, growing usage, and expanding adoption of new products is the largest lever in the company plan.
• You'll lead the team that owns everything post sales: activation, retention, expansion, and support. This is a hands-on role. You'll coach, mentor, and grow the team while also interfacing directly with the largest enterprise customers alongside the Enterprise CSM.
• There's real building to be done too. The playbooks are young. You'll inherit a foundation and take it from working to repeatable.

Why You Should Join

• Own the Post-Sale Motion: Retention, expansion, activation, and support all land in the Customer Success team. Each has an individual owner, and it's up to you to manage the big picture.
• Nurture and Lead the Team: You'll lead an established customer success team. You'll coach and develop the team, work with the executive team to define high level goals, craft the strategy to achieve those goals, and execute against your plans.
• Enterprise Work, Not Just Oversight: You'll support the largest relationships personally alongside the Enterprise CSM.
• Real Product, Real Pain: The platform solves a problem agencies feel every single day. The ROI is tangible and easy to put in front of a customer.
• A+ Team and Backers: Backed by top investors and industry insiders. The founding team is full of multiple time builders, insurance experts, and A+ talent. They're looking for more of the same.
• Momentum: Post PMF. Revenue generating. Growing fast. The base is big enough to matter and the product surface is expanding every month.

What You'll Do

Own Retention and Expansion

• Own net dollar retention across the customer base. Renewals, expansion, and churn prevention all report into this seat.
• Set the team's quarterly goals against the company plan, and hold the team to the pacing that gets there.
• Know where revenue is at risk before it shows up in a billing report, and say so early.

Lead and Grow the Team

• Run the customer success team day to day: goals, 1:1s, performance conversations, career paths.
• Mentor and coach the people already in seat. Your job as a manager is to empower and unblock your team, getting them the resources they need to shine.

Build and Run the Post-Sale Operating System

• Define SOPs and best practices, collaborating with the team to put processes in place and strengthen the infrastructure.

Manage High-Stakes Enterprise Relationships

• Partner with the Enterprise CSM on the largest accounts, personally overseeing enterprise customer relationships and pilots.
• Provide strategic guidance and support, including hands-on execution for critical accounts.

Partner Cross-Functionally

• Build clean handoffs with sales.
• Carry the highest signal customer feedback into the product roadmap.
• Identify risks and opportunities across the customer base to present a holistic post-sale picture, owning the full customer experience.

Must Have Requirements:

• 7+ years in customer success or account management at B2B SaaS or fintech, including 2+ years managing CSMs directly.
• You've owned a retention number and hit it. Real accountability for NDR or GRR, with the metrics to back it up.
• You've run enterprise relationships yourself: renewals with real dollars attached, exec sponsors, and the occasional bad quarter you had to overcome.
• You've built process where none existed. Playbooks, health scoring, SLAs, comp structures, hiring bars.
• You're technically fluent and tool forward. Data analysis and AI assisted building are how you work. You prototype what your team needs instead of filing a ticket and waiting.
• You're high agency and thrive in ambiguity. You're excited about having a goal to hit, the latitude to build a plan for how to achieve that goal, and the responsibility to own the outcome.

Nice-to-have

• Insurance, financial services, or another trust heavy vertical. You understand how risk averse buyers adopt new things.
• You've been an early customer success leader and taken a small team through a growth phase.
• Startup experience. You've been part of an all hands on deck team and will do whatever it takes.