Senior Customer Success Manager

About Fulcrum

The $1.5 trillion insurance industry is powered by brokers. Every business needs insurance, and the brokerage industry is hamstrung by account management capacity. Account managers are constantly pulled in multiple directions—keying information into systems, chasing documents, doing mundane work—rather than focusing on the client interactions that actually matter. Most brokerages either outsource this work or grind through it manually.

We're building an AI platform to automate this insurance drudgery. Our platform already saves customers thousands of hours and millions of dollars every year. Our customers love the product— we have deep penetration within enterprise brokerages and genuinely enjoy making our customers' lives better. We just raised our Series A and are just getting started.

Why Fulcrum

• Rocket-ship growth. We’ve achieved multiple seven figures in ARR in just over a year, serving large enterprise clients including 30% of the top 50 brokers in the country.

• Extreme ownership. You’ll work directly with enterprise users and ship end-to-end products that save them hours every week.

• Bleeding-edge problems, real impact. Tackle tough AI and product challenges whose wins show up immediately in customer workflows.

• In-person collaboration. Join a lean, staff-level team (ex-Affirm, Uber, DoorDash, McKinsey) working side-by-side in San Francisco; we believe the best ideas are fostered in an in-person environment.

• Top-of-market rewards. Competitive base salary plus meaningful founding-team equity.

About the Role

You will carry a book of roughly 25-30 brokerage accounts and own them from go live through renewal: the relationship, onboarding, ongoing adoption, and the renewal itself. Adoption at a brokerage is not a login count. It is an account manager who has checked policies by hand for nineteen years deciding to trust our output on a Tuesday afternoon when she is behind. Your job is to make that happen at scale, across every team in your book, and to know exactly why it did or did not.

This role sits alongside our AI Deployment Strategists, who lead AI transformation strategy with brokerage executives and own expansion into new teams, subsidiaries, and workflow families. You are the operator who makes the deployment stick, and the person the customer calls first. Gross retention and renewal on your book is your number. Expansion is a number you feed with evidence and champions.

Customer Success at Fulcrum is three people including you. You will build the function while carrying the book. What you write becomes how Fulcrum runs Customer Success for the next hundred customers.

What You'll Own

The relationship. You are the named owner for your accounts, from the operations lead who sponsored the purchase to the branch manager who never wanted it. Trusted enough that bad news reaches you early, and senior enough to hold a hard conversation with a COO without escalating it.

Onboarding and time to first value. Taking the handoff from Sales and Deployment, running the go live plan, and driving each account to real production usage on a defined timeline. You are accountable for the date, not for explaining the slip.

Adoption against real exit criteria. Breadth (active users against contracted seats), depth (document volume against contracted allowance), and workflow coverage. You will know your accounts' numbers cold, know what moved each one, and be able to defend the call when the number and the customer's mood disagree.

Product Expert. You know the product inside and out, and solution for customer needs appropriately.

The change management. Enablement plans, workflow level training, champion development, office hours, and the unglamorous follow up that turns a provisioned seat into a weekly habit. Most of the value in this job is created in the fourth conversation, not the first.

Renewals. Building the case across the year rather than in the last sixty days, quantifying delivered ROI in the customer's own numbers, and closing the renewal in partnership with Sales.

Business reviews that hold up. Operations leaders and C suite at top 100 brokerages, working from real usage data and quantified outcomes rather than slideware.

Technical partnership. Working with our forward deployed engineers, deployment strategists, and product team on AMS integrations such as Applied Epic, SSO and provisioning, tenant and subsidiary structure, and coverage line mapping. You will also be the loudest, best evidenced voice for what your accounts need from the product.

The function itself. Health scoring, onboarding curriculum, business review standards, escalation paths, playbooks.

Who You Are

Required

• 6+ years in customer success, strategic account management, implementation, or post sales consulting at a B2B software company, including enterprise accounts with multiple stakeholders and multiple user groups.

• A record of owning commercial outcomes. Retention or renewal targets you can talk about with real numbers, including the ones you missed and why.

• Fluency with data. You can pull usage, build a defensible metric, and talk a customer out of a vanity number. Comfortable in spreadsheets and BI tools. SQL is a plus, not a requirement.

• Demonstrated change management with non technical operators who did not ask for new software and are good at their current way of doing things.

• Enough technical literacy to hold your own on integrations, provisioning, and data flow. You do not need to write code. You do need to never be the bottleneck in a technical conversation.

• Written precision. A lot of the influence here happens over email and in documents that executives read without you in the room.

• Based in San Francisco or willing to relocate. This role is in office five days a week.

Preferred

• Insurance brokerage, insurtech, or another regulated vertical such as healthcare, financial services, or legal, where the customer's operation is the whole context for the product.

• Experience as an early or founding CSM, first or second person in a function.

• AI or automation products, where value depends on users trusting output they used to produce by hand.

• Experience carrying a renewal number alongside a partner who owns expansion on the same account.

What Will Make This Hard

We would rather tell you now than in month three.

• The playbook does not exist yet. You will be writing the process while carrying the book, and the first version will be wrong.

• Our customers are conservative by design. Brokerages are regulated, relationship driven, and full of people whose expertise is threaded through the manual process you are asking them to give up. Persuasion here is slow, specific, and earned.

• You will be measured on adoption you influence but do not fully control. Integration timelines, customer staffing, competing priorities. The job is to move the number anyway, and to be straight about it when you cannot.

• You share accounts. Deployment Strategists, forward deployed engineers, and Sales all touch your customers. Getting the outcome requires coordinating people who do not report to you.

• We are in the office five days a week and we move fast. Speed here means shipping a rough version of the business review template this week instead of a polished one next month.

If that reads as a warning, this is not the right role for you. If it reads as the reason to take it, we should talk.

Your First Year

• 30 days. You know your accounts' usage, contracts, and integration state cold, and you have met every champion and every skeptic who matters.

• 90 days. You own your book end to end, you have run your first business reviews, and you have shipped at least one artifact the team keeps using.

• 12 months. Your accounts have cleared adoption criteria, you have closed your renewals, and Customer Success has a repeatable model with your fingerprints on it.

How We Work

• Ship, learn, improve, repeat

• Approach challenges with curiosity

• Find joy in hard problems

• Actions before words

• Growth for one means growth for all

• Care for our customers, care for each other

Our Team and Philosophy

• Builders at heart. You don't wait for a process to exist—you create it, refine it, and own it.

• Bias toward action. You have an internal sense of urgency. You'd much rather get something done today than tomorrow.

• Owners, not renters. You treat the company's money and decisions like your own. You hold yourself accountable to outcomes, not just outputs.

• Ambitious about the opportunity. You're excited about building the defining AI company in the insurance industry—and you understand that great finance is a competitive advantage.

What We Offer

• Competitive salary + meaningful equity.

• Full health, dental & vision.

• High-ownership, high-trust culture with lightning-fast executors.

• Regular team off-sites, dinners, and an office stocked for builders.