Customer Success Manager

About TruckerCloud

TruckerCloud connects commercial fleets' telematics data to the insurers who cover them. We integrate with more than 200 telematics, dash camera, and ELD providers, normalize the data, and deliver it to roughly 70 insurance carriers and MGAs for underwriting, loss control and claims.

The role

We are hiring a Customer Success Manager to own the relationship with our carrier and MGA customers after they sign.

This is a growth job, not a support job. Most of our new revenue comes from existing customers connecting more fleets and adopting new products. You will be the reason that happens: you'll keep accounts healthy, get fleets connected and data flowing, and help customers get real value from what we build.

You will report to the Director of Customer Success. You will work daily with our onboarding team, Product, Engineering and our commercial team, and with the internal AI assistants that are part of how this team operates.

What you will do

• Own a book of carrier and MGA accounts: recurring customer meetings, quarterly business reviews and renewal readiness
• Present to customers regularly: QBRs, product walkthroughs and rollouts, and training for underwriting, loss control and claims teams
• Grow connected fleets and vehicles inside every account
• Drive adoption of new products across your book
• Run pilot programs from kickoff to conversion: agree on success criteria up front and build the case for a full contract before the pilot ends
• Move customers toward self-serve: the dashboard, help center and automated onboarding, so your time goes to growth conversations rather than manual work
• Track every commitment we make to a customer and raise anything at risk before it's missed
• Be the customer's point person when data issues come up: route them to the right team, keep the customer informed and close the loop
• Bring structured customer feedback to Product, with the account and revenue impact attached

What you bring

• 3+ years in a customer-facing role: customer success, account management, sales or BDR, or commercial insurance (agent, underwriter, broker). If you've been in insurance and want to move to the technology side of the industry, we'd like to hear from you
• You present well and enjoy it. People leave meetings with you energized and clear on next steps
• AI-first. You reach for AI tools by default: to research a customer's data question, draft a QBR, or work through a problem before you bring it to someone else. You'll have internal AI assistants with direct access to our data and documentation, and we expect you to use them daily
• Precise. Customers act on what we tell them about their data. You verify before you answer, and you never guess
• Enough technical fluency to understand how fleets connect their telematics providers, how data flows and why a fleet's data might show gaps. You do not need to write code, but you should be able to explain a data issue clearly to a non-technical customer
• Comfort leading commercial conversations about expansion and renewal
• A genuine enjoyment of customer relationships. You're the person a program manager, underwriter, loss-control lead or claims adjuster is glad to see on their calendar

Additional Qualifications

• Familiarity with how carriers and MGAs use telematics across underwriting, loss control and claims
• Insurance, insurtech, or fleet and transportation background
• Experience at a telematics, ELD or dash camera provider
• Experience with Attio or other CRM, Claude or ChatGPT, Intercom, Slack, Google Suite, Notion
• You have helped build or support a Customer Success function: playbooks, QBR formats, health scoring

Compensation and benefits

Base salary is $80,000 to $100,000 depending on experience, with on-target earnings (OTE) of $100,000 to $125,000. Variable compensation is tied to net revenue retention and connected-vehicle growth across your book of accounts.

• Health, dental and vision insurance
• 401(k)
• Paid time off
• Flexible work environment