Customer Success Manager (Client Success Champion | Fleet Software Sherpa | Retention & Growth Strategist )
RTA FleetDo you get a real charge out of watching a client go from confused to confident with software they used to dread logging into? Do you know which accounts need a check-in before the CRM reminds you? Do you spot a renewal date approaching and take action before anyone asks? Good. Keep reading. This is a traditional Customer Success Manager (CSM) role. Internally, we call it Fleet Success. As our Fleet Software Sherpa, you will own customer relationships, product adoption, retention, renewals, and growth across an assigned book of business. You will report to the Director of Fleet Success and work alongside the Fleet Success team. Our customers keep school buses, emergency vehicles, ambulances, public transportation, and essential delivery fleets running. Helping them succeed matters. We are also an AI-forward company: using AI regularly and responsibly to prepare, spot patterns, and work smarter is part of this job. Your Top 3 Objectives Drive Adoption, Measurable Outcomes & Strategic Engagement: Help customers set SMART goals, realize value from RTA software, and stay engaged. Complete quarterly business reviews with 100% of top-tier accounts and at least one structured touchpoint each quarter with every other account. Grow Accounts & Improve the Customer Experience: Identify and pitch at least one upsell or expansion opportunity per quarter across your portfolio, with annual goals set by the Director of Fleet Success. Partner with Support, Product, Sales, Training, and Onboarding to remove barriers and improve outcomes. Own Retention, Renewals & Account Health: Build trusted relationships across customer organizations, manage renewal dates and contract terms, recognize usage and engagement risks early, and confidently navigate difficult conversations, price increases, and renewals. Target at least 90% annual gross client retention across your assigned book. What You’ll Actually Own Strategic Customer Relationships Build relationships at multiple levels, ask strong discovery questions, and guide customers toward SMART goals. Account Health & Risk Track usage, engagement, support trends, and renewal signals; intervene before a concern becomes churn. Business Reviews & Engagement Lead valuable QBRs and structured customer touchpoints; document outcomes and next steps. Expansion & Commercial Conversations Identify upsell opportunities, discuss pricing and objections, and collaborate with internal partners to close opportunities. Book of Business & Renewals Manage assigned accounts, renewal schedules, commercial conversations, and growth opportunities. Cross-Functional Customer Advocacy Coordinate Support, Product, Sales, Training, and Onboarding to deliver customer outcomes. CRM & Execution Discipline Keep account history, contracts, activity, next steps, and renewal information accurate and current. AI-Enabled Work Use AI tools weekly for meeting preparation, account-history summaries, communication drafts, and pattern analysis, with human review and appropriate data safeguards. What We’re Looking For At least two years in a Customer Success Manager role at a SaaS company; direct experience with renewals, price increases, and upsells or expansions. Demonstrated ownership of a book of business and accountability for customer outcomes and retention. Strong business acumen, discovery skills, relationship management, objection handling, and follow-through. Ability to conduct customer business reviews and use CRM and account-health information effectively. Comfort using AI tools weekly to prepare calls, draft communications, and analyze account information. Excellent verbal and written communication; confident with phone and video meetings. Self-directed, team-oriented, adaptable, and willing to travel domestically 10–15%. No bachelor’s degree required; relevant experience and breadth of knowledge matter more. You’ll Really Stand Out If... You know fleet operations, fleet maintenance, automotive, transpor…