Revenue Operations Manager, Expansion and Retention at Fleetio

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation! More about our team and company: • Fleetio overview video: [Upgrade to PRO to see link] • Our careers page: [Upgrade to PRO to see link] As a Revenue Operations Manager, Expansion and Retention you will be the operational backbone of Fleetio’s post-sales organizations. This role is critical to how we retain and expand revenue across our post-sales lifecycle. You will partner closely with Customer Success, Account Management, Finance, and GTM Systems to improve visibility, streamline workflows, and create repeatable processes across the customer lifecycle. You’ll work day-to-day with Customer Success and Account Management leaders and collaborate closely with the CRO and VP of Customer Experience to ensure customer health, renewals, and expansion are supported by strong data and operational discipline. Who you are You’re a strong operator who blends analytical depth with business judgment. You’re comfortable navigating ambiguity, asking hard questions, and translating complex data into clear insights that leaders can act on. You thrive in high-growth B2B SaaS environments and enjoy building structure where it doesn’t yet exist. Your impact In this role, you will: • Own reporting and dashboards that provide a clear view into ARR performance across churn, contraction, reactivation, and expansion • Analyze churn, contraction, and expansion trends to identify root causes and inform changes to GTM plays, segmentation, or customer coverage • Fine-tune renewal and expansion forecasting by improving process, data hygiene, and visibility into at-risk and growth accounts • Facilitate weekly and quarterly business reviews in partnership with Customer Success and Account Management leaders to support renewals, NRR, and GRR • Design scalable post-sales processes, including customer handoffs, account ownership, and lifecycle milestones • Partner with GTM Systems to continuously improve Salesforce, Gainsight, and supporting tools to better enable revenue teams Your experience • 4+ years in Revenue Operations, Customer Success Operations, Account Management Operations, or Business Operations within a B2B SaaS environment • Experience building reporting, analyzing trends, and managing workflows in Salesforce and/or Gainsight; SQL or advanced analytics experience is a plus • Familiarity with customer health metrics, retention drivers, and leading indicators for churn and expansion • A track record in cross-functional collaboration, driving strategic projects from ideation to gaining process adoption • A track record in structuring problems (e.g., breakdown in funnel conversion rates, decline in pipeline generation), deriving insights from data, and recommending revenue opportunities • Strong communication skills, with the ability to present forecasts, insights, and narratives to senior leaders Benefits • Multiple health/dental coverage options (100% coverage for employee, 50% for family) • Vision insurance • Incentive stock options • 401(k) match of 4% • PTO - 4 weeks (increases at year two!) • 12 company holidays + 2 floating holidays • Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid) • FSA & HSA options • Short and long term disability (short term 100% paid) • Community service funds • Professional development funds • Wellbeing fund - $150 quarterly • Business expense stipend - $125 quarterly • Mac laptop + new hire equipment stipend • Fully stocked kitchen with tons of drinks & snacks (BHM only) • Remote working friendly since 2012 #LI-REMOTE Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need. This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will. If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.