Senior Revenue Operations Analyst - 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: https://www.youtube.com/watch?v=YoXyXTFWbkg
• Our careers page: https://www.fleetio.com/careers

The Opportunity

We’re looking for a versatile Senior Revenue Operations Analyst who enjoys connecting the details to the bigger business picture. You’ll own sales compensation and tackle a range of other analytical and operational challenges that help Fleetio’s go-to-market teams perform at their best.

You’ll run the monthly commission process, maintain accurate plans, and help our teams understand and trust their payouts. Alongside that ownership, you’ll analyze performance trends, strengthen reporting, and improve the processes that support our revenue organization.

You might trace a commission discrepancy back to its source, investigate why conversion changed across a sales segment, or turn a manual workflow into a repeatable process using automation. You’ll identify problems, recommend solutions, and work with partners to implement those improvements.

This role is a strong fit for someone who thrives on variety, takes pride in precise execution, and wants to build both deep expertise and broad business understanding. You’re curious about how things work, comfortable learning unfamiliar processes, and motivated by making them better.

You’ll report to the Revenue Operations Manager and partner with Sales, Account Management, Finance, People Operations, Marketing, Enablement, and GTM Systems.

Your Impact

You’ll work across sales compensation, funnel analytics, and process improvement to help our revenue teams operate effectively and make informed decisions.

• Own the monthly sales commission process from data preparation and payout validation through handoff to Payroll, ensuring accuracy, timeliness, and clarity for our teams.
• Translate approved compensation plans into precise payout calculations and comp letters, seamlessly managing updates for new hires, role transitions, and plan changes.
• Resolve data and payout discrepancies by identifying root causes, clearly explaining findings, and maintaining records of adjustments.
• Lead investigative funnel analyses from exploration to practical recommendations, uncovering growth drivers and shaping the team’s focus.
• Empower sales leadership with a clear view of pipeline health, conversion velocity, and revenue attainment through high-impact reports and executive dashboards.
• Collaborate across teams on territory design, capacity planning, and target-setting, using data to evaluate options and trade-offs.
• Streamline recurring workflows in partnership with systems and operational teams, leveraging AI to reduce manual effort and maintain high accuracy.
• Document processes and business rules to ensure scalability, repeatability, and strong cross-functional trust.

What You Bring

• 4+ years in Revenue Operations, Sales Operations, Business Operations, Compensation Operations, Finance, or a similar analytical role in B2B SaaS or a recurring-revenue business.
• You can explain a payout calculation to a rep, a performance trend to a leader, or a business requirement to a systems partner.
• You’re comfortable asking questions and respectfully challenging assumptions when the data points elsewhere.
• You’ve owned a recurring process or project from start to finish and made it better along the way.
• You can take an open-ended question, structure the analysis, check your assumptions, and land on a recommendation with clear trade-offs.
• You have a proven track record of building and auditing spreadsheet models using formulas, lookups, pivot tables, and quality checks.
• You have hands-on experience with Salesforce (or a similar CRM) and QuotaPath (or similar commissions software).
• You learn unfamiliar areas quickly and can move between detailed operational work and broader business problems.
• You prioritize well, keep partners informed, and raise risks or decisions early.
• You’re curious about AI and automation and can spot practical ways to improve analysis and workflows, with thoughtful validation of the results.

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
• Remote working friendly since 2012