Senior Manager, Deal Desk

New Remote - USA 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 We are seeking a strategic, commercially minded Senior Manager of Deal Desk to own and evolve the deal desk function at scale. This role sits at the intersection of Sales, Partnerships, Finance, Revenue Operations, and Legal — serving as a senior commercial partner who not only ensures deals are structured efficiently and evaluated consistently, but also shapes the strategy, systems, and policies that drive sustainable, profitable growth. Who you are As the Senior Manager of Deal Desk, you will be the owner of Fleetio's commercial deal infrastructure and serve as a trusted strategic partner to Sales, Partnerships, and Finance leadership. You don't just review deals — you build and continuously refine the commercial policy framework, approval architecture, and deal governance systems that allow revenue teams to move with speed and confidence. You bring deep expertise in SaaS business models, and you operate with the executive presence to drive alignment across a complex, fast-moving organization. This role will report to the Director of Revenue Operations. We believe AI will fundamentally change how revenue organizations operate. The ideal candidate is actively incorporating AI and automation into their workflow to eliminate manual work, accelerate deal reviews, and scale their impact. The ideal candidate also demonstrates versatility beyond the deal desk function — stepping into strategic initiatives and cross-functional challenges as the business changes. Your impact In this role, you will: Own and operate Fleetio's Deal Desk function end-to-end — including deal review, approval routing, and exception management — while continuously improving the systems and processes that support deals at every size and level of complexity Own the commercial policy framework, including discount guardrails, approval matrices, and escalation paths that allow Sales to move fast with the right controls Serve as a senior commercial advisor to Sales, Partnerships, and executive leadership on complex, strategic, and non-standard deals — bringing independent commercial judgment and clear recommendations, not just process facilitation Support the full commercial lifecycle by reviewing new business, expansion, and renewal deals, ensuring consistent application of pricing policies and approval workflows across all GTM motions Analyze pricing, discounting, and deal performance data trends to surface opportunities for productivity improvements Leverage AI and automation tools to automate deal review triage, summarize non-standard contract terms, generate pricing scenario models, and reduce manual approval coordination Collaborate with the Partnerships teams to develop the commercial framework for partner-sourced and partner-influenced deals,...