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 Fleetio is leading the charge with raving fans and new customers signing up every day. The company raised $450M in Series D funding in March 2025 and is on an exciting trajectory. Fleetio is also a proud founding member of the Rails Foundation. More about the team and company:

• Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
• Careers page: https://www.fleetio.com/careers

Who you are

As the Senior Manager of Deal Desk, you will own Fleetio's commercial deal infrastructure and serve as a trusted strategic partner to Sales, Partnerships, and Finance leadership. You will 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 operate with executive presence to drive alignment across a complex, fast-moving organization. This role reports to the Director of Revenue Operations. The ideal candidate actively incorporates AI and automation into workflows to eliminate manual work, accelerate deal reviews, and scale impact. They also demonstrate versatility beyond the deal desk function by stepping into strategic initiatives and cross-functional challenges as business needs evolve.

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 systems and processes supporting deals at every size and complexity level.
• Own the commercial policy framework including discount guardrails, approval matrices, and escalation paths enabling Sales to move fast with appropriate controls.
• Serve as a senior commercial advisor to Sales, Partnerships, and executive leadership on complex, strategic, and non-standard deals — providing independent commercial judgment and clear recommendations beyond 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 identify 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 Partnerships teams to develop commercial frameworks for partner-sourced/influenced deals including deal registration, pricing rules, margin structures.
• Define/report on internal metrics for Deal Desk function such as deal approval SLAs and ARPU floors; use data to continuously improve speed and quality of deals.

Your experience

• 6+ years in Deal Desk, Revenue Operations or commercial finance within B2B SaaS
• Minimum 2 years in senior individual contributor or leadership role
• Experience owning deal review processes, approval workflows or discounting policy management for SMB,... Mid-Market & Enterprise deals
• Strong understanding of SaaS business models,... contract structures & discounting methodologies
• Proven ability to evaluate deal economics balancing growth,... profitability & risk
• Strong analytical skills; experience using Salesforce & financial modeling tools
• Demonstrated ability incorporating AI-powered tools into workflows for efficiency & accelerated analysis
• Strong communication skills simplifying complex concepts for diverse audiences
• Proven track record operating autonomously in fast-moving environments; setting priorities & making sound judgments under ambiguity; proactively driving outcomes without direction

Benefits

• Multiple health/dental coverage options (100% employee coverage; 50% family coverage)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks (increases after year two)
• 12 company holidays + 2 floating holidays
• Parental leave: birthing parent (16 weeks paid), non-birthing (4 weeks paid)
• FSA & HSA options
• Short & 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 drinks/snacks (BHM office only)
• Remote working friendly since 2012 #LI-Remote