Senior Manager, Deal Desk

Role Overview

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.

What You Will Do

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. Serve as a senior commercial advisor to Sales, Partnerships, and executive leadership on complex, strategic, and non-standard deals.

Why It Might Be a Fit

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.

Requirements

• 6+ years of experience in Deal Desk, Revenue Operations, or commercial finance within a B2B SaaS environment, with at least 2 years in a senior individual contributor or lead capacity
• Experience owning deal review processes, approval workflows, or discounting policy management for SMB, Mid-Market, and Enterprise deals
• Strong understanding of SaaS business models, contract structures, and discounting methodologies
• Proven ability to evaluate deal economics and make recommendations that balance growth, profitability, and risk
• Strong analytical skills with experience using Salesforce and financial modeling tools
• Demonstrated ability to incorporate AI-powered tools into day-to-day workflows to improve efficiency and accelerate analysis
• Strong communication skills with the ability to simplify complex commercial concepts for a variety of audiences in Sales, Partnerships, and Finance
• Proven track record of operating with high autonomy in a fast-moving environment — setting your own priorities, making sound judgment calls under ambiguity, and proactively driving outcomes without waiting to be directed

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

Tagged as: Deal Desk