fleetio senior manager deal desk

Remote Senior Manager, Deal Desk at Ironwood Digital
Senior Manager, Deal Desk
A little about us…Ironwood Digital 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. Ironwood Digital is also a proud founding member of the Rails Foundation!
More about our team and company:
– Ironwood Digital overview video:
– Our careers page:
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 Ironwood Digital'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 Ironwood Digital'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, including deal registration, pricing rules, and margin structures
– Define and report on internal metrics for the Deal Desk function — including deal approval SLAs and ARPU floors — and use data to continuously raise the bar on both speed and deal quality
Your experience
– 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
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About Ironwood Digital
Company profile
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