Senior Manager of Deal Desk, Fleetio
+ Stock Options
More information about location
Fleet management software
Be an early applicant
Fleet management software
201-500 employees
Be an early applicant
+ Stock Options
More information about location
201-500 employees
Company mission
To help organizations track, analyze and improve their fleet operations.
Role
Who you are
- 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
What the job involves
- 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
- 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, 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
Our take
Fleetio offers software that helps organizations track, analyze, and improve their fleet operations. Fleet management is a famously complex and challenging task, so Fleetio's services unburden organizations of this, enabling them to focus time and energy on their own mission.
The company makes it easier for businesses to lease a fleet of vehicles with an app which allows managers, drivers and mechanics to access and update information, relieving users of outdated fleet software and complicated spreadsheets. This simple solution has proven effective with the start-up seeing nearly 400% growth in a three-year margin.
The company had a successful 2025 too, having raised over $450M early in the year, which also included the acquisition of Auto Integrate. With moves like this, Fleetio can certainly expect to continue its growth, especially given its stable position in a market estimated to be worth $52.4 billion by 2027.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
18% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2025
$450m
SERIES D
May 2023
$144.7m
SERIES C
Total funding: $620m
Company benefits
- Health & Wellness: Taking care of you and your family is important to us. Our healthcare plans deliver choice and value so you can prioritize your health
- 401k Match: Plan for your future. We match your retirement contributions up to 4% of your salary each pay period
- PTO/Holidays: Four weeks of paid time off (PTO), two floating holidays, as well as 12 company holidays
- Parental Leave: We provide all our team members (birthing & non-birthday parents) time off to care for and bond with their newborn or newly adopted children
- Stock Options: At Fleetio, we grant all our team members options to acquire an ownership stake in Fleetio
- Professional Development: Team members get an annual professional development allowance to invest in their own professional growth
Company HQ
Central City, Birmingham, AL
Leadership
Jon Meachin
(CEO)Jon initially joined Fleetio as COO in 2022, becoming CEO in 2023. Prior to this, they were COO at A Cloud Guru and held VP roles at Campaign Monitor and McKissock.
Matthew Mandel
(CFO & COO)Prior to joining Fleetio in 2023, Matthew was the COO & Co-CEO at Cometeer. They also spent 3 years at Wayfair in various General Manager roles.
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