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Deal Desk Manager

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We are actively seeking a Deal Desk Manager to join our Finance team. You will be the first point of contact for all deal desk inquiries from AEs, managers, and the other teams. You will work with other teams (Rev Ops, Sales, CSMs, Legal, Accounting, and FP&A) to evolve our deal desk processes and systems.

In this role, you will have a unique opportunity to impact the growth, direction, and future of Fleetio. Ideal candidates will have deep past deal desk experience at a B2B SaaS that has scaled well from $50M ARR or more. We value enterprise deal experience. You are a natural problem-solver with a strong ability to navigate ambiguity.

What’s Fleetio?

Fleetio (pronounced "flee-tee-oh”) is a leading provider of fleet management SaaS that helps organizations of all sizes track, analyze, automate, and manage their vehicles and equipment. With a purpose-built, easy-to-use, and comprehensive suite of tools and features, Fleetio makes it easy for fleet managers to optimize their operations, reduce costs, and improve safety and compliance.

We’ve become a trusted partner for thousands of businesses across the globe, from small startups to large enterprises. With a focus on innovation, customer success, and sustainable growth, Fleetio is on a mission to transform fleet management.

What makes us special, you might ask? We’ve been remote-friendly since 2012 and have been recognized as Birmingham Alabama’s Best Places to Work five years in a row. We have over 200 employees all over the United States, Canada, and Mexico, and have over 5,000 paying customers in 70+ countries. It’s an exciting time at Fleetio as we’re growing 50+% year on year and have just closed our Series C round led by our incredible investment partner, Elephant. We’re building the fleet management platform of the future – the single screen for fleet managers to drive their businesses forward.

More about our product and company:

This is a full-time role that can be held at our HQ in Birmingham, Alabama, or remotely anywhere in the continental United States. Be sure to mention espresso in your cover letter so we know you actually read this.

What you’ll be doing

The Deal Desk Manager will be responsible for scaling and running the Deal Desk function. In this role, you will be the go-to person to ensure we are winning the best deals within the parameters of our ideal customer profile principles, internal bookings guidelines, and GAAP. This role requires a highly detail-oriented individual. Curiosity, flexibility, and the ability to operate with a “one team” attitude alongside a cross-functional team are non-negotiable attributes for this role.

Key Responsibilities:

  • Scale our deal desk function and continuously evolve it with the help of other stakeholders (Rev Ops, Sales, CSMs, Legal, Accounting, and FP&A).
  • Ensure compliance with our sales and business approval policies, as well as legal and revenue recognition policies.
  • Support our Sales team on contract objection-handling techniques, alternative contract options, compensation impacts, and value propositions to drive clean deals and close new revenue.
  • Help develop tools that help the Sales team effectively price and structure deals while managing certain business metrics and requirements.
  • Maintain a holistic view of deals during contract negotiations to be able to drive internal stakeholder discussions and alignment on customer concerns or key business issues that arise during negotiations.
  • Collaborate with Legal to develop pre-approved clause libraries for use in our CLM.
  • Possess knowledge of when to escalate deal negotiations to Legal to comply with revenue recognition, risk mitigation, and operational policies.
  • Conduct analysis in partnership with FP&A on discounting and pricing strategy to measure effectiveness (discounting/pricing and how that may be impacting close rates, future churn, etc.).
  • Create internal reports to drive transparency and improve behavior changes through reporting, dashboards, and analytics with high-quality data.
  • Collaborate with Product Marketing, Marketing, and Sales on new product and packaging roll-outs.
  • Be an expert on our company ARR recognition and sales compensation plans, and proactively flag any concerns on deal structure and escalate to Accounting/Finance or AEs as necessary.
  • Develop and drive initiatives to improve productivity, streamline company deal policies, and simplify processes.
  • Recommend new deal desk-related tools to improve the process and collaborate with other Business Operations on selection, implementation, and roll-out.
  • Help Sales Enablement to deliver training to new and existing AEs on deal desk policies and best practices.
  • Partner with Revenue Operations, Sales, Enablement, Legal, Finance, and Accounting, to drive process improvements, automation, and team enablement.

What’s in it for you?

  • Be part of a fast-growing B2B SaaS company in an enormous market. There has not been anyone in Deal Desk Manager role in the history of the company so you will be able to say you were the first!
  • Be a part of an incredible team of “A” players who go above and beyond to make Fleetio a successful company. We’re a customer-centric team with a great product, excellent support, and countless happy customers.
  • Work remotely (within the United States), or at our Birmingham, AL HQ. We strive to promote a strong remote working culture and have done so since the beginning.

Our team

Your future fellow team members currently live in Birmingham, Chicago, Los Angeles, and along the Gulf Coast. The Birmingham group periodically works out of the HQ building when the flow is right, but also works digitally first along with much of our company. In a nutshell, we want the best talent located wherever they happen to be. We can usually catch each other for quick Slack pings or Zoom calls from roughly the core hours of 9 am to 3 pm Central. We rely heavily on asynchronous communication through Asana, our company-wide project management system.

From a systems standpoint, we use a lot of them. We rely on the saying: “a great solution today can become a problem tomorrow.” We are constantly thinking about if processes or systems will scale. If we can get a few years from a system before we need to replace it, then we’ll implement it. We rely heavily on automated integrations between our systems so we can keep manual work down.


  • Experience with a B2B SaaS that has scaled well from $50M+ ARR. We need someone who understands how a modern software company servicing thousands of organizations worldwide should operate at scale.
  • 6+ years of professional experience, with 3+ years in a deal desk function, including complex enterprise deal experience.
  • Prefer experience with Ironclad (or other enterprise CLM).
  • Expert knowledge of Salesforce.
  • Working experience with NDAs, RFP responses, subscription agreements, and pilot agreements. Fleetio has an in-house legal team and outside experts.
  • Good understanding of software revenue recognition (including ASC 606) and order process principles.
  • Highly organized, customer-focused, innovative, and attention to details.
  • Ability to multitask and prioritize at times of high volume during end of month and quarter.
  • Experience with building deep partnerships with Rev Ops, Sales, CSMs, Legal, Accounting, and FP&A.
  • Ability to analyze, model, and recommend the best course of action for complex pricing, negotiations, and business situations; quantitative experience required.
  • Ability to manage multiple variables, and adjust approach within defined parameters as well as the ability to drive rapid, but fact-based decision-making with imperfect data.
  • You’re confident operating autonomously and comfortable escalating when required.
  • You lean into problem-solving, educating, and providing an empathetic, but opinionated perspective that drives alignment across partners and teams.
  • Ability to work in a fast-paced, dynamic environment with changing priorities and tight deadlines.
  • Be sure to mention coffee in your application so we know you actually read this.


  • 100% health/dental coverage (50% coverage for family)
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks
  • 10 company holidays + 2 floating holidays
  • Parental and bonding leave
  • Dependent care and medical FSA
  • Short and long term disability
  • Community service funds
  • Professional development funds
  • Health and wellness initiatives
  • Mac laptop + new hire equipment stipend
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • Remote working friendly since 2012

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