Fleet Development Specialist

Tommy's•Holland, MI

10d•Onsite

About The Position

Tommy’s is looking for a Fleet Development Specialist to help build and scale our fleet program. In this role, you will establish the foundation of a fleet and dealership B2B sales program across the Tommy’s Express franchise network. You’ll partner closely with marketing and franchise teams to design and implement the strategy, tools, and processes that enable locations to build lasting relationships with commercial fleets, auto dealerships, and other business accounts. This is a great opportunity for someone who loves connecting strategy, sales, and systems and is energized by building something that can grow and scale across a large network.

Requirements

Advanced degree or equivalent formal training/certifications and experience required
3+ years of B2B inside sales experience, preferably in fleet services, automotive, hospitality, or a franchise-based industry
Technical savvy and proficient in Microsoft Office and CRM platforms (Salesforce, HubSpot, or equivalent); experience within sales outreach and digital marketing tools a plus
Strong written and oral communication skills with the ability to present confidently to business owners, fleet managers, and executives
Demonstrated ability to develop new sales programs, territories, or markets from scratch
Highly organized self-starter who can manage multiple initiatives across a distributed franchise network
Collaborative mindset with experience working cross-functionally alongside marketing, operations, or franchise development teams
Experience selling to commercial fleets, auto dealerships, or multi-vehicle account holders
Background working within or supporting a franchise system
Comfort with travel to attend franchise partner meetings, industry events, or dealership visits as needed
Strong organizational and time management skills; ability to multitask and prioritize workload
Highly adaptable with strong problem-solving and critical thinking skills; ability to exercise good judgment and make sound data-backed decisions
High level of integrity and dependability with a strong sense of urgency and results-orientation
Views customer care as high priority; exhibits a positive can-do attitude
Displays a strong initiative and drive to identify gaps and fill them

Nice To Haves

experience within sales outreach and digital marketing tools a plus

Responsibilities

Design and develop the Tommy’s Express fleet and dealership B2B sales program, including scalable processes, tools, KPIs, reporting, and tracking systems.
Create and deliver franchise-ready playbooks, pitch materials, onboarding resources, and outreach strategies to support execution in local markets.
Partner with leadership to define target markets, fleet segments, and partnership criteria, and translate strategy into actionable plans.
Serve as the primary resource for franchise partners by providing coaching, sales support, training, and guidance on outreach, objection handling, and account development.
Lead or support the full B2B sales lifecycle, including prospecting, outreach, discovery, presentations, proposals, closing agreements, and transitioning accounts to franchise partners.
Build, manage, and nurture a pipeline of qualified fleet and dealership prospects through proactive outreach and ongoing engagement.
Coordinate multi-location and national opportunities while supporting franchise partners with corporate-led sales efforts when needed.
Partner with marketing to develop and execute B2B campaigns, contribute to collateral and promotional strategy, and coordinate co-branded opportunities.
Leverage CRM and automation tools to support outreach, pipeline tracking, and follow-up across the network.
Build strong relationships with key accounts, provide performance reporting, and gather insights to continuously refine and improve the program
Other duties as assigned; duties and responsibilities may change at any time with or without notice.

Benefits

Base pay and eligibility for annual profit-sharing bonus
Full insurance package including Health, Dental, Vision, Life, Disability, Employee Assistance
Dependent Care FSA with on-site Daycare options
401k match and complimentary financial planning services
Paid time off and paid holidays
Opportunity for continued education and tuition assistance
Valuable learning and development program
Significant ability to grow internally for motivated and strong performing team members
Fun, energetic, family-oriented work culture with an emphasis on team member morale
Growing nationwide brand / presence