Wheelbase - Sales Development Representative (SDR)

The Ride Platform, Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly. We're named for the thing every part of our business runs on: the ride — the single transaction where an operator meets a renter. We're the only company building end-to-end for the Operator Economy: the marketplaces to book (Outdoorsy, Ride), the enterprise SaaS to manage (Wheelbase), and the insurtech (Roamly) to protect the assets people turn into profitable businesses. We enable millions of people to explore the world, while helping independent operators build generational wealth. Our mission is to build the essential infrastructure for the mobility economy.

At Roamly and Wheelbase Pro, we are redefining mobility, fleet management, and insurance for the modern world. Wheelbase is the premier fleet management SaaS ("the operating system") for auto rental, carshare, RV, and mobility fleets. Deeply embedded into our software is Roamly—a pioneering InsurTech platform providing proprietary, real-time commercial insurance that protects fleets during downtime, active rentals, and rideshare periods.

Together, we eliminate operational friction and help fleet owners scale from simple asset owners to high-performing commercial operators.

As an SDR at Wheelbase, you will be the tip of the spear for our sales growth engine. You’ll engage prospect fleet owners, pitch our all-in-one software solution, and book qualified meetings for our Account Executives. This is an onsite role where you’ll collaborate directly with sales leadership, iterate quickly on messaging, and build the foundational skills needed for a fast-track career in SaaS sales.

• Drive Pipeline: Outbound prospect via cold calls, personalized emails, and LinkedIn to fleet owners.
• Qualify Leads: Conduct discovery calls to evaluate potential customers' fleet sizes, current software stack, and business needs.
• Set Meetings: Schedule high-quality product demos for Account Executives.
• Master the Product: Develop a deep understanding of the outdoor travel industry and the Wheelbase platform capabilities.
• Manage CRM Data: Maintain accurate, up-to-date records of all outreach and deal stages in Salesforce/HubSpot.

• Based in (or relocating to) San Francisco and excited to work in a collaborative, in-office environment.
• 1–2 years of experience in sales, business development, or customer-facing roles (SaaS experience is a plus, but grit and coachability matter most).
• Excellent verbal and written communication skills—you’re comfortable picking up the phone.
• Resilient, high-energy mindset with a track record of meeting or exceeding targets.
• Genuine curiosity about tech, SMB software solutions, or the outdoor travel space.

• Competitive Compensation & Uncapped Commissions: On Target Earnings (OTE) of $90-$110K.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off.
• Fun Office Atmosphere: Lively office, stocked with endless snacks, regular Happy Hours, catered lunches, and team building events.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.
• Schedule: This is a full-time hybrid position.