SDR - OTR Fleet

About PistonPay PistonPay is a payments company starting by revolutionizing how fleets manage their fuel payments. We're a Series A company backed by some of the best investors in the world, including Pear, Spark, and FPV (the same firms behind Anthropic, Dropbox, DoorDash, and Canva). We're building the financial backbone for the trucks and fleets that move the economy, and we're just getting started. Role overview We're hiring a Sales Development Representative dedicated to over-the-road (OTR) trucking fleets, long-haul carriers running fuel-intensive routes across the country. You'll be the first conversation a prospect has with PistonPay, prospecting into accounts, qualifying inbound interest, and booking discovery calls for our Account Executives. This is a builder's role. You'll work closely with sales leadership and AEs to shape the outbound playbook for this segment, not execute someone else's script. Key Responsibilities Prospect into OTR fleet target accounts through a disciplined mix of cold calls, cold email, and LinkedIn outreach, sustaining a high-volume, high-quality outbound motion (100+ calls per day). Qualify inbound leads against our ideal customer profile and convert qualified conversations into booked discovery calls for Account Executives. Partner with marketing on campaign development, messaging testing, and ongoing refinement of the OTR fleet ideal customer profile. Maintain accurate, up-to-date records in Salesforce and Outreach, and bring a clear point of view on what messaging and tactics are working. Travel occasionally (1 to 3 week sprints) to support in-market pushes and events. Contribute directly to the outbound playbook other SDRs will follow as the team scales. What Success Looks Like In the first 30 days: You have completed onboarding and have a working knowledge of PistonPay's product, ICP, and the OTR trucking market. You are comfortable with our tech stack (Salesforce, Outreach, Slack, G-Suite) and running a full daily outbound cadence. You have made your first calls and sent your first sequences, and are actively building pipeline. You have booked your first discovery calls for an Account Executive. In the first 90 days: You are consistently hitting daily and weekly activity targets (100+ calls/day) and booking a steady, predictable volume of qualified meetings. You have a clear, data-backed point of view on what messaging, lists, and channels are working in the OTR segment. You are a trusted partner to marketing and AEs, actively shaping campaigns and ICP refinement rather than just executing them. You have helped document or improve the outbound playbook for this segment. Qualifications & Requirements Must-have: A genuine desire to build a long-term career in sales. This is a launchpad role, not a stopgap. Strong written and verbal communication skills. Ability to thrive on a high-volume outbound cadence (100+ dials/day) and work…