Description
Job Overview
We're hiring a Sales Development Representative dedicated to ground contractor fleets, independent service providers, and contracted delivery operators running their own trucks. 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.
Key Responsibilities
- Prospect into Ground contractor 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 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.
- 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 contractor fleet 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 fleet 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 cross-functionally with marketing, AEs, and leadership.
- Coachable, competitive, and energized by building something from the ground up.
Nice-to-have:
- Prior SDR, BDR, or summer sales experience.
- Door-to-door sales experience.
- Competitive athletics or sports background.
- Immersive, high-discipline experience such as a religious mission, military service, or similar.
- Curiosity about or prior exposure to fintech, payments, or trucking/logistics.
- Familiarity with Salesforce, Outreach, Slack, or G-Suite.
Compensation & Benefits
- $55,000 to $60,000 OTE
- Meaningful early-stage equity
- Medical insurance
- All hardware and software needed to do your best work
- A front-row seat to building a category-defining payments company from its earliest days