Director of Sales

RoadSync•Atlanta, GA

6d•Hybrid

About The Position

RoadSync is revolutionizing the logistics industry with intelligent, simple, and innovative financial solutions. Our digital platform streamlines payment processes for warehouses, carriers, brokers, and repair/tow operators, dramatically reducing processing time and maximizing revenue collection. Reporting to the CRO, the Director of Sales leads a team of 8–10 Account Executives selling RoadSync Checkout. This is a player-coach role: you own your team's number and get there through disciplined Coaching, fast new-hire ramp, and consistent execution. You'll partner closely with RevOps, Customer Success, and Marketing, and you'll own pipeline health, forecast accuracy, and the development of every AE on your team.

Requirements

5+ years in B2B sales with 2+ years leading a quota-carrying AE team (8+ reps)
Demonstrated track record of hitting and exceeding team revenue targets
Hands-on coaching leader comfortable on calls, in demos, and in the deal
Strong CRM discipline; fluency in HubSpot (or comparable) for pipeline inspection, forecasting, and process enforcement
Experience hiring, onboarding, and ramping new AEs at speed
Data-driven approach to pipeline, forecasting, and performance management

Nice To Haves

SaaS, payments, fintech, or logistics/transportation industry experience
Experience selling into SMB and mid-market, with exposure to longer-cycle enterprise deals
Familiarity with sales enablement tooling and structured call-coaching frameworks

Responsibilities

Lead, coach, and develop a team of 8–10 AEs to hit individual and team quota consistently.
Run a consistent coaching cadence: weekly 1:1s, call evaluations, & pipeline reviews.
Use call recordings & structured scorecards to drive measurable improvement in discovery, demo, and objection handling.
Manage performance directly and fairly, including progressive Coaching and accountability when reps are off track.
Own new-hire onboarding and time-to-productivity; ensure every new AE follows the formal onboarding checklist.
Get new reps shadowing experienced AEs in Week 1 and ramping against clear 30-60-90-day expectations.
Surface and remove ramp obstacles early.
Own an accurate, defensible forecast and a healthy, well-qualified pipeline across your team
Inspect pipeline rigorously in HubSpot; enforce data quality, stage discipline, and playbook completion.
Hold the line on process adherence; dispositioning, required fields, deal gates and Cross-functional partnership.
Raise CRM and process friction early and help drive solutions with RevOps.
Provide structured input to Marketing on lead quality and quantity.
Coordinate with Customer Success on clean deal-to-onboarding handoffs.