Director of Sales

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.

Team leadership & Coaching

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  Lead, coach, and develop a team of 8–10 AEs to hit individual and team quota consistently.

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  Run a consistent coaching cadence: weekly 1:1s, call evaluations, & pipeline reviews.

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  Use call recordings & structured scorecards to drive measurable improvement in discovery, demo, and objection handling.

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  Manage performance directly and fairly, including progressive Coaching and accountability when reps are off track.

Hiring & Ramp

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  Own new-hire onboarding and time-to-productivity; ensure every new AE follows the formal onboarding checklist.

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  Get new reps shadowing experienced AEs in Week 1 and ramping against clear 30-60-90-day expectations.

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  Surface and remove ramp obstacles early.

Pipeline, Forecast & Quota

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  Own an accurate, defensible forecast and a healthy, well-qualified pipeline across your team

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  Inspect pipeline rigorously in HubSpot; enforce data quality, stage discipline, and playbook completion.

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  Hold the line on process adherence; dispositioning, required fields, deal gates and Cross-functional partnership.

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  Raise CRM and process friction early and help drive solutions with RevOps.

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  Provide structured input to Marketing on lead quality and quantity.

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  Coordinate with Customer Success on clean deal-to-onboarding handoffs.

• First 30 days — Know your team. Complete 1:1s with every AE, review each rep's pipeline and recent calls, learn RoadSync Checkout and the buyer, and establish your coaching cadence.

• First 60 days — Own the forecast. Deliver an accurate team forecast, identify your top 2–3 ramp and performance priorities, and have a concrete plan for any underperforming reps and open headcount.

• First 90 days — Drive results. The team is tracking to quota, new hires are ramping up on plan, and Coaching is producing measurable improvements in call quality.

• 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

Preferred

• 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

RoadSync is a team of passionate professionals who care deeply about what we do and bring our best every day. We value being a diverse and inclusive team and company. In addition to joining an innovative and passionate team, you will get:

• Competitive compensation package and company equity awarded on day 1!

• RoadSync employees enjoy three weeks (15 working days) of PTO annually

• Medical, dental, and vision benefits - premiums paid for employees

• Leadership role reporting directly to the CRO

• Hybrid office, Downtown Atlanta, Georgia
  
  

RoadSync is proud to be an Equal Opportunity Employer and an Affirmative Action Employer. We do not discriminate based on race, creed, color, ethnicity, national origin, religion, sex, sexual orientation, gender expression, age, height, weight, veteran status, military obligations, pregnancy, marital status, or any other legally recognized protected basis under federal, state, or local law. Every day, our team is honored to work with individuals from all walks of life. We aim to build a team that reflects the diversity of our customers. Each individual at RoadSync brings their own perspectives, work experiences, lifestyles, and cultures. We believe that a more diverse team creates more innovative products, provides a better service to our customers, and helps us grow and learn as individuals.