Director of Sales

The Role Reporting to the CRO, the Director of Sales leads a team of 8–10 Account Executives. 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. What You’ll Own Team leadership & coaching Lead, coach, and develop a team of 8–10 AEs to consistently hit individual and team quota Run a consistent coaching cadence — weekly 1:1s, call evaluations, and pipeline reviews Use call recordings and 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 Hiring & ramp 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 Pipeline, forecast & quota 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, and deal gates 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 What Success Looks Like First 30 days — Know your team. Complete 1:1s with every AE, review each rep’s pipeline and recent calls, learn client’s digital payment and invoicing platform, 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. Team is tracking to quota, new hires are ramping on plan, and coaching is producing measurable call‑quality improvement. Qualifications Required 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 What We Offer Competitive base salary plus performance‑based incentive (range to be specified) Leadership role reporting directly to the CRO #J-18808-Ljbffr