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

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