Director of Sales, Enterprise

Responsibilities

As a Player (roughly 50% of your time)

• Personally hunt, own and close a named list of strategic enterprise accounts mid-market and enterprise banks, credit unions, payment processors, lenders, and platform fintechs.
• Carry a direct, individual quota in addition to your team's number.
• Run discovery, scoping, demo, technical evaluation support, commercial negotiation, redlines, and contract close with assists from Solutions, Product, Legal, and Finance.
• Drive measurable pipeline yourself through outbound, network, partner channels, and event work — you are not waiting on marketing or SDRs to feed you.
• Be the senior voice in the room on Worth's biggest deals including ones your AEs are running and step in to unblock at any stage.

As a Coach (roughly 50% of your time)

• Hire, develop, and retain a high-performing team of Enterprise AEs and supporting SDRs raise the bar with every hire.
• Run weekly 1:1s, pipeline reviews, deal reviews, and call coaching. Listen to recorded calls, ride along on live ones, and give specific, actionable feedback within 24 hours.
• Own forecasting accuracy. Submit a weekly call to the CRO that you can defend deal-by-deal.
• Partner closely with Marketing on ABM, with Product on roadmap signal from the field, with CS on handoff and expansion, and with Partnerships on co-sell motions.
• Build the operating cadence: pipeline generation targets, stage conversion targets, cycle-time targets, win-rate targets — and hold the team to them.
• Present sales performance, pipeline health, competitive intel, and strategic recommendations to the executive team and board as needed.

Requirements

• 8+ years of enterprise B2B SaaS sales experience, with at least 4 years in a frontline sales leadership role managing AEs.
• Documented, repeatable track record of personally closing six- and seven-figure ACV deals — you can name the logos, the deal sizes, and the cycle times.
• Direct experience selling into financial institutions, fintechs, payment processors, lenders, or adjacent regulated industries. Familiarity with KYB, KYC, IDV, AML, fraud, underwriting, or onboarding tooling.
• Genuine player/coach disposition you have run deals while leading a team and can point to AEs whose careers you have measurably advanced.
• Operating fluency in a modern sales stack: HubSpot (our CRM), Outreach/Salesloft, Gong/Chorus, LinkedIn Sales Navigator, ZoomInfo or similar.
• Mastery of a structured enterprise sales methodology (MEDDPICC, Command of the Message, Challenger, Force Management, or similar) and the ability to teach it.
• Sharp commercial instincts on pricing, packaging, paper, and procurement. You know when to hold, when to concede, and when to walk.
• Executive presence and writing that holds up in front of a Chief Risk Officer or a board.

Benefits

• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k)
• Life Insurance
• Flexible Paid Time Off
• 9 paid Holidays
• Free Food & Snacks in Orlando office