Job Description

Worth is a B2B SaaS fintech platform that consolidates SMB onboarding and underwriting into a single AI-powered system for financial institutions, credit unions, fintechs, lenders, payment processors, and ISVs. We are hiring a Director of Sales, Enterprise to own new logo acquisition and expansion across our enterprise segment — financial institutions, top-tier fintechs, payment processors, ISVs, and lenders writing the biggest checks in our pipeline. This is a player/coach role: you will personally carry a quota and run our largest, most complex deals while building, coaching, and scaling a small team of senior Enterprise AEs and SDRs underneath you.

If you only want to manage from a forecast spreadsheet, this is not the job. If you want to sit in the deal, sharpen the message, build the playbook, and develop the next generation of Worth sellers while you do it — read on.

Responsibilities

• As a Player (roughly 50% of your time)
• As a Coach (roughly 50% of your time)

Requirements

• 8+ years of enterprise B2B SaaS sales experience, with at least 4 years in a frontline sales leadership role managing AEs.
• A 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
• A 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