Director of Sales, Enterprise

Worth AI; Orlando (FL); On-site; USD 130,000 - 180,000; Full time

Benefits offered by this job

Health Care Plan (Medical, Dental & Vision)

Retirement Plan (401k)

Life Insurance

Flexible Paid Time Off

9 paid Holidays

Free Food & Snacks in Orlando office

Job summary

Worth AI in Orlando is seeking a Director of Sales to lead the enterprise sales strategy targeting financial institutions, fintechs, and payment processors. This player/coach role requires 8+ years in B2B SaaS sales, strong leadership skills, and a proven record of closing significant deals. Responsibilities include direct sales, team development, and achieving sales targets. Worth AI offers a comprehensive benefits package, including health care and a retirement plan.

Qualifications

• 8+ years of enterprise B2B SaaS sales experience, with 4 years in sales leadership.
• Documented track record of closing six- and seven-figure ACV deals.
• Direct experience with financial institutions, fintechs, or payment processors.
• Player/coach disposition with a focus on team advancement.

Responsibilities

• Hunt and close strategic enterprise accounts.
• Manage a team of Enterprise AEs and support their development.
• Own forecasting accuracy and present to executive teams.
• Drive pipeline generation through various channels.

Skills

Enterprise B2B SaaS sales experience

Team leadership

Sales methodology mastery

Commercial instincts

Tools

HubSpot

Outreach/Salesloft

Gong/Chorus

LinkedIn Sales Navigator

ZoomInfo

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)
  • 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.

Qualifications

• 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