# Director of Sales, Enterprise

**Company:** [Worth AI](https://hotfix.jobs/companies/worth-ai)
**Location:** Remote
**Role:** Account Executive
**Experience:** 8+ years
**Skills:** HubSpot, Outreach, Salesloft, Gong, Chorus, LinkedIn Sales Navigator, ZoomInfo, MEDDPICC, ABM, Outbound Sales
**Posted:** 2026-05-14

> Leads enterprise sales for B2B SaaS fintech platform, personally closing six- and seven-figure deals with financial institutions while building and coaching a team of AEs and SDRs. Requires 8+ years B2B SaaS sales experience, 4+ in leadership, and expertise in regulated industries.

## Job Description

## 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

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