Director of Sales, Enterprise

🕒 May 14

🐊 Florida – Remote

🐊 Florida – Remote

⏰ Full Time

🔴 Lead

🤑 Sales

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Worth AI

WebsiteLinkedInAll Job Openings

11 - 50 employees

💼 Consulting

🛡️ Insurance

🤖 Artificial Intelligence

Consulting • Insurance • Artificial Intelligence

Worth AI is a company that specializes in enhancing financial security and risk management through advanced AI-driven solutions. Their platform offers a suite of tools designed for seamless onboarding, compliance, and credit risk assessment. They help banks, fintech companies, and credit unions streamline operations by automating processes such as KYC/KYB compliance, reputation monitoring, and automated credit underwriting. Worth AI's technology provides real-time risk monitoring, predictive analytics, and AI-generated insights to improve decision-making, safeguard institutions, and boost revenue. Key offerings include Worth Score™, an AI-driven credit score solution, and unique AI underwriting systems that enhance the accuracy and efficiency of financial assessments.

📋 Description

• 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. • 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. • 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