Director of Sales – Enterprise

This is a fully remote position, open to applicants in Florida.

📋 Description

• Take ownership of hunting, managing, and closing a designated list of strategic enterprise accounts that include mid-market and enterprise banks, credit unions, payment processors, lenders, and platform fintechs.

• Maintain a direct individual quota in addition to the overall team goal.

• Conduct discovery sessions, scoping, demonstrations, technical evaluations, commercial negotiations, redlining, and contract closures with support from Solutions, Product, Legal, and Finance teams.

• Generate measurable pipeline via outbound efforts, networking, partner channels, and event participation.

• Act as the senior representative on Worth's largest deals and facilitate the progress of deals at any stage.

• Recruit, develop, and retain a high-performing team of Enterprise Account Executives and supporting Sales Development Representatives.

• Hold weekly one-on-one meetings, pipeline reviews, deal evaluations, and call coaching sessions; review recorded calls, participate in live calls, and provide constructive feedback within 24 hours.

• Take responsibility for forecasting accuracy and deliver a well-supported weekly forecast to the Chief Revenue Officer.

• Collaborate with Marketing on Account-Based Marketing (ABM), Product on roadmap indicators, Customer Success on handoff and expansion, and Partnerships on co-selling strategies.

• Establish the operational rhythm around pipeline creation, stage transitions, cycle duration, and win-rate objectives.

• Present sales performance metrics, pipeline status, competitive insights, and strategic recommendations to the executive team and board as required.

⛳️ Requirements

• 8+ years of experience in enterprise B2B SaaS sales, including at least 4 years in a frontline sales leadership role overseeing Account Executives.

• A proven, documented track record of personally closing six- and seven-figure annual contract value (ACV) deals — you can recall the companies, deal sizes, and timelines.

• Direct experience selling to financial institutions, fintechs, payment processors, lenders, or similar regulated sectors.

• Knowledge of Know Your Business (KYB), Know Your Customer (KYC), Identity Verification (IDV), Anti-Money Laundering (AML), fraud prevention, underwriting, or onboarding tools.

• A true player/coach mentality; you have successfully led deals while managing a team and can cite AEs whose careers you have significantly advanced.

• Proficiency in a modern sales technology stack: HubSpot (our CRM), Outreach/Salesloft, Gong/Chorus, LinkedIn Sales Navigator, ZoomInfo or equivalent tools.

• Expertise in a structured enterprise sales methodology (such as MEDDPICC, Command of the Message, Challenger, Force Management, or comparable) and the capability to teach it effectively.

• Strong commercial acumen regarding pricing, packaging, contracting, and procurement processes.

• Executive presence and writing skills that resonate with a Chief Risk Officer or a board of directors.

🏝️ 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