Director of Sales – Enterprise

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

📋 Description

• Lead new customer acquisition and growth within Worth's enterprise segment.

• Actively seek, manage, and finalize strategic enterprise accounts, including banks, credit unions, payment processors, lenders, and platform fintechs.

• Maintain a direct individual sales quota in addition to the team's overall target.

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

• Generate measurable pipeline through outbound efforts, networking, partner channels, and events.

• Serve as the lead voice in Worth's most significant deals and resolve issues at any stage of the process.

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

• Conduct weekly one-on-ones, pipeline assessments, deal evaluations, and coaching sessions.

• Ensure accurate forecasting and provide a justifiable weekly forecast to the Chief Revenue Officer.

• Collaborate with Marketing on Account-Based Marketing, Product on roadmap insights, Customer Success on transitions and growth, and Partnerships on co-selling strategies.

• Establish an operational rhythm focused on pipeline generation, stage transitions, cycle times, and win-rate objectives.

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

⛳️ Requirements

• Over 8 years of experience in enterprise B2B SaaS sales, with a minimum of 4 years in frontline sales leadership overseeing Account Executives.

• A proven, repeatable history of personally closing six- and seven-figure Annual Contract Value deals—able to specify the client names, deal sizes, and timelines.

• Direct experience in sales to financial institutions, fintech companies, payment processors, lenders, or other regulated industries.

• Familiarity with 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 managed deals while leading a team and can identify AEs whose careers you have significantly advanced.

• Proficient in using a modern sales technology stack: HubSpot, Outreach/Salesloft, Gong/Chorus, LinkedIn Sales Navigator, ZoomInfo, or similar tools.

• Expertise in a structured enterprise sales methodology (such as MEDDPICC, Command of the Message, Challenger, Force Management, or similar) and the ability to instruct others in it.

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

• Executive presence and writing skills that are effective in communications with a Chief Risk Officer or board members.

🏝️ 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