Director of Sales, Enterprise

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

📋 Description

• Proactively identify, manage, and secure a designated list of strategic enterprise accounts within mid-market and enterprise sectors, including banks, credit unions, payment processors, lenders, and fintech platforms.

• Maintain a personal quota alongside your team's overall targets.

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

• Generate measurable pipeline independently through outbound efforts, networking, partner channels, and events — taking initiative rather than relying on marketing or SDRs for leads.

• Serve as the senior representative in major deals at Worth, including those led by your Account Executives, providing support to remove obstacles at any phase.

• Recruit, nurture, and retain a high-performing team of Enterprise Account Executives and supporting Sales Development Representatives, continuously raising the standards with each new hire.

• Conduct weekly one-on-ones, pipeline evaluations, deal assessments, and call coaching sessions. Review recorded calls, accompany live calls, and provide specific, actionable feedback within 24 hours.

• Take ownership of forecasting accuracy. Deliver a weekly report to the Chief Revenue Officer that you can substantiate on a deal-by-deal basis.

• Collaborate closely with Marketing on Account-Based Marketing (ABM), with Product on roadmaps based on field insights, with Customer Success on handoffs and expansions, and with Partnerships on co-selling strategies.

• Establish operational metrics: pipeline generation objectives, stage conversion rates, cycle-time benchmarks, and win-rate targets — and ensure the team adheres to them.

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

⛳️ Requirements

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

• A proven, repeatable history of personally closing six- and seven-figure Annual Contract Value (ACV) deals — you should be able to reference the company names, deal sizes, and sales cycles.

• Direct experience selling to financial institutions, fintechs, payment processors, lenders, or other closely regulated sectors. Knowledge of KYB, KYC, IDV, AML, fraud prevention, underwriting, or onboarding tools is preferred.

• A genuine player/coach mindset; you have successfully closed deals while leading a team and can identify Account Executives whose careers you have significantly advanced.

• Proficiency with a modern sales technology stack: HubSpot (our CRM), 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 comparable) and the capability to teach it to others.

• Strong commercial acumen regarding pricing, packaging, contracts, and procurement. You possess the judgment to know when to stand firm, when to compromise, and when to walk away.

• Executive presence and writing skills that are suitable for presentation to 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