Director of Sales, Enterprise

📋 Description

• Take personal responsibility for identifying, securing, and managing a designated list of strategic enterprise accounts, including mid-market and enterprise banks, credit unions, payment processors, lenders, and platform fintech companies.

• Maintain an individual quota alongside your team's overall targets.

• Conduct discovery sessions, scope out requirements, provide demo and technical evaluation support, negotiate commercially, handle redlines, and finalize contracts with assistance from Solutions, Product, Legal, and Finance teams.

• Generate a quantifiable sales pipeline independently through outbound efforts, networking, partner channels, and event participation — you will not rely on marketing or Sales Development Representatives (SDRs) for leads.

• Serve as the leading authority in discussions on Worth's most significant deals, including those managed by your Account Executives (AEs), and intervene to resolve any obstacles at any point in the process.

• Recruit, nurture, and retain a high-performing team of Enterprise AEs and supporting SDRs, continuously elevating standards with each new hire.

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

• Ensure accuracy in forecasting. Deliver a weekly report to the Chief Revenue Officer (CRO) that you can substantiate on a deal-by-deal basis.

• Collaborate closely with Marketing on Account-Based Marketing (ABM), with Product on gathering field signals for the roadmap, with Customer Success (CS) on handoffs and expansions, and with Partnerships on co-selling initiatives.

• Establish the operational rhythm: targets for pipeline generation, stage conversion, cycle times, and win rates — and hold the team accountable to these metrics.

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

⛳️ Requirements

• 8+ years of experience in enterprise B2B SaaS sales, including a minimum of 4 years in a frontline sales leadership role managing Account Executives (AEs).

• A proven, documented history of successfully closing six- and seven-figure Annual Contract Value (ACV) deals — you can specify the associated logos, deal sizes, and sales cycles.

• Direct experience selling to financial institutions, fintech companies, payment processors, lenders, or related regulated industries, with knowledge of KYB, KYC, IDV, AML, fraud prevention, underwriting, or onboarding tools.

• A genuine player/coach mentality; you have actively closed deals while leading a team and can identify AEs whose careers you have significantly advanced.

• Proficient use of a modern sales tech stack: HubSpot (our CRM), Outreach/Salesloft, Gong/Chorus, LinkedIn Sales Navigator, ZoomInfo, or similar platforms.

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

• Strong commercial acumen regarding pricing, packaging, documentation, and procurement. You understand when to stand firm, when to compromise, and when to walk away.

• Possess executive presence and writing skills that resonate with Chief Risk Officers 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 the Orlando office