Director, Large Enterprise Sales

DailyPay

Director of Large Enterprise Sales at DailyPay, leading a team focused on acquiring enterprise customers. Driving strategic sales motions and coaching enterprise sellers in complex sales cycles.

Posted 6/8/2026full-timeRemote • 🇺🇸 United StatesLead💰 $163,000 - $250,000 per yearWebsite

About the role

Key responsibilities & impact

Lead and coach a team of Large Enterprise Account Executives focused on acquiring net new enterprise customers within the 5,000–20,000 employee segment
Drive disciplined pipeline generation, strategic account planning, and execution across complex enterprise sales cycles with multiple stakeholders and long procurement processes
Ensure consistent execution of MEDDPICC, Sandler, and consultative sales methodologies throughout the sales process
Build a culture of accountability, operational rigor, forecasting accuracy, and performance excellence through regular pipeline reviews, deal coaching, and performance management
Coach sellers on enterprise discovery, executive engagement, multi-threading, negotiation strategy, objection handling, and value-based selling
Partner cross-functionally with Legal, Security, Finance, Product, Marketing, and Customer Success teams to remove deal blockers and accelerate strategic opportunities
Elevate the team’s ability to deliver compelling executive-level storytelling and business cases tied to workforce outcomes, ROI, and financial wellness impact
Support strategic relationship management within existing enterprise customers to strengthen partnerships and identify expansion opportunities

Requirements

What you’ll need

10+ years of enterprise SaaS, fintech, HCM, payroll, or related technology sales experience, including 3–5+ years leading high-performing enterprise sales teams
Proven success selling into and leading teams focused on enterprise organizations with 5,000–20,000 employees
Demonstrated experience managing complex enterprise sales cycles involving executive buyers, procurement, legal, security, and multiple decision-makers
Strong expertise in MEDDPICC, Sandler, and consultative enterprise sales methodologies, with a track record of improving team execution and sales performance
Proven ability to coach, develop, and hold enterprise sales teams accountable while fostering a high-performance culture
Exceptional executive communication, relationship-building, and storytelling skills, with the ability to articulate business value and differentiate within competitive enterprise environments.

Benefits

Comp & perks

Exceptional health, vision, and dental care
Opportunity for equity ownership
Life and AD&D, short- and long-term disability
Employee Assistance Program
Employee Resource Groups
Fun company outings and events
Unlimited PTO
401K with company match

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enterprise SaaSfintechHCMpayrollMEDDPICCSandlerconsultative sales methodologiespipeline generationstrategic account planningnegotiation strategy

Soft Skills

coachingrelationship-buildingexecutive communicationstorytellingobjection handlingvalue-based sellingperformance managementaccountabilityoperational rigorforecasting accuracy