Director, Large Enterprise Sales

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DailyPay

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2015

💳 Fintech

🤝 B2B

👥 HR Tech

Fintech • B2B • HR Tech

DailyPay is a financial technology company that provides an On-Demand Pay platform, allowing employees to access their earned wages before payday. This service empowers employees by giving them financial control, which in turn increases engagement, motivation, and overall happiness at work. DailyPay aims to help organizations improve recruitment and retention rates while reducing employee turnover through its innovative financial wellness solutions.

📋 Description

• 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

• 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

• 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