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DailyPay

Hard work pays off on the daily.

Director, Large Enterprise Sales

SalesSalesFull TimeRemoteLeadTeam 501-1,000Since 2015H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

11 days ago

Salary

$163K - $250K / year

Seniority

Lead

Bachelor Degree10 yrs expEnglish

Job Description

Director, Large Enterprise Sales

DailyPay

• 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

Job 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

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