Note: The job is a remote job and is open to candidates in USA. DailyPay is transforming the way people get paid as a leading worktech company. They are seeking a high-impact Director of Large Enterprise Sales to lead a team focused on acquiring new enterprise logos within the 5,000–20,000 employee market segment, driving a disciplined and strategic sales motion.
Responsibilities
- 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
Skills
- 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
Company Overview