Director, Large Enterprise Sales
New
D
DailyPayFintech Worktech
US-RemoteFull-TimeDirector
Salary$163K - $250K; $163K – $250K • Offers Equity • Offers Commission • Multiple Ranges; New York City: $190K – $250K • Offers Equity • Offers Commission; Remote Premium: $171K – $226K • Offers Equity • Offers Commission; Remote Standard: $163K – $215K • Offers Equity • Offers Commission
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Job Details
- Experience
- 10+ years
- Required Skills
- Account Management
Requirements
- 10+ years of enterprise SaaS, fintech, HCM, payroll, or related technology sales experience
- 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
- Proven ability to coach, develop, and hold enterprise sales teams accountable
- Exceptional executive communication, relationship-building, and storytelling skills
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
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