DailyPay

Worktech

Director,LargeEnterpriseSales

$163–250k United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Director candidates.

The Brief

“Director, Large Enterprise Sales at DailyPay. Skills: Enterprise sales, Sales leadership, Consultative selling. Lead and coach sales team. Acquire net new enterprise customers”

Industry & Context.

Worktech
Problems you'll solve

Uncovering business pain

What They're Looking For.

Must Have

10+ years enterprise SaaS sales experience, 3-5+ years leading sales teams, Experience selling to 5,000-20,000 employee organizations, Experience managing complex enterprise sales cycles, Expertise in MEDDPICC, Expertise in Sandler sales methodology, Expertise in consultative enterprise sales

Nice to Have

Fintech sales experience, HCM sales experience, Related technology sales experience

What You'll Do.

Lead and coach sales team

Acquire net new enterprise customers

Drive pipeline generation

Execute strategic account planning

Manage complex enterprise sales cycles

Ensure MEDDPICC execution

Ensure Sandler execution

Ensure consultative sales execution

Build accountability culture

Improve forecasting accuracy

Coach sellers on discovery

Coach sellers on executive engagement

Coach sellers on multi-threading

Coach sellers on negotiation strategy

Coach sellers on objection handling

Coach sellers on value-based selling

Partner cross-functionally

Accelerate strategic opportunities

Deliver executive storytelling

Develop business cases

Support relationship management

Strengthen partnerships

Identify expansion opportunities

How You'll Work.

Team & Collaboration

Partner with Legal; Partner with Security; Partner with Finance; Partner with Product; Partner with Marketing; Partner with Customer Success

Communication Scope

Executive storytelling; Business value articulation

Full Job Description

About Us: DailyPay is transforming the way people get paid. As a worktech company and the industry’s leading on demand pay solution, DailyPay uses an award-winning technology platform to help America’s top employers build stronger relationships with their employees. This voluntary employee benefit enables workers everywhere to feel more motivated to work harder and stay longer on the job while supporting their financial well-being outside of the workplace. DailyPay is headquartered in New York City, with operations throughout the United States as well as in Belfast. For more information, visit DailyPay's Press Center. http://www.dailypay.com/press THE ROLE: DailyPay is 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. This leader will drive a disciplined, consultative, and highly strategic sales motion focused on complex enterprise organizations with long sales cycles, multiple stakeholders, and sophisticated procurement processes. The ideal candidate is a proven enterprise sales leader with deep experience building and coaching high-performing sales teams, driving accountability, and leading through structured sales methodologies including MEDDPICC and Sandler. This role requires a leader who can develop enterprise sellers into trusted advisors capable of uncovering business pain, navigating complex buying committees, building executive relationships, and delivering compelling business-value storytelling. While the primary focus is net new logo acquisition, this leader will also ensure Account Executives maintain strong executive relationships within existing client accounts to support expansion opportunities, retention, and long-term strategic partnerships. If this opportunity excites you, we encourage you to apply even if you do not meet all of the qualifications. HOW YOU WILL MAKE AN IMPACT: - Lead and coach a team of Large Enterprise Account Executiv

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