Enterprise Sales Director

About the role

The Director of Enterprise Sales provides strategic leadership to the Account Executive team, directly driving net-new revenue growth and maximizing DailyPay’s market expansion across key enterprise segments. Serving as a principal advisor and escalation point, this role reconciles complex stakeholder perspectives across multi-threaded enterprise deals to secure high-value partnerships. The Director establishes functional sales objectives, implements metrics-based management cultures, and aligns team execution with broader corporate growth targets. By cultivating a high-performance culture, this leader significantly impacts the competitive positioning and long-term operational effectiveness of the sales function.

Responsibilities

• Team Leadership: Recruit, develop, and manage a high-performing Account Executive team, focusing on continuous performance elevation and talent retention.
• Strategic Deal Orchestration: Serve as the executive escalation point for complex enterprise prospects, designing innovative deal strategies to accelerate sales cycles.
• Revenue Forecasting: Deliver highly accurate weekly, quarterly, and annual revenue forecasts to the VP of Sales, utilizing metrics-based management data.
• Market Expansion: Define and execute tactical plans to maximize DailyPay's penetration across target market segments and enterprise verticals.
• Cross-Functional Collaboration: Partner closely with Sales Operations, Marketing, Product, and Legal teams to ensure seamless alignment on go-to-market strategies and resource deployment.
• Process Optimization: Develop, refine, and enforce scalable sales methodologies, playbooks, and value propositions tailored for complex financial technology solutions.
• CRM & Tech Governance: Drive the strict adoption of CRM strategies, sales enablement technologies, and data analytics to optimize pipeline health and visibility.
• Brand Advocacy: Serve as a principal market evangelist, educating the broader labor and corporate marketplace on the strategic benefits of DailyPay’s platform.

Requirements

• Proven Leadership: 7+ years of professional sales experience, with at least 3+ years successfully managing and scaling a high-performing B2B enterprise sales team.
• Domain Expertise: Demonstrated track record of success selling complex SaaS, HR Tech, FinTech, or Enterprise Business Intelligence solutions.
• Strategic Execution: Proven ability to translate high-level corporate goals into actionable sales plans, structured processes, and measurable revenue outcomes.
• Advanced Tech Literacy: Exceptional proficiency utilizing Salesforce and modern sales tech stacks (e.g., Clari, Gong, Salesloft) for predictable pipeline management.
• Stakeholder Management: Elite communication, negotiation, and public speaking skills, with a verified capability to influence and close deals at the C-suite level.

Qualifications

• Bachelor’s degree in Business Administration, Marketing, Communications, or a related professional field.

Skills

• Exceptional communication and interpersonal skills.
• Ability to lead and mentor a team.
• Strong analytical and problem-solving skills.
• Experience with Salesforce and other CRM tools.
• Knowledge of SaaS, HR Tech, FinTech, or Enterprise Business Intelligence solutions.

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.

Pay

Competitive compensation package including base salary and bonus opportunities.

Schedule

Full-time position with flexible working hours.