Director, Enterprise Sales

Ladders; United States; Remote; USD 370,000 - 490,000; Full time

Benefits offered by this job

100% health coverage for employees and

Monthly stipends for tech setup and 健康

Flexible time off and generous holiday

Employee stock purchase plan (ESPP)

Job summary

Ladders is seeking a Director, Enterprise Sales to lead a high-performing enterprise sales team focused on complex partnerships and revenue growth. This role shapes the enterprise retail motion, guides senior sales talent, and partners with cross-functional teams to drive commercial results. Location: Remote - US based candidates only.

Compensation: $370,000 – $490,000 annually. 10+ years in enterprise sales, proven success with large retail merchants in payments/fintech, and strong executive

Qualifications

• 10+ years in enterprise sales or commercial leadership with senior teams.
• Experience managing senior, quota-carrying Account Executives.
• Proven success in large, complex sales cycles with executive stakeholders.
• Strong alignment with the organization's mission and value proposition.
• Experience selling to large retail merchants in payments or fintech.
• Excellent judgment and communication skills with executive presence.
• Track record of developing high-performing sales talent and discipline.
• Proficient in data, AI, and modern sales tools for improved effectiveness.

Responsibilities

• Lead and develop a team of senior Account Executives, driving performance and accountability.
• Own team performance metrics, including pipeline health and revenue outcomes.
• Coach AEs through complex strategic opportunities and negotiations.
• Build relationships with senior leaders at major retail merchants.
• Shape enterprise retail go-to-market strategy and objectives.
• Drive commercial outcomes by collaborating with cross-functional teams.
• Leverage data and modern tools to enhance sales effectiveness and operational excellence.
• Travel as needed for merchant meetings and industry events.

Skills

Enterprise sales leadership

Executive presence

Coach senior AEs

Cross-functional collaboration

Data-driven selling

Job description

For our client, we are seeking a Director, Enterprise Sales to join the team of a leader in the Finance & Insurance space.

This role will lead a high-performing enterprise sales organization focused on complex merchant partnerships and revenue growth. You will shape strategy for the enterprise retail motion, guide senior sales talent, and partner closely with cross-functional teams to drive commercial results. The position requires strong executive presence, disciplined execution, and the ability to influence outcomes across sophisticated sales cycles in a fast-moving financial services environment.

Location: Remote - US based candidates only, no visa sponsorship available

Compensation: $370,000 – $490,000 annually

Responsibilities

• Lead and develop a team of senior Account Executives, driving performance and accountability
• Own team performance metrics, including pipeline health and revenue outcomes
• Coach AEs through complex strategic opportunities and negotiations
• Build relationships with senior leaders at major retail merchants
• Shape enterprise retail go-to-market strategy and objectives
• Drive commercial outcomes by collaborating with cross-functional teams
• Leverage data and modern tools to enhance sales effectiveness and operational excellence
• Travel as needed for merchant meetings and industry events

Qualifications

• 10+ years in enterprise sales or commercial leadership, with a focus on senior sales teams
• Experience managing and developing senior, quota-carrying Account Executives
• Proven success in large, complex sales cycles with executive stakeholders
• Strong alignment with the organization's mission and understanding of its value proposition
• Experience selling to large retail merchants in payments or fintech
• Excellent judgment and communication skills, with executive presence
• Track record of developing high-performing sales talent and operational discipline
• Proficient in data, AI, and modern sales tools for improved effectiveness

Benefits

• 100% health coverage for employees and their dependents
• Monthly stipends for tech setup and health/wellness options
• Flexible time off and generous holiday calendars
• Employee stock purchase plan (ESPP) allowing purchase of company stock at a discount

Our client is an equal opportunity employer.