Regional Sales Director, Enterprise

Regional Sales Director, Enterprise

At AbsenceSoft, we're transforming the employee experience. Our secure, intuitive technology helps employers bring humanity, certainty, and efficiency to some of the most complex moments in the workplace. Built by HR professionals for HR professionals, we're proud of where we've been and even more excited about where we're going.

The Regional Sales Director leads and develops a team of Enterprise Account Executives to drive new business growth across an assigned region, ensuring consistent execution of revenue goals and high-quality sales delivery within AbsenceSofts B2B SaaS environment. This role provides hands-on leadership, coaching, performance management, and operational rigor to support the attainment of revenue goals, while partnering closely with Marketing, Sales Operations, Customer Success, and Product to maintain pipeline health and refine sales strategies. This position is instrumental in scaling and optimizing AbsenceSofts sales engine while developing the next generation of sales talent. The ideal candidate is an experienced sales leader with a proven track record of coaching and developing enterprise Account Executive teams in high-growth SaaS environments.

This is a remote, Central US region-based role that requires travel.

WHAT YOULL DO

• Lead, manage, and coach a team of Enterprise Account Executives to achieve individual and team quota objectives
• Oversee day-to-day sales activities, including pipeline development, opportunity management, and forecasting accuracy
• Conduct regular one-on-ones, deal reviews, and performance assessments to support skill development and accountability
• Implement and reinforce standardized sales processes, methodologies, and best practices across the team
• Partner with Sales Operations to analyze key performance metrics and identify areas for improvement
• Collaborate with Marketing to ensure campaign alignment, lead quality, and pipeline coverage
• Work with Product and Revenue leadership to communicate market feedback and inform product strategy and positioning
• Monitor the competitive landscape and guide Account Executive strategy to differentiate AbsenceSofts value proposition
• Actively participate in key deals, providing coaching and deal strategy support to help Account Executives close business
• Drive consistent usage and optimization of CRM and sales tools, including Salesforce, Salesforce CPQ, Gong, Outreach, and Ironclad
• Support hiring, onboarding, and continuous development of Account Executives to build a strong talent pipeline
• Coach the team on MEDDPICC methodology and ensure its applied consistently across deal reviews and pipeline management

WHAT YOULL BRING

• 3-5 years of experience managing Account Executive teams in B2B SaaS sales
• Bachelors degree in Business, Marketing, Communications, or related field, or equivalent practical experience
• Demonstrated ability to provide hands-on deal coaching and support to help Account Executives navigate complex sales cycles
• Proven track record of leading teams to meet or exceed revenue targets
• Proficiency in pipeline management, opportunity qualification, and forecasting
• Strong working knowledge of CRM systems (e.g., Salesforce) and sales-enablement tools
• Demonstrated ability to lead, influence, and develop enterprise SaaS Account Executives
• Experience selling leave management, HR, or workforce management solutions into large enterprise organizations (10,000+) is a plus
• Knowledge of compliance, labor, and leave laws (FMLA, ADA, PWFA, etc.) is a plus
• Formal training in or understanding of sales methodologies like MEDDICC, Challenger, or Sandler is a plus
• Experience working in a high-growth, scaling SaaS environment is a plus

Why join us

At AbsenceSoft, we LEAD with our values:

Lead with Innovation - We create meaningful change through intelligence, focus and passion. We embrace curiosity, data, and insight to shape the future of our industry. Always innovating, learning and evolving.

Elevate Every Voice - Every perspective matters. We listen, learn, and build a culture where diversity of thought and experience drives better solutions and smarter decisions.

Achieve Together - The customer fuels everything we do. We share knowledge, collaborate, celebrate wins, and face challenges as one team because success is always a collective achievement.

Drive Outcome - Every action we take delivers measurable value to our teams, our customers, and the employees they support. Accountability is non-negotiable. We honor our commitments, take responsibility for results, and see every success and setback as a chance to grow stronger.

We offer:

• Impact that matters. You'll do work that shapes the future of the modern workplace
• Flexibility and trust. We're remote-first and results driven. You'll have the freedom and flexibility to do your best work, wherever you do it best.
• Growth and development. We believe the best work happens when people are growing. You'll have access to learning resources, leadership programs, and real opportunities to take on new challenges and expand your impact.
• Competitive rewards. We offer comprehensive benefits, a performance-based bonus program, and equity opportunities - because when we grow, you should too.
• Time for life. Recharge and reconnect with flexible time off, paid holidays, and flexible leave programs designed to support every season of life.
• Belonging and balance. We're building an inclusive culture where every voice is valued, collaboration is celebrated, and success is shared.

We're committed to building a team as diverse as the customers we serve. If your experience doesn't align perfectly with every qualification, we still encourage you to apply you might be exactly what we're looking for. If this sounds like a fit, apply today, we'd love to meet you!

Compensation: Compensation: Base salary range for this full-time position is $120,000 - $140,000 annually + bonus/commission + benefits. The expected On-Target Earnings (OTE) for this role is $260,000 - $280,000.

Final compensation is determined based on a candidates relevant experience, skills, education, and geographic location. This position is also eligible for annual bonus.

The pay range for this role is:

107,107 - 133,883 USD per year (US National)

117,818 - 147,272 USD per year (US High)

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Sales

Chicago, IL

WI

IN

MI

OH

IA

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