Regional Sales Director, Enterprise

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 AbsenceSoft's 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 AbsenceSoft's 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.

Responsibilities

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 AbsenceSoft's 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 it's applied consistently across deal reviews and pipeline management

Requirements

3-5 years of experience managing Account Executive teams in B2B SaaS sales; Bachelor's 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

Nice to have

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

Benefits

Remote-first work; Impactful work; Learning resources and leadership programs; Comprehensive benefits; Performance-based bonus program; Equity opportunities; Flexible time off; Paid holidays; Flexible leave programs; Inclusive culture