Regional Sales Director, Mid-Market (SaaS)

TL;DR

Regional Sales Director, Mid-Market (SaaS): Leading and developing a team of Mid-Market Account Executives to drive new business growth across assigned regions with an accent on revenue goals, coaching, and operational rigor. Focus on scaling the sales engine, implementing MEDDPICC methodology, and optimizing pipeline health through cross-functional collaboration.

Location: Remote (Must be based in the United States)

Company

B2B SaaS company providing secure and intuitive technology to help employers manage complex employee leave and workplace experiences.

What you will do

• Lead, manage, and coach Mid-Market Account Executives to achieve individual and team quota objectives.
• Oversee day-to-day sales activities, including pipeline development, opportunity management, and forecasting accuracy.
• Implement and reinforce standardized sales processes and MEDDPICC methodology across the team.
• Partner with Marketing, Sales Operations, and Product to align lead quality, pipeline coverage, and product strategy.
• Conduct regular deal reviews and provide hands-on coaching to help Account Executives navigate complex sales cycles.
• Support hiring and onboarding to build a strong talent pipeline of sales professionals.

Requirements

• Must be based in the United States.
• 3-5 years of experience managing Account Executive teams in B2B SaaS sales.
• Proven track record of leading teams to meet or exceed revenue targets.
• Proficiency in pipeline management, opportunity qualification, and CRM systems (e.g., Salesforce).
• Bachelor's degree in Business, Marketing, Communications, or equivalent practical experience.

Nice to have

• Experience selling leave management, HR, or workforce management solutions.
• Knowledge of compliance, labor, and leave laws (FMLA, ADA, PWFA, etc.).
• Formal training in sales methodologies like MEDDICC, Challenger, or Sandler.
• Experience working in a high-growth, scaling SaaS environment.

Culture & Benefits

• Remote-first and results-driven work environment with flexibility and trust.
• Comprehensive benefits package including full medical, dental, vision, and life insurance.
• 401(k) with company match available after the first year.
• Support for professional growth, including industry training and certifications.
• Flexible time off, paid holidays, and inclusive culture where diversity of thought is valued.