Director, Mid-Market Sales

Job Overview

We are seeking a dynamic Sales Manager to lead a team of Account Executives focused on acquiring new accounting and tax firms (16–49 employees). This leader will be responsible for driving team performance, developing territory strategies, and ensuring the achievement of aggressive growth targets. The ideal candidate has a proven track record in sales leadership, understands consultative selling, and is passionate about enabling firms with technology solutions that address security, compliance, and operational efficiency.

• Team Leadership
  • Recruit, coach, and develop a high-performing team of Account Executives.
  • Foster a culture of accountability, collaboration, and continuous improvement.
  • Conduct regular pipeline reviews, forecast updates, and performance evaluations.
• Sales Strategy & Execution
  • Define and implement strategies to penetrate new markets and achieve revenue goals.
  • Support reps in building territory plans and executing prospecting strategies.
  • Monitor KPIs and ensure alignment with organizational objectives.
• Event & Market Engagement
  • Oversee team participation in association events, trade shows, and networking opportunities.
  • Build relationships with key industry stakeholders to enhance brand presence.
• Operational Excellence
  • Ensure accurate and timely reporting of forecasts and sales metrics.
  • Collaborate with marketing, product, and customer success teams to optimize go-to-market efforts.

• Experience
  • 5+ years of sales leadership experience, preferably in technology or managed services.
  • Proven success in leading teams selling cloud hosting, security, compliance solutions, or managed IT services.
  • Experience with in the accounting or tax industry is highly desirable.
• Skills
  • Strong leadership and coaching abilities with a focus on developing talent.
  • Strategic thinker with excellent territory planning and execution skills.
  • Ability to manage complex sales cycles and drive consultative selling practices.
• Other
  • Willingness to travel for team support, events, and client meetings.
  • Highly motivated, results-driven, and adaptable to a fast-paced environment.
  • Proficient in CRM tools and sales analytics platforms.

• This role is open to US Citizens or permanent residents authorized to work in the United States. Rightworks LLC is unable to offer visa sponsorship.
• Due to specific state regulations, we are unable to accept applications from residents of California, Hawaii, or Alaska.
• Relocation will not be offered for this position.

Compensation for this position is up to $250,000 OTE

To provide best-in-class solutions, we need a best-in-class team. We offer competitive salaries to recruit the best talent. We provide company-paid short and long-term disability insurance, life insurance and a generous 401K match. We offer highly affordable medical, dental, vision coverage, and many other valuable benefits. We offer flexible PTO, and numerous paid holidays, affording you the time to be there for what is important in your life.

We encourage giving back to our communities by providing paid volunteer time off. We are proud to be an Equal Opportunity Employer.

This job description may not be inclusive of all assigned duties, responsibilities, or aspects of the job described, and may be amended at any time at the sole discretion of the employer.