Director of Sales

WHO WE ARE

At ProService Hawaii, we're not just another company-we're a tribe of passionate people committed to empowering employers and their employees across Hawaii.

People are at the heart of everything we do. We know that running a business in Hawaii comes with challenges-from regulatory complexity to high costs.

That's why we're dedicated to supporting both our clients and our team, fueling the "Why" behind everything we do.

We're the largest local HR partner trusted by over 3,000 employers and 50,000 employees, providing expert HR consulting, training, benefits, payroll, risk support, and more.

We help organizations effectively hire, manage, and grow their teams with confidence. Headquartered in Hawaii with offices on Oahu, Maui, Kauai, and the Big Island, we've been voted Best Place to Work for over 17 years.

Join our diverse and resilient team, and together, we'll make an impact.

WHAT YOU'LL DO

As the Director of Large Market Sales , you'll play a pivotal role in driving bold growth and setting new standards for success at ProService Hawaii.

Your leadership will be essential in crafting and executing robust, sustainable sales strategies, enabling the company to achieve its ambitious goals.

You'll build and nurture a high-performing, high-energy sales team dedicated to surpassing customer acquisition and revenue targets.

In this role, you'll focus on coaching, empowering, and refining strategies to help your team reach their full potential.

Your passion for fostering a culture of excellence will be instrumental in positioning ProService for impactful, scalable success.

If you thrive on challenges, are results-driven, and are ready to make a significant mark on our company's growth, we invite you to lead our large market sales efforts and shape our exciting future.

Responsibilities include :

• Participate in hiring Business Development Managers (BDMs), actively interviewing and collaborating with other leaders to select top candidates.
• Evolve sales processes and strategies within the large market sales segment.
• Develop programs and initiatives to train and enable both new and existing BDMs.
• Create quantitative and qualitative reporting to assess individual BDM strengths and weaknesses, and assist Sales Managers in coaching and development.
• Work closely with Sales Managers and leadership to ensure consistent communication and drive sales activity metrics.
• Actively manage and coach BDMs to meet or exceed monthly sales production targets, addressing performance issues as necessary.
• Collaborate with sales, implementation, and service teams to improve the quality of new business, measured by metrics like days to first payroll and deal completion rates.
• Oversee key performance metrics : dollars sold, breadth of participation, staffing, first meetings set, and deals that don't materialize.

WHAT YOU BRING TO THE TEAM

• 5+ years of experience in people management within a sales team.
• Hawaii-based, or open to relocation.
• Proven experience working across an organization to drive holistic success.
• Sales, sales support, or account management experience, with the ability to relate to and coach consultative sales professionals.
• Strong ability to consult, teach, and develop others in a positive and growth-oriented manner.
• Deep understanding of sales metrics, strategy, and content; comfortable working on projects that require both visual and numerical skills.
• Proven success in B2B large account sales.
• Preferred industry experience in PEO, HCM (Human Capital Management), HR, payroll, or employer insurances.

Your unique background, perspectives, and experience matter to us. Even if you don't check every box, we encourage you to apply and share your story.

WHY YOU'LL LOVE PROSERVICE

At ProService Hawaii, we don't just talk about growth-we live it. We offer a dynamic, inclusive environment where your voice matters, your ideas are celebrated, and your potential is limitless.

Here's what you can expect :

• A Purpose-Driven Culture : Join a team that values integrity, collaboration, and continuous improvement. We are passionate about making a difference for our clients and our community.
• Empowerment & Innovation : We encourage bold thinking, challenge the status quo, and empower you to take ownership of meaningful projects that drive change.
• Growth & Development : With our focus on learning and growth, you'll have access to leadership development programs, mentorship opportunities, and a path to advance your career.
• Competitive Pay & Benefits : The base compensation for this role is $160,000.00 - $190,000.00 per year depending on experience and qualifications.

This role is eligible for an additional compensation incentive in the form of performance based commissions / bonuses.