Business Development Manager, Mid Market

Career Opportunities with Pro Service Hawaii

Rated One Of Hawaii's Best Places To Work for 18 Years

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At Pro Service 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 18 years.

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

At Pro Service Hawaii, we partner with over 3,000 local businesses to help them manage HR, payroll, and benefits — so they can focus on what they do best. We’re Hawaii’s largest HR solutions provider, and we’re growing. That growth depends on sales professionals who can build real relationships in Hawaii’s close-knit business community and consistently bring in new clients.

The Business Development Manager I owns the full sales cycle for small market prospects — from outbound prospecting and canvassing to discovery, proposal, and close. Most of your time will be spent out in the community: meeting business owners where they are, earning their trust, and connecting Pro Service solutions to real operational challenges. Success here means hitting an aggressive revenue quota through disciplined activity, strong pipeline management, and the persistence to earn a reputation in the market.

• Own the full B2B sales cycle from cold outreach and canvassing through proposal, negotiation, and close for small business prospects across Hawaii.
• Execute a high-volume outbound prospecting rhythm — including in-person canvassing, cold calling, networking events, and referral development — to generate qualified opportunities.
• Lead consultative discovery meetings that uncover client pain points and clearly articulate how Pro Service HR, payroll, and benefits solutions drive business outcomes.
• Build and manage a sales pipeline that provides consistent visibility into progress toward monthly and annual revenue targets.
• Represent Pro Service in the community at networking events, local business gatherings, and client interactions, including occasional evenings or weekends.
• Collaborate with sales leadership and peers to share what’s working, apply coaching, and contribute to a high-performance team culture.

This role is a strong fit if you thrive in a metrics-driven environment and genuinely enjoy the grind of new business development. The activity requirements — outbound prospecting, canvassing, daily follow-up — are not optional; they’re the job. You’ll have a defined sales operating rhythm and be expected to execute it consistently.

Hawaii’s business community is relationship-driven and word travels fast. You’ll need to earn credibility quickly and protect it with every interaction. Our sales managers provide active coaching and the team shares best practices openly — but you’ll need to bring the energy, follow-through, and competitive drive to turn that support into results.

We’re looking for someone with a proven track record in B2B new business development and the discipline to execute a high-activity sales process independently. Strong communicators who quickly establish credibility with small business owners and navigate to a close will thrive here.

• Consistent quota attainment: You’ve hit or exceeded your number in a B2B sales role focused on new business acquisition and can walk through exactly how you did it.
• You can point to a specific year, your…