Business Development Representative, Mid Market

At ProService, we empower employers to succeed in Hawaii. For more than 30 years, local businesses have trusted us with their payroll, HR, and benefits so they can focus on growing. Every one of those partnerships starts with a conversation, and our Business Development team is where those conversations begin.

As a Business Development Representative on our Mid Market team, you'll be one of ProService's most visible brand ambassadors. Hawaii's Mid Market is a connected community of a few thousand organizations, so you'll build pipeline the way the best local networkers do: showing up at chamber events, industry associations, and community functions across the islands, knowing who's connected to whom, and earning introductions to owners, executives, and HR and finance leaders. Success looks like a steady flow of highly qualified meetings for our Mid Market Business Development Managers, results that exceed Closed Won pipeline targets each year, and a reputation in the business community as someone worth knowing.

IN THIS ROLE YOU WILL

• Build relationship-driven account plans across assigned Mid Market segments and industries, finding warm paths into each target account
• Represent ProService at chamber events, industry associations, trade shows, and community functions to grow your network and generate qualified leads
• Qualify owners, executives, and HR and finance leaders by uncovering business needs, urgency, and fit before handing off to Mid Market Business Development Managers
• Speak confidently to the full ProService bundle, including healthcare, payroll, workers' compensation, HR, and technology, and position value instead of price
• Manage your pipeline and follow-up in Salesforce, and partner with Marketing on value-add outreach that builds our reputation
• Coach and support newer BDR teammates through call shadowing, objection handling feedback, and best-practice sharing
  
  

IS THIS ROLE RIGHT FOR YOU?

This is a metrics-driven role with high expectations for both activity and quality. Booking six to eight qualified meetings a week, maintaining your Hawaii State Resident Producer License, and showing up at community and industry events are not optional — they're the job. You'll have the support of your Inside Sales Manager, the Mid Market sales team, Marketing, and the training to help you hit those marks.

This role is built for someone ready for more autonomy and visibility. You'll be trusted to make your own calls on targeting and messaging, and every interaction reflects on ProService. If you prefer high-volume, transactional outreach, this may not be the right fit. If you have high EQ, care about Hawaii's business community, and are ready to own your results and help others win too, you'll find real growth here.

What You’ll Bring To The Team

You bring proven, sustained success in outbound B2B sales or business development, with a track record of turning cold and warm prospects into high-quality meetings. You're fluent in Salesforce and prospecting platforms such as Outreach, Gong, HubSpot, ZoomInfo, or Sales Navigator, and you pair strong relational instincts and listening skills with sound judgment and a high bar for your own work.

You're Probably a Fit If

• You're the person everyone seems to know. You became a regular at a few industry associations, and when a target company's CFO was hard to reach, a board member you'd met at an event offered to make the introduction.
• You sell value, not just price. You walked an owner through how the full offering would save her time and cost instead of quoting a rate, and she agreed to a meeting because she finally saw the whole picture.
• You listen first and qualify with judgment. You picked up on an HR director's frustration with their current provider, asked the right follow-up questions, and handed off a meeting where the prospect felt understood from the first minute.
• You've coached or supported peers without formal authority. You shadowed a newer rep's calls and shared a better way to handle a common objection, and within a few weeks they booked their best month yet.
• You protect relationships while hitting your numbers. You chose a thoughtful follow-up over another cold email, and a prospect who wasn't ready came back six months later and asked for you by name.
  
  

WORK LOCATION

Hawaii Kai — Hybrid

This role is based out of our Hawaii Kai office. We offer a flexible hybrid schedule that gives you the structure of in-person collaboration with the flexibility of remote work.

In office: Tuesday – Thursday | Remote Option: Monday & Friday

Compensation

The base salary range for this role is $70,000.00 – $80,000.00, plus commission, commensurate with experience.

Variable compensation: $30,400.00 at 100% of plan — commissions are uncapped.

At ProService, compensation is tied to performance. Strong results are recognized and rewarded, and there are clear paths to advance within the business development track and across the broader sales team.

WHY YOU'LL LOVE PROSERVICE

ProService is a Hawaii-based PEO combining payroll, HR, and benefits expertise with purpose-built technology — all backed by the best local service in the islands. Backed by Silver Lake and recognized as one of Hawaii’s Best Places to Work for 20 consecutive years, we’re a team of high performers united by one mission: Empowering Employers to Succeed in Hawaii.

• A PROhana unlike any other. We assume the best in each other, give feedback focused on what’s right—not who’s right—and show up every day. This isn’t just a workplace. It’s a community.
• Do work that matters. You’ll see exactly how your contributions move the needle—meaningful problems, real decisions, and a seat at the table.
• Grow without a ceiling. Internal roles post first, and we reimburse certifications, conferences, and memberships. Your growth is our growth.
• Compete, collaborate, and win together. High expectations, real accountability, and a team of experts ready to help you push through any obstacle.
• Total rewards built around your whole life. Fully paid healthcare, 401(k) matching, paid parental leave, student loan assistance, employee assistance programs, and paid time off—just to name a few.