Business Development Representative, Mid Market

At Pro Service, 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 Pro Service'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 Pro Service 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 Pro Service 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 Pro Service. 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, Hub Spot, Zoom Info, 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…