Inside Sales Manager

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, and many of those relationships started with someone who showed up, listened, and earned trust long before a deal was on the table. Our inside sales team is where those relationships begin.

As our Inside Sales Manager, you'll lead our Business Development Representatives and build the cultivation motion that turns Hawaii's business community into qualified pipeline, with a special focus on our Mid Market team. Hawaii is a small, connected market where our Mid Market and large-business universe is a few thousand accounts, so every outreach either builds our reputation or costs us a relationship.

Success means BDRs who are known and trusted across the islands as Pro Service's brand ambassadors, playbooks that reach the right decision-makers through the right relationships, and steady qualified pipeline for our Business Development Managers.

IN THIS ROLE YOU WILL

Build and run the cultivation motion for SBO and Mid Market BDRs, with account plans that map who knows whom and how to earn an introduction to each target account

Coach BDRs to be the friendly, informed face of Pro Service at chamber events, industry associations, golf tournaments, and community functions across the islands

Create playbooks, talk tracks, and value-add outreach with Marketing so every touch gives business owners something useful

Raise the team's command of the Pro Service bundle, including healthcare, aligned pricing, payroll, workers' compensation, HR, and technology, so reps sell value instead of price

Run weekly 1:1s, call reviews, and pipeline reviews using Gong and Salesforce, and set clear activity, quality, and handoff standards for Business Development Managers

Recruit, onboard, and develop reps with Talent Acquisition, and build a path for strong BDRs to grow into closing roles

IS THIS ROLE RIGHT FOR YOU?

This is a coaching role in a relationship-driven market. You can't switch to a new territory or buy a bigger list when pipeline runs thin, so strategic account planning, patience, and protecting Pro Service's reputation in every interaction are not optional — they're the job. You'll partner closely with Marketing on events and content, and with sales leadership and Business Development Managers on account strategy.

Our BDRs are brand ambassadors who care about Hawaii's businesses, and that care has to come through in every conversation. If your instinct is high-volume, transactional outreach, this may not be the right fit. If you have high EQ, lead with authenticity, and are energized by working a connected market one relationship at a time and teaching others to do the same, you'll find real ownership here.

WHAT YOU’LL BRING TO THE TEAM

You've led or coached SDRs, BDRs, or inside sales reps in a B2B environment, and you've done the work yourself, from prospecting and relationship building to qualification. You bring strong relational instincts, ideally from Hawaii or another small, relationship-dense market, along with the ability to build playbooks, coach to a high bar, and use Salesforce and call recording data to improve results.

You're probably a fit if:

You've built pipeline in a market where every account counts. You mapped a limited target list by relationships instead of volume, found warm paths into accounts that had ignored cold outreach, and your team started meeting decision-makers who welcomed the conversation.

You coach reps to become trusted faces in the community. You got your reps showing up consistently at the same chambers and associations, and within months business owners were greeting them by name and referring them to peers.

You teach reps…