Inside Sales Manager

ProService Hawaii; East Honolulu (HI); Hybrid; USD 100,000 - 125,000; Full time

Benefits offered by this job

Fully paid healthcare

401(k) matching

Paid parental leave

Student loan assistance

Employee assistance programs

Paid time off

Job summary

ProService Hawaii is seeking an Inside Sales Manager to lead BDRs and shape the cultivation motion for SBO and Mid Market opportunities in Hawaii. You will coach BDRs to represent the ProService bundle—healthcare, payroll, HR, and technology—at events, associations, and community functions across the islands.

This is a hybrid role based in Hawaii Kai with a mix of in-office and remote work. You will drive playbooks, talk tracks, and value-added outreach with Marketing, ensuring reps sell value

Qualifications

• Coaching BDRs/SDRs in a B2B environment with a relationship-driven approach.
• Proven ability to build pipeline and manage a cultivation motion.
• Experience using Salesforce and call recording data to improve results.

Responsibilities

• Build and run the cultivation motion for SBO and Mid Market BDRs with account plans.
• Coach BDRs to be the friendly, informed face of ProService at events and associations.
• Create playbooks, talk tracks, and value-add outreach with Marketing.
• Increase product knowledge of ProService bundle (healthcare, payroll, HR, benefits) to sell value over price.
• Lead weekly 1:1s, call reviews, and pipeline reviews; set activity and handoff standards.
• Recruit, onboard, and develop reps with Talent Acquisition.

Skills

Coaching

Sales leadership

Account planning

Relationship building

Event networking

Tools

Salesforce

Gong

Job description

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, 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 ProService'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 ProService 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 ProService 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 ProService'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 to sell value, not price. You noticed reps leaning on discounts, built a simple value story around the full offering, and prospects began asking about the bundle instead of just the rate.

You partner with Marketing to make outreach worth receiving. You worked with Marketing on an event and content series for a target industry, and your reps' follow-ups turned into conversations because owners had already gotten something useful.

You lead with high EQ and hold a high bar. You set clear standards and coached every rep to them, and the team stayed motivated through a tough quarter because they knew you were invested in their growth.

WORK LOCATION

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

Base salary: $100,000 – $125,000, commensurate with experience.

Variable compensation: $27,650.00 at 100% of plan

At ProService, compensation is directly tied to performance. Strong results are recognized and rewarded — top performers consistently exceed plan through uncapped commissions. There are clear paths to advance within the sales function and into senior sales roles as you build your portfolio and demonstrate sustained results.

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.