Director, Mid Market Sales

ProService Hawaii; East Honolulu (HI); Hybrid; USD 171,000 - 209,000; 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 seeks a Director of Mid Market Sales to own the segment’s new business revenue and lead the team of Business Development Managers. Hawaii relationships, strategic quota design, and disciplined forecasting drive growth and trusted partnerships.

You’ll guide a senior sales team, recruit top talent, and negotiate complex multi-stakeholder deals with executives while aligning pricing and implementation for client success.

Qualifications

• Experience leading mid-market B2B sales teams.
• Proven ability to forecast and manage pipelines.
• Strong negotiation and deal-closing skills.
• Track record of recruiting and developing top performers.
• Established relationships with Hawaii business community a plus.

Responsibilities

• Own Mid Market revenue and achieve quarterly/annual targets.
• Set strategy for target industries, territories, and quotas.
• Lead weekly operating rhythm: 1:1s, pipeline review, deal reviews.
• Recruit and maintain top-performing sellers and address underperformance.
• Build executive relationships with owners/CFOs to protect margin.
• Collaborate with Pricing, Implementation, and Account Management for client fit.

Skills

Mid Market sales leadership

Forecasting

Deal negotiation

Team recruitment

Executive relationship building

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 today we serve as a partner to established organizations across the islands. Our Mid Market segment is where some of our most consequential partnerships are built, and we're looking for the leader who will take it to the next level.

As Director of Mid Market Sales, you'll own the segment's new business revenue and lead the team of Business Development Managers who win it. Mid Market deals are fewer, larger, and more complex, and in Hawaii they're won through relationships and reputation as much as through process. Success means a team that runs on a disciplined weekly rhythm, a forecast leadership can trust, a bench of A players who win the right clients at the right price, and a leader the local business community knows and respects.

IN THIS ROLE YOU WILL

Own Mid Market new business revenue and deliver against quarterly and annual targets with an honest, accurate forecast

Use pipeline, win/loss, and competitor data to set the segment's strategy, including ideal client profile, target industries and islands, territory design, and quota, and decide what the team should stop doing

Run a weekly operating rhythm of 1:1s, pipeline inspection, and deal reviews so every deal has an owner, a next step, and a date

Recruit and keep a bench of top-performing sellers, set clear written standards, and address underperformance within weeks, not quarters

Build executive relationships across Hawaii's business community and lead complex, multi-stakeholder negotiations with owners and CFOs that protect margin

Partner with Pricing, Implementation, and Account Management so every new client is a good fit, sold the right solution, and set up to succeed.

IS THIS ROLE RIGHT FOR YOU?

This is a senior leadership role with direct accountability for results. A single win or loss can swing the team's quarter, so disciplined pipeline inspection, accurate forecasting, and personal involvement in key deals are not optional — they're the job. We also expect transparency: bad news shared early, with the number, the cause, and the plan. You'll hold experienced sellers to a high bar and make hard people decisions when coaching doesn't turn performance around, with the partnership of sales executive leadership, Sales Operations, and Pricing.

In Hawaii's close-knit business community, reputation is everything. You'll need existing relationships with mid-market executives or the ability to build them quickly, and you'll represent ProService through industry associations and occasional evening or weekend events. A mainland playbook that ignores how relationships work here won't succeed. If you want to shape a segment, rebuild where needed, and earn the trust of local executives, this role offers real ownership.

WHAT YOU'LL BRING TO THE TEAM

You've led and scaled teams of quota-carrying B2B sellers who consistently hit new business targets, including turning around an underperforming team, and you've personally closed complex deals with owners and senior executives, ideally in PEO, HR, payroll, benefits, insurance, or professional services. You bring data-driven strategic thinking, strong negotiation skills, a proven record of recruiting A players, and a reputation for integrity with your numbers. Relationships in Hawaii's business community are a strong plus.

You're probably a fit if:

You turn strategy into a weekly cadence that never slips. You put a weekly pipeline inspection and deal review rhythm in place, and your leadership team stopped bracing for end-of-quarter surprises and started planning with confidence.

You've rebuilt an underperforming team. You reset standards, kept your strongest sellers, made the hard calls on the rest, and within a year the team was hitting plan and strong candidates were asking to join.

You recruit A players and always keep a bench. You stayed connected to top sellers even when you weren't hiring, so when a seat opened you filled it in weeks and clients never felt the gap.

You tell the truth about your numbers. You pulled a large deal from commit when the signals weren't there, told leadership early, and earned the trust that made every forecast conversation after that easier.

You treat clients as partners after the signature. You owned a messy first-year handoff with Implementation, fixed the process, and new clients went from confused in their first month to referring to other businesses.

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

The base salary for this role is $190,000.00 per year, commensurate with experience.

Variable compensation: $185,00.00 at 100% of plan.

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

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.