Weekend Cold Calling Jobs in Hawaii (NOW HIRING)

At ProService Hawaii, we partner with over 3,000 local businesses to help them manage HR, payroll, and benefits — so they can focus on what they do best. We’re Hawaii’s largest HR solutions provider, and we’re growing. That growth depends on sales professionals who can build real relationships in Hawaii’s close-knit business community and consistently bring in new clients.

The Business Development Manager I owns the full sales cycle for small market prospects — from outbound prospecting and canvassing to discovery, proposal, and close. Most of your time will be spent out in the community: meeting business owners where they are, earning their trust, and connecting ProService solutions to real operational challenges. Success here means hitting an aggressive revenue quota through disciplined activity, strong pipeline management, and the persistence to earn a reputation in the market.

IN THIS ROLE YOU WILL

• Own the full B2B sales cycle from cold outreach and canvassing through proposal, negotiation, and close for small business prospects across Hawaii.
• Execute a high-volume outbound prospecting rhythm — including in-person canvassing, cold calling, networking events, and referral development — to generate qualified opportunities.
• Lead consultative discovery meetings that uncover client pain points and clearly articulate how ProService HR, payroll, and benefits solutions drive business outcomes.
• Build and manage a sales pipeline that provides consistent visibility into progress toward monthly and annual revenue targets.
• Represent ProService in the community at networking events, local business gatherings, and client interactions, including occasional evenings or weekends.
• Collaborate with sales leadership and peers to share what’s working, apply coaching, and contribute to a high-performance team culture.

IS THIS ROLE RIGHT FOR YOU?

This role is a strong fit if you thrive in a metrics-driven environment and genuinely enjoy the grind of new business development. The activity requirements — outbound prospecting, canvassing, daily follow-up — are not optional; they’re the job. You’ll have a defined sales operating rhythm and be expected to execute it consistently.

Hawaii’s business community is relationship-driven and word travels fast. You’ll need to earn credibility quickly and protect it with every interaction. Our sales managers provide active coaching and the team shares best practices openly — but you’ll need to bring the energy, follow-through, and competitive drive to turn that support into results.

WHAT YOU’LL BRING TO THE TEAM

We’re looking for someone with a proven track record in B2B new business development and the discipline to execute a high-activity sales process independently. Strong communicators who quickly establish credibility with small business owners and navigate to a close will thrive here.

You’re probably a fit if:

• Consistent quota attainment: You’ve hit or exceeded your number in a B2B sales role focused on new business acquisition and can walk through exactly how you did it.

• You can point to a specific year, your activity level, and what made the difference getting to close.

• High-volume outbound execution: You’re comfortable with canvassing, cold calling, and networking as core daily activities — not occasional tactics.

• You’ve managed pipelines with 50+ active opportunities and kept deals moving without a manager pushing you.

• Consultative discovery skills: You can quickly build rapport with decision-makers and translate their operational challenges into a compelling business case.

• Business owners describe feeling understood before you ever pitch them.

• Self-driven competitiveness: You don’t need external motivation to prospect every day, and your peers describe you as someone who finds a way to win even when the territory is tough.

• You bring the same energy on a slow Tuesday in January as you do at the end of a strong quarter.

• Community presence: You understand that in Hawaii, your reputation is your pipeline — and you treat every interaction as an opportunity to build trust.

• You’re professionally polished at a chamber event and equally comfortable walking into a small business cold.

WORK LOCATION

Hawaii Kai — Primarily Field-Based

This role is based out of our Hawaii Kai office, but the majority of your working hours will be spent in the field — canvassing businesses, attending networking events, and meeting clients across Oahu. We offer a flexible hybrid schedule that gives you the structure of in-person collaboration alongside the freedom to manage your time in the community.

In office: Tuesday – Thursday | Field/Remote: Monday & Friday

COMPENSATION

Base salary: $90,000 – $110,000, commensurate with experience.

Variable compensation: $118,280.00 at 100% of plan — commissions are uncapped.

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.