Business Development Representative, SBO

At Pro Service, we empower employers to succeed in Hawaii. For more than 30 years, local small businesses have trusted us with their payroll, HR, and benefits so they can spend less time on paperwork and more time running their business. 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 Small Business (SBO) team, you'll be the first voice many local business owners hear from Pro Service. Through calls, emails, social outreach, and event follow-up, you'll spark interest, learn what owners need, and book qualified meetings for our SBO Business Development Managers. Success looks like mastering our value proposition within your first 90 days, booking five or more qualified meetings a week, and building the pipeline that helps more Hawaii businesses grow.

IN THIS ROLE YOU WILL

• Conduct high-volume outbound prospecting by phone, email, and social platforms to engage small business owners and decision-makers
• Qualify leads against our Ideal Client Profile and book meetings for SBO Business Development Managers
• Follow up quickly on inbound, marketing, and event-generated leads within defined response times
• Manage daily activity and track engagement in Salesforce, Outreach, Gong, Zoom Info, and Hub Spot
• Partner closely with full-cycle sales reps to ensure smooth handoffs and follow-through on every opportunity
• Represent Pro Service at small business events and conferences to meet and engage potential clients

IS THIS ROLE RIGHT FOR YOU?

This is a high-volume, highly measured role. Hitting daily and weekly activity targets, making cold calls, and bouncing back quickly from a “no” are not optional — they’re the job. Business owners are busy, so you’ll need persistence, resilience, and the drive to keep showing up. You won’t do it alone: you’ll get structured training on the Pro Service value proposition, coaching from your Sales Manager and senior reps, and tools that help you work smarter.

This role is a strong starting point for a career in sales. If you’re looking for a quiet, low-pressure role, this may not be the right fit. If you’re energized by competition, clear goals, and seeing your effort turn into results each week, you’ll find a team that will invest in your growth.

WHAT YOU’LL BRING TO THE TEAM

You bring demonstrated success in outbound B2B sales or lead generation, along with real comfort with cold outreach and turning first contacts into booked meetings. You’re familiar with CRM and prospecting tools like Salesforce, Zoom Info, Gong or Hub Spot, and you pair strong communication and listening skills with a high bar for your own work and the tenacity to see it through.

You’re probably a fit if:

• You thrive on cold outreach and don’t let rejection slow you down. You kept dialing through a tough morning, and your twentieth call reached a café owner who’d been struggling with payroll and was glad someone finally reached out.
• You consistently push past your activity goals. You set a personal target above your weekly quota, hit it, and your closers had a fuller calendar of conversations with owners ready to talk.
• You listen first and ask good questions. You let a busy contractor share his frustrations before pitching anything, and he agreed to a meeting because he felt heard, not sold to.
• You follow up quickly and consistently. You called an event lead the next morning while the conversation was still fresh, and that small business owner got the help she needed weeks sooner.
• You communicate clearly with owners and executives. You explained a complex service in plain, simple terms, and a skeptical owner walked away understanding exactly…