| Location | HONOLULU, HI |
| Salary | $100,000–$125,000 Per Year |
At ProService, we empower employers to succeed in Hawai?i. For more than 30 years, local businesses have trusted us with their payroll, HR, and benefits, and our sales team is how they find us. As we grow, the way we develop our sellers matters more than ever.
As Sales Training & Enablement Manager, you'll formalize how every ProService seller is onboarded, certified, and upskilled, from SDRs to SBO and Mid Market Business Development Managers to our channel team. Your biggest focus will be value selling: helping reps explain how our full bundle, from healthcare to payroll, workers' compensation, HR, and technology, saves businesses money and makes running them easier. Success means a certification program ready for our 2027 hires and clear proof that training is working, such as hearing reps apply value selling on their Gong calls within weeks of completing a program.
IN THIS ROLE YOU WILL
Design, launch, and improve role-based onboarding, ramp plans, and certification for SDRs, BDMs, and channel sellers, replacing ride-along learning with a structured path
Build a value selling curriculum on the ProService bundle, partnering with Marketing and Product to turn our healthcare offerings, aligned pricing, and service model into a clear value story
Create digestible, testable training materials with role plays, assessments, and certifications that confirm reps can apply what they learn
Deliver ongoing training on prospecting, discovery, qualification, proposals, objection handling, and negotiation tailored to each sales motion
Measure impact in Gong and Salesforce, including whether reps use value selling language on calls after training, and report results on ramp time, conversion, and quota attainment
Partner with sales leaders on coaching standards, call reviews, and manager guides so training sticks in the field
IS THIS ROLE RIGHT FOR YOU?
This role drives results through people you don't manage, and it is measured by application, not attendance. Earning credibility with experienced sellers, building materials reps actually use, and proving with Gong and Salesforce data that behavior is changing are not optional — they're the job. You'll have the partnership of sales leadership, Sales Operations, Marketing, and Product.
Many of our reps learned by riding along with a colleague, so you'll be building much of this from the ground up, and quickly, to support a wave of 2027 hires. ProService sells a complex offering to very different buyers, so one-size-fits-all training won't work. If you prefer to deliver polished content and move on, this may not be the right fit. If you want to turn the way our best sellers win into a repeatable, measurable system, this role offers real impact.
WHAT YOU’LL BRING TO THE TEAM
You've built and run a sales onboarding, certification, or training program that measurably shortened ramp time or improved results, and you've carried a quota or sold B2B services yourself, ideally in PEO, HR, payroll, benefits, insurance, or professional services. You bring hands-on experience teaching value selling, strong coaching and presentation skills, sharp analysis, and the ability to lead change and inspire sellers to adopt new habits.
You're probably a fit if:
You've replaced ride-along onboarding with a real program. You built a structured certification path, and new reps walked into their first prospect meetings confident instead of overwhelmed.
You teach value selling that shows up on calls. After a six-week value selling program, you heard reps leading with business outcomes on their Gong calls instead of price, and prospects started asking deeper questions about the full offering.
You turn cross-functional knowledge into training reps can use. You pulled product and marketing expertise into short, testable modules, and reps who used to avoid complex topics started explaining them clearly to prospects.
You influence experienced sellers and leaders without authority. You won over a skeptical veteran rep by coaching one deal with them, and they became the strongest advocate for your program on the floor.
You measure application, not attendance. You tracked certification results against call behavior and conversion, and showed leadership exactly which training moved results and which needed rework.
WORK LOCATION
Hawaii Kai — Hybrid
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 range for this role is $100,000.00 – $125,000.00, commensurate with experience.
At ProService, compensation is tied to performance. Strong results are recognized and rewarded, and there are clear paths to advance within the enablement track and across the broader sales 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 Hawai?i’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 Hawai?i.