Vice President, Sales

Who We Are

At ProService Hawaii, we empower businesses and employees across the islands. As Hawaii’s largest local HR partner, we provide innovative HR solutions in payroll, benefits, risk management, and more. With over 18 years as a Best Place to Work, we’re dedicated to fostering a purpose-driven, inclusive, and high-performing culture.

What You’ll Do

As the Vice President of Sales, you will lead the charge in building high-performing, high-volume sales teams and developing well-defined sales plans to drive $8M in new logo ARR from approximately 500 SMBs. Your role will focus on ensuring the team is well-planned, well-managed, well-trained, and well-staffed, with an annual growth expectation of 20%.

• Lead and develop high-performing sales teams. Build, coach, and mentor 3-4 sales teams to ensure high productivity and success in meeting revenue targets.
• Act as a player-coach. Work alongside sales teams to win deals, particularly focusing on medium and large accounts, while directly contributing to achieving team quotas.
• Improve proposal quality and win rates. Drive a cultural and operational shift in sales execution to enhance critical thinking, collaboration, and deal strategy.
• Refine and execute strategic sales processes. Improve forecasting, lead nurturing, and competitive positioning to increase first-call opportunities and conversion rates.
• Prepare for future growth. In collaboration with the CSO and sales leadership, develop staffing, planning, and training initiatives to ensure sales teams are fully prepared to hit the ground running in the following year.
  
  

What You Bring

• 10 years of sales leadership experience, including managing multi-team sales organizations in high-growth environments.
• Proven track record of scaling sales teams and achieving aggressive revenue targets in a B2B or SMB-focused business.
• Experience developing and executing sales strategies that drive increased close rates, enhance proposal effectiveness, and improve competitive positioning.
• Strong leadership and coaching ability, with demonstrated success in mentoring and developing sales managers and reps.
• Background in consultative sales, business development, or account management, with deep expertise in solving client pain points and building long-term relationships.
• Data-driven decision-making skills, with proficiency in using sales analytics, CRM tools, and forecasting techniques.
• Experience collaborating cross-functionally, aligning sales with marketing, product, and customer success to drive holistic growth
  
  

Your unique background, perspectives, and experience matter to us. Even if you don’t check every box, we encourage you to apply and share your story.

WHY YOU’LL LOVE PROSERVICE

At ProService Hawaii, we’re not just about work—we’re about creating a community where people thrive. Here’s what makes us stand out:

• Purpose-Driven Culture: Integrity, collaboration, and continuous improvement are at our core. Join a team passionate about making a meaningful impact for our clients, community, and one another.
• Empowerment & Innovation: We encourage bold thinking, challenge the status quo, and empower you to take ownership of projects that drive real change.
• Growth Opportunities: With access to leadership development programs, mentorship, and clear career paths, you’ll have the tools and support to reach your full potential.
• Flexibility: We offer hybrid work options for Hawaii-based candidates. For mainland based candidates interested in this role, you must be willing to relocate to Hawaii.
• Competitive Pay & Benefits: We believe in recognizing and rewarding your hard work with competitive compensation, comprehensive benefits, and a commitment to your well-being. The pay range for this role is $200,000.00 - $250,000.00 per year. In addition this role is eligible for variable compensation.