Sales Enablement

Job Purpose
We're looking for an energetic, self-motivated Sales Enablement & Training Manager to take Hawaiian Telcom's Sales Organization to the next level. This is your chance to lead training and enablement across multiple business units and sales channels, shaping how our teams sell, grow, and win. You'll design and deliver engaging online and in-person training programs, build impactful sales curriculums, and use roleplaying and hands-on coaching to develop top-tier sales talent. If you thrive on inspiring teams, driving performance, and making a real impact, this is the role for you.

This is a hands-on, high-impact leadership role for someone who loves building programs, energizing teams, and shaping a winning sales culture. If you're ready to elevate Hawaiian Telcom's sales organization and lead the charge in sales excellence, this role is for you

Essential Functions

• Create & Deliver World-Class Training

• Design, launch, and manage comprehensive training curriculums for both virtual and in-person learning.

• Incorporate high-energy roleplay and real-world scenarios into every training to build confidence and execution skills.
• Lead onboarding programs for new hires to ensure rapid ramp-up and success.

• Provide ongoing development programs that keep tenured sales reps sharp and motivated.

• Sales Enablement & Content Development

• Build and maintain a centralized enablement library of sales tools, resources, and playbooks.

• Partner with marketing and product teams to ensure all training content is current, accurate, and aligned with go-to-market strategy.

• Continuously refresh training materials to reflect market trends and business needs.

• Coaching & Field Engagement

• Conduct ride-alongs and shadowing to deliver in-the-moment coaching.

• Reinforce training in real-world selling environments to drive measurable performance improvement.

• Strategic Collaboration

• Work with sales leaders to identify gaps, design targeted training programs, and improve overall effectiveness.

• Act as a trusted advisor to leadership, providing feedback from the field to influence strategy and product development.

• Measurement & Impact

• Use sales performance data, feedback, and assessments to measure training effectiveness.

• Continuously iterate programs to accelerate sales performance and enhance customer experience.

Education

• Four years of College resulting in a Bachelor's Degree or equivalent experience
• Bachelor's degree in Business, Marketing, Communications, or related field (or equivalent practical experience).

Certifications, Accreditations, Licenses

• Sales methodology certifications (Sandler, Challenger, SPIN, MEDDPICC, etc.)
• Training certifications (ATD, CPTD, Train-the-Trainer, Kirkpatrick, etc.)
• Bonus for project management credentials (PMP, Agile).

Relevant Work Experience

• 5 to 7 years in related field
• 5+ years in sales enablement, sales training, or sales leadership, preferably in telecom, tech, or high-growth industries.
• Experience in developing structured training curriculums (online & classroom) and facilitating engaging roleplay-based learning.
• Background in multiple sales channels: B2B, SMB, Enterprise, Retail, Inside Sales.
• Proven success in driving sales performance through training and coaching.

Special Knowledge, Skills And Abilities

• A high-energy, self-starter attitude with a passion for developing sales talent.
• Exceptional communication and presentation skills with the ability to inspire.
• Creativity and adaptability to make learning both fun and impactful.
• Proficiency in LMS systems and training tech.
• Ability to travel statewide to connect and train teams in person.

Supervisory Responsibility

• No Supervisory Responsibilities

Salary Range: $80k-$120k