Head of Sales Enablement & Leadership Development

Insperity Services, L.P.; Kingwood (WV); On-site; USD 110,000 - 170,000; Full time

Job summary

Insperity leads the strategy, design, development, and execution of sales talent development and enablement programs across all product lines. This role requires deep cross-functional collaboration with service, Pricing & Review, and Competitive Intelligence to empower sales teams with the right information to meet performance targets.

The position drives training, certification, new-hire and product-launch initiatives, while leveraging AI-enabled tools to personalize learning and accelerate

Qualifications

• Bachelor’s Degree or 10+ years of related experience in sales/revenue enablement.
• 10+ years designing, developing and implementing companywide sales enablement programs.
• 5 years of corporate leadership/talent development experience preferred.
• ATD or related certification required; adult learning and facilitation skills.
• Deep understanding of B2B sales cycles and sales process value.

Responsibilities

• Leads the talent strategy, sales leadership development, and training programs to build skills across all sales teams.
• Oversees design, development, and delivery of sales training and certification programs.
• Develops comprehensive training strategies aligned to sales processes and market trends.
• Leads adoption of AI-enabled tools to personalize learning and improve efficiency.
• Assesses capabilities and learning needs to implement development solutions that boost performance.
• Builds partnerships across Sales, HR, Learning & Development, and Sales Operations.
• Sets standards for training effectiveness, measures ROI, and reports results.
• Facilitates learning sessions, workshops, and sales kickoff events to align teams with goals.
• Shapes messaging and content for sales collateral with Marketing and Service teams.
• Provides coaching and develops direct reports to nurture a high-performing culture.

Skills

Sales enablement

Leadership development

Coaching

Cross-functional collaboration

Instructional design

Education

Bachelor’s degree

ATD certification

Tools

CRM

LMS

AI-enabled training tools

Content management platforms

Job description

Insperity leads the strategy, design, development, and execution of sales talent development and enablement programs across all product lines. This role requires deep cross-functional collaboration with service, Pricing & Review, and Competitive Intelligence to empower sales teams with the right information to meet performance targets.

The position drives training, certification, new-hire and product-launch initiatives, while leveraging AI-enabled tools to personalize learning and accelerate