Managing Director, Sales Performance & Development

About the Company

Insperity provides the most comprehensive suite of scalable HR solutions available in the marketplace with an optimal blend of premium HR service and technology. With more than 90 locations throughout the U.S., Insperity is currently making a difference for thousands of businesses and communities nationwide. We value diversity, inclusivity, and a sense of belonging, celebrating work and life events while partnering with clients and communities to make great things happen. Insperity has earned recognition as a top place to work by organizations like Glassdoor and U.S. News & World Report and is proud to be recognized for one of the country’s Top 50 Midsize Early Talent Programs through RippleMatch’s Campus Forward Awards.

Why Insperity?

• Flexibility: Over 80% of Insperity’s jobs offer flexibility to balance time with coworkers, clients, family, or community.
• Career Growth: Continuous learning programs, mentorship opportunities, and ongoing training support professional development.
• Well-Being: Total rewards package includes generous paid time off, top-tier medical, dental, and vision benefits, health & wellness support, paid volunteer hours, and more.

About the Role

This position leads the strategy, design, development, and execution of sales talent development and enablement programs that strengthen capability, improve productivity, and build readiness across all sales teams in the organization, encompassing all products and solutions sold by Insperity. The role requires deep knowledge and cross-functional collaboration with all parts of service and product to effectively train sales staff and support both sellers and sales leaders through targeted initiatives that enhance individual performance, leadership effectiveness, and long-term sales success.

Responsibilities

• Leads the talent strategy, sales leadership development, and training programs to build skills and capabilities that drive sales performance across all sales teams and products.
• Demonstrates deep functional knowledge and collaborates cross-functionally with service, Pricing & Review, Competitive Intelligence, and other teams to train sales staff on sales performance expectations.
• Oversees the design, development, and delivery of sales training and certification programs, including Sales Administrator and operations training, Insperity Sales Leadership Development (ISLD), the Certified Business Performance Advisor (CBPA) program, new hire training, new product launches, competencies, and marketing and selling initiatives.
• Develops and continuously improves comprehensive training strategies for all sales roles, aligning content to defined sales processes, evolving business needs, and external market trends.
• Leads the adoption of innovative training methods and AI-enabled tools to improve content development, personalize learning experiences, and increase the efficiency and effectiveness of sales enablement initiatives.
• Assesses organizational capabilities, skill gaps, and learning needs to recommend and implement development solutions that improve sales performance.
• Builds strong partnerships with stakeholders across Sales, HR, Learning and Development, Sales Operations, and other GTM teams to align enablement initiatives with business goals, accelerate ramp to productivity, and support corporate sales processes.
• Establishes standards and measures for training effectiveness, monitors program impact on sales goals and metrics, and owns the Sales Training and Development budget, ROI measurement, and executive reporting on investments and results.
• Facilitates learning sessions, workshops, and sales kickoff events to educate teams on products, sales techniques, and market trends while aligning leaders and team members around sales goals.
• Shapes messaging and content for sales collateral by partnering with Marketing and Service organizations to co-create materials and ensure alignment between field sales execution and go-to-market messaging.
• Provides coaching and constructive feedback to team members and participants and develops direct reports to build a high-performing team culture.
• Supervises others: Yes.

Requirements

• Bachelor’s Degree or ten or more years of related experience is required.
• Ten or more years of experience in designing, developing, and implementing companywide sales and/or revenue enablement programs aimed at enhancing the capabilities of sellers or sales leadership, with a proven development track record.
• Five years of corporate leadership/talent development experience is preferred.
• ATD (Association Talent Development) or other associated training and talent development certification required, specific to adult learning and facilitation skills.
• Deep understanding of B2B sales cycles, sales functions, common sales methodologies, and the value of the sales process within a selling organization.
• Strong knowledge of adult learning principles, instructional design, facilitation techniques, blended and e-learning approaches, and other performance development frameworks.
• Excellent written, verbal, and interpersonal communication skills, with the ability to adapt messaging to different audiences and communicate clearly and persuasively across all levels of the organization.
• Demonstrated ability to collaborate effectively across functions, business units, and regions, and to build strong working relationships with diverse stakeholders.
• Strong leadership, coaching, and mentoring skills, with the ability to lead teams, provide direction, and develop others.
• Knowledge of sales enablement technologies, including CRM, LMS, content management platforms, AI and automation tools, and communication and project management applications.
• Strong business acumen, presentation skills, and openness to testing new ideas and innovative training approaches.
• Experience designing and implementing innovative sales training and learning strategies in large organizations, including facilitation of group instruction and coordination of large-scale or national events.
• Travel required: up to 30% of the time.