Head of Sales Enablement & Leadership Development

60 Insperity Services, L.P.; Houston (TX); On-site; USD 100,000 - 140,000; Full time

Job summary

Insperity seeks a seasoned Sales Talent Development Lead to drive strategy, design, and delivery of sales training across all products. You will partner with Sales, HR, Learning and Development, and Marketing to create scalable programs that raise readiness and performance.

The role emphasizes executive coaching, content development with AI-enabled tools, and measuring impact on sales metrics, while enabling rapid onboarding and leadership development.

Qualifications

• 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 the 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, listen for insight, 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.
• Travels: Yes, up to 30% of time.

Responsibilities

• Leads the talent strategy, sales leadership development, and training programs needed to build the skills and capabilities that drive sales performance across all sales teams in the organization, spanning every product and solution sold by Insperity.
• Demonstrates deep functional knowledge and cross-functional collaboration with all areas of service, Pricing & Review, Competitive Intelligence and others across the organization in order to effectively lead and train the sales staff with an appropriate level of information to execute on sales performance expectations for each product.
• 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 and objectives.
• Shapes messaging and content for sales collateral by partnering with the Marketing and Service organizations, co-creating materials and understanding what resonates with buyers through the sellers’ approach, ensuring alignment between the 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.

Skills

Sales enablement

Leadership

Strategic thinking

Communication

Collaboration

Adult learning

Education

Bachelor’s Degree

10+ years experience

Tools

CRM

LMS

Content management

AI tools

Job description

Insperity seeks a seasoned Sales Talent Development Lead to drive strategy, design, and delivery of sales training across all products. You will partner with Sales, HR, Learning and Development, and Marketing to create scalable programs that raise readiness and performance.

The role emphasizes executive coaching, content development with AI-enabled tools, and measuring impact on sales metrics, while enabling rapid onboarding and leadership development.