Insperity

Managing Director, Sales Performance & Development

Insperity$150K — $180K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's Degree or ten years of related experience required.
  • 10+ years in designing and implementing companywide sales enablement programs.
  • 5+ years in corporate leadership or talent development preferred.
  • ATD or equivalent training certification required.
  • Deep understanding of B2B sales cycles and methodologies.
  • Strong knowledge of adult learning principles and instructional design.
  • Excellent communication skills with the ability to adapt messages.
  • Proven ability to collaborate across functions and build relationships.
  • Strong leadership, coaching, and mentoring capabilities.
  • Familiarity with sales enablement technologies and tools.

Responsibilities

  • Leads talent strategy and sales leadership development programs for all sales teams.
  • Collaborates cross-functionally to train sales staff on product execution.
  • Designs and delivers comprehensive training and certification programs.
  • Implements and improves training strategies aligned with business needs.
  • Adopts innovative training methods and AI tools for efficiency.
  • Assesses capabilities and skill gaps to enhance sales performance.
  • Builds relationships across various teams to align enablement initiatives.
  • Establishes standards for training effectiveness and monitors impacts on sales goals.
  • Facilitates learning sessions and workshops for product and sales techniques.
  • Shapes messaging for sales collateral in alignment with marketing.

Benefits

  • Comprehensive sales training and certification programs.
  • Opportunities for professional development and continuing education.
  • Ability to collaborate with diverse teams across the organization.
  • Access to innovative training tools and methodologies.
  • Flexibility in work arrangements with up to 30% travel.
Full Job Description
SUMMARY

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. Deep knowledge and cross-functional collaboration with all parts of service and product are required in order to effectively lead and train the sales staff to execute on sales performance expectations. The role supports both sellers and sales leaders through targeted training and development initiatives that enhance individual performance, leadership effectiveness, and long-term sales success through people capabilities, skill building, coaching and leadership development.

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


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

About Insperity

Insperity, Inc. provides human resources (HR) and business solutions to enhance business performance for small and medium-sized businesses in the United States. The company offers its HR services through its Workforce Optimization and Workforce Synchronization solutions, which include a range of human resources functions, such as payroll and employment administration, employee benefits, workers' compensation, government compliance, performance management, and training and development services. Insperity, Inc. was founded in 1986 and is headquartered in Kingwood, Texas.
Learn more about Insperity
Size
3,600 employees
Market Cap
$4.2 billion
Industry
Net Income
$138.2 million
Founded
1986
5 Year Trend
+11.1%
Revenue
$4.2 billion
NASDAQ

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