Director, Retail Training & Development

About Us

We’re a fast-growing, privately held insurance company on a path to becoming a leading U.S. retail platform. We believe every client and customer relationship holds the potential to become something great and the same is true for our people. As we grow, we’re redefining how great talent connects with meaningful work, enabling our ambitious strategy while building a culture of high performance, creativity, and partnership. If designing impactful training strategies, strengthening retail sales effectiveness, and enabling growth across life insurance and annuities distribution excites you, this role offers the opportunity to make a meaningful impact.

About The Role

We’re looking for a Director of Retail Training & Development responsible for the strategy, design, and execution of enterprise training and development programs that support retail distribution, sales performance, and marketing effectiveness across our life insurance and annuities business.

This role serves as the centralized leader for training initiatives supporting internal/external sales teams, distribution partners, and marketing stakeholders. The Director of Training partners closely with Sales, Marketing, Product, Compliance, and Operations to ensure training programs are aligned with business objectives, regulatory expectations, and evolving market needs. In addition, the ability to partner with outside training vendors to curate content will be important for this role.

What You’ll Do

Training Strategy & Program Development

• Develop and execute a comprehensive training strategy supporting retail sales, marketing, and distribution objectives across life insurance and annuities products, including onboarding.
• Design, implement, and continuously enhance training programs for all sales teams, distribution partners, and marketing stakeholders
• Ensure training curriculum addresses product knowledge, sales effectiveness, market positioning, compliance standards, territory management, technology utilization and company policies
• Translate business priorities and growth strategies into scalable, practical training solutions
  
  

Retail Sales & Marketing Enablement

• Partner closely with Sales, Retail Distribution, and Marketing leadership to identify training needs and performance gaps
• Support sales enablement initiatives through structured onboarding, ongoing education, and targeted development programs along with reinforcement throughout
• Collaborate with Marketing to align training content with brand standards, messaging, and go-to-market strategies
• Support new product launches through coordinated training plans and field readiness initiatives
  
  

Field Training & Partner Engagement

• Conduct live, virtual, and on-site training sessions as needed, including sales meetings, conferences, and field workshops
• Monitor field feedback and performance metrics to refine and improve training effectiveness
  
  

Operational & Risk Awareness

• Ensure all training programs, materials, and communications comply with regulatory requirements and internal policies within a life insurance and annuities environment
• Partner with Compliance and Legal to review training content, product materials, and sales practices
• Maintain governance over training documentation, process, certifications, and completion tracking as required
• Support consistent, compliant sales practices across retail and institutional channels
  
  

Team Leadership & Collaboration

• Lead, mentor, and develop training professionals or contributors supporting retail, sales, and marketing initiatives
• Foster collaboration across Sales, Marketing, Product, Operations, and Distribution teams
• Support talent development, succession planning, and knowledge sharing across the organization
• Drive a culture of continuous learning, performance improvement, and accountability
  
  

What You’ll Bring

• 8 years of experience in sales training, sales development, or distribution enablement within life insurance and/or annuities
• Proven experience designing and delivering training programs for retail sales and distribution organizations
• Strong understanding of life insurance and annuity products, sales processes, and compliance requirements
• Experience partnering with Sales, Marketing, and Distribution leadership to support growth initiatives
• Demonstrated ability to translate complex concepts into clear, engaging training content
• Excellent organizational, facilitation, and stakeholder management skills
• Strong written, verbal, and presentation communication skills
• Ability to adapt to a dynamic, fast-paced environment and manage competing priorities
• Austin, TX location preferred, relocation available; If not based in Austin, this role will require ability to travel for business 25-35% of the time
  
  

Technical Skills

• Proficiency in Microsoft Office (Outlook, Word, Excel, PowerPoint)
• Experience with learning management systems (LMS), virtual training platforms, and content delivery tools
• Ability to analyze training effectiveness using performance metrics and feedback
• Strong instructional design and curriculum development capabilities
• Strong content creation skills required
• Ability to learn, utilize and teach sales technologies
  
  

Core Competencies

• Learning Strategy & Execution: Designs and delivers impactful training aligned with business goals
• Business Partnership: Collaborates effectively with Sales, Marketing, and Distribution leadership
• Communication & Facilitation: Engages diverse audiences through clear, compelling instruction
• Compliance & Risk Awareness: Ensures training supports compliant sales practices
• Continuous Improvement: Uses data, feedback, and market insights to evolve training programs
• Leadership & Influence: Builds credibility and trust across internal teams and external partners
  
  

What We Offer

• A collaborative, inclusive environment that values authenticity, accountability, and partnership
• The opportunity to join the company at an exciting stage of growth, where colleagues are empowered to build what’s next
• A variable compensation package with a base range of $140,000 - $160,000 annually
• A competitive benefits package including comprehensive medical, dental, and vision coverage; an HSA and 401(k) company match; paid time off; and employer-paid life and disability insurance
• Remote/hybrid work arrangement
  
  

At Prosperity, we are committed to equal employment opportunity and encourage people from all backgrounds to apply. We make hiring decisions based on merit and do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, age, disability, or any other protected status.

We strive for a meaningful interview experience for all candidates. If you need an adjustment or accommodation due to a disability or medical condition during the hiring process, please let your recruiter know.