Sales Training Leader

We Insure, LLC. is an independent insurance franchise that takes immense pride in providing like-minded entrepreneurs with successful agency ownership. With more than 200 agency locations in 35 states, We Insure continues to grow rapidly and supports our agency owners, customers, and carriers by facilitating faster service, greater efficiencies, better choices, and improved bottom lines. What makes We Insure stand out: we are data-driven for better value and people-led for better service. And our leadership is seeking more highly motivated, career-driven people to help lead our efforts!

We Insure has received countless awards including Jacksonville Business Journal’s Best Places to Work and Fastest-Growing Private Companies, and Inc.’s 5000 Fastest Growing Companies. If you are looking for a long-term career in a supportive, goal-driven, growth environment with a company that believes in developing its people, We Insure is the right fit for you and we encourage you to apply today!

The Sales Training Leader is responsible for designing, developing, and delivering comprehensive training programs to enhance the performance, effectiveness, and productivity of the sales team. This role ensures that all sales professionals are equipped with the necessary skills, product knowledge, and tools to achieve organizational goals and deliver outstanding customer experiences. The Sales Training Leader will collaborate with cross-functional teams, benchmark best practices, and utilize innovative training techniques to drive measurable results.

This position will work out of our Austin, TX office.

Remote candidates up for consideration.

Key Responsibilities:

Training Program Development:

• Design and implement creative and effective sales training programs catering to new hires, tenured reps, and leadership.
• Develop curriculum and materials, including presentations, role-play scenarios, product guides, and e-learning modules.
• Align training initiatives with the company’s sales goals, strategic objectives, and organizational values.
  
  

Team Onboarding:

• Lead onboarding processes for new sales employees to ensure they quickly learn product knowledge, sales methodology, and company tools.
• Provide hands-on coaching and mentoring for new team members during their initial ramp-up phase.
  
  

Sales Methodology & Skill Development:

• Instruct sales teams on industry best practices, consultative selling techniques, objection handling, closing strategies, and customer relationship management.
• Create workshops focused on honing specific sales skills, such as prospecting, negotiation, and lead qualification.
  
  

Performance Monitoring & Assessment:

• Evaluate the effectiveness of training programs through assessments, feedback sessions, and performance metrics.
• Conduct ongoing analysis to identify gaps in knowledge and skills and recommend targeted initiatives for improvement.
  
  

Collaboration & Communication:

• Partner closely with Sales Leaders, HR, Product Teams, and Marketing to ensure training is aligned with company goals and customer needs.
• Act as a key advisor to leadership on sales enablement strategies and initiatives.
  
  

Sales Enablement & Tools:

• Provide education on CRM systems, sales technologies, and other tools to improve efficiency and accountability.
• Stay informed about the latest trends and technologies in sales training to continually improve the learning experience.
  
  

Coaching & Mentorship:

• Lead one-on-one and group coaching sessions to provide actionable feedback and guidance to sales team members.
• Cultivate a culture of continuous learning and professional growth within the sales organization.
  
  

Qualifications and Experience:

• Bachelor’s degree in business, Marketing, Education, or a related field; advanced degree preferred.
• 5+ years of experience in sales, training, or a related leadership role, preferably in a fast-paced organization.
• Deep understanding of sales processes, methodologies (e.g., SPIN, Challenger, or Sandler), and customer relationship management.
• Proven track record of developing and executing impactful training programs that deliver quantifiable results.
• Experience with training tools, platforms, and technologies (e.g., LMS systems, e-learning tools).
• Excellent project management, communication, and interpersonal skills.
• Ability to motivate and inspire teams while fostering a positive, learning-oriented environment.
  
  

Preferred Skills:

• Experience leveraging data and analytics to assess training effectiveness and identify areas of improvement.
• Familiarity with e-commerce, SaaS, B2B, or other relevant industries.
• Strong public speaking and facilitation skills.
• Certification in sales methodologies or training (e.g., Train-the-Trainer, Certified Professional in Learning and Performance).
  
  

Key Competencies:

• Leadership and Team Building
• Strong Communication and Presentation Skills
• Strategic Thinking and Problem-Solving
• Adaptability and Resilience
• Results-Oriented Mindset
  
  

Why join the We Insure Team?

The We Insure Difference:

• Medical, Dental, Vision, Life, Pet; Flexible Spending Account
• Competitive Salaries
• 401K Match
• Work-Life Balance: Personal Days, PTO Days, 12 Paid Holidays, Two Paid Days for Volunteer Service, Paid Parental Leave
• Short and Long-Term Disability
• Employee Support Programs, Including Mental Health
• Tuition Reimbursement
• Matching Charitable Gift Program
• Lucrative Referral Program
• Flexibility: Remote and Hybrid Opportunities Available
  
  

This position is not able to be performed in California, Colorado, New York or Washington.

EEO

We Insure Group is an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

Disability

We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hrinfo@peak6insurtech.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

Note to applicant: It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment. Please know that our company does not use lie detector tests in our hiring process.

Base Salary Range:

$91,200-$114,000