Sales Training LeadChicago, IL

As the Sales Academy Lead, you will play a pivotal role in shaping the sales training landscape within our organization. Your primary responsibility will be to develop and execute comprehensive sales training programs aimed at enhancing the skills and capabilities of our sales teams. You will be instrumental in designing and delivering both standardized and customized sales training modules.

In this dynamic role, you will collaborate closely with key stakeholders across various departments to understand the unique needs and challenges of our sales force. Drawing upon your expertise in sales methodologies and adult learning principles, you will tailor training content to address specific skill gaps and drive continuous improvement in sales performance.

Joining our team as the Sales Academy Lead offers a unique opportunity to get in on the ground floor of a transformative initiative. You'll have the chance to shape the direction of our sales training efforts from the outset and grow alongside our team as we expand and evolve. If you're ready to make a significant impact and advance your career in sales leadership, we invite you to join us on this exciting journey.

Key Responsibilities:

Sales Academy

  • Develop and implement comprehensive training programs tailored for new and seasoned producers focusing on foundational sales techniques and strategies as well as exploring sales pipelines, diverse marketing strategies, and innovative approaches to maximize sales outcomes.

  • Establish training modules focusing on handling intricate insurance scenarios, equipping sales professionals with the skills required for effectively presenting risks, negotiating deals, and cultivating long-term client relationships.

  • Create leadership strategies and training modules aimed at enabling sales managers to drive results through their teams, emphasizing motivational techniques and effective team management strategies.

  • Develop a framework for nurturing a high-performance sales culture, encompassing approaches to inspire, engage, and retain top talent within the sales force.

  • Implement metrics-based strategies to track team productivity and effectiveness, leveraging data-driven insights to continuously enhance sales performance.

Sales Modules

  • Create a comprehensive roadmap of training modules tailored to the specific requirements of the company, addressing key areas identified for skill development and sales improvement.

  • Develop sales training programs that can be delivered both in-person and virtually.

  • Customize training to optimize engagement and understanding.

  • Map training programs directly to desired business outcomes, aligning learning objectives with the overarching goals of the company.

  • Continuously evaluate the effectiveness of training modules in achieving these outcomes and Implement a system of regular assessment and evaluation to gauge the effectiveness of the training roadmap.

Sales Coaching

  • Conduct coaching sessions aimed at refining sales behavior, emphasizing effective client engagement, and nurturing relationship-building skills.

  • Develop techniques and strategies to equip sales professionals in handling objections confidently and closing deals effectively.

  • Implement mechanisms to assess the application of sales fundamentals taught in the academy during coaching sessions.

  • Track improvements in sales metrics and performance, establishing clear benchmarks for progress.

  • Evaluate the success of coaching interventions through measurable outcomes, linking coaching efforts directly to enhanced sales performance and behavioral improvements.


  • Bachelor's degree in Business Administration, Marketing, or related field; advanced degree preferred.

  • Proven track record of success in sales leadership roles, with a strong understanding of sales methodologies and techniques.

  • Demonstrated experience in designing and delivering sales training programs

  • Exceptional communication and interpersonal skills, with the ability to engage and inspire diverse audiences.

  • Licensed in commercial property & casualty or life health preferred

  • Strong analytical skills, with the ability to interpret data and translate insights into actionable training strategies.

  • Certification in sales training or coaching (e.g., SPIN Selling, Challenger Sales) is a plus.

  • Proficiency in remote learning platforms and digital collaboration tools.

  • Ability to thrive in a fast-paced, dynamic environment and adapt quickly to changing priorities.

The expected salary range for this position is $90K to $110K and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. Specialty Program Group is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.

Department Sales

Required Experience: 5-7 years of relevant experience

Required Travel: Up to 50%

Required Education: High school or equivalent

HUB International Limited is an equal opportunity and affirmative action employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations. The EEO is the Law poster and its supplement is available here at

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