Live In Insurance Sales Trainer Jobs (NOW HIRING)

What You'll Do

Onboarding & Ramp

• Facilitate all onboarding sessions for new SDRs and AEs - product knowledge, sales process, tool training, and market context
• Run certification assessments before reps go live - cold call roleplays, discovery simulations, demo run-throughs - and give specific, actionable feedback
• Track new hire progress through ramp milestones and flag concerns early
• Refine delivery continuously based on what's working across cohorts

Tools Training

• Deliver hands-on training for HubSpot, Gong, and our enablement platform for new hires and existing reps
• Build and maintain role-specific tool guides and SOPs
• Run refresher sessions when tools update and track adoption across the team

Process Training

• Train reps on the full sales process - SDR prospecting through AE close - as defined by enablement and RevOps
• Deliver SDR-to-AE handoff training and CRM hygiene expectations
• Run refreshers when processes change and surface breakdowns you observe back to enablement

Campaign Training

• Train SDRs on new campaign plays before they go live - messaging, sequencing, scripts, and objection handling
• Run live practice sessions so reps execute confidently from day one
• Debrief early results and feed observations back to enablement and Marketing

Ongoing Skill Development

• Run scheduled sessions on specific skills: cold calling, discovery, objection handling, demo delivery
• Facilitate call reviews and roleplays at the team level
• Maintain a library of exercises and practice materials reps can use independently

What We're Looking For

Hard Skills

• Proven ability to facilitate engaging training sessions for salespeople - not just present, but teach
• Enough sales process knowledge to train credibly on prospecting, discovery, demo, and close
• Comfortable in HubSpot and Gong; can teach others and troubleshoot in the moment
• Experience running structured roleplays and delivering specific behavioral feedback
• Familiar enough with healthcare markets (provider, life science, or payer) to make examples relevant
• Organized enough to manage multiple training tracks simultaneously without dropping anything

Soft Skills

• Credible with salespeople - ideally you've carried a bag or been customer-facing; reps need to believe you understand their job
• High energy and strong presence - you can hold a room of skeptical reps who'd rather be selling
• Honest and direct in feedback - you can tell someone what they need to improve without crushing their confidence
• Adaptable - you read the room and adjust when a session isn't landing
• Collaborative - you work well with enablement managers, take direction on what to train, and stay in your lane without being told twice

Nice to Have

• Background as an SDR, AE, or sales coach in a healthcare technology or SaaS environment
• Experience training across multiple buyer segments simultaneously
• Familiarity with provider, life science, or payer sales motions specifically

Compensation for this job is subject to market conditions, geographic considerations, the candidate's unique skills and experience, state and local laws, and budget. Our commitment to pay transparency is a testament to our dedication to creating a fair, equitable, and inclusive workplace. By continuously analyzing market trends, staying abreast of changes in state laws, and making budgetary adjustments accordingly, we strive to ensure that our compensation practices reflect the value we place on our associates' unique contributions and support their professional growth.

Enhancing Lives and Building Careers

Veradigm believes in empowering our associates with the tools and flexibility to bring the best version of themselves to work and to further their professional development. Together, we are In the Network. Interested in learning more?

Take a look at our Culture, Benefits, Early Talent Program, and Additional Openings.

Visa Sponsorship is not offered for this position.

At Veradigm, our greatest strength comes from bringing together talented people with diverse perspectives to support the needs of healthcare providers, life science companies, health plans, and the patients they serve. The Veradigm Network is a dynamic, open community of solutions, external partners, and cutting-edge artificial intelligence technologies that provide advanced insights, technology, and data-driven solutions. Veradigm offers a comprehensive compensation and benefits package, including holidays, vacation, medical, dental, and vision insurance, company paid life insurance and retirement savings.

Veradigm's policy is to provide equal employment opportunity and affirmative action in all of its employment practices without regard to race, color, religion, sex, national origin, ancestry, marital status, protected veteran status, age, individuals with disabilities, sexual orientation or gender identity or expression or any other legally protected category. Applicants for North American based positions with Veradigm must be legally authorized to work in the United States or Canada. Verification of employment eligibility will be required as a condition of hire. Veradigm is proud to be an equal opportunity workplace dedicated to pursuing and hiring a diverse and inclusive workforce.

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