Sales & Client Success Trainer

Job Description:

Job Title: Sales & Client Success Trainer

About Us:

On a mission to deliver affordable, delightful healthcare for all, First Stop Health provides connected, whole-person virtual care to employers 24/7 through app, website, or phone in all 50 states. First Stop Health prioritizes an engaging and easy-to-use experience, setting people on healthier journeys through care at multiple stages.

First Stop Health offers a comprehensive benefits package that includes various health and medical coverage options, dental and vision coverage, disability and life coverage, making healthcare easily accessible. For those that choose to waive medical coverage a monthly medical waiver allowance will be provided.

First Stop Health offers a remote-first work environment and flexible paid time off, including Summer Fridays. Furthermore, the employer match 401k plan and monthly phone stipend demonstrate the company's commitment to employee financial well-being. The First Stop Health membership benefit is another added perk for employees and provides our virtual care solutions - Urgent Care, Mental Health, and Primary Care - from their very first day!

Job Description:

The Sales & Success Trainer will own, design, and deliver scalable onboarding and ongoing enablement for our Sales and Customer Success teams. As a senior individual contributor, this role is ideal for an experienced educator passionate about coaching, curriculum, and GTM performance enablement. You’ll be part of the Solutions Consulting team, reporting initially to the VP of Solutions Consulting.

Key Responsibilities:

Onboarding & Curriculum Design 

• Build and maintain repeatable onboarding programs for Directors of Sales and Customer Success team members
• Create modular, role-specific training materials for live and asynchronous learning

Ongoing Training & Field Enablement 

• Design and deliver training across key themes: Salespersonship, Client Engagement, Product Fluency, and Strategic Selling
• Run pitch practices, mock scenarios, QBR prep, and refreshers for ongoing skill development

Performance Analysis & Optimization 

• Partner with RevOps to analyze ramp time, attainment, and pipeline health to inform training priorities
• Establish quarterly training cadences across Sales and CS tied to product, process, and performance

Cross-Functional Collaboration 

• Serve as a bridge between Sales, CS, Marketing, Product, and RevOps to ensure unified GTM readiness
• Support strategic enablement initiatives that increase quota attainment and team confidence

Requirements:

• Bachelor’s degree required
• 10+ years in B2B sales, sales training, enablement, or solutions consulting
• Demonstrated ownership of onboarding and ongoing development programs for quota-carrying teams
• Experience training both Sales (new business) and CS (retention and upsell) teams
• Familiarity with GTM tech stack including Salesforce, Gong, and Highspot
• Healthcare or employer benefits background preferred
• Experience in PE-backed or high-growth environments is a plus
• Exceptional facilitation and content creation skills (live and async)
• Strong understanding of consultative selling, choice architecture, and sales psychology
• Fluency in enablement best practices and adult learning principles
• Ability to build scalable training systems and track performance impact

First Stop Health is committed to diversity, equity, inclusion, and belonging.  Research shows that women, people of color and other historically underrepresented groups tend to only apply to jobs in which they meet all of the job requirements.  Unsure if you check every box?  Apply.  We’d love to consider your unique experiences and how you could make First Stop Health even better.

To learn more about First Stop Health, visit https://www.firststophealth.com/ and if you require any assistance during the application process or have questions, please don't hesitate to contact our talent acquisition team via email at careers@fshealth.com.