Telecommute Insurance Sales Trainer

The Sales Trainer is a net new role at Relativity — and intentionally so. It is a dedicated expert in the craft of changing seller behavior: live facilitation, deliberate practice, real-time coaching, and training design that respects how adults learn under pressure. This person owns the training roadmap and is the field-facing half of a content partnership with the Learning Experience Designer. the LXD builds the assets and infrastructure.

Facilitate live training that changes behavior — onboarding, product launches, sales methodology, tactics, and advanced selling workshops for both new hires and tenured reps
~ Design and run deliberate practice: role plays, objection drills, discovery coaching, and deal review simulations with real-time feedback
~ Own the annual training roadmap — sequencing programs to align with commercial priorities, product launches, and sales cycle rhythms
~ Co-design training programs with the Learning Experience Designer, bringing field observations and rep feedback into the content build
~ Partner with sales operations business partners to understand segment needs and translate them into training priorities
~ Measure training effectiveness through behavior change, not attendance — and adjust the roadmap based on what the data shows
5+ years in sales training or a quota-carrying sales role — you have trained sellers professionally or been one; Deep experience training on structured sales methodology — can learn a framework cold, coach it live, and build practice that creates muscle memory
~ Experience designing deliberate practice: role plays, call simulations, and coaching frameworks that build muscle memory, not just awareness
~ Experience owning a training roadmap end-to-end — diagnosing gaps, sequencing programs, and measuring behavior change
Experience in a high-growth SaaS or legal tech environment
~ Experience with AI-assisted roleplay and coaching tools
~ Annual training roadmap built and socialized with sales leadership in the first 60 days
~ New hire onboarding delivery running consistently, with measurable ramp improvement
~ At least two tenured seller skill programs launched in partnership with the LXD
~ Sellers and managers actively requesting more — training has a reputation for being useful, not obligatory
This position is eligible for total compensation which includes a competitive base salary, an annual performance bonus, and long-term incentives.
116,000 and $174,000 The final offered salary will be based on several factors, including but not limited to the candidate's depth of experience, skill set, qualifications, and internal pay equity.

Hiring at the top end of the range would not be typical, to allow for future meaningful salary growth in this position. Change Management, Content Development, Facilitation, Leadership, Process Improvements, Program Management, Project Management, Stakeholder Management, Strategic Planning, Vendor Management