Sales Trainer

PowerToFly; Illinois; Hybrid; USD 116,000 - 174,000; Full time

Benefits offered by this job

Flexible work arrangements

Winter break

401k matching

Paid parental leave

Job summary

Relativity in the United States is hiring a Sales Trainer to own the training roadmap, deliver live facilitation, and design deliberate practice for sellers in a fast-paced environment. You will co-design with the Learning Experience Designer and partner with sales operations to translate insights into structured programs and measurable improvements.

The role includes a competitive base salary ranging from $116,000 to $174,000, plus an annual bonus and long-term incentives, with a hybrid work

Qualifications

• 5+ years in sales training or a quota-carrying sales role — you have trained sellers professionally or been one; ideally both
• Demonstrable facilitation craft: can hold a room of skeptical sellers, create energy without losing substance, and make hard skills feel learnable
• 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

Responsibilities

• 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
• Deliver manager enablement that teaches frontline leaders how to coach the skills being trained
• 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

Skills

Change Management

Content Development

Facilitation

Leadership

Process Improvements

Program Management

Project Management

Stakeholder Management

Strategic Planning

Vendor Management

Job description

Posting Type

Hybrid

Job Overview

The Sales Trainer is a net new role at Relativity — and intentionally so. This is not a repackaged program manager. 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 Trainer knows what sellers need because they are in the room with them; the LXD builds the assets and infrastructure. Together they co-design and co-deliver across the full learning cycle.

Job Description and Requirements

KEY RESPONSIBILITIES

• 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
• Deliver manager enablement that teaches frontline leaders how to coach the skills being trained
• 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

QUALIFICATIONS

Required

• 5+ years in sales training or a quota-carrying sales role — you have trained sellers professionally or been one; ideally both
• Demonstrable facilitation craft: can hold a room of skeptical sellers, create energy without losing substance, and make hard skills feel learnable
• 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

Differentiators (Preferred)

• Experience in a high-growth SaaS or legal tech environment
• Familiarity with the e-discovery market or Relativity’s product ecosystem
• Experience with AI-assisted roleplay and coaching tools
• Comfort operating globally across time zones and regional selling motions

WHAT SUCCESS LOOKS LIKE IN YEAR ONE

• 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

Relativity is committed to competitive, fair, and equitable compensation practices.

This position is eligible for total compensation which includes a competitive base salary, an annual performance bonus, and long-term incentives.

The expected salary range for this role is between following values:

$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.

Required Skills:

Change Management, Content Development, Facilitation, Leadership, Process Improvements, Program Management, Project Management, Stakeholder Management, Strategic Planning, Vendor Management

What Relativity Has to Offer

Relativity's software helps users organize data and quickly identify key issues during litigation, internal investigations, and compliance projects. They offer their employees great benefits like:

• Flexible work arrangements
• Winter break (office closed from Christmas through New Year's Day)
• 401k matching
• Paid parental leave