Director, Sales Enablement

PowerToFly; Illinois; Hybrid; USD 162,000 - 242,000; Full time

Benefits offered by this job

Flexible work arrangements

Winter break

401k matching

Paid parental leave

Job summary

Relativity is seeking a Director of Sales Enablement to lead a modern, AI-forward, microlearning-driven enablement function. Reporting to the Sr Director of Global Revenue Operations, this leader will build a proactive, segment-led program and manage four direct reports.

They will define a global strategy, drive cross-functional collaboration with sales leadership, and oversee the enablement tech stack (Highspot, Gong, Salesforce, AI platforms) with KPI tracking.

Qualifications

• 5+ years in commercial enablement with team leadership.
• Modern learning design: microlearning and AI-enabled content.
• Proven impact on ramp time, quota attainment or retention.
• Executive presence and ability to influence sales leadership without direct authority.
• Experience with Highspot, Gong, Salesforce, and AI enablement platforms.
• Change management guiding teams through transitions and adoption.

Responsibilities

• Define and execute a global sales enablement strategy aligned to priorities.
• Build and lead a team of 4 with clear work-stream ownership.
• Champion AI-powered, microlearning-first approaches with role plays and pods.
• Partner with sales ops and leadership to ensure segment-aligned enablement.
• Define and track KPIs including ramp time, adoption, and revenue impact.
• Manage vendor relationships and enablement tech stack budget.
• Model a modern operating cadence with quarterly planning and reviews.

Skills

Commercial enablement leadership

Microlearning design

AI-enabled content

Executive presence

Sales tools management

Change management

Tools

Highspot

Gong

Salesforce

AI platforms

Job description

Job Overview

Posting Type: Hybrid

The Director of Sales Enablement leads the modernization of Relativity’s sales enablement function. Reporting to the Sr Director of Global Revenue Operations, this leader will build an AI-forward, microlearning-led enablement organization that enables sellers to keep pace with the speed of commercial and product innovation.

This director will shape how the team operates — moving from reactive program delivery to a proactive, segment-led model anchored in modern learning design. They will manage four direct reports and serve as the strategic partner to sales leadership across all segments.

Key Responsibilities

• Define and execute a global sales enablement strategy aligned to Relativity’s commercial priorities and segment needs
• Build and lead a team of 4 — with clear work-stream ownership
• Champion AI-powered, microlearning-first approaches — role plays, practice pods, assessments, and in-flow delivery
• Partner with sales ops business partners and sales leadership globally to ensure enablement is anchored to commercial priorities — segment context flows from the sales ops BPs, not owned directly by this team
• Define and track KPIs including ramp time, program adoption, seller confidence scores, and revenue impact
• Manage vendor relationships, tools budget, and the enablement tech stack (Highspot, Gong, Salesforce, AI platforms)
• Model a modern operating cadence — quarterly planning, monthly cross-functional reviews, continuous feedback loops

Qualifications

Required

• Deep experience in enablement roles in high-growth SaaS or legal tech, including 5+ years in commercial enablement with team leadership
• Modern learning design expertise: microlearning, AI-assisted content, spaced repetition, and in-flow delivery
• Track record of building enablement programs that directly impact ramp time, quota attainment, or retention
• Strong executive presence and ability to influence sales leadership without direct authority
• Experience with Highspot, Gong, Salesforce, and AI enablement platforms
• Change management expertise — history of guiding teams through transitions and driving adoption

Differentiators (Preferred)

• Experience in legal tech, law firm sales, or professional services market
• Familiarity with Relativity’s product ecosystem or e‑discovery space
• Experience building or scaling an enablement function from a low‑maturity baseline

Compensation & Benefits

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 $162,000 and $242,000. 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, Leadership, Process Improvements, Program Management, Project Management, Relationship Building, Sales Enablement, Stakeholder Management, Strategy Development.

What Relativity Has to Offer

Relativity’s software helps users organize data and quickly identify key issues during litigation, internal investigations, and compliance projects.

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