Director, AI-Driven 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

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.