Director, GTM AI Enablement

Iterable•Chicago, GA

2d•Remote

About The Position

As Director of GTM AI Enablement at Iterable, you will own the strategy, design, and continuous evolution of how our entire GTM team learns, ramps, and sells. You'll lead a team responsible for building AI-powered, just-in-time enablement programs, accelerating field ramp time, and raising business acumen across every customer-facing function, while creating the compelling content, training, and systems that reduce friction across the sales process. This leadership role merges enablement program design with high-level GTM strategy, cross-functional orchestration, and team development to execute high-impact initiatives. You will implement structural rigor, scalable systems, and a culture of continuous learning across the global revenue organization — and build a high-performing enablement team in the process.

Requirements

7+ years in revenue enablement, sales training, or GTM strategy, with at least 2–3 years in a team leadership role
Proven track record of building and leading high-performing enablement or content teams
Demonstrated track record of reducing ramp time and improving quota attainment
Experience building or deploying AI/ML-enhanced enablement programs
Experience in B2B SaaS, ideally martech or an adjacent space
Deep fluency with enablement platforms (Guru, Momentum, Salesforce)
Strong analytical skills - measure everything and iterate fast
Excellent program management across a high-volume, fast-moving roadmap
Skilled content producer who can set a high editorial bar for the team
Strong executive communication and cross-functional influence
Strategic thinker who can zoom out to set vision and zoom in on a single talk track
Strong leader who builds trust with their team and credibility with senior stakeholders
Comfortable with ambiguity — builds structure and clarity where it doesn't yet exist
Collaborative and low-ego, energized by cross-functional work

Nice To Haves

Former SC / sales engineer background a plus — can speak the technical language

Responsibilities

AI-Powered Enablement: Design and deploy a just-in-time learning system using AI tools that delivers relevant content, talk tracks, and competitive intelligence in the flow of work.
Stay ahead of AI-driven enablement trends and continuously evaluate new tools and approaches that improve rep performance.
Partner with RevOps to embed AI-assisted guidance directly into Salesforce and the broader sales tech stack.
Field Ramp & Onboarding: Own end-to-end onboarding for AEs, SCs, SDRs, and CSMs by defining milestone-based ramp calendars, certification criteria, and accountability frameworks.
Establish a test-and-learn culture for onboarding, with a structured roadmap to continuously reduce time-to-productivity.
Partner with Sales leadership to reinforce Iterable's sales methodology through coaching, call reviews, and live practice.
GTM Business Acumen: Build a GTM-wide learning track covering financial modeling basics, industry vertical knowledge, buyer persona fluency, and economic value selling.
Translate business objectives from sales, marketing, and product leadership into enablement initiatives with clear scope, timelines, and success metrics.
Content, Training & Sales Systems: Lead a team producing high-quality battle cards, playbooks, demo scripts, objection-handling guides, and training programs designed to reduce friction at every deal stage.
Proactively audit the sales process to identify where reps lose time, confidence, or momentum — then build the tools, templates, and workflows that remove those blockers.
Maintain consistent messaging, brand, and quality standards across all enablement assets.
Team Leadership: Build and lead a high-performing GTM AI enablement team: recruit, mentor, and grow a team of enablement specialists, content creators, and program managers.
Set clear priorities and remove blockers so the team can move quickly without sacrificing quality, balancing reactive field needs with proactive program work.
Build a team culture that values craft, data-informed decisions, rapid iteration, and genuine partnership with the field.
Partner with recruiting and HR to scale the team as the business and enablement needs evolve.
Develop future leaders within the team through coaching, stretch assignments, and clear growth paths.
Analytics & Reporting: Define and own the GTM AI enablement measurement framework — ramp speed, quota attainment, win rate, deal velocity, and content utilization.
Report regularly to GTM leadership on enablement performance, with clear linkage to pipeline and revenue impact.
Identify trends and opportunities in performance data and translate them into prioritized enablement initiatives.