About this role
The Role:
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.
Key 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
What We’re Looking For:
Experience & Background
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
Skills & Competencies
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
Personal Attributes
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
Former SC / sales engineer background a plus — can speak the technical language
Success Metrics
Quota attainment and win rate improvements tied to enablement programs
Team health, retention, and on-time delivery against roadmap
Ramp time to productivity across AE, SC, SDR, and CSM roles
Business acumen assessment scores across the GTM org
Enablement program velocity and field satisfaction (NPS)
Content utilization and adoption across the field
Perks & Benefits:
Paid parental leave
Competitive salaries, meaningful equity, & 401(k) plan
Medical, dental, vision, & life insurance
Community Impact Days
Fertility & Adoption Assistance
Paid Sabbatical
Flexible PTO
Monthly Employee Wellness allowance
Monthly Professional Development allowance
Pre-tax commuter benefits
Complete laptop workstation
The US base salary range for this position at the start of employment is $168,000 - $240,000. Within this range, individual pay is determined by specific US work location, as well as additional factors, including job-related skills, experience, relevant education or training, and internal equity considerations.
Please note that the range listed above reflects only base salary. The total compensation package includes variable pay (where applicable), equity, plus a range of benefits, including medical, dental, vision, and financial. In addition, we offer perks such as generous stipends for health & fitness and learning & development, among others.