Director, GTM AI Enablement

Director, GTM AI Enablement

Iterable is the leading AI-powered customer engagement platform that helps leading brands like Redfin, SeatGeek, Priceline, Calm, and Box create dynamic, individualized experiences at scale. Our platform empowers organizations to activate customer data, design seamless cross-channel interactions, and optimize engagement—all with enterprise-grade security and compliance. Today, nearly 1,200 brands across 50+ countries rely on Iterable to drive growth, deepen customer relationships, and deliver joyful customer experiences.

Our success is powered by extraordinary people who bring our core values—Be an Owner, Growth Mindset, Run as One, Transparency—to life. We foster a culture of innovation, collaboration, and inclusion, where ideas are valued and individuals are empowered to do their best work. That's why we've been recognized as one of Inc's Best Workplaces and Fastest Growing Companies, and were recognized on Forbes' list of America's Best Startup Employers in 2022. Notably, Iterable has also been listed on Wealthfront's Career Launching Companies List and has held a top 10 ranking on the Top 25 Companies Where Women Want to Work.

With a global presence—including offices in San Francisco, New York, Denver, London, and Lisbon, plus remote employees worldwide—we are committed to building a diverse and inclusive workplace. We welcome candidates from all backgrounds and encourage you to apply. Learn more about our story and mission on our Culture and About Us pages. Let's shape the future of customer engagement together!

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