Director, GTM AI Enablement

Iterable is the AI customer engagement platform built for enterprise scale loved by teams and trusted by global brands like Redfin SeatGeek Priceline Calm and Box. Our platform empowers organizations to activate customer data from any source design seamless cross-channel experiences and optimize engagement with Nova Intelligence the AI layer of our platform all with enterprise-grade security and compliance. Today nearly 1200 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 to life every day: Be an Owner Growth Mindset Run as One and Transparency. And the market has noticed: G2 recognizes Iterable as a Leader globally spanning the Americas EMEA APAC ANZ and Latin America with category leadership in Personalization Marketing Automation Push Notifications and Mobile Marketing and a 4.5/5-star rating from hundreds of users. Gartner named Iterable a Challenger in the Gartner Magic Quadrant for Multichannel Marketing in both 2024 and 2025. Weve also earned TrustRadius Top Rated honors in 2024 and 2025 were named a TrustRadius Buyers Choice for 2026 and were featured in Snowflakes Modern Marketing Data Stack 2026.

With a global presence that includes offices in San Francisco Denver London Sydney 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. Lets 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. Youll 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 Iterables 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 Were Looking For:

Experience & Background

• 7 years in revenue enablement sales training or GTM strategy with at least 23 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 doesnt 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 $168000 - $240000. 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 addition we offer perks such as generous stipends for health & fitness and learning & development among others.

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