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!
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.
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
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
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.
Please be aware that Iterable, Inc. (“Iterable”) and our official professional recruiting agencies and platforms do not:
Send job offers from free email services like Gmail, Yahoo mail, Hotmail, etc.
Request money, fees, or payment of any kind from prospective candidates to apply to Iterable, for employment, or for the recruitment process (e.g. for home office supplies, or training, etc.).
Request or require personal documents like bank account details, tax forms, or credit card information as part of the recruitment process prior to the candidate signing an engagement letter or an employment contract with Iterable.
You may see all job vacancies on our official Iterable channels:
Official Iterable website, Careers page: https://iterable.com/careers/
Official LinkedIn Jobs page: https://www.linkedin.com/company/iterable/jobs/
Iterable is not affiliated in any way to these impostors and we hereby confirm that such individuals/entities are not authorized, encouraged, or sponsored to act on behalf of Iterable. Such job opportunities are entirely fake and not valid. Therefore, please disregard any written or oral request for a job offer or an interview that you believe is or might be fraudulent or suspicious and immediately reach out to us via email at talent-ops@iterable.com upon receiving a suspicious job offer.
Criminal and/or civil liabilities may arise from such actions, and Iterable expressly reserves the right to take legal action, including criminal action, against such individuals/entities whenever such phenomena occur. In any case, please note that under no circumstances shall Iterable and any of its affiliates be held liable or responsible for any claims, losses, damages, expenses or other inconvenience resulting from or in any way connected to the actions of these impostors.
Iterable is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Iterable does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender-identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Iterable also strives for a healthy and safe workplace and strictly prohibits harassment of any kind. Pursuant to the San Francisco Fair Chance Ordinance and other similar state laws and local ordinances, and its internal policy, Iterable will also consider for employment qualified applicants with arrest and conviction records.
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Iterable is a customer communication platform that enables businesses to deliver personalized, data-driven experiences across multiple channels. The AI-powered platform helps companies engage customers through email, SMS, push notifications, and other touchpoints.
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