Director of GTM AI Enablement, Iterable
$168-240k
+ Equity
AI-powered customer communication platform
Be an early applicant
AI-powered customer communication platform
501-1000 employees
Be an early applicant
$168-240k
+ Equity
501-1000 employees
Company mission
To connect people with products that bring them joy.
Role
Who you are
- 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
- Former SC / sales engineer background a plus — can speak the technical language
What the job involves
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
Our take
Iterable is a growth marketing platform that enables brands to create, execute and optimize cross-channel campaigns. The company aims to complement and support marketers in creating effective user engagement campaigns throughout the sales funnel, and across all channels.
The global omnichannel retail commerce platform market is huge, and the opportunity within this sector has bought with it considerable competition for Iterable. Despite this, the company has firmly established a name for itself and now has over 1000 customers (including DoorDash, Fender, Calm, Box, and Cars.com).
After raising significant funding in 2021, and a change in leadership that same year, Iterable has invested in several sales-focused AI technologies in order to appeal to enterprise companies. In 2025 it achieved the feat of surpassing one trillion customer interactions, demonstrating that its momentum is still very strong.
Steph
Company Specialist at Welcome to the Jungle
Insights
-3% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jun 2021
$200m
SERIES E
Dec 2019
$60m
SERIES D
Total funding: $342.2m
Company benefits
- Medical, Dental & Vision Insurance
- Life & Disability Benefits
- Flexible Spending Accounts
- Health Savings Accounts with Employer Contributions
- Premium Calm Membership
- Health and Fitness Stipend
- Paid Parental Bonding Leave
- Paid Sabbatical
- Internet and Mobile Phone Reimbursement
- Learning and Development Stipend
- Family Forming Benefits
- Paid Holidays
- Flexible Time Off
- Balance Days
Company HQ
Financial District, San Francisco, CA
Leadership
Andrew Boni
(Founder & Chief Scientist)Was CEO of the company for 4 years. Previously an Application Services Developer at Boston College and Lead Web Developer at Kollaboration Boston.
Sam Allen
(CEO)Accomplished executive who has managed $3B+ P&Ls. Spent almost 11 years at Salesforce and previously co-founded and was CEO at ScanCafe.
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