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The AI Transformation Factory is Asana’s internal engine for evolving the Customer Experience organization to drive customer adoption of our AI platform. It operates at the intersection of Revenue, Product, and Engineering — redesigning post-sales motions, running strategic customer engagements, and driving cross-functional change to accelerate net retention and AI revenue growth. We are looking for a Head of Customer AI Transformation to build and lead this Factory. This is not a traditional professional services or customer success leadership role. You will be the operational leader for the AI Transformation Factory, responsible for evolving Asana’s post-sales organization into an AI-activation model — redesigning how our customer success, renewal, and services teams operate; running proofs of concept and generating validated ROI proof points with strategic customers; and driving cross-functional operationalization across the company to ensure changes ship at speed. This role will report to the Chief Customer Officer.
Responsibilities
Evolve the customer success team to drive consumption of AI products — define and operationalize new motions, equipping the team to plan workflow agentification with customers, deploy AI capabilities to demonstrate value, and cultivate champions for cross-team expansion
Drive the development of an ROI-validated AI use case library structured by persona, vertical, and AI capability, and embed it into customer success tooling so the field can make a concrete value case in every customer conversation
Enable seat-to-AI conversion across the renewal motion — equip renewal managers with the playbooks, commercial tools, and streamlined processes to convert seats into AI products as part of the standard renewal workflow
Evolve services delivery for the AI era — transition the core services entitlement to AI activation, redefine and upskill the implementation team, update pricing and packaging for our Services Produts, and build partner delivery infrastructure so certified partners deliver implementation at scale
Run initial targeted proofs of concept with strategic customers to validate AI use cases in real environments, producing documented outcome reports and packaging ROI proof points for the field
Serve as the escalation hub and product liaison for the field on all customer experience issues tied to AI products, and aggregate voice of customer feedback into structured input for Product
Drive cross-functional operationalization across Product, Marketing, Engineering, Finance, Legal, Deal Desk, Channel, and Support to ship changes on aggressive timelines
Own measurement and reporting — AI consumption tracking pre- and post-engagement, net retention impact, and macro-level AI product adoption across the installed base
Establish the operating cadence and steering committee model, keeping senior leadership aligned on progress, risks, and decisions
Requirements
8+ years of leadership experience in customer success, professional services, revenue operations, product management, or technical consulting, with significant expertise in enterprise SaaS
Proven track record of transforming how internal teams operate — you’ve redesigned motions, redefined roles, upskilled large teams, and shipped new operating models across complex organizations
Deep understanding of post-sales motions — customer success, renewals, professional services, and partner delivery. You understand how these functions interlock and how to evolve them simultaneously
Deep customer empathy with the ability to build consensus with senior technology leaders at large enterprises by translating complex AI capabilities into clear business outcomes
Strong technical fluency in AI and generative AI technologies — including AI workflow design, agent orchestration, LLM-based products, and enterprise AI platforms. You don’t need to train models, but you understand agentic AI architectures and how they transform enterprise workflows
Direct experience with revenue targets, pricing and packaging strategy, services P&L management, or renewal and expansion motions
Exceptional at driving change across Product, Engineering, Sales, Finance, Legal, and Channel — unblocking dependencies and holding cross-functional partners accountable on aggressive timelines
You can do the hands-on work in the early phases while simultaneously designing the scalable operating model for the long term
Track record of developing top-tier talent, upskilling existing teams through role transitions, and inspiring high-achieving teams
Nice-to-haves
If you're interested in this role and don't meet every listed requirement, we still encourage you to apply.
Benefits
Mental health, wellness & fitness benefits
Career coaching & support
Inclusive family building benefits
Long-term savings or retirement plans
In-office culinary options to cater to your dietary preferences
