Head of Customer AI Transformation

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. This role can either be fully remote depending on which US state you live in, or based in our San Francisco or New York office with an office-centric hybrid schedule. If based in-office: The standard in-office days are Monday, Tuesday, and Thursday. Most Asanas have the option to work from home on Wednesdays. Working from home on Fridays depends on the type of work you do and the teams with which you partner. If you're interviewing for this role, your recruiter will share more about the in-office requirements.  What you’ll achieve 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 About You Experience: 8+ years of leadership experience in customer success, professional services, revenue operations, product management, or technical consulting, with significant expertise in enterprise SaaS Organizational transformation: 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 Post-sales depth: 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 Executive presence: 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 AI fluency: 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 Commercial acumen: Direct experience with revenue targets, pricing and packaging strategy, services P&L management, or renewal and expansion motions Cross-functional operator: Exceptional at driving change across Product, Engineering, Sales, Finance, Legal, and Channel — unblocking dependencies and holding cross-functional partners accountable on a