Head of Digital and Scaled Customer Success

At Asana, we’re building agentic work management software to help every organization in the world become more effective in working together and realizing their goals. Our Customer Experience team is committed to helping customers in their post-sales journey to deploy, adopt, and use Asana as both a technology product and a holistic way of working. We strive to help our customers, across geographies, industries, and functions, get off on the right foot, experience the most value out of the tool over time, and ultimately renew & grow their subscription.

We are looking for a senior leader for the Head of Digital & Scaled Customer Success. In this role you will lead a team that designs and leads automated, data-driven programs to retain, engage, and grow large groups of smaller-tier customers without relying on one-on-one human management. You will build tech-touch strategies, manage digital engagement tools, and optimize operations to drive low-cost customer lifetime value.

This role can either be fully remote depending on which US state you live in, or based in our San Francisco, Chicago, or New York City 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

• Define and own scale & digital strategy: Own the scale and digital CS strategy, defining the digital customer journey, determining engagement motions for each stage, and establishing how customers transition as their needs evolve.

• Design digital success programs: Launch self-serve onboarding, lifecycle communications, and in-product nudges that drive activation and habitual software usage with minimal to no human coverage.

• Build AI-powered engagement plays: Implement AI-driven plays to scale team impact, partnering closely with Product to clarify platform capabilities versus team-built automation.

• Accelerate customer time-to-value: Develop strategic customer plays centered on relationship building, deep discovery, and solution alignment, serving as a key advisor and escalation point for complex issues.

• Establish metrics frameworks: Define customer activation milestones across every stage of the journey, identify leading indicators, and build instrumentation to measure program success.

• Drive data-informed experimentation: Run a rigorous experimentation program to identify motions that effectively shift customer behavior, using data insights to continually iterate on playbooks.

• Lead cross-functional vision: Lead and develop a high-leverage team while partnering cross-functionally across the organization to align stakeholders on the digital CS vision and operating model.

• 7-10+ years of experience in Customer Success or client-facing leadership roles within the SaaS industry, with a proven track record of managing large-scale regional organizations.

• Demonstrates curiosity about AI tools and emerging technologies, with a willingness to learn and leverage them to enhance productivity, collaboration, or decision-making.

• Proven track record in customer success leadership, specifically in building, executing, and scaling digital or programmatic customer success strategies.

• Demonstrated experience establishing metrics frameworks, tracking leading indicators, and running rigorous data-driven experimentation programs.

• Strong cross-functional partner with experience collaborating across Product,