Head of Digital and Scaled Customer Success

United States Digital Space LLC; United States; Remote; USD 223,000 - 262,000; Full time

Benefits offered by this job

Mental health benefits

Career coaching

Inclusive family building benefits

Long-term savings / retirement plans

In-office culinary options

Job summary

United States Digital Space LLC is seeking a Senior Leader for Head of Digital & Scaled Customer Success. You will design and lead automated, data-driven programs to retain, engage, and grow large groups of customers with minimal human management, building tech-touch strategies and optimizing operations for low-cost CLV.

The role can be fully remote or hybrid with offices in San Francisco, Chicago, or New York.

Qualifications

• 7-10+ years of experience in Customer Success or similar senior leadership roles in SaaS.
• Experience building digital/programmatic customer journeys and scalable programs.
• Proven ability to mentor and develop high-performing teams.

Responsibilities

• Define and own scale & digital CS strategy and the customer journey.
• Design self-serve onboarding and lifecycle communications to drive activation.
• Build AI-driven engagement plays to scale team impact with Product alignment.
• Accelerate time-to-value through strategic plays and deep discovery.
• Establish metrics and instrumentation to measure program success.
• Lead cross-functional teams and align stakeholders on the digital CS vision.

Skills

Leadership

Digital CS

Data-driven

AI tools interest

Cross-functional

Customer success

Mentoring teams

Tools

CRM systems

Product metrics

Job description

At the company, 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 the company 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.

About you

• 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, Marketing, and Operations to design product-led and program-led journeys.

• Proven capability as an advisor for complex customer issues, with strong problem-solving skills to manage senior customer escalations effectively.

• Track record of leading, mentoring, and developing high-performing teams while driving strategic operating models.

At the company, we’re committed to building teams that include a variety of backgrounds, perspectives, and skills, as this is critical to helping us achieve our mission. If you're interested in this role and don't meet every listed requirement, we still encourage you to apply.

What we’ll offer

Our comprehensive compensation package plays a big part in how we recognize you for the impact you have on our path to achieving our mission. We believe that compensation should be reflective of the value you create relative to the market value of your role. To ensure pay is fair and not impacted by biases, we're committed to looking at market value which is why we check ourselves and conduct a yearly pay equity audit.

For this role, the estimated base salary range will vary based on your location. Locations in the US are categorized into one of three geographic pay zones, and the ranges for the zones are as follows:

Zone A: $223,200 - $262,400

Zone B: $200,800 - $236,000

Zone C: $178,400 - $210,000

For more information about which locations fall into each pay zone, please visit https://the company.com/usa-pay-zones. Please also consult your recruiter to confirm the applicable pay zone for your specific location.

The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process. The listed ranges above are a guideline, and the base salary range for this role may be modified.

In addition to base salary, your compensation package may include additional components such as equity, sales incentive pay (for most sales roles), and benefits. If you're interviewing for this role, speak with your recruiter to learn more about the total compensation and benefits for this role.

We strive to provide equitable and competitive benefits packages that support our employees worldwide and include:

• 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

These are just some of the benefits we offer, and benefits may vary based on role, country, and local regulations. If you're interviewing for this role, speak with your Talent Acquisition Partner to learn more about the total compensation and benefits for this role.

#LI-Hybrid

About us

the company is a leading platform for human + AI collaboration. Millions of teams around the world rely on the company to achieve their most important goals, faster. the company has been named to Fortune's Best Workplaces for 7+ years and recognized by Fast Company, Forbes, and Gartner for excellence in workplace culture and innovation. We offer an exceptional office-centric culture while adopting the best elements of hybrid models to ensure that every one of our global team members can work together effortlessly. With 13+ offices all over the world, we are always looking for individuals who care about building technology that drives positive change in the world and a culture where everyone feels that they belong.

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