Senior Director, Digital Customer Success

About 1Password

At 1Password, we’re building the foundation for a safe, productive digital future. Our mission is to unleash employee productivity without compromising security by ensuring every identity is authentic, every application sign-in is secure, and every device is trusted. We innovated the market-leading enterprise password manager and pioneered Extended Access Management, a new cybersecurity category built for the way people and AI agents work today. As one of the most loved brands in cybersecurity, we take a human-centric approach in everything from product strategy to user experience. Over 175,000 businesses and millions of people trust us to provide seamless, secure access to their most critical information. 

If you're excited about the opportunity to contribute to the digital safety of millions, to work alongside a team of curious, driven individuals, and to solve hard problems in a fast-paced, dynamic environment, then we want to hear from you. Come join us and help shape a safer, simpler digital future.

We are seeking a Head of Digital Customer Success to build and lead our digital-first customer success motion for our self-serve segment. This business represents customers who primarily sign up and transact via credit card, and while their spend may be smaller individually, they represent a critical growth engine for our company.

In this role, you will be accountable for engagement, activation, expansion, and retention of these customers. You’ll work as a close partner to Product to design in-app experiences that drive success at scale, and with Marketing to deliver lifecycle communications and campaigns that deepen customer value. When digital success plays fall short, you’ll coordinate seamless human interventions to ensure outcomes are achieved.

This is a dynamic and highly collaborative role—you’ll embrace experimentation, measurement, and iteration to continuously evolve our approach. You’ll balance strategy and execution: shaping the long-term vision for scaled success while running agile tests that deliver immediate impact. Your work will be instrumental in ensuring customers adopt our solutions, expand into new products, and stay loyal over time.

What to expect:

Strategy & Leadership
Design and own the digital customer success strategy, including segmentation, engagement models, success and expansion plays for our self-serve customer base.

• Partner with Product to embed customer success into the product experience (in-app guidance, lifecycle flows, nudges, and usage triggers).

• Collaborate with Marketing on lifecycle communications, campaigns, and content that support adoption, expansion, and retention at scale.

• Establish a digital escalation model, ensuring the right human intervention when product-led motions are not sufficient.
  

Customer Engagement & Growth

• Drive activation of existing services, ensuring customers realize ongoing value from our platform.

• Own expansion motions (upsell, cross-sell) through coordinated digital campaigns, lifecycle marketing, and product-driven recommendations.

• Work with cross-functional stakeholders (Sales, Success, Marketing, Product) to align digital programs with broader go-to-market strategies.

• Monitor health across the customer base and proactively address churn risks through scaled interventions.
  

Operations & Insights

• Run a test-and-learn approach to digital programs—experimenting with new engagement tactics, lifecycle journeys, and interventions.

• Continuously measure program effectiveness using adoption, retention, and revenue metrics; refine strategies based on what works.

• Partner with Product and Marketing to pilot and scale new engagement methods, ensuring the customer experience evolves with the business.

• Provide actionable insights back to Product, Marketing, and Customer Success leadership to inform and influence roadmap and strategy.
  

Team & Program Development

• Build and lead a high-performing team. Coach and mentor direct reports, maintain a deep understanding of the team’s talent, and implement plans to hire, develop and optimize talent for current business needs.

• Build repeatable, automated customer journeys leveraging email, in-app messaging, knowledge base, community, and AI/automation.
  

What we're looking for:

• Minimum 7+ years of experience in Customer Success, Digital Programs, or Product-Led Growth at a SaaS company (500 employees+).

• Minimum 3+ years leading teams during the above years.

• Proven track record of driving activation, expansion, and retention in a digital-first or scaled-success model.

• Strong partnership skills with Product and Marketing to align on customer outcomes and deliver seamless digital experiences.

• Experience with customer success and lifecycle tools like; Gainsight, Salesforce, Iterable, Marketo

• Experience with analytics tools like; Pendo, Mixpanel, Amplitude

• Comfort with APIs, integrations, and working alongside engineering/ops teams to automate at scale.

• Analytical mindset with the ability to measure impact, identify trends, and turn data into action.

• Excellent communication skills with the ability to influence stakeholders and executive leadership.

• Strong leadership skills with experience building or leading a program team.
  

Measure of Success:

• Increased product activation and engagement rates across self-serve customers, achieved through effective product-led and marketing-supported programs.

• Improved net revenue retention (NRR) and reduced churn in the long-tail customer segment.

• Demonstrated expansion revenue growth (upsell, cross-sell) driven by digital campaigns, lifecycle communications, and in-product experiences.

• Evidence of a strong test-and-learn culture—regular experimentation with digital success plays, with measurable improvements from iteration.

• Documented cross-functional impact through successful collaboration with Product (e.g., in-app engagement) and Marketing (e.g., lifecycle campaigns).

• Scaled customer coverage and engagement touchpoints without significant increases in human resource costs.

• Positive recognition internally (from Product, Marketing, Success, and Leadership) for contributions to customer insights and growth strategy.

USA-based roles only: The annual base salary for this role is between $211,000 USD and $285,000 USD, plus immediate participation in 1Password's benefits program (health, dental, 401k and many others), utilization of our generous paid time off, an equity grant and, where applicable, participation in our incentive programs.

Canada-based roles only: The annual base salary for this role is between $202,000 CAD and $274,000 CAD, plus immediate participation in 1Password’s generous benefits program (health, dental, RRSP and many others), utilization of our generous paid time off, an equity grant and, where applicable, participation in our incentive programs.

At 1Password, we approach each individual's compensation with a promise of fair market value and internal equity commensurate with experience and specific skill set.

Our culture

At 1Password, we prioritize collaboration, clear and transparent communication, receptiveness to feedback, and alignment with our core values: keep it simple, lead with honesty, and put people first.

You’ll be part of a team that challenges the status quo, and is excited to experiment and iterate in search of the best solution. That said, 1Password is not for everyone . Our work is demanding, we strive for excellence, and the pace is fast. We need people who are keen to take on challenging problems, who seek feedback to grow, and who are driven to make an impact. If you're looking for a place where you can settle into a comfortable routine, this might not be the right fit for you. We’re looking for individuals who are proven experts in their fields, as well as those who are highly adaptable, can thrive in ambiguity and through change, are curious, and above all deliver results.

We are committed to leveraging cutting-edge technology—including AI—to achieve our mission. We also understand that thinking critically about AI in its current forms will help us create better solutions for our customers and ourselves with its future forms, which will help us continue to close the gap between security and privacy and achieve our mission. We want team members at all levels to take the approach of actively learning AI best practices, identifying opportunities to apply AI in meaningful ways, and driving innovative solutions in their daily work. Embracing the future of AI isn't just encouraged at 1Password—it's an essential part of how we will be successful at 1Password.

Our approach to remote work

We believe in the power of remote work, but recognize that in-person connection is important to help us achieve our mission. While we are a remote-first company, travel for in-person engagement is a part of almost all roles, and we require our employees to be ready and willing to take part. Frequency will depend on role and responsibilities, and may include, but is not limited to: annual department-wide offsites, team meetings, and customer/industry events.

What we offer

We believe in working hard, and rewarding that hard work through our benefits. While not an exhaustive list, here is a glance at what we currently offer:

Health and wellbeing

👶 Maternity and parental leave top-up programs

🩺 Competitive health benefits

🏝 Generous PTO policy

Growth and future

📈 RSU program for most employees

💸 Retirement matching program

🔑 Free 1Password account

Community

🤝 Paid volunteer days

🏆 Peer-to-peer recognition through Bonusly

🌎 Remote-first work environment

*Some roles in our GTM team are currently being hired for in-person hybrid work in Toronto and Austin. These roles will specify on the posting.

You belong here.

1Password is proud to be an equal opportunity employer. We are committed to fostering an inclusive, diverse and equitable workplace that is built on trust, support and respect. We welcome all individuals and do not discriminate on the basis of gender identity and expression, race, ethnicity, disability, sexual orientation, colour, religion, creed, gender, national origin, age, marital status, pregnancy, sex, citizenship, education, languages spoken or veteran status. Be yourself, find your people and share the things you love.

Accommodation is available upon request at any point during our recruitment process. If you require an accommodation, please speak to your talent acquisition partner or email us at [email protected] and we’ll work to meet your needs.

Remote work is a part of our DNA. Given that our company was founded remotely in 2005, we can safely say we're experts at building remote culture. That said, remote work at 1Password does mean working from your home country. If you've got questions or concerns about this, your talent partner would be happy to address them with you.

Successful applicants will be required to complete a background check that may consist of prior employment verification, reference checks, education confirmation, criminal background, publicly available social media, credit history, or other information, as permitted by local law.

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