Director, Customer Success (Enterprise)

1Password is growing. We’ve surpassed $400M in ARR and we’re continuing to accelerate, earning a spot on the Forbes Cloud 100 for four years in a row and teaming up with iconic partners like Oracle Red Bull Racing.

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 Unified 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 180,000 businesses, from Fortune 100 leaders to the world’s most innovative AI companies, trust 1Password to help their teams securely adopt the SaaS and AI tools they need to do their best work.

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.

Our Enterprise Customer Success team is responsible for protecting and growing the revenue relationships with 1Password's largest, most strategically significant customers. We are customer-obsessed, commercially rigorous, and committed to building the long-term executive partnerships that make 1Password an indispensable part of every enterprise's identity security strategy.

As Enterprise Director of Customer Success, you will lead a team of Enterprise CSMs across experience levels – and own the Enterprise segment's NRR outcomes, engagement model, and team performance. You will be accountable for the full post-sale success motion in the Enterprise segment: retention, expansion pipeline generation, executive business review quality, success plan coverage, and forecasting accuracy. You are a player-coach and organizational architect who shapes how Customer Success operates at scale, develops exceptional talent, and serves as a senior cross-functional partner to Enterprise Sales, RevOps, Solutions Engineering, and Product.

This role requires deep customer success expertise, strong commercial acumen, a high standard for operational rigor, and genuine passion for building high-performing teams. Adaptability, executive presence, systems thinking, and a relentless focus on customer and revenue outcomes will define your success.

How we’re using AI today

Across GTM, we’re transforming the way we work with AI. We expect every seller, CSM, and team member to become a power user, using it daily to work smarter and move faster. AI is already embedded in how we operate – from real-time coaching that sharpens how we sell and interact with customers, to surfacing insights that help us anticipate needs – creating more time for meaningful customer engagement. If you’re excited to reshape how you think, make decisions, and drive growth with AI, you’ll feel right at home here.

This is a remote opportunity within Canada and the US.

What we're looking for

Experience & Background

10+ years in Customer Success, enterprise account management, or a strategic post-sale function in SaaS, with a demonstrated track record of owning NRR and expansion outcomes

10+ years of people management experience, with demonstrated progression in leading and developing CSMs at multiple levels; experience managing managers is a strong plus

Proven ability to lead Enterprise-focused CS teams through complex renewals, executive stakeholder engagement, and commercial expansion motions

Deep familiarity with CS operating frameworks – success planning, EBR design, risk CTA management, renewal and expansion forecasting – and how they connect to segment-level NRR performance

Strong familiarity with Gainsight and Salesforce; experience using CS platforms to manage team performance, customer health, and pipeline visibility at scale

Background in cybersecurity, identity security, IAM, strongly preferred; former 1Password power user or practitioner is a meaningful advantage

Leadership & Team Development

Demonstrated ability to build, develop, and scale high-performing Enterprise CSM teams across levels

Sets and reinforces clear performance standards aligned to the CS KPIs – territory planning, EBRs, expansion pipeline, forecasting hygiene, risk management, CSAT, and advocacy

Structures coaching and development deliberately: formal deal reviews, call debriefs, and development plans that produce measurable improvement in CSM commercial performance

Champions AI capability and enablement adoption across the team; models responsible, high-quality AI-assisted workflows in their own practice

Drives succession planning, hiring strategy, and internal growth paths; builds a team culture of accountability, curiosity, and continuous improvement

Commercial & Revenue Leadership

Owns the Enterprise segment's NRR targets and the discrete Renewals and Pipeline Generation motions that contribute – including gross retention rate, expansion pipeline volume, amendment win rates, renewal upsell win rates, and forecasting accuracy

Partners with Enterprise AEs to define and evolve the CS-Sales collaboration model: joint account planning, QL handoff standards, pipeline attribution, and deal strategy norms for the segment's most complex accounts

Understands and coaches on multi-stakeholder executive business reviews, C-suite renewal negotiations, multi-year expansion business cases, and competitive retention conversations

Drives forecasting rigor at the team level: maintains forecasting hygiene standards, identifies renewal risks with sufficient lead time, and provides CS leadership with accurate, forward-looking segment visibility

Uses Gainsight and Salesforce to manage segment health, track CTA resolution, monitor expansion pipeline, and report on team-wide RFS KPI performance

Strategic & Operational Excellence

Designs, documents, and scales Enterprise CS engagement models, success planning standards, EBR methodologies, and playbooks that improve team-wide performance and create repeatable outcomes

Aligns CS capacity, segment coverage models, and role deployment to ARR growth targets and Enterprise customer complexity

Identifies operating gaps and cross-functional friction; drives structured improvements that reduce risk, accelerate activation, and increase expansion velocity

Contributes to CS OKR development; brings data-backed recommendations that influence CS and GTM strategy, organizational design, and investment priorities

Promotes and models an AI-first approach to commercial execution; builds AI-assisted systems for account intelligence, risk monitoring, and engagement preparation that multiply team capacity at scale

Customer & Cross-Functional Collaboration

Serves as senior escalation owner for the Enterprise segment's most critical, high-stakes customer situations; partners with cross-functional leaders to drive resolution and ensure learnings are captured and embedded

Trusted partner to Enterprise Sales, Solutions Engineering, RevOps, Support, and Product leadership; aligns stakeholders at all levels, including executive audiences, on customer priorities and segment strategy

Aggregates customer intelligence from the Enterprise book and channels it into GTM positioning, product roadmap input, and CS commercial model design with documented influence on business decisions

Represents the Enterprise CS organization with confidence in leadership forums and strategic planning conversations

Communication, Enablement & Influence

Excellent written and verbal communication skills with strong executive presence across internal and customer-facing audiences

Communicates team performance, renewal risk, expansion opportunity, and strategic priorities with clarity and commercial discipline to CS and GTM leadership

Confident leading with influence rather than authority; navigates organizational ambiguity, drives clarity, and aligns cross-functional partners through expertise and relationship

Champions a culture of enablement, documentation, and shared learning; ensures that high-impact workflows, playbooks, and best practices created within the team are made available and usable across the broader CS organization

What you can expect

Onboard & Orient (Month 1)

Develop deep fluency in 1Password's product suite, CS methodology, Enterprise customer profiles, and the commercial motion connecting retention and expansion

Build strong working relationships with your team, key internal partners (Enterprise Sales leadership, RevOps, Solutions Engineering, CS leadership), and the segment's most strategic customer relationships

By the end of Month 1, you will have clear, documented visibility into team health, open renewal risks, expansion pipeline status, and RFS KPI performance across the Enterprise segment

Establish the Standard (Month 3)

All direct reports have clear performance expectations, active development plans, and structured coaching rhythms in place

Enterprise CS engagement model is defined or refined: EBR cadence, success plan coverage standards, forecasting hygiene, and CS-Sales collaboration norms are operating with consistency

By Month 3, the team is tracking to NRR targets, forecasting hygiene meets team standards, and expansion pipeline is being sourced and progressed with documented commercial context

Drive Performance & Organizational Impact (Month 6)

Enterprise segment NRR is tracking to plan; the team's renewal, expansion, and CSAT outcomes are visible and positive in CS and GTM leadership reporting

Playbooks, AI workflows, and team enablement contributions are in active use and improving measurable outcomes

By Month 6, you are recognized as a strategic cross-functional partner by Enterprise Sales, RevOps, and CS leadership, and your team is developing and performing with clear upward trajectory

USA-based roles only: The annual base salary for this role is between $168,000 USD and $252,000 USD, and is commission-eligible. This role is also eligible for 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 $169,000 CAD and $254,000 CA, and is commission-eligible. This role is also eligible for 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.

This posting is for an existing vacancy.

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.

How we work with AI

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—it's an essential part of how we will be successful at 1Password.

This approach extends to our hiring process—candidates are welcome to use AI tools responsibly and thoughtfully during the application process.

Our approach to work

We recognize the power of both in person collaboration and remote work. Some roles are designated as remote-first, with an expectation that individuals work from their homes majority of the time, while others are designated as in-office roles, with an expectation of being on-site on a regular basis. We recognize that certain roles benefit from regular, in-person connection to support collaboration, team cohesion, and customer engagement.

For all roles, occasional travel may be required. This includes things like: department-wide offsites, quarterly department meetings and periodic customer events. These events are typically held in varying locations across Canada, USA and/or EMEA. In leadership roles, you can expect to travel once per month on average.

Note: All go-to market roles will have an in-person onboarding in Toronto.

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