Scaled Customer Success Manager

Open Role

Scaled Customer Success Manager

• Remote - Canada: Select locations
• Remote
• Customer Experience and Success
• Full Time

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

As a Scaled Customer Success Manager at Dropbox, you will drive adoption, value realization, and renewal readiness across a portfolio of mid-market and small business managed customers. You will use customer and product signals to identify where engagement can have the greatest impact, then deliver timely, relevant experiences through targeted campaigns, group programs, digital touchpoints, and selective personalized outreach.

You will play a central role in connecting our Programmatic and Digital Customer Success team with the Renewals Desk for scaled segment accounts. You will ensure customer health, sentiment, risk, and adoption signals translate into clear renewal-readiness actions, while identifying and qualifying customer-backed growth opportunities as Customer Success Qualified Leads (CSQLs) for handoff to Sales.

Within the scaled portfolio, you will provide more focused engagement for a priority group of customers and translate customer health, retention, renewal, and growth signals into regular executive-level updates that support forecasting and business decisions. You will also own shared inbound customer channels, ensuring questions and requests are triaged, resolved, or routed to the right partner with clear follow-through.

The successful candidate is a customer-focused operator who is equally comfortable analyzing a portfolio, building repeatable engagement programs, writing clear customer communications, and speaking directly with customers to understand their experience.

You will bring recent experience managing or materially influencing customer renewals, including the ability to interpret retention metrics, identify churn and contraction risk, execute save plays, and surface customer-backed growth levers. You will help Dropbox scale Customer Success while retaining the judgment, curiosity, and customer voice that come from real customer conversations.

Responsibilities

• Own adoption, customer health, and renewal readiness across a scaled customer portfolio, using lifecycle, product usage, engagement, sentiment, and retention signals to prioritize action and improve renewal outcomes.
• Provide focused engagement for a priority group of customers, partnering closely with Renewal Managers and other account stakeholders to coordinate retention and growth actions and deliver regular executive-level portfolio and forecast updates for top accounts in the scaled portfolio.
• Design and execute targeted campaigns and scaled touchpoints that help customers adopt key capabilities, realize value, prepare for renewal, and address common risks at the right moments in their journey.
• Serve as the coordination point between Programmatic and Digital Customer Success and the Renewals Desk, ensuring timely handoffs, shared visibility, clear ownership, and coordinated save plays for customers with renewal-readiness gaps or identified churn and contraction risk.
• Own and manage shared inbound customer email channels, triaging questions and requests, coordinating timely responses, and ensuring issues are resolved or routed to the appropriate partner with clear follow-through.
• Use data to segment customers, identify patterns, test engagement strategies, measure impact, and continuously improve playbooks, content, workflows, and automation.
• Engage customers directly when a focused 1:1 conversation is needed to validate a signal, understand sentiment, address risk, gather product feedback, or capture a representative customer example.
• Synthesize customer voice across the portfolio and share actionable insights with Product, Marketing, Sales, Support, and Customer Experience partners to improve the product and customer journey.
• Partner cross-functionally to operationalize repeatable customer programs, resolve gaps in the customer experience, and identify customer-backed growth levers such as broader adoption, new use cases, license utilization, or additional product fit. Qualify relevant opportunities as Customer Success Qualified Leads (CSQLs) and route them to Sales with clear customer context and supporting signals.

Requirements

• 4+ years of experience in B2B SaaS Customer Success, Account Management, Digital Customer Success, lifecycle programs, or a comparable post-sale customer role.
• Recent experience directly managing or materially influencing customer renewals across a book of business, with measurable examples of save plays, churn or contraction mitigation, and retention outcomes.
• Demonstrated success managing customer outcomes across a broad or high-volume portfolio through a combination of one-to-many programs and targeted 1:1 engagement.
• Strong analytical judgment and fluency in SaaS retention metrics, including renewal rate, gross revenue retention, net revenue retention, churn, contraction, and expansion, with experience using those measures alongside customer signals to identify risk and growth levers.
• Experience designing or executing customer lifecycle, adoption, retention, or renewal-readiness campaigns and measuring their impact on customer behavior or business outcomes.
• Excellent written and verbal communication skills, including the ability to create clear customer-facing content and lead effective discovery or feedback conversations.
• Demonstrated ability to coordinate across Customer Success, Renewals, Sales, and other teams, clarify ownership, and move shared retention and growth outcomes forward while managing concurrent programs and changing priorities.
• Experience with Customer Success platforms, CRM systems, marketing automation, business intelligence tools, or related customer-data systems.

Preferred Qualifications

• Experience working in a Customer Success model that partners with a centralized Renewals Desk or specialized renewals team.
• Experience facilitating webinars, office hours, group enablement, customer communities, or other one-to-many programs.
• Experience applying test-and-learn methods to improve engagement, adoption, retention, or conversion outcomes.
• Experience supporting collaboration, productivity, content, or AI-enabled SaaS products.

Durable Skills

• AI fluency means using these tools to amplify human judgment, not replace it.
• We believe people with these skills will thrive as work and technology continue to evolve:
• Awareness: Understand yourself and others.
• Judgment: Evaluate information and make decisions in complex situations.
• Adaptability: Learn, adjust, and stay effective through change.
• Connection: Communicate, collaborate, and build trust.
• To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.

Compensation

Canada Pay Range

$142,400—$192,600 CAD

The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.

Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

Read more about our benefits here.

Company Description

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships.

With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox Customer Experience and Success (CXS) Team shapes how more than 700 million users and 575k teams worldwide interact with our products. We turn insights into actions, bringing empathy and expertise to every touchpoint.

Our team embraces resourcefulness and curiosity, pushing boundaries—and ourselves—to improve the customer experience and ensure our customers achieve their desired outcomes with our products, leading to increased customer lifetime value, retention, and growth. Every team member contributes their unique perspective as we collaborate across the organization to amplify the customer voice.

If you're passionate about bringing joy, humanity, and simplicity to how people interact with Dropbox, join our Customer Experience and Success team.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings.

While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

AI Fluency

AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.

We look for four key behaviors in candidates:

• Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
• Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
• Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team’s.
• Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.

Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. To learn more, see our approach to AI in hiring .

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.

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