Scaled Customer Success Manager

Canada
Remote
Posted Oct 4, 2026
1 position

$142,400–$192,600 / year

Opens an external site

Employment type: Full-time
Experience level: Mid-level · 4+ years
Posting language: English
Working hours: 40 hours per week

Job summary

You will manage a portfolio of mid-market and small business customers to drive product adoption, ensure renewal readiness, and mitigate churn risk. Additionally, you will design targeted engagement campaigns and serve as a key coordinator between internal teams to facilitate customer growth and retention.

Job details

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

What you’ll do

Requirements

Candidates must have 4+ years of experience in B2B SaaS Customer Success or account management with a proven track record in managing renewals and retention metrics. Strong analytical skills and the ability to coordinate across cross-functional teams are essential for success in this role.