Success Jobs in Whitby, ON (NOW HIRING)

We are currently seeking a Manager, Scaled Success to join our Customer Success team to lead the build and implementation of Clio's next-generation Scaled Success. The Scaled Success team is responsible for driving retention, adoption, and growth outcomes across our varied customer segments. The team delivers proactive, timely intervention to support customers in realizing value from Clio's platform.

The legal profession is being redefined by AI, and Clio is leading that shift. Our mission to transform the legal experience for all now depends on more than giving firms powerful software. It means helping them put AI to work, grounded in their own matters and the law, to win the right business, do their best legal work, and run more efficient firms. Clio's platform spans a wide range of products and packages whose full value takes time and guidance to unlock, so Scaled Success uses data, automation, and AI to engage thousands of firms with the right message at the right moment, coaching them to evolve their operations and workflows to transform in how they work.

This team plays a central role in reimagining what Customer Success looks like at scale. We support the 1:1 component of the Scaled Success journey. We identify signals of risk or opportunity across large customer cohorts and act on them systematically. We also serve as an innovation center for the broader Customer Success organization, piloting new scaled engagement models before they're rolled out more broadly.

We are a dedicated team who enjoy what we do and are serious about making a positive impact on our customers' businesses, at scale.

As the Manager of Scaled Success, you will lead a growing team responsible for the retention, growth, and adoption of Clio's suite of products across our largest customer segments by volume. You'll play a critical role in building the future of Customer Success at Clio by designing and scaling data-driven engagement models.

You are a strategic, tech-forward leader with experience managing individual contributors in high-velocity SaaS environments, with a background rooted in customer success and focused on expansion. You thrive at the intersection of process excellence, automation, and people leadership, bringing a data-driven approach to segmentation, scoring, and lifecycle engagement design. An innovator at heart, you possess a healthy obsession for the customer experience, having designed AI-first, one-to-many Customer Success workflows from the ground up. You leverage cohort trends, funnel analytics, and behavioral triggers to drive strategic decisions, actively coaching your team toward an AI-driven mindset that unlocks new efficiencies in reach and impact. Beyond the metrics, you are a dedicated mentor who uses situational leadership to develop talent. Whether refining a digital engagement journey or troubleshooting a systemic adoption gap, you bring the analytical rigor and grit required to excel in a dynamic, fast-paced environment.

You will report to the Director of Account Management and serve as a key cross-functional partner on customer initiatives and operational improvements, driving progress against the department's key priorities in Scaled Success and Payments.

• Champion Deep Practice Area & Industry Knowledge: Maintain a strong command of the legal industry's evolving landscape (practice area workflows, firm economics, and the operational realities of running a modern legal practice) to ensure the team's engagement strategies are grounded in genuine legal industry expertise that speak credibly to the specific workflows and pain points of each segment.

• Architect Engagement Strategies, Plays & Campaigns: Design and continuously refine a portfolio of engagement strategies, playbooks, campaigns, and talk tracks that guide customers toward value realization across Clio's ecosystem, tailored by segment, lifecycle stage, and practice area.

• Guide Team and Customers Through the AI Transformation of Legal Work: Help how Scaled Success helps the legal industry thrive in the AI age. Position the Scaled Success team as a strategic consultant helping firms rethink how they operate, navigate change management and design AI first workflows.

• Build Trust and Confidence in AI: Help firms build confidence in accuracy, confidentiality, and professional responsibility by demonstrating how Clio's AI is grounded in their own matters and the authoritative law. Position the team as a credible, honest guide that turns skepticism into confidence and strengthens the legal industry's trust in AI.

• Architect Scaled Workstreams: Partner cross-functionally to refine current Scaled Success processes and build new internal frameworks to support the launch of upcoming programs, pilots, and self-serve or one-to-many initiatives.

• Institutionalize a Data-Driven Operating Model: Continuously assess engagement effectiveness, customer outcomes, and operational efficiency, leveraging cohort-level insights to evolve service strategy and optimize resource deployment.

• Optimize Team Process to : Lead and enable the adoption of modern customer engagement platforms and CRM tools (e.g., Salesforce, ChurnZero, Gong, Salesloft, Claude) to track behavior at scale, trigger interventions, and automate reporting.

• Cross-Functional Collaboration: Work closely with Scaled Customer Programs, Product, Marketing, Customer Education, CSOps, S&A, CS Leadership to improve reporting, account assignments, in-app guidance, reduce time to value, and expand the reach of automated touchpoints.

• Build AI-First Workflows with Strategic Intent: Design, deploy, and govern AI-driven solutions, from automated health scoring to intelligent triage, that create measurable impact on reach, efficiency, and customer outcomes and expansion revenue across large cohorts. You build with a strategy, instrument for results, and iterate based on evidence.

• Oversee Escalations: Provide leadership guidance for customers escalated out of Scaled Success and Payments channels, ensuring the right cases are triaged to the right level of support, and that systemic issues are identified and resolved at the root.

• Develop Retention Strategies at Scale: Create and implement proactive strategies to drive high levels of adoption, satisfaction, and retention across large customer populations.

• Identify Upsell/Cross-sell Opportunities at Scale: Train the team to identify and surface expansion signals across the customer engagements. Partner with Customer Sales Leadership to increase lead generation as outcome of customer engagements.

• Forecasting and Reporting: Own the team's pipeline funnel forecast and core scaled-success and Payments metrics (reach, engagement rate, activation rate, retention, efficiency). Report on team and program performance to senior leadership.

• Optimize the Growth Funnel: Collaborate with cross-functional partners to expand lead generation from the the team

• Foster a Positive Team Culture: Cultivate a collaborative, results-oriented, and customer-centric team environment. Set clear Quarterly roadmap for the team identifying direct impact of their work to key business and customer outcomes.

• Recruit, Hire, and Onboard: Identify, recruit, and train new team members, ensuring they are equipped with the product knowledge and analytical skills to succeed in a scaled, data-driven environment.

• Coaching and Mentoring: Act as a coach and mentor to the team, providing personalized feedback based on call reviews and customer funnel oversight/review. Set short and long term growth goals to help grow your team to the next level of their careers.

• Performance Management: Set clear goals and KPIs for the team. Build, manage, and iterate performance management frameworks. Conduct performance reviews, provide proactive/constructive feedback, and manage performance improvement plans as needed.

• Proactively Address and Action Team Survey Responses: Secure learning corners, guest speakers, and Q&As to drive clarity and confidence in any areas that flag.

• Own and Manage Program Reviews & Feedback Cycles: Manage the review of campaign and playbook performance to ensure continued growth and refinement of scaled programs.

• 3+ years of management experience leading individual contributors

• Proven track record in a dynamic, fast-moving SaaS startup environment

• Experience scaling teams and programs at velocity. Scaling reach, tools, and workflows while maintaining and building culture

• Experience building and deploying cutting-edge Customer Success AI workflows and applications, particularly at a one-to-many scale

• Experience with Salesforce or other SaaS/CS tools, including CRMs and lifecycle engagement platforms

• Experience managing a team that contributes to lead generation and revenue. Sales fundamentals influence your coaching strategies

• A passion for people management. Developing and enabling a team-oriented culture through individualized and situational leadership

• A healthy obsession for customers, and an incessant drive to innovate

• Excitement and motivation to solve complex, high-volume business problems through automation and data

• Experience in owning customer escalations and outcomes

• Data/target-driven management and strategy

• Experience working with Customer Success tools such as ChurnZero, SFDC, Salesloft, Gong, or similar

• Experience in FinTech or Account Management is an asset

• Bachelor's degree or equivalent experience