Director, Customer Success

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead, mentor, and enhance the capabilities of the Customer Success, Implementation, and Customer Success Operations teams.

• Set performance benchmarks, operational rhythms, and accountability measures to encourage adoption, value realization, executive involvement, retention, and readiness for renewal.

• Recognize customer risks proactively and facilitate actionable recovery strategies.

• Serve as an executive sponsor for strategic, complex, and at-risk customer relationships.

• Supervise the implementation process for new customers, ensuring quality at launch, timely value delivery, training, and smooth transition to Customer Success.

• Collaborate with Customer Success Operations to enhance enablement, reporting, portfolio insights, data integrity, workflows, and the Customer Success knowledge base.

• Leverage customer and operational data to spot trends, prioritize actions, and provide recommendations to executive leadership.

• Streamline processes, automate repetitive tasks, and free up capacity for strategic customer engagement.

• Set expectations for AI utilization within Customer Success to enhance preparation, analysis, communication, and workflow efficiency.

• Collaborate with Account Management, Support, Sales, Product, Engineering, Finance, and Operations.

• Advocate for the customer perspective in company strategic planning and product prioritization discussions.

• Foster a high-performance culture rooted in ownership, sound judgment, transparency, and continuous improvement.

⛳️ Requirements

• Over 8 years of experience in Customer Success, customer operations, implementation, account leadership, or a related SaaS discipline.

• More than 4 years of experience in people leadership.

• Proven track record of enhancing customer retention, adoption, health, and team performance.

• Experience guiding teams through organizational growth, operational transformations, or evolving processes.

• Capability to prioritize, simplify tasks, and enhance outcomes in a resource-conscious environment.

• Experience in establishing Customer Success operational rhythms, performance metrics, and scalable procedures.

• Strategic account management and executive-level customer engagement experience.

• Experience in leading or closely collaborating with Implementation and Customer Success Operations.

• Ability to convert reporting and customer data into actionable insights.

• Cross-functional leadership experience involving Sales, Account Management, Product, Engineering, Support, and Finance.

• Practical experience utilizing AI and automation to boost productivity, team effectiveness, or customer workflows.

• Exceptional executive communication skills, analytical thinking, judgment, and follow-through.

• Familiarity with Gainsight, Salesforce, HubSpot, or a similar Customer Success or CRM platform; Gainsight experience is a bonus.

🏝️ Benefits

• Remote work and flexible working hours.

• Mentorship and professional development opportunities.

• Comprehensive medical and dental benefits.

• Healthcare spending account.

• $3,000 annual Health and Wellness Spending Account.

• Employee Assistance Program (EAP).

• Flexible (Unlimited) Time Off.