Head of Customer Success

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Customer Success based in Canada.

This is a senior leadership opportunity to shape and scale the customer experience within a fast-growing B2B SaaS environment focused on software security and developer tools. As Head of Customer Success, you will lead Technical Account Management and Customer Success functions, building strong teams and scalable programs that help customers achieve lasting value. You will oversee the entire customer journey, from technical evaluation and onboarding through adoption, retention, and expansion. Working closely with Sales, Product, Engineering, and Support, you will turn customer insights into better experiences and measurable business outcomes. You will also establish the operating models, performance metrics, and leadership structures needed to support continued growth. This remote-first role offers the opportunity to influence customer strategy and build a high-performing global organization.

Accountabilities:

Build, lead, and develop high-performing teams across Technical Account Management and Customer Success, including hiring, coaching, and developing functional leaders.

• Establish clear team responsibilities, accountability structures, and a culture of continuous improvement.

• Design and oversee a seamless customer journey covering technical evaluation, onboarding, product adoption, and ongoing engagement.

• Develop scalable customer success programs that accelerate time-to-value, increase product engagement, and improve customer retention.

• Partner with Sales to identify customer risks, strengthen renewal strategies, and uncover opportunities for account growth and expansion.

• Collaborate with Product, Engineering, and Support teams to communicate customer needs and translate feedback into product and service improvements.

• Define and implement scalable processes, performance metrics, and operating rhythms to support organizational growth.

• Monitor customer health, adoption, retention, and team performance data to guide strategic decisions and strengthen accountability.

• Continuously improve the customer experience while supporting long-term customer relationships and business growth.

Requirements:

• At least 12 years of experience in Customer Success, Account Management, or related customer-facing functions, including at least five years in senior leadership roles.

• Proven experience building and scaling technical, customer-facing organizations within a B2B SaaS environment.

• Demonstrated success developing strong leaders, building high-performing teams, and fostering a culture of ownership and accountability.

• Track record of improving customer adoption, retention, and measurable business outcomes.

• Strong commercial judgment and experience partnering with Sales teams on renewals, customer risk management, and expansion opportunities.

• Data-driven approach to evaluating customer health, measuring organizational performance, and making strategic decisions.

• Excellent executive presence, sound judgment, and the ability to influence senior stakeholders and manage competing priorities across functions.

• Strong cross-functional leadership and communication skills, with the ability to operate effectively in a distributed environment.

• Nice to have: Experience in developer tools, application security, software supply-chain security, or DevSecOps.

• Nice to have: Experience leading multiple customer-facing functions across pre-sales and post-sales.

• Nice to have: Experience managing distributed teams across different customer segments or geographic regions.

Benefits:

• Estimated on-target earnings: USD $300,000–$350,000, with compensation adjusted for candidates outside the United States according to local market salary data.

• Meaningful equity opportunities.

• Comprehensive health benefits for employees and their families, with 99% coverage.

• Flexible paid time off and holidays.

• Winter shutdown to support rest and recharging.

• Paid parental leave.

• Remote-first work environment.

• Quarterly team off-sites.

• Opportunity to build and lead a growing customer-facing organization in an innovative technology environment.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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