Head of Customer Success

Canada
Remote
Posted Nov 5, 2026
1 position

US$300,000–US$350,000 / year

Opens an external site

Employment type: Full-time
Experience level: Lead · 12+ years
Posting language: English
Working hours: 40 hours per week

Job summary

Lead Customer Success and Technical Account Management strategy, teams, and operating structures, overseeing the customer journey from technical evaluation and onboarding through adoption and ongoing engagement. Partner with Sales, Product, Engineering, and Support to improve customer outcomes, renewals, retention, and expansion while establishing scalable processes and performance metrics.

Job details

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. As Head of Customer Success, you will shape and lead the teams responsible for helping customers successfully evaluate, adopt, and maximize the value of a technical SaaS platform. You will oversee Technical Account Management and Customer Success, building strong leadership capabilities and scalable operating structures. Your mission will be to create a seamless customer journey, strengthen long-term relationships, and drive measurable improvements in adoption and retention. Working closely with Sales, Product, Engineering, and Support, you will turn customer insights into business growth and product improvements. You will also establish the processes, performance metrics, and organizational culture needed to support continued expansion. This is a senior leadership opportunity within a remote-first, fast-growing technology environment. \n Accountabilities You will lead the overall Customer Success strategy, develop high-performing teams, and ensure customers receive consistent value throughout their relationship with the organization. Recruit, coach, and develop leaders across Technical Account Management and Customer Success. Establish clear responsibilities, accountability structures, and a culture of continuous improvement. Design and oversee a connected customer journey, from technical evaluation and onboarding through adoption and ongoing engagement. Develop scalable 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 expansion. Collaborate with Product, Engineering, and Support to communicate customer feedback and drive meaningful product improvements. Establish 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 maintain accountability. Requirements: The ideal candidate is an experienced customer success executive with a strong background in scaling technical, customer-facing organizations in B2B SaaS. You should combine strategic leadership, commercial judgment, and a data-driven approach with the ability to build strong teams and influence stakeholders across functions. 12+ years of experience in Customer Success, Account Management, or related customer-facing roles. At least 5 years of experience in senior leadership positions. Proven experience building and scaling technical customer-facing organizations within B2B SaaS. Demonstrated ability to develop effective leaders, build high-performing teams, and foster 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 on renewals, customer risks, and expansion opportunities. Data-driven approach to customer health analysis, performance measurement, and strategic decision-making. Strong executive presence, sound judgment, and the ability to influence stakeholders and manage competing priorities across functions. Nice to have: Experience in developer tools, application security, software supply-chain security, or DevSecOps. Experience leading multiple customer-facing functions, including pre-sales and post-sales teams. Experience managing distributed teams across different customer segments or geographic regions. Benefits: Estimated on-target earnings of $300,000–$350,000 USD, with compensation adjusted according to local market data for candidates outside the United States. Meaningful equity program. Comprehensive health benefits for employees and their families, with 99% coverage. Flexible paid time off, company holidays, and a winter shutdown. Paid parental leave. Remote-first working environment. Quarterly team off-sites. \n 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. #LI-CL1

What you’ll do

Requirements

Requires 12+ years in Customer Success, Account Management, or related customer-facing roles, including at least five years in senior leadership, with a record of scaling technical customer-facing organizations in B2B SaaS. Candidates should demonstrate strong team development, customer adoption and retention results, commercial judgment, data-driven decision-making, and the ability to influence cross-functional stakeholders.