Head of Customer Success

CanadaRemoteFull-timeexecutive

OperationsManagement

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Quick Summary

Requirements Summary

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,

Technical Tools

OperationsManagement

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.

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

~1 min read

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

~1 min read

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.

What We Offer

~1 min read

✓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.

Location & Eligibility

Where is the job

Canada

Remote within one country

Who can apply

About this job

Pay per year: $300,000–$350,000 a year; 160% above the $124,925 median for Management jobs on Jobera (1,127 salaries).
Who can apply: Canada
Posted: Today
Employer: has 6,376 open jobs on Jobera in 42 countries.