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Strategy & Operations, Customer Success

Job in Winnipeg, Manitoba, Canada
Listing for: Ashby
Full Time position
Listed on 2026-11-05
Job specializations:
  • Business
    Customer Success Management, CRM Systems & Management
  • Customer Service/HelpDesk
    Customer Success Management, CRM Systems & Management
Salary/Wage Range or Industry Benchmark: 168500 CAD Yearly CAD 168500.00 YEAR
Job Description & How to Apply Below
Role Overview
In this Strategy and Operations, Customer Success role, you will drive the strategy, processes, and data-driven insights that empower our Customer Success Team to deliver exceptional outcomes for our customers. Reporting to the Manager of Strategy and Operations, and partnering closely with Customer Success leadership, you will define strategies and execute improvements that optimize customer health, retention, and revenue growth.

Role Overview
In this Strategy and Operations, Customer Success role, you will drive the strategy, processes, and data-driven insights that empower our Customer Success Team to deliver exceptional outcomes for our customers. Reporting to the Manager of Strategy and Operations, and partnering closely with Customer Success leadership, you will define strategies and execute improvements that optimize customer health, retention, and revenue growth.

Our Customer Success team is consistently praised by our customers for their deep expertise, responsiveness, and dedication—a testament to how much we Care Deeply About Customers, one of our core Operating Principles. As we continue to scale, it’s critical that we preserve and enhance this high standard of customer care while ensuring our processes, tools, and insights evolve to support sustainable growth.

You will play a crucial role in our operations, including process improvements, planning, and reporting. This is both a strategic and tactical role in which you’ll design frameworks and programs, uncover actionable insights, and create data-informed recommendations across our Customer Success functions.

What You'll Do At Ashby

Operationalize CS Strategy:
Develop and refine processes, tools, and workflows to scale Customer Success operations. This includes customer segmentation, onboarding workflows, lifecycle mapping, and playbook development.

Analyze Business Dynamics:
Partner with internal stakeholders on reporting & analysis of metrics such as NRR, GRR, churn, product adoption, health score, and customer sentiment. Use these insights to provide early warnings and refine CS strategies.

Optimizate the Customer Journey:
Enhance the end-to-end customer journey, ensuring smooth transitions across all post-sales touch points from onboarding through support and renewal.

Support Strategic Planning:
Collaborate with Finance and CS leadership on planning cycles, including headcount planning, capacity modeling, and quota setting. Provide relevant historical data for informed decision making.

Drive Process Improvements:
Identify inefficiencies and implement improvements to CS workflows, customer onboarding, account transitions, and renewal processes. Implement & deploy KPIs to measure performance against strategic initiatives.

Optimize CS Systems:
Define the business requirements to improve Customer Success efficiency, efficacy, and scalability. Partner with Rev Ops teammates to implement changes to tools (CRM, health scoring platforms, etc)

Collaborate Cross-functionally:
Ensure alignment with Sales, Product, and other teams to align resources with customer needs and forecasted growth.

Support Change Management:
Lead the roll-out and adoption of new processes or workflows to the CS team. Partner with Enablement on larger scale change programs.

You Could Be a Great Fit If

Are a self-starter, innately curious in your approach

Bring both SaaS & financial literacy, offering an informed perspective on CS benchmarks (e.g.ideal book sizes)

Have a strategic mindset, with the ability to distill data into actionable recommendations

Are detail-oriented and committed to data accuracy and process quality

Have experience in fast-growth SaaS environments, ideally in a Customer Success or Revenue Operations role

Are skilled in CRM…
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