Strategy & Operations, Customer Success

Ashby; Canada; On-site; CAD 236,000 - 310,000; Full time

Benefits offered by this job

Stock options (10-year window)

Unlimited PTO

Family leave (12 weeks)

Equipment budget

Education budget

Health insurance for US-based staff

Job summary

Ashby, Inc. is seeking a Strategy and Operations leader for Customer Success to shape the strategy, processes, and data-driven insights that drive customer health, retention, and revenue growth.

Reporting to the Manager of Strategy and Operations and partnering with CS leadership, you will design frameworks, run planning cycles, and implement KPIs across onboarding, lifecycle, renewal, and cross-functional collaboration.

Qualifications

• Experience in fast-growth SaaS environments, ideally in a Customer Success or Revenue Operations role.
• Skilled in CRM reporting, with preference for HubSpot experience.
• Strategic mindset with ability to distill data into actionable recommendations.
• Detail-oriented and committed to data accuracy and process quality.
• Willing to manage both high-level strategy and hands-on execution.

Responsibilities

• Operationalize CS Strategy: Develop and refine processes, tools, and workflows to scale CS operations.
• Analyze Business Dynamics: Partner on reporting & analysis of metrics like NRR, GRR, churn, health, and sentiment.
• Optimize Customer Journey: Enhance end-to-end customer journey across onboarding, support, and renewal.
• Support Strategic Planning: Collaborate on headcount planning, capacity modeling, and quota setting.
• Drive Process Improvements: Identify inefficiencies and deploy KPIs to measure performance.
• Optimize CS Systems: Define requirements to improve CS efficiency and work with RevOps on tool changes.
• Collaborate Cross-functionally: Align with Sales, Product, and other teams for growth forecasting.
• Support Change Management: Lead rollout of new processes and enablement programs.

Skills

Self-starter

Data-driven

Strategic mindset

Excellent communicator

Tools

HubSpot

CRM systems

Job description

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 RevOps 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 reporting, with preference for HubSpot experience
• Work autonomously, managing multiple tasks and deadlines effectively
• Are an excellent communicator, both verbally and in writing

This Role May Not Be a Fit If

• You're unwilling to manage both high-level strategy and hands-on execution
• You're uncomfortable with ambiguity and prefer structured, predefined assignments
• You prefer focused work on a single project at a time
• You prefer working within a single team rather than across multiple teams

Interview Process

Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows:

Role

• Recruiter Screen with Talent Acquisition Team - 30 minutes
• Hiring Manager Interview - 45 minutes
• Challenge Interview - 45 minutes
• Virtual Onsite - 90 min

Benefits

• 10-year exercise window for stock options. You shouldn't feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.
• Unlimited PTO with four weeks recommended per year. Expect "Vacation?" in our one-on-one agenda until you start taking it.
• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.
• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!
• $100/month education budget with more expensive items (like conferences) covered with manager approval.
• If you're in the US, top-notch health insurance for you and your dependents, with all premiums covered by us.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

Compensation Range: $168,500 - $221,875