Strategy & Operations, Customer Success

Big Internet Seller Services Inc; Canada; On-site; CAD 85,000 - 110,000; Full time

Benefits offered by this job

Unlimited PTO

Four weeks vacation

Twelve weeks family leave in the US

Equipment budget

Education budget

Health insurance (US)

Equal employment opportunities

Job summary

Ashby is seeking a Strategy and Operations, Customer Success leader to drive CS strategy, processes, and data-informed insights. Reporting to the Manager of Strategy and Operations, you will shape programs that optimize health, retention, and revenue growth while partnering with CS leadership.

You'll operationalize CS workstreams, analyze key metrics, and design scalable processes. This role blends strategic thinking with hands-on execution in a fast-growth SaaS environment.

Qualifications

• Self-starter with strong curiosity and initiative.
• Experience in fast-growth SaaS environments.
• Ability to distill data into actionable recommendations.
• Experience with CRM reporting and HubSpot.

Responsibilities

• Operationalize CS strategy and scale CS operations.
• Analyze metrics like NRR, GRR, churn, and health score.
• Improve end-to-end customer journey from onboarding to renewal.
• Collaborate with Finance and CS leadership on planning.
• Lead change management and roll-out new processes.

Skills

Self-starter

SaaS literacy

Strategic thinking

Data-driven decision making

Excellent communication

Tools

HubSpot CRM

Job description

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 you:

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:

Recruiter Screen with Talent Acquisition Team - 30 minutes

Virtual Onsite - 90 min

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.