eState Planner is on a mission to improve estate planning for Canadians by empowering professionals with modern, intuitive tools.

Our platform helps legal and financial professionals deliver a more client-focused experience while improving efficiency and accuracy. Built with deep domain expertise, eState Planner combines intelligent, rule-based technology with a user-friendly interface to support the drafting of both simple and complex estate plans.

About the role We’re looking for a

Customer Success Manager

to ensure our customers are set up for long-term success with eState Planner.

This role is focused on

onboarding, retention, and customer relationships . You’ll work closely with Sales and Marketing to deliver a seamless customer journey, from initial conversion through ongoing engagement.

You’ll play a key role in helping our customers get the most value from our product, while also acting as a voice of the customer to inform our product and go-to-market strategy.

What you’ll do: Customer onboarding & activation

Own the onboarding experience for new customers after they convert from trial

Ensure smooth handoff from Sales to Customer Success

Guide customers through setup and early usage to set them up for success

Proactively identify and address risks during the early lifecycle

Retention & relationship management

Build and maintain robust relationships with customers

Regularly engage customers to ensure they are getting value from the product

Identify risks early and take action to prevent churn

Analyze data to spot churn signals and opportunities

KPIs: Churn rate, churned revenue,



customer engagement Customer advocacy & insights

Act as the voice of the customer internally

Gather feedback, insights, and product requests from customers

Share learnings with Product, Sales, and Marketing to inform roadmap and messaging

Help identify trends across customer segments

Billing & account health

Ensure customer accounts remain in good standing

Monitor and follow up on failed payments

Work with customers to resolve billing issues promptly

Cross-functional collaboration

Collaborate with Sales to ensure smooth transitions and aligned expectations

Partner with Marketing to share customer insights and success stories

Contribute to improving onboarding and customer experience processes

What we’re looking for

2–3 years of experience in Customer Success , or

2+ years in Account Management or a similar customer-facing role

Strong interpersonal and communication skills

Comfortable building relationships and working directly with customers

Organized and proactive, with strong follow-up habits

Ability to identify problems and take initiative to solve them

Experience in SaaS is a plus

Experience in legaltech or a background in the legal industry is a strong plus

Play a key role in shaping the customer experience and retention strategy

Work closely with Sales, Marketing, and Product

High ownership and autonomy in your role

Our commitment eState Planner is an equal opportunity employer. We believe diverse teams build better companies and are committed to creating an inclusive environment for all.

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📌 Customer Success Manager (Winnipeg)
🏢 eState Planner
📍 Winnipeg