Job Postings
Customer Success Specialist/Manager (Onboarding & Retention)
remote
Toronto, Ontario, Canada .
full-time . April 9, 2026
Toronto, Ontario, Canada .
full-time . April 9, 2026
Description
About eState Planner
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 Specialist/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
👉 KPI: Early churn/activation
Retention & relationship management
- Build and maintain strong relationships with customers
- Regularly engage customers to ensure they are getting value from the product
- Identify risks early and take action to prevent churn
- Spot opportunities for expansion and upsells where relevant
👉 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
Compensation & Benefits
- Base salary: $50,000 – $65,000 CAD
- Optional performance bonus tied to retention and customer success metrics
- Fully remote role with flexibility
Why join us
- Play a key role in shaping the customer experience and retention strategy
- Work closely with Sales, Marketing, and Product
- Be part of a growing company with real impact on customers
- 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.
Compensation
$50,000.00 - $65,000.00 per year