Customer Success Associate – Remote in Toronto, Ontario at Spade Recruiting

We’re more than an insurance organization — we’re a team built around purpose, service, and opportunity. For over 60 years, we’ve supported working families across North America by helping them access benefit programs designed to protect what matters most.

We believe strong careers are built through the right combination of training, mentorship, integrity, and personal growth. That’s why our environment is focused on helping people develop professionally while creating flexibility, balance, and long-term opportunity.

Through our partnerships with unions and associations across the U.S. and Canada, we’re able to serve families who have already requested information about their benefits. Every client conversation gives us the chance to provide clarity, support, and peace of mind to the people who keep our communities moving.

This role is more than just a position — it’s an opportunity to become a trusted resource for the families we serve. As a representative, you’ll connect with clients who have shown interest in learning more about their available benefits. Your job is to answer questions, explain options clearly, and help each family make confident decisions about their coverage.

This is not about pressure-based sales or aggressive scripts. It’s about listening, educating, and guiding people through an important process with professionalism and care. Along the way, you’ll build valuable communication, leadership, and client service skills that can support long-term career growth.

Build strong relationships with clients through clear communication and consistent follow-up

Explain benefit options in a simple, professional, and easy-to-understand way

Help families review their needs and make informed decisions about coverage

Provide support throughout the process with patience, empathy, and professionalism

Work with leadership and team members to improve the overall client experience

Participate in hands-on training, mentorship, and ongoing professional development

Strong communication and relationship-building skills

A people-focused attitude and genuine interest in helping others

Self-motivation, discipline, and accountability in a remote work setting

Good organization, follow-through, and time management

Positive mindset with a willingness to learn and grow

Customer service, sales, or insurance experience is helpful but not required

Must be legally authorized to work in the U.S. or Canada

Remote-first work environment with flexibility

Weekly pay plus monthly performance-based bonuses

Personalized training and mentorship from experienced leaders

Clear advancement opportunities through a leadership development track

Supportive team culture focused on growth, integrity, and collaboration

The opportunity to make a meaningful impact while building a long-term career