Enterprise Customer Success Manager

Location:

Hybrid (Montréal, QC | Toronto, ON | Halifax, NS)

Reports to:

Head of Customer Support & Success

About Us Trolley is the payouts platform for the internet economy. Our mission is to unlock the global economic opportunity of the internet by building a truly borderless payouts ecosystem. Through our platform and API, Trolley enables businesses to pay people anywhere in the world, supporting creators, on‑demand workers, and suppliers at scale. Companies rely on Trolley as mission‑critical infrastructure to automate payouts, collect tax and banking information, and reduce fraud and risk, all in one place. Today, Trolley is the trusted payouts solution for hundreds of businesses, including Canva, SoundCloud, and Envato. We've processed millions of payments globally, helping creators, artists, and suppliers get paid quickly, securely, and with confidence. As we continue to grow, we're looking for a customer‑focused technical expert who is passionate about building strong client relationships, solving complex challenges, and helping customers realize the full value of the Trolley platform. This role can be based in

Montréal, Toronto, or Halifax , working in a hybrid environment alongside our collaborative and globally distributed team.

What You'll Do

Own and manage a portfolio of high‑value and complex customers and act as their strategic business partner.

Deliver a world‑class customer experience to your customers and evangelize the benefits and value of our solutions.

Develop and maintain strong relationships with customers, becoming a trusted advisor and advocate for their success.

Become a solution expert to instate a high level of customer confidence in you and our Trolley solutions.

Gain a deep understanding of our customers’ operational workflows and use cases to provide more tailored and impactful client guidance.

Gain deep industry knowledge in end‑to‑end payment automation, tax regulations, and the unique challenges facing our key market segments to earn the right to become a trusted advisor.

Grow your customers' depth of understanding by providing enablement sessions on new and existing features and capabilities, and translate complex concepts into easy to understand solutions that align with your customers’ business workflows and goals.

Provide a strong functional consultative approach to customer management with a passion for identifying solutions to meet customers' business goals (understanding how complex solutions work in practice).

Drive engagement across multiple customer stakeholders by understanding their unique goals/business outcomes, supporting their internal change management process during implementation/onboarding, and continually monitoring KPIs and changing business needs through quarterly business reviews.

Build and maintain influential relationships with customers with highly complex use cases, from end users to executive sponsors, to ensure they achieve their business goals and have a best‑in‑class experience.

Actively monitor adoption, analyze data/metrics/industry trends, and implement strategies that showcase how customers can enhance their workflows and use our product to derive value.

Collaborate with support, product and other internal stakeholders to help resolve customer issues and ensure timely resolution.

Advocate for customers' needs (product features, bug fixes and potential improvements), working cross‑functionally with internal teams to champion projects and product enhancements.

Effectively engage multiple customer stakeholders in discussing organizational goals, uncovering additional business problems/opportunities, and exploring potential up/cross‑sell solutions.

Driving strategic growth for both Trolley and the customers.

Proactively identify and close up/cross‑sell opportunities by thoroughly understanding client needs and aligning additional products with those needs; contributing to revenue growth while ensuring clients achieve their desired outcomes.

What We're Looking For

10+ years of progressive and consultative experience in customer‑facing account management roles.

5+ years of experience in Customer Success in B2B SaaS/Software managing large mid‑market accounts.

The highest degree of initiative, courtesy, and professionalism to build valuable customer relationships that you will leverage to generate a positive feel in the market and contribute significantly to revenue and company growth.

Bonus points for having experience in financial services, SaaS payment automation, and the internet economy/music royalties.

The ability to learn and pivot quickly in a fast‑paced, often ambiguous environment.

Experience managing multiple stakeholders, departments, and implementation cycles.

A high