At a Glance
- Tasks: Deliver exceptional customer experiences and solve complex technical challenges.
- Company: Join Trolley, a leading payouts platform for the internet economy.
- Benefits: Competitive salary, equity program, extended healthcare, and generous vacation time.
- Other info: Work in a hybrid environment with a diverse team and excellent growth opportunities.
- Why this job: Make a real impact by helping customers maximize their use of innovative technology.
- Qualifications: Experience in customer success or technical support with strong problem-solving skills.
The predicted salary is between 82800 - 101200 $ per year.
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.
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.
The Opportunity
As a Senior Technical Customer Success Manager, you will play a critical role in delivering an exceptional customer experience throughout the customer lifecycle. You will combine deep technical product knowledge with strong relationship management skills to support customers, drive product adoption, and act as a trusted advisor for some of our most strategic accounts.
What You’ll Do
- Deliver Exceptional Customer Experiences
- Deliver world-class customer experiences with professionalism, empathy, and a customer-first mindset.
- Build trusted relationships with customers by understanding their business goals and helping them maximize the value of Trolley’s platform.
- Manage a portfolio of assigned customer accounts, providing proactive guidance, personalized support, and ongoing account management.
- Handle challenging customer conversations with confidence, influencing positive outcomes while maintaining strong relationships.
- Technical Product Expertise
- Serve as a subject matter expert across Trolley’s products, including Pay, Tax, Trust, and Sync.
- Troubleshoot complex product, integration, and API-related issues, acting as a Level 2 technical resource before escalating to Product or Engineering.
- Collaborate closely with Product and Engineering teams to resolve customer issues efficiently while keeping customers informed throughout the process.
- Customer Success & Adoption
- Monitor customer adoption and platform usage to identify opportunities for increased engagement and long‑term success.
- Help customers optimize their use of Trolley’s products through education, onboarding support, and ongoing consultation.
- Operational Excellence
- Manage a high volume of customer inquiries while consistently meeting or exceeding established service level agreements (SLAs).
- Ensure customer issues are followed through to resolution, coordinating effectively with internal teams when escalation is required.
- Drive Continuous Improvement
- Identify recurring customer issues and emerging trends to improve processes, documentation, and service delivery.
- Gather and synthesize customer feedback to influence product enhancements and service improvements.
What We’re Looking For
- Required Experience
- Several years of experience in Customer Success, Technical Support, Solutions Engineering, or a similar customer-facing SaaS role.
- Strong experience supporting enterprise B2B software products.
- Demonstrated experience troubleshooting APIs, integrations, and technical product issues.
- Excellent written and verbal communication skills with the ability to explain technical concepts to both technical and non-technical audiences.
- Preferred Experience
- Experience within fintech, payments, or financial technology.
- Familiarity with REST APIs, JSON, webhooks, API testing tools (such as Postman), and technical troubleshooting methodologies.
What We Offer
- Join an amazing team of diverse people working together on a common mission.
- Competitive salary.
- ESOP Program: Meaningful equity and ownership that aligns your success with ours.
- Extended healthcare benefits from Day 1.
- 4 weeks paid vacation per year + public holidays (+ 1 extra vacation day per year of service).
- 30 days remote work from anywhere.
- Gym membership allowance.
- 1/2 day Fridays off during summer.
- Company‑provided use of Apple MacBook Pro and Mac gear.
Senior Technical Support & Success Manager in Halifax employer: Trolley
Trolley is an exceptional employer that fosters a culture of innovation and collaboration, making it an ideal place for an Executive Product Leader to thrive. With a strong focus on employee growth and development, Trolley offers unique opportunities to shape the future of fintech while working in vibrant cities like Toronto or Montréal. The hybrid work model promotes flexibility, ensuring a healthy work-life balance while driving impactful product strategies in a supportive environment.
