Senior Technical Support & Success Manager

Trolley; Toronto; Hybrid; CAD 90,000 - 130,000; Full time

Benefits offered by this job

ESOP Program

Extended healthcare benefits

4 weeks paid vacation + holidays

Remote work: 30 days

Gym membership allowance

Half-day Fridays in summer

MacBook Pro equipment

Job summary

Trolley is seeking a Senior Technical Customer Success Manager to drive exceptional experiences across the customer lifecycle. You’ll blend deep product knowledge with relationship management to support strategic accounts, drive product adoption, and act as a trusted advisor.

Collaborating with Product, Engineering, Sales, and Customer Success teams, you’ll resolve complex technical issues, identify optimization opportunities, and advocate for platform improvements while delivering measurable

Qualifications

• Several years in Customer Success, Tech Support, Solutions Engineering, or similar SaaS roles.
• Experience supporting enterprise B2B software products.
• Proven API, integrations, and technical product issue troubleshooting.
• Ability to manage customer relationships with consultative guidance.
• Strong analytical and problem-solving skills; capable of explaining technical concepts clearly.
• Excellent written and verbal communication with multiple stakeholders.

Responsibilities

• Deliver world-class customer experiences with a customer-first mindset.
• Build trusted relationships and help customers maximize value of Trolley platform.
• Manage a portfolio of accounts with proactive guidance and ongoing support.
• Provide consultative recommendations to improve workflows and business outcomes.
• Resolve complex issues and escalate when needed with Product/Engineering.

Skills

Customer Success

API troubleshooting

Relationship management

Cross-functional collaboration

SaaS expertise

Problem-solving

Tools

Salesforce

Intercom

Jira

Notion

Job description

Senior Technical Support & 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.

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.

Working closely with Product, Engineering, Sales, and Customer Success teams, you'll resolve complex technical issues, identify opportunities to improve customer outcomes, and advocate for enhancements that strengthen our platform.

This is an ideal opportunity for someone who enjoys balancing technical problem-solving with consultative customer engagement and is passionate about helping customers succeed.

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.
• Deliver consultative recommendations that help customers improve workflows and achieve business objectives.
• 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.
• Diagnose technical challenges, identify root causes, and provide timely, effective solutions.
• Collaborate closely with Product and Engineering teams to resolve customer issues efficiently while keeping customers informed throughout the process.
• Develop a deep understanding of Trolley's platform and emerging capabilities to effectively support customers and internal teams.

Customer Success & Adoption

• Monitor customer adoption and platform usage to identify opportunities for increased engagement and long-term success.
• Analyze customer data, trends, and usage metrics to proactively recommend improvements and best practices.
• Help customers optimize their use of Trolley's products through education, onboarding support, and ongoing consultation.
• Identify opportunities to improve customer health, satisfaction, retention, and expansion.

Operational Excellence

• Manage a high volume of customer inquiries while consistently meeting or exceeding established service level agreements (SLAs).
• Prioritize work effectively while maintaining exceptional quality, responsiveness, and attention to detail.
• Ensure customer issues are followed through to resolution, coordinating effectively with internal teams when escalation is required.
• Maintain accurate documentation and contribute to internal knowledge sharing.

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.
• Advocate for customers by partnering with Product and Engineering to prioritize bug fixes, feature requests, and platform improvements.
• Lead discussions around customer experience improvements and contribute to operational excellence initiatives across the organization.
• Share knowledge and mentor team members on technical troubleshooting, customer communication, and best practices.

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.
• Proven ability to manage customer relationships while delivering consultative guidance.
• Strong analytical and problem-solving skills with the ability to diagnose complex technical issues.
• Excellent written and verbal communication skills with the ability to explain technical concepts to both technical and non-technical audiences.
• Exceptional organizational skills with the ability to manage multiple priorities in a fast-paced environment.
• Passion for delivering outstanding customer experiences.

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.
• Experience working with Salesforce, Intercom, Jira, Notion, or similar customer support and collaboration platforms.
• Experience analyzing customer usage metrics and driving product adoption.
• Experience working cross-functionally with Product, Engineering, and Go-to-Market teams.

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.