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Added 1 hour ago
Toronto Showroom - Expression of Interest
CullenUS
Toronto, ON
A supportive, collaborative team and clear paths to grow from Client Advisor into senior and leadership roles in a global business
Added 3 hours ago
A
Everyday Banking Advisor - Spirit River
ATB
Spirit River, AB · Rycroft, AB
- Full-time
Be a Trusted Advisor: Provide personalized advice on personal banking products, services, and solutions. You'll match clients with the right products and escalate complex needs to senior…
Added 4 hours ago
A
Regional Service Agent
Allstate
Thunder Bay, ON
- Full-time
The Customer Service Senior Associate handles basic to complex telephone/email/chat/fax inquiries from internal and external customers in an efficient, professional, and accurate manner.…
Added 4 hours ago
Senior Lending Advisor - Cochrane, AB
Scotiabank
Cochrane, AB
As a Senior Lending Advisor, you’ll help clients achieve their homeownership goals by delivering expert mortgage advice, strengthening relationships, and driving lending growth.
Added 5 hours ago
EC
Health and Safety Advisor - Atlantic Canada
EnGlobe Corp.
Dartmouth, NS
- Full-time
…accountability, and continuous improvement. As a Health & Safety Advisor, you will play a key role in supporting our commitment to providing a safe and healthy workplace for our employees,…
Added 5 hours ago
K
Senior Consultant, Financial Services-Insurance & Wealth & Asset Management
KPMG
ON · Toronto, Ontario
- Full-time
…distribution and advice effectiveness, operational improvement, customer and advisor experience, cost optimization, business architecture, AI use case development, and transformation…
Added 6 hours ago
IW
Senior Manager, Living Plan Portal - Canada
IG Wealth Management
MB · Manitoba, Canada
- Full-time
We are looking for a Living Plan Portal specialist (Senior Manager) to join our Advanced Financial Planning team. We are open to considering candidates located in all provinces. Although…
Added 6 hours ago
IW
Senior Manager, Living Plan Portal - Canada
IG Wealth Management
ON · Ontario, Canada
- Full-time
We are looking for a Living Plan Portal specialist (Senior Manager) to join our Advanced Financial Planning team. We are open to considering candidates located in all provinces. Although…
Added 6 hours ago
B
Director of Finance
BackStretch
Vancouver, BC
- Full-time
Serve as a trusted financial advisor to the CEO, executive leadership team, and other senior stakeholders.
Added 6 hours ago
MU
Associate Director, Digital Infrastructure Strategy
McMaster University
Hamilton, ON
- Full-time
Our University Technology Services team mission is to provide exceptional customer service and a high level of support to the McMaster community. Critical to the success of this role we…
Added 7 hours ago
EF
Senior Financial Advisor (Chilliwack City Branch)
Envision Financial
Chilliwack, BC
- $56,800 to $72,800 USD / year
- Full-time
The Senior Financial Advisor provides exceptional customer service to a portfolio of members by offering a full range of investment, deposit and complex lending services. The Senior…
Added 7 hours ago
C
Sr. Financial Advisor - CIRO-ID (Urban)
CIBC
Burnaby, BC · Vancouver, BC · Richmond, BC
- Full-time
…comprehensive financial plans and providing exceptional client service. As a Senior Financial Advisor in the Imperial Service Team, you’ll expertly deliver on CIBC’s Imperial Service…
Added 7 hours ago
AC
Regional Service Agent
Allstate Canada
Thunder Bay, ON
- Full-time
The Customer Service Senior Associate handles basic to complex telephone/email/chat/fax inquiries from internal and external customers in an efficient, professional, and accurate manner.…
Added 7 hours ago
Manager, Strategic Business Partnering (Operations)
Pembina Pipeline Corporation
Calgary, AB
…Director, Strategic Business Partnering within the Human Resources Service Unit. This role leads strategic HR business partnering for the Pembina Operations and Project Delivery & Technical…
Added 8 hours ago
EC
Senior Account Manager, Prairies
Esri Canada
AB · Edmonton, AB
- Full-time
Demonstrated ability to operate as a trusted advisor to senior customer stakeholders.
Added 8 hours ago
M
Bilingual Client Success Manager
Maple
Toronto, ON
- Full-time
Build and maintain trust-based relationships across your portfolio, acting as the primary point of contact and strategic advisor - in both French and English.
Added 8 hours ago
SS
Roving Sales Advisor - Ottawa - 12 month contract
Sienna Senior Living
Markham, ON
- Full-time
Reporting to the Senior Director, Sales Strategy and Support, the Roving Sales Advisor plays a critical role in promoting and maintaining the occupancy of the retirement homes in the region…
Added 8 hours ago
Senior Financial Advisor (Chilliwack City Branch)
First West
Chilliwack, BC
The Senior Financial Advisor provides exceptional customer service to a portfolio of members by offering a full range of investment, deposit and complex lending services. The Senior…
Added 8 hours ago
Senior Financial Advisor - West Vancouver Branch - West Vancouver, BC
Scotiabank
West Vancouver, BC · Vancouver, BC
Our Advisors are customer-centric and able to connect with people in a relatable way. As an essential member of the Canadian Banking Branch network, our focus is to provide exceptional…
Added 8 hours ago
C
Sr. Financial Advisor CIRO-ID (Urban)
CIBC
Thunder Bay, ON
- Full-time
As a member of the Imperial Service Team, you’ll manage and grow a dedicated client portfolio through key relationship management, creating comprehensive financial plans and providing…
Added 8 hours ago
C
Sr. Financial Advisor - CIRO-MFD/AMF
CIBC
Golden, BC
- Full-time
…comprehensive financial plans and providing exceptional client service. As a Senior Financial Advisor in the Imperial Service Team, you’ll expertly deliver on CIBC’s Imperial Service…
Added 9 hours ago
S
Director, Deployment Operations
Solink
Remote, Canada
- $156,696 to $195,870 CAD / year
- Full-time
- Remote
Partner across the organization: Work closely with senior leaders in Sales, Customer Success, Support, Product and Finance to align on planning, resolve cross-functional friction and make…
Added 9 hours ago
CT
Director, Technology Communications & Organizational Change Management (14 month contract)
Canadian Tire Corporation
Toronto, ON
- Full-time
As a trusted advisor to Technology leadership, you will translate complex priorities into clear narratives, embed the employee perspective into critical decisions, and create the conditions…
Added 9 hours ago
Y
Client Onboarding Specialist - SaaS
YuJa
Toronto, ON · North York, ON
- $50,000 to $60,000 CAD / year
- Full-time
…strategic upselling and renewals. You'll serve as a trusted advisor to our clients, ensuring they achieve maximum value from our solutions while identifying opportunities to expand their…
Added 9 hours ago
KL
Deputy Chief Administrative Officer
Kawartha Lakes
Kawartha Lakes, ON
- Full-time
Champion business modernization and organizational transformation initiatives that improve service delivery, operational effectiveness and customer experience.

Trolley

Senior Technical Support & Success Manager

Toronto, ON, Canada
Montreal, QC, Canada
Halifax, NS, Canada

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Job details

Posting language: English
Posted: Oct 1, 2026

Original 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.

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More about this job

Responsibilities

The Senior Technical Customer Success Manager will manage a portfolio of strategic accounts, providing proactive guidance and technical support to ensure customer success. They will collaborate with internal teams to resolve complex API and integration issues while advocating for product enhancements based on customer feedback.

Requirements

Candidates must have several years of experience in customer-facing SaaS roles with a strong background in troubleshooting APIs and technical product issues. Excellent communication skills and the ability to manage complex enterprise B2B relationships are essential for this position.

Skills

Technical support
Customer success
API troubleshooting
SaaS
Relationship management
Fintech
REST APIs
JSON
Webhooks
Postman
Salesforce
Intercom
Jira
Notion
Data analysis
Problem-solving

Benefits

Competitive salary
ESOP program
Extended healthcare benefits
4 weeks paid vacation
30 days remote work
Gym membership allowance
1/2 day Fridays off during summer
Apple MacBook Pro

Visa sponsorship

Not detected in the job text

Keywords

SaaS
Fintech
Payments
API
REST APIs
JSON
Webhooks
Postman
Salesforce
Intercom
Jira
Notion
Technical Support
Customer Success
Solutions Engineering
Enterprise B2B
Troubleshooting
Product Adoption
Account Management
Data Analysis
SLA
Integration
Infrastructure
Consultative Engagement
Mentorship

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