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Added 1 min ago
W
Senior Manager, Software Development - Clients & Accounts
Wealthsimple
Canada
- Full-time
…of. We build the uncompromising, simple, fully digital in-app onboarding experience Wealthsimple is known for, guiding clients from sign-up through funded accounts in minutes, not days, and…
Added 47 mins ago
VM
Sales Representative- Permanent Full-Time - (Supply Chain and Logistics B2B) - Alberta
Venture Media
Calgary, AB
- From $60,000 CAD / year
- Full-time
Reporting to the Sales Manager – Business Development, the Sales Representative will contribute directly to revenue growth by turning qualified opportunities into active shipping clients…
Added 47 mins ago
VM
Sales Representative- Permanent Full-Time - (Supply Chain and Logistics B2B) - Ontario
Venture Media
Toronto, ON
- From $60,000 CAD / year
- Full-time
Reporting to the Sales Manager – Business Development, the Sales Representative will contribute directly to revenue growth by turning qualified opportunities into active shipping clients…
Added 1 hour ago
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Retail Operations Manager
PetSmart
Ottawa, ON
- Full-time
Facilitates the associate experience and supports associate development. This includes but is not limited to training, onboarding, mentoring, and coaching for growth as well as providing…
Added 1 hour ago
MC
Retail Location Coordinator
Midwest co-operative services
Saugeen Shores, ON
- $21 to $25.5 CAD / hour
- Full-time
…Location Coordinator. Under the direction of the Retail Location Manager, the Retail Location Coordinator supports the daily operations of a single MCS retail location specializing in farm…
Added 1 hour ago
TL
Driver Recruiter
Transx Ltd
Rosser, MB
- Full-time
…Recruitment team in Winnipeg. Reporting to Driver Recruiting Manager, and under the guidance of the Team Lead, the Driver Recruiter is responsible for sourcing, screening, qualifying, and…
Added 1 hour ago
MS
Account Executive, Cardiology
Myant Shared Service Corp.
Mississauga, ON
- Full-time
…grounded in the economics and operational realities of each customer: helping practices increase study capacity, improve report turnaround and generate additional value from their existing…
Added 1 hour ago
HC
Print / Press Room Manager
Hartmann Canada Inc
Brantford, ON
- $110,000 to $115,000 CAD / year
- Full-time
We require the talent of a Print / Press Room Manager to join our team.
Added 1 hour ago
VI
Branch Manager
VPI INC.
Hamilton, ON
- Up to $72,100 CAD / year
- Full-time
The Branch Manager is responsible for the day-to-day operation of the branch and for ensuring key performance indicators, as set out internally by the organization and by the government…
Added 1 hour ago
BS
Regional Manager (Food Service)
Bento Sushi
Ottawa, ON
- Up to $60,000 CAD / year
- Full-time
The Franchise Regional Manager will oversee the operations of franchise stores within a designated region in Ottawa. This role ensures that franchisees meet Bento's operational standards,…
Added 1 hour ago
BG
Estimator, Senior
BV GLAZING
Niagara Falls, ON
- $85,000 to $95,000 CAD / year
- Full-time
We will provide training and onboarding sessions to ensure that you’ve got everything you need to succeed in your new role.
Added 1 hour ago
BG
Purchasing Agent
BV GLAZING
Concord, ON
- $50,000 to $60,000 CAD / year
- Full-time
We will provide training and onboarding sessions to ensure that you’ve got everything you need to succeed in your new role.
Added 1 hour ago
BG
JR DESIGNER
BV GLAZING
Concord, ON
- $50,000 to $65,000 CAD / year
- Full-time
Assist in taking organic designs from customer vision to commercialization
Added 1 hour ago
BG
Junior Project Operations Manager
BV GLAZING
Niagara Falls, ON
- $50,000 to $80,000 CAD / year
- Full-time
Direct quality aspects and quality control for Group factories, suppliers, and third parties in coordination with the Project Quality Manager.
Added 3 hours ago
A
Assistant Front Office Manager
AccorHotel
Calgary, AB
- Full-time
We invite you to join the world of hospitality at Sheraton Suites Calgary Eau Claire as our new Assistant Front Office Manager. The Assistant Front Office Manager is a key leader within the…
Added 4 hours ago
TC
Service Manager / Field Supervisor (Plumbing Operations)
TR Construction Group
Field, BC
- Full-time
TR Construction Group, LLC seeks an experienced Service Manager / Field Supervisor to direct daily workflow and oversee the quality, safety, and productivity of our residential plumbing…
Added 4 hours ago
G
QUALITY MANAGER
GreenSupply
Quebec, QC
- Full-time
In-Process Quality Inspection, Document Maintenance & Reduce Rejection. Customer Complaint Handling & Swift Resolution.
Added 5 hours ago
T
R&D Engineer- Data Scientist
Tenova
Mississauga, ON
- Full-time
The R&D Engineer - Data Science, under the direction of the R&D Manager, is responsible for analyzing operational and test data, developing algorithms, and researching, building,…
Added 6 hours ago
SD
Senior Manager, Specialty Pharmacy-2
Shoppers Drug Mart Specialty Health Network
Calgary, AB
- Full-time
Reporting to the Director, Clinic and Specialty Programs, the Senior Manager, Specialty Pharmacy is responsible for the successful operation of our Shoppers Drug Mart Specialty Health…
Added 6 hours ago
Produce - Clerk Department Second Produce
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Fall River, NS
…Supervise the Produce Department and staff in the absence of the Manager. Actively contribute to an environment of employee and customer…
Added 7 hours ago
TE
Branch Administrator
TK Elevator
Sudbury, ON · Greater Sudbury, ON
- Full-time
Respond to customer inquiries and/or redirect to the appropriate department
Added 7 hours ago
MS
Merchandise Manager PT
Michaels Stores
Winnipeg, MB
- Part-time
Store - WINNIPEG-GARDEN CITY, MBThe Merchandise Manager drives merchandising and operational execution, including truck processing, inventory routines, planogram sets, and visual standards.…
Added 7 hours ago
MS
Merchandise Manager
Michaels Stores
Saskatoon, SK
- Part-time
Store - SASKATOON, SKThe Merchandise Manager drives merchandising and operational execution, including truck processing, inventory routines, planogram sets, and visual standards. This role…
Added 8 hours ago
CH
Seasonal Holiday Retail Manager - Kildonan Place
Cherry Hill Programs
Winnipeg, MB
- Part-time
As our Local Manager, you'll lead the team responsible for creating magical holiday memories for children and families. You'll oversee daily photo operations, drive sales and service…
Added 8 hours ago
UO
Urban Outfitters Assistant Manager
Urban Outfitters
Richmond, BC
- $24 CAD / hour
- Full-time
Acts as a brand representative reflective of the company values and partners with the Visual Merchandising Manager on the creation of an engaging visual experience that appeals to the UO…

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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