Senior Enterprise Customer Success Lead

Trolley; Toronto; Hybrid; CAD 101,000 - 123,000; Full time

Benefits offered by this job

Competitive base salary and bonus

ESOP program with equity ownership

Extended healthcare benefits from Day

4 weeks paid vacation per year

30 days remote work from anywhere

Gym membership allowance

MacBook Pro and gear provided

Job summary

Trolley is looking for a customer-focused technical expert to manage a portfolio of high-value clients across Montréal, Toronto, or Halifax, acting as their strategic partner. You will drive adoption, translate needs into product improvements, and help customers realize full platform value.

You’ll build strong relationships, lead enablement sessions, and collaborate with support, product, and sales to ensure joint success in a fast-paced, hybrid environment.

Qualifications

• 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 and contribute to revenue and growth.
• Bonus points for experience in financial services, SaaS payment automation, and the internet economy/music royalties.

Responsibilities

• Own and manage a portfolio of high-value and complex customers as their strategic business partner.
• Deliver a world-class customer experience and evangelize the value of our solutions.
• Develop and maintain strong relationships, becoming a trusted advisor for their success.
• Become a solution expert to instill confidence in our products and workflows.
• Understand customer workflows to provide tailored guidance and outcomes.
• Monitor KPIs and engage stakeholders through quarterly business reviews to drive outcomes.
• Provide enablement sessions on features and capabilities to align with customer goals.

Skills

Account management

Customer success

SaaS experience

Data analysis

Communication

Negotiation

Problem solving

Tools

Salesforce

Google Workspace

Job description

Trolley is looking for a customer-focused technical expert to manage a portfolio of high-value clients across Montréal, Toronto, or Halifax, acting as their strategic partner. You will drive adoption, translate needs into product improvements, and help customers realize full platform value.

You’ll build strong relationships, lead enablement sessions, and collaborate with support, product, and sales to ensure joint success in a fast-paced, hybrid environment.