Enterprise Customer Success Manager

Trolley is the payouts platform for the internet economy. Our vision is to unlock the collective economic opportunity of the internet – for everyone – by building a truly global payouts ecosystem. Through our powerful platform and API, Trolley enables businesses to reach workers from all corners of the world and offer creators, on-demand workers, and suppliers the ability to bring their specialized talents to a global market. Businesses use Trolley to automate and manage payouts, collect recipient tax and banking information, and mitigate fraud and risk. The payouts solution of choice for hundreds of businesses, Trolley has made payouts to over 1.1 million different musicians, artists, makers, vendors, and suppliers around the world.

Trolley is looking for a dynamic, highly personable, opportunity-driven, and resourceful Customer Success Manager to join our talented team in Halifax or Montreal! You’ll be a key partner to our customers’ success team, helping to get them up and running on our platform and transforming their businesses.

Our customers love our platform and service, you can see it for yourself here.

In this role, you will:

• Manage a portfolio of high-value, complex customers, acting as their strategic partner and trusted advisor.
• Become a solution expert to instate a high level of customer confidence in you and our Trolley solutions.
• Gain a deep understanding of our customers’ operational workflows and use cases to provide more tailored and impactful client guidance.
• Drive engagement across multiple customer stakeholders by understanding their unique goals/business outcomes, and supporting their internal change management process during implementation/onboarding.
• Actively monitor adoption, analyze data, and industry trends, to implement strategies that drive value.
• Collaborate with internal teams to resolve issues and advocate for customer needs.
• Identify and pursue up-sell and cross-sell opportunities by aligning solutions with customer needs, driving growth and ensuring success.

About you:

• Demonstrate initiative, professionalism, and relationship-building skills to drive revenue and company growth.
• 10+ years in consultative account management and 5+ years in Customer Success for B2B SaaS, managing large mid-market accounts; experience in financial services, SaaS payment automation, or internet economy/music royalties is a plus.
• Quick learner, adaptable in fast-paced, ambiguous environments, with proven success managing multiple stakeholders, departments, and implementation cycles.
• Strong communication, interpersonal, and presentation skills, with experience conducting product demos and training sessions.
• Analytical mindset, using data to drive decisions and improve customer success, with strong problem-solving, negotiation, and commercial skills.
• Proven success in customer retention, proactively mitigating churn for at-risk customers.
• Exceptional written and spoken English, with experience working with SaaS business/enterprise applications.
• Detail-oriented, organized, able to multitask and prioritize in dynamic environments, and a confident, proactive team player.
• Familiar with CRM best practices (Salesforce preferred) and proficient in Google Apps (Gmail, Docs, Calendar).

What we offer:

• Competitive salary and meaningful equity (ESOP).
• Join an amazing team of diverse people working together on a common mission.
• Extended Healthcare benefits including dental, vision, LTD, etc. 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.