Full-Time

Senior Engineering Manager

Posted on 9/12/2025

Trolley

Trolley

51-200 employees

Global payment processing for businesses

No salary listed

Remote in Canada

Remote

Category
Engineering Management (1)
Requirements
  • 10+ years of progressive experience in software engineering and leadership, with a clear trajectory of taking on more complex challenges over time.
  • Minimum of 3+ years in direct people management, including a proven track record of successfully managing other Engineering Managers.
  • Demonstrated experience in developing, recruiting, and mentoring top-tier senior talent.
  • Strong technical background from time as a hands-on Senior Engineer, with architectural depth to guide and challenge senior engineers.
  • History of thriving in environments that demand a high degree of precision and quality, such as fintech, healthcare, or other regulated industries.
  • Capability of both long-term strategic planning and short-term tactical execution, translating a high-level vision into a concrete roadmap.
  • Exceptional communication skills, capable of articulating complex technical ideas with clarity to any audience.
  • Solid intellectual curiosity, a principled approach to decision making, and a relentless desire for excellence.
Responsibilities
  • Lead a multi-squad domain, managing both engineering managers and individual contributors with clear ownership and accountability.
  • Translate the company vision into a clear technical roadmap, making deliberate priority calls that balance immediate business needs with long-term architectural integrity.
  • Hire and develop exceptional talent, fostering a culture of continuous growth where every member is empowered to master their craft.
  • Set the technical direction for the domain, championing best practices in security, testing, and observability to ensure systems are scalable, compliant, and resilient.
  • Establish and refine the group's operating rhythms to ensure high-velocity, predictable delivery without compromising on quality or due diligence.
  • Forge strong partnerships with leaders across the business, ensuring teams deliver maximum impact for customers.

Trolley provides global payment processing tailored for businesses of all sizes. It offers tools to automate sending and receiving payments, with features for tax compliance, recipient management, and integration with other financial systems. The platform processes transactions securely and streamlines payment workflows, helping businesses save time and reduce complexity. It differentiates itself through a user-friendly interface, strong security measures, and robust customer support, including transparent incident history and status updates. The company’s goal is to enable reliable, efficient cross-border payments to support growth for SMEs, freelancers, and large corporations, and it generates revenue mainly from transaction fees, with optional premium plans for larger or more complex needs.

Company Size

51-200

Company Stage

Series B

Total Funding

$30.7M

Headquarters

Westmount, Canada

Founded

2015

Simplify Jobs

Simplify's Take

What believers are saying

  • $23M Series B in 2023 fuels global expansion and Trust enhancements.
  • CD Baby, Spare Music, OpenPlay partnerships capture music royalties.
  • Trolley Plus launches enterprise SaaS for higher-margin contracts.

What critics are saying

  • Stripe's payouts API undercuts fees by 20-30% in 6-12 months.
  • Wise Business API seizes 40% cross-border volume in 12-18 months.
  • Payoneer poaches CD Baby with zero-fee payouts in 6-12 months.

What makes Trolley unique

  • Trolley's one-line code APIs enable embedded payouts for platforms.
  • DAC7 compliance product creates switching costs in EU markets.
  • RecipientOps centralizes onboarding, verification, and tax compliance.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Company Equity

Paid Vacation

Remote Work Options

Gym Membership

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

1%

2 year growth

0%
Spare Music
Jul 14th, 2025
Faster Payouts, Lower Fees: Spare Music Partners with Trolley

SpareMusic LTD has partnered with Trolley to bring you faster payouts, lower fees, and a much smoother experience - so you can spend less time waiting and more time creating.

Nationwide Report
Jun 17th, 2025
OpenPlay and Trolley Sign Partnership to Streamline Royalty Payments for the Global Music Industry

Music catalog management platform and business engine OpenPlay has announced a new collaboration with Trolley, the end-to-end payouts platform for the internet economy.

Business Wire
Nov 15th, 2024
Trolley Secures $23 Million USD Series B to Accelerate Global Payout Platform Expansion

Trolley, a leading global payouts platform, today announced it has raised $23 million USD in a Series B growth equity funding round led by Wavecrest G

Business Wire
Nov 13th, 2024
Trolley Secures $23 Million USD Series B to Accelerate Global Payout Platform Expansion

Trolley secures $23 million USD Series B to accelerate global payout platform expansion.

BetaKit
Nov 13th, 2024
Trolley raises $32M CAD Series B

Montréal-based FinTech startup Trolley raised $32 million CAD ($23 million USD) in Series B funding to expand its global payout platform. The round was led by Boston's Wavecrest Growth Partners, with support from New York's Pace Capital. The funds will enhance Trolley's payout features, focusing on quicker, safer transactions and global expansion. The investment emphasizes Trolley's Trust product for ID and phone authentication. This round brings Trolley's total funding to approximately $42 million CAD.

INACTIVE