Chief Revenue Officer

Overview

Chief Revenue Officer (CRO)

Location :
Toronto, Ontario (Hybrid) or Montreal, Québec (Hybrid)

Reports to : CEO

Level :
Executive / C-Suite

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 panies use Trolley 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.

We are seeking an experienced Chief Revenue Officer (CRO) to lead Trolley’s revenue growth and go-to market execution. This individual will unify Sales and Marketing while providing operational leadership across Customer Success, Account Management, and Partnerships to ensure scalable, durable growth. This is a critical executive role at a pivotal stage of Trolley’s growth, requiring a proven operator who can translate strategy into execution, align teams around clear priorities, and build the systems, processes, and accountability required for scale.

The CRO will own the end-to-end customer journey, from demand generation and acquisition through onboarding, retention, expansion and long-term value creation. This individual will ensure a cohesive and disciplined approach to how Trolley engages, converts, retains, and grows our customer base, with clear ownership of revenue performance and growth outcomes. The CRO will work closely with the CEO and functional leaders to drive alignment, operational rigor, and translate company strategy into predictable, scalable growth outcomes.

This role requires a balance of strategic leadership and hands‑on execution, particularly in resource‑conscious, execution‑driven environments, where prioritization, focus, and cross‑functional alignment are essential. The ideal candidate is a senior go‑to‑market executive with a demonstrated track record of leading Sales and Marketing simultaneously within B2B SaaS, enterprise software, or fintech organizations. They bring a strong understanding of how Customer Success, Account Management, and Partnerships contribute to sustainable growth.

• Own and execute the company’s end-to-end GTM and growth strategy, aligning Sales, Marketing, Customer Success, Account Management, and Partnerships into a cohesive operating model across the full customer lifecycle.
• Drive predictable revenue growth across enterprise segments, with clear accountability for pipeline performance, bookings, ARR, retention, and expansion.
• Build, lead, and develop high‑performing Sales and Marketing leadership teams, while providing strategic oversight and direction to Customer Success, Account Management, and Partnerships.
• Establish, own, and maintain strong forecasting discipline, operating cadence, and performance accountability across all growth‑related functions.
• Refine market positioning, pricing, segmentation, and channel strategy to support efficient customer acquisition and long‑term value creation.
• Ensure thoughtful prioritization and ROI focused use of GTM resources across acquisition, retention, and expansion initiatives.
• Partner closely with Product, Finance, and Customer teams to ensure market feedback, customer insights, and financial discipline inform decision‑making.
• Own pipeline generation strategy and performance (volume, quality, conversion).
• Align positioning, ICP definition, segmentation, and messaging with revenue goals.
• Ensure tight handoffs and accountability between Marketing and Sales.
• Optimize CAC, payback, and channel mix as the business scales.
• Serve as a trusted strategic advisor to the CEO and executive leadership team on growth strategy and execution.

10+ years of experience in senior B2B revenue or growth leadership roles, with responsibility…