Chief Revenue Officer (CRO)
Location: Toronto, Ontario (Hybrid) or Montreal, Québec (Hybrid)
Reports to: CEO
Level: Executive / C-Suite
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 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.
The Role
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.
Key Responsibilities
- 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.
Ideal Candidate Profile
- 10+ years of experience in senior B2B revenue or growth leadership roles, with responsibility across Sales, Marketing, and broader GTM functions.
- 2+ years serving as the single executive owner of both Sales and Marketing, with direct experience partnering closely with or providing leadership to Customer Success, Account Management, and/or Partnerships (e.g., CGO, CRO, SVP Sales & Marketing).
- Proven experience leading end-to-end GTM and growth in companies with approximately$10M–$75M USD in revenue, including accountability for acquisition, retention, and expansion.
- Background in organizations that require hands-on leadership, disciplined execution, and clear prioritization to drive results.
Industry & Domain
- Strong background in B2B Enterprise software.
- Fintech and/or payments experience is a significant advantage.
- Deep understanding of enterprise buying cycles, complex sales motions, and long-term customer value creation.
- Experience working with partners, channels, or ecosystem relationships that support enterprise growth.
Leadership & Execution
- Proven ability to align Sales and Marketing into a single, cohesive GTM engine, with strong integration across Customer Success, Account Management, and Partnerships.
- Comfortable driving results in execution focused environments, with an emphasis on cost-efficiency, prioritization, and impact.
- Data driven, commercially sharp, and execution oriented, with a strong focus on outcomes and accountability.
- Strong people leader with a track record of building, developing, and retaining high performing GTM teams.
What Success Looks Like in 12–18 Months
Within 12 To 18 Months, The Chief Revenue Officer Will Have Established a Clear, Disciplined, And Scalable Growth Engine That Supports The Full Customer Lifecycle And Drives Predictable, Sustainable Results. Success Will Be Reflected In
- Sales, Marketing, Customer Success, Account Management, and Partnerships operating as a fully aligned growth organization, with shared accountability across the customer journey.
- Improved revenue predictability, including high quality pipeline, increased forecasting confidence, and clear visibility into retention and expansion performance.
- More effective enterprise sales execution, demonstrated by improved win rates, deal quality, and customer fit.
- Clear ownership and leadership depth across all growth-related functions.
- Efficient growth discipline, with strong ROI across acquisition, retention, and expansion initiatives.
- Strong cross functional alignment with Product and Customer teams, ensuring market and customer insights consistently inform strategy.
A scalable operational foundation that positions Trolley for its next phase of growth.
By this stage, the CRO will be viewed as a trusted executive leader who brings clarity, focus, and operational rigor to Trolley’s end-to-end growth strategy.
What we offer:
- Competitive salary, performance based bonus/commission.
- 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.
