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 people 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. It is the go-to payouts solution for hundreds of businesses like Canva, Soundcloud, and Envato, ensuring creators, artists, and suppliers get paid efficiently. Trolley has processed millions of payments, supporting musicians, artists, makers, vendors, and suppliers worldwide.
Reports to: Director, Demand Generation
Interview stages: preliminary/recruiter interview, hiring manager interview, case study + presentation.
We want to ship fast, test, learn, and iterate to build a pipeline that converts. This is a technical and creative role focused on rapid marketing and sales campaign execution, AI-powered automation, and measurable results. You’ll work backward from pipeline goals to build what we need: campaigns, workflows, custom landing pages, autonomous chat solutions, and experimental growth plays.
You own the full cycle—from idea to post-ops—including sprint management, reporting, automation, and operational excellence across our GTM stack. You’ll help ensure our campaigns, systems, data, and processes work together to drive efficient pipeline growth.
70% Building: Executing campaigns, setting up automation, and shipping experiments.
20% Data & Reporting: Tracking metrics, analyzing performance, and optimizing.
10% Syncs: Cross-functional coordination and planning.
Campaign Ownership: Build AI-enabled campaigns end-to-end, managing tooling, deployment, and delivery against deadlines.
Experimentation: Build a monthly roadmap of experiments focused on hitting pipeline targets.
Technical Execution: Own technical changes to demo forms, landing pages, and trial experiences, and campaign infrastructure.
GTM & ABM Operations: Own account and contact data quality, segmentation, routing, enrichment, and audience management across Trolley’s GTM systems.
Data & Insights: Build campaign-level reporting to measure impact from top-of-funnel to closed-won; be the expert on the data.
Troubleshooting: Diagnose tooling issues and optimize workflows day-to-day.
Collaboration: Work cross-functionally with sales, product, and content teams to deliver cohesive, high-impact campaigns.
Open Curiosity: Be open and willing to collaborate. You act with intention, stay humble, seek feedback to improve. Focus on winning as a team, but speak up to share feedback when you have an opinion
Growth/Demand Gen Experience: A track record of building A-Z campaigns focused on bottom-of-funnel pipeline or customer expansion.
AI Proficiency: You don’t just "use" AI, you treat it as a core component of your toolkit for automation and scaling.
Technical Fluency: Comfortable with marketing automation tools and no-code stacks. You focus on iterating and improving existing systems.
Marketing & Revenue Ops Experience: Experience managing CRM and marketing automation systems, including lead routing, attribution, lifecycle management, tracking, and reporting.
CRO Mindset: You are both creative and technical, focused on increasing conversion rates, pipeline velocity, and lead experience.
Data-Driven: You love nerding out with the data team but can synthesize complex metrics into actionable "what's next" plans.
Startup DNA: You’ve worked in fast-growth environments, are egoless, and celebrate building impactful, scalable solutions.
Sales Fluency: You understand the sales funnel, core metrics, and how to align marketing output with sales needs.
Background in B2B SaaS or fintech.
Previous experience in a GTM Engineering or similar hybrid technical-marketing role.
Strong meme game (we’re a team, let’s have fun).
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.
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Trolley (formerly Payment Rails) is a Toronto-based fintech offering an end-to-end global payouts platform for the internet economy. It helps businesses onboard, verify, and pay creators, musicians, freelancers, and contractors across 210+ countries while managing tax compliance.
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