GTM Operations Engineer About Trolley 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 payo…
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Full-time
Competitive Salary, Equity (ESOP), Extended Healthcare, Dental Insurance, Vision Insurance, Long Term Disability
Posted 44d ago
~40 hrs/week
Responsibilities
The role focuses on executing AI-powered marketing and sales campaigns to drive pipeline growth. Responsibilities include managing the GTM stack, optimizing conversion rates, and building campaign-level reporting.
Requirements
Candidates need a proven track record in demand generation and revenue operations with high proficiency in AI tools and no-code stacks. Experience in fast-growth startup environments and a data-driven mindset are essential.
Full job description
GTM Operations Engineer
About Trolley
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.
About the Role
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.
Your Standard Week:
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.
What You'll Be Doing:
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.
What you'll need to be successful:
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.
Bonus points:
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).
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.
Payout infrastructure for the internet economy. Unify PayoutOps and RecipientOps. Pay people in 210 regions worldwide.
Industry
Software Development
Company size
51-200 employees
Founded
2015
Headquarters
Toronto, Ontario
LinkedIn followers
7,646
Total funding
$32M
Trolley is payout infrastructure built for modern internet businesses. It unifies payout and recipient operations into a single embeddable platform, enabling companies to onboard, verify, and pay millions of recipients globally—while maintaining full compliance and operational control.
Since 2015, Trolley has processed billions in payouts and filed over 1.2M tax statements across 210 countries and territories. Leading platforms including Envato, Canva, SoundCloud, and Bugcrowd rely on Trolley to run mission-critical payout operations at scale.
Trolley consolidates payment delivery, tax compliance, identity verification, fraud detection, reconciliation, and reporting into one unified system. Finance and operations teams strengthen governance and reduce manual workflows, while product and engineering teams embed compliant global payouts directly into their products through APIs, SDKs, and pre-built UI components.
In the internet economy, every payout is a trust moment. Trolley ensures those moments are compliant, reliable, and globally scalable.
Offices: 1 University Ave, 3rd Floor, Toronto, Ontario M5J 2P1, CA · 1100 Atwater Ave, Suite 4300, Montreal, Quebec H3Z 2Y4, CA · 1791 Barrington St, 20th Floor, Halifax, Nova Scotia B3J 3K9, CA · 8 Devonshire Square, London, England EC2M 4PL, GB · Didžioji 18, Vilnius, LT-01128, LT
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