About ZayZoon
Who We Are
- At ZayZoon, we are on a mission to save 10 million hardworking employees 10 billion dollars. We’ve created a financial empowerment platform that helps businesses of all sizes make a big impact on employee financial wellness.We offer a variety of financial wellness services, like earned wage access, allowing employees to access their earned wages ahead of payday. With 74% of ZayZoon customers reporting reduced financial stress, we know our solutions help lead to happier and more productive employees. Our recent funding extension has raised our Series B funding round to nearly $50 million USD. Join us in shaping the future of employee financial wellness. We’re fully remote and hire across Canada and the U.S.About The Role
As our GTM Automation Specialist, you’ll help us get more out of our systems and find smarter ways to automate, connect, and scale. You’ll focus on improving how we prospect, enrich data, personalize outreach, and measure what’s working using both our existing tools and new AI capabilities. You’ll work closely with Sales, Marketing, and RevOps to spot what’s clunky or manual today and turn it into something more streamlined and reliable. This role is for the builder who loves connecting complex GTM systems, constantly experimenting with the latest automation and AI technologies, and is focused on driving measurable impact for our teams.Your Impact
Evaluate and evolve our existing GTM tech stack by identifying opportunities to better leverage automation and AI across prospecting, enrichment, sequencing, personalization,



and reportingDesign and orchestrate workflows across our GTM tools (e.G., enrichment platforms, sequencing tools, AI tools) to automate and simplify outbound executionIntegrate AI-enabled tooling with our CRM, first‑party data, and third‑party vendors to ensure clean, enriched, and actionable data flowsBuild and optimize automated prospecting and enrichment pipelines to improve targeting accuracy, segmentation, and message relevanceEnable AI‑assisted, multi‑channel outbound programs (email, LinkedIn, etc.) that increase personalization while maintaining scale and consistencyPartner closely with Sales, RevOps, and Marketing to operationalize outbound strategies and reduce day‑to‑day execution friction for repsEstablish and support a GTM experimentation framework, incorporating AI‑driven testing across messaging, targeting, sequencing, and channelsBuild and refine dashboards and reporting that measure performance, adoption, and ROI of automation and AI‑driven GTM initiativesDocument workflows, tooling, and AI best practices to drive adoption and long‑term scalability across the teamYou Bring
4+ years of experience in Go‑to‑Market Automation, Revenue Operations, Sales Operations,



or Growth Operations within a SaaS environmentStrong experience working with HubSpot, including automation, workflows, data models, and reporting that support scalable GTM operationsStrong understanding of data hygiene, enrichment, segmentation, and how they impact targeting and performanceExperience building dashboards and running experiments to improve GTM performance, messaging, and pipeline outcomesHands‑on experience designing, building and optimizing GTM automation across tools like Clay, Apollo, Outreach, Salesloft, and enrichment platformsAbility to apply AI and LLM tools to GTM workflows including prospect research, message personalization, enrichment, and automated decisioning within outbound and lifecycle motionsExperience integrating tools and systems using APIs, webhooks, or platforms like Zapier, Make, n8n, or WorkatoWhy You’ll Love Working At ZayZoon
Permanently Remote: Work from a desk, a coffee shop, or in the great outdoors – our jobs are fully remote, foreverFlexible Time Off: Up to 6 weeks vacation and a “You‑do‑You” time off program that caters to diverse lifestylesInstant Advantages: All full‑time employees get access to medical, vision, and dental benefits from their first day, including increased mental health coverage and a wellness stipendInclusive parental leave top‑up, earned wage access, real‑time market data for salaries, a supportive culture for lifelong learners, and moreCompensation
CA$102 K – CA$140 K
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📌 Go To Market (Gtm) Automation Specialist (Winnipeg)
🏢 ZayZoon
📍 Winnipeg