Go to Market (GTM) Automation Specialist II

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, that allows 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. ZayZoon was also recognized for its growth in the 2025 Deloitte Technology Fast 50, 2025 Deloitte Technology Fast 500, and top-10 growth companies in Canada by CIX awards. 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 and building services that address the immediate needs of today's employees.

You might see a few cities listed, but no need to be in any of them! 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 - you’ll be raising the bar on how our systems work and how our teams use them. This role is for the builder who loves connecting complex GTM systems, constantly experiments 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 reporting

• Design and orchestrate workflows across our GTM tools (e.g., enrichment platforms, sequencing tools, AI tools) to automate and simplify outbound execution

• Integrate AI-enabled tooling with our CRM, first-party data, and third-party vendors to ensure clean, enriched, and actionable data flows

• Build and optimize automated prospecting and enrichment pipelines to improve targeting accuracy, segmentation, and message relevance

• Enable AI-assisted, multi-channel outbound programs (email, LinkedIn, etc.) that increase personalization while maintaining scale and consistency

• Partner closely with Sales, RevOps, and Marketing to operationalize outbound strategies and reduce day-to-day execution friction for reps

• Establish and support a GTM experimentation framework, incorporating AI-driven testing across messaging, targeting, sequencing, and channels

• Build and refine dashboards and reporting that measure performance, adoption, and ROI of automation and AI-driven GTM initiatives

• Document workflows, tooling, and AI best practices to drive adoption and long-term scalability across the team

You bring:

• 4+ years of experience in Go-to-Market Automation, Revenue Operations, Sales Operations, or Growth Operations within a SaaS environment

• Strong experience working with HubSpot, including automation, workflows, data models, and reporting that support scalable GTM operations

• Strong understanding of data hygiene, enrichment, segmentation, and how they impact targeting and performance

• Experience building dashboards and running experiments to improve GTM performance, messaging, and pipeline outcomes

• Hands-on experience designing, building and optimizing GTM automation across tools like Clay, Apollo, Outreach, Salesloft, and enrichment platforms

• Ability to apply AI and LLM tools to GTM workflows including prospect research, message personalization, enrichment, and automated decisioning within outbound and lifecycle motions

• Experience integrating tools and systems using APIs, webhooks, or platforms like Zapier, Make, n8n, or Workato

Research shows that while men apply to jobs when they meet an average of 60% of listed criteria, women and other marginalized folks tend to only apply when they check every box. Think you have what it takes, but not sure you check every box? Apply to the role anyways. We’d love to talk and determine together whether you could be a great fit!

• Permanently Remote: Work from a desk, a coffee shop, or in the great outdoors - our jobs are fully remote, forever

• Flexible Time Off: Whether it's a longer vacation to explore new horizons, a series of short breaks for regular rejuvenation, or stepping away for a new level of mastery in a skillset – our “You-do-You” time off program caters to the diverse and evolving lifestyles of our team with a maximum of 5 weeks vacation

• Instant Benefits: All full-time employees get access to medical, vision, and dental benefits from their very first day including increased mental health coverage and a wellness stipend

• Plus: Inclusive parental leave top-up, earned wage access, real time market data for salaries, a supportive culture for lifelong learners and more

Every application will be reviewed by our team - we're committed to giving each application the attention it deserves because we know how important this step is for you. We want to make sure you're always in the loop and will respond to every application.

So go ahead and hit that apply button with confidence, knowing that we’re here for you every step of the way! We can't wait to hear from you.

#LI-REMOTE