Go to Market (GTM) Automation Specialist

About the role

You will evaluate and evolve the existing GTM tech stack to better leverage automation and AI across prospecting, enrichment, sequencing, personalization, and reporting. You will design and orchestrate workflows across GTM tools such as enrichment platforms, sequencing tools, and AI tools to automate and simplify outbound execution. You will integrate AI-enabled tooling with the CRM, first-party data, and third-party vendors to ensure clean, enriched, and actionable data flows. You will build and optimize automated prospecting and enrichment pipelines to improve targeting accuracy, segmentation, and message relevance. You will enable AI-assisted, multi-channel outbound programs including email and LinkedIn to increase personalization while maintaining scale and consistency. You will partner closely with Sales, RevOps, and Marketing to operationalize outbound strategies and reduce day-to-day execution friction for reps. You will establish and support a GTM experimentation framework that incorporates AI-driven testing across messaging, targeting, sequencing, and channels. You will build and refine dashboards and reporting that measure performance, adoption, and ROI of automation and AI-driven GTM initiatives.

Key facts

What you'll do

• Evaluate and evolve the existing GTM tech stack to better leverage automation and AI across prospecting, enrichment, sequencing, personalization, and reporting.
• Design and orchestrate workflows across GTM tools such as enrichment platforms, sequencing tools, and AI tools to automate and simplify outbound execution.
• Integrate AI-enabled tooling with the 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 including email and LinkedIn to 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 that incorporates 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.
• Research and test emerging automation and AI technologies that can enhance GTM efficiency and effectiveness.
• Collaborate with cross-functional stakeholders to translate business requirements into technical automation solutions.
• Monitor automation performance, identify bottlenecks, and implement improvements to increase reliability and outcomes.

Requirements

• 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.
• Proven ability to work independently and collaboratively in a fast-paced, remote-first environment.

Practical notes

• No official apply page mentioned in SOURCE, so no URL is provided.

The role is fully remote, and the company hires across Canada and the United States, so location flexibility is built into the position. There are no specific hours, travel requirements, visa conditions, or application deadlines outlined in the current description. You are encouraged to apply if you believe you possess the core qualifications and are excited by the opportunity to contribute to a high-growth, mission-driven organization that is focused on financial empowerment for employees. If you are a builder who thrives on solving complex system challenges and leveraging cutting-edge automation and AI to move the needle for GTM outcomes, this position is a strong fit. The company's recent funding extension and recognition in major industry awards highlight its momentum and commitment to innovation in the financial wellness space. Joining now means partnering with cross-functional teams to establish the foundation for scalable, data-driven GTM strategies that will define the future of the platform.