GTM Automation Engineer — AI Revenue Ops

The Opportunity

At Riverside Insights, we are building the world's highest-performing double bottom line business, one where strong business performance and real impact for learners make each other stronger. Our research-backed assessments help educators and clinicians discover the unique strengths and challenges of each learner, and grow the potential in every student. As we scale in revenue, growth is how that impact reaches more schools, more districts, and more kids.

That is where you come in. As our GTM Engineer, you will build the AI and automation layer behind our go-to-market organization. This is a hands-on individual contributor role at the intersection of GTM, AI, and revenue operations. You will design, build, and ship the agents, workflows, and integrations that take manual work off the plates of our sales, marketing, customer success, and GTM Operations teams, and you will put practical AI tools in the hands of everyone who sells and supports our products.

Every hour you give back is an hour our people can spend with the students and educators we serve, and a way to reach K-12 districts, schools, and clinical professionals with more precision without growing headcount at the same rate. That is our double bottom line at work: capacity that powers both revenue and mission.

Selling into education has its own rhythm: fiscal-year budget cycles, federal and state funding streams, RFP-driven procurement, buying committees that span superintendents, assessment directors, and school psychologists, and strict expectations for protecting student data. You will build systems tuned to that reality, so our teams show up at the right district, with the right message, at the right point in the buying cycle.

You will be GTM Operations' builder. You will partner with our Revenue Analytics, Systems & Rev Tech, Deal Operations, and Global Operations owners to find the highest-leverage opportunities, ship in short sprints, measure the hours and revenue impact of every build, and teach the team to use and extend what you create. You will see your work adopted, measured, and felt across the company.

This role reports to the VP, GTM Operations.

What You'll Do

• Find and prioritize the work. Map manual workflows with Sales, Marketing, Customer Success, and GTM Operations, and deliver a prioritized automation backlog in sprints.
• Build AI agents and workflows. Design, build, and maintain production automations using Hub Spot, workflow platforms, LLM APIs, and agent tooling.
• Power K-12 account intelligence. Enrich district and school data in Hub Spot and route buying signals, like RFPs, funding, and renewal windows, to the right rep at the right time.
• Equip sellers with AI. Deploy AI assistants for account research, call prep, CRM meeting notes, proposal and RFP first drafts, and renewal-risk alerts.
• Automate revenue operations. Automate lead routing, CRM data hygiene, quote and order handoffs, and forecast prep with Systems & Rev Tech and Deal Operations.
• Keep data trusted and documented. Keep data flows across GTM systems reliable with Revenue Analytics, and document every build so the team can support it.
• ·Measure and invest wisely. Baseline every build and report hours saved, adoption, and pipeline impact, while recommending build-versus-buy decisions on new tools.
• Enable the team. Coach GTM teammates to use AI and build their own simple automations, backed by a shared prompt and skills library.
• Govern AI responsibly. Set standards for monitoring and human review, and ensure every workflow meets FERPA, COPPA, and state student-privacy requirements.

Must-Have Qualifications

• 4+ years in GTM systems roles such as revenue operations, sales or marketing operations, GTM engineering, or solutions engineering,…