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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 & RevTech, 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 HubSpot, workflow platforms, LLM APIs, and agent tooling.
Power K-12 account intelligence. Enrich district and school data in HubSpot 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 & RevTech 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.
Requirements
Must-Have Qualifications
4+ years in GTM systems roles such as revenue operations, sales or marketing operations, GTM engineering, or solutions engineering, including 2+ years building production automations and integrations, and deep hands-on HubSpot (or Salesforce) experience with workflows, custom objects and properties, and APIs, owning integration points rather than only consuming data from them.
A track record of shipping AI/LLM-powered workflows or agents in a business setting (prompt design, LLM APIs, agent or MCP tooling), with examples you can walk us through, and proficiency with at least one workflow automation or iPaaS platform (e.g., n8n, Zapier, Make, Workato, Tray.io).
Working knowledge of SQL and a scripting language (Python or JavaScript), comfort with REST APIs, webhooks, and JSON, and experience with data enrichment and orchestration (e.g., Clay or comparable waterfall enrichment tools) and a cloud data warehouse (Snowflake preferred).
Business fluency in funnel and revenue metrics, the habit of tying every build to a measurable outcome, and sound judgment about data privacy and security when connecting systems and AI tools.
The ability to turn loosely defined problems into shipped systems, work autonomously, and manage several stakeholders' priorities at once, with clear written and verbal communication and the patience to teach non-technical users.
What You'll BringGTM experience in EdTech, K-12, higher education, or public-sector SaaS, including district budget cycles, RFP and procurement processes, and funding sources such as Title I and IDEA, plus familiarity with K-12 market data sources (e.g., NCES, MDR, state education agency data, bid and RFP feeds).
Working knowledge of FERPA, COPPA, and state student-privacy requirements.
Experience at a company scaling through a growth inflection point (e.g., $100M to $200M in revenue) and experience leading AI adoption or enablement programs for non-technical teams.
Exposure to CPQ or quoting tools, planning tools such as Pigment, conversation intelligence (e.g., Gong), or sales enablement platforms (e.g., Seismic).
Physical Requirements
Remote
Travel 1–2 times a year for off-site team meetings or conference.
May require stationary positions (sitting or standing) for extended periods.
Disclaimer
The above statements describe the general nature and level of the work performed by people assigned to this work. This list does not cover all possible duties, tasks, or responsibilities. Riverside Insights may amend or change responsibilities to meet the needs of the business and organization as necessary
Benefits
Why Join Our Team?
At Riverside Insights , achieving real results for students and educators is more than talk, it is what we do. As we grow, so will you, offering the chance to expand your skills on an ambitious, solution-focused team. Join us in making great work possible, where your well-being and dedication to making an impact go hand in hand. If you are ready for an ambitious, collaborative environment, Riverside is the place for you.
Benefits
Medical, Dental, and Vision plans
Company paid basic life and AD and D insurance
Company paid long-term disability
Paid Parental Leave
Supplemental life insurance options
Company paid Employee Assistance Program (EAP)
Retirement plan with discretionary company matching
Flexible Spending Account (FSA) and Health Savings Account (HSA) options
Premium subscription to Calm for employee and dependents
33 days of company paid time off (PTO, Holidays, Winter Break, Summer Fridays, Wellness Days)
Weekly Focus Wednesdays
Flexible work arrangements
Tuition Reimbursement Program
Company orientation and 30, 60, 90 Day Onboarding
Compensation
A reasonable estimate of the salary range for this position is $120,000 to $140,000 USD.
This compensation range is specific to the United States, and it incorporates many factors including but not limited to an applicant's skills and prior relevant experience and training; licensures, degrees, and certifications; internal pay ranges; and market data or range parameters.
Riverside Insights is an Equal-opportunity Employer
Riverside Insights provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.