GTM Engineer

Riverside Insights

16h•$120,000 - $140,000•Remote

About The Position

Riverside Insights is hiring a hands-on individual contributor to build the AI and automation layer behind its go-to-market organization. The role sits at the intersection of GTM, AI, and revenue operations, and designs, builds, and ships agents, workflows, and integrations that reduce manual work for Sales, Marketing, Customer Success, and GTM Operations teams. The work also puts practical AI tools in the hands of employees who sell and support Riverside products, with the aim of increasing capacity, revenue, and impact for learners without growing headcount at the same rate. The GTM Engineer will build systems suited to the education market, including district budget cycles, funding streams, RFP-driven procurement, buying committees, and student-data privacy requirements. They will partner with Revenue Analytics, Systems & RevTech, Deal Operations, and Global Operations to identify high-impact opportunities, deliver work in short sprints, measure time and revenue impact, and teach colleagues to use and extend the systems created. This role reports to the VP, GTM Operations. The position is remote and includes travel one to two times a year for off-site team meetings or conferences. The role may require sitting or standing for extended periods. The stated U.S. salary range is $120,000–$140,000.

Requirements

At least 4 years in GTM systems roles such as revenue operations, sales or marketing operations, GTM engineering, or solutions engineering, including at least 2 years building production automations and integrations.
Deep hands-on HubSpot or Salesforce experience with workflows, custom objects and properties, and APIs, including ownership of integration points rather than only consuming data from them.
Track record of shipping AI/LLM-powered workflows or agents in a business setting, including prompt design, LLM APIs, and agent or MCP tooling; able to discuss examples.
Proficiency with at least one workflow automation or iPaaS platform, such as n8n, Zapier, Make, Workato, or Tray.io.
Working knowledge of SQL and Python or JavaScript; comfort with REST APIs, webhooks, and JSON.
Experience with data enrichment and orchestration, such as Clay or comparable waterfall enrichment tools, and a cloud data warehouse; Snowflake is preferred.
Business fluency in funnel and revenue metrics, and a habit of tying builds to measurable outcomes.
Sound judgment regarding data privacy and security when connecting systems and AI tools.
Ability to turn loosely defined problems into shipped systems, work autonomously, manage several stakeholders' priorities, communicate clearly in writing and verbally, and teach non-technical users.

Nice To Haves

GTM 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.
Familiarity with K-12 market data sources such as NCES, MDR, state education agency data, and bid and RFP feeds.
Working knowledge of FERPA, COPPA, and state student-privacy requirements.
Experience at a company scaling through a growth inflection point, such as $100M to $200M in revenue.
Experience leading AI adoption or enablement programs for non-technical teams.
Exposure to CPQ or quoting tools, planning tools such as Pigment, conversation intelligence tools such as Gong, or sales enablement platforms such as Seismic.

Responsibilities

Map manual workflows with Sales, Marketing, Customer Success, and GTM Operations, and deliver a prioritized automation backlog in sprints.
Design, build, and maintain production automations using HubSpot, workflow platforms, LLM APIs, and agent tooling.
Enrich district and school data in HubSpot and route buying signals, such as RFPs, funding, and renewal windows, to the appropriate representative.
Deploy AI assistants for account research, call preparation, CRM meeting notes, proposal and RFP first drafts, and renewal-risk alerts.
Automate lead routing, CRM data hygiene, quote and order handoffs, and forecast preparation with Systems & RevTech and Deal Operations.
Keep GTM system data flows reliable in collaboration with Revenue Analytics, and document each build so the team can support it.
Baseline each build and report hours saved, adoption, and pipeline impact; recommend build-versus-buy decisions for new tools.
Coach GTM teammates in using AI and building simple automations, supported by a shared prompt and skills library.
Set standards for AI workflow monitoring and human review, and ensure workflows meet FERPA, COPPA, and state student-privacy requirements.

Benefits

Medical, dental, and vision plans.
Company-paid basic life and AD&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 Calm subscription for employees and dependents.
33 days of company-paid time off, including PTO, holidays, Winter Break, Summer Fridays, and Wellness Days.
Weekly Focus Wednesdays.
Flexible work arrangements.
Tuition reimbursement program.
Company orientation and 30-, 60-, and 90-day onboarding.