[Hiring] GTM Engineer @Riverside Insights

Role Description

At Riverside Insights, we are building the world's highest-performing double bottom line business, where strong business performance and real impact for learners make each other stronger. 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.

• Design, build, and ship agents, workflows, and integrations to reduce manual work for sales, marketing, customer success, and GTM Operations teams.
• 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 to the right rep at the right time.
• Deploy AI assistants for account research, call prep, CRM meeting notes, proposal and RFP first drafts, and renewal-risk alerts.
• Automate lead routing, CRM data hygiene, quote and order handoffs, and forecast prep with Systems & RevTech and Deal Operations.
• Keep data flows across GTM systems reliable with Revenue Analytics and document every build.
• Baseline every build and report hours saved, adoption, and pipeline impact.
• Coach GTM teammates to use AI and build their own simple automations.
• Set standards for monitoring and human review, ensuring compliance with FERPA, COPPA, and state student-privacy requirements.

Qualifications

• 4+ years in GTM systems roles such as revenue operations, sales or marketing operations, GTM engineering, or solutions engineering.
• 2+ years building production automations and integrations, with deep hands-on HubSpot (or Salesforce) experience.
• Track record of shipping AI/LLM-powered workflows or agents in a business setting.
• 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.
• Business fluency in funnel and revenue metrics.
• Ability to turn loosely defined problems into shipped systems.
• Clear written and verbal communication skills.

Requirements

• GTM experience in EdTech, K-12, higher education, or public-sector SaaS.
• 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).
• Exposure to CPQ or quoting tools, planning tools such as Pigment, conversation intelligence, or sales enablement platforms.

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