GTM Engineer

HopSkipDrive

1d•$120,000 - $130,000•Remote

About The Position

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country. Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date. We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. As a lean, high-impact Revenue Operations team, we build the scalable infrastructure and intelligent systems that power HopSkipDrive’s growth engine. We are an AI-first team obsessed with clean data, connected tools, and workflows that just work — and you will join us as the technical backbone who makes that possible. We do, and you will, support the business through the following responsibilities:

Requirements

5+ years of experience in a GTM Engineering, RevOps Systems, or Salesforce Admin role within a high-growth B2B SaaS or marketplace environment
Salesforce Administrator certification or equivalent hands-on expertise, with deep proficiency in flows, validation rules, permission sets, custom objects, and reporting
Demonstrated AI-first mindset — a track record of incorporating LLMs, automation agents, or AI-assisted enrichment tools (e.g., Clay, n8n, Gemini, Claude, or similar) into GTM workflows to meaningfully reduce manual lift
Hands-on experience managing a SaaS GTM tool stack, including renewal tracking, vendor evaluation, and ROI analysis across tools like ZoomInfo, Outreach, Gong, Spiff, or comparable platforms
Strong technical aptitude for system integrations, including experience connecting tools via REST APIs, native connectors, or iPaaS platforms such as Zapier, Make, or Workato
A builder’s mentality and ‘owner’ mindset — you proactively identify gaps, architect scalable solutions from scratch, and take pride in systems that others rely on without thinking twice
Comfortable building automations, debug integrations, and working with APIs — you don't need to ship production code daily, but you can read docs, use AI tools like Claude Code to close gaps fast.
Build AI agents and workflows that help reps prep for calls, auto-populate CRM after meetings, surface deal risk signals, and automate district research — shipping tools reps actually use

Responsibilities

Administer and continuously optimize Salesforce — owning user management, custom objects, flows, validation rules, permission sets, and reporting dashboards to ensure it operates as a reliable single source of truth
Own the GTM tool stack end-to-end: maintain a live inventory of all tools, manage vendor relationships, track contract renewal timelines, and provide data-driven recommendations on consolidation, expansion, or replacement
Design and deploy new tool workflows and cross-system integrations that eliminate manual handoffs and increase velocity across Sales, Marketing, and Customer Success
Champion an AI-first approach to GTM operations — proactively identifying opportunities to leverage LLMs, automation agents, and intelligent enrichment pipelines to reduce manual effort and surface actionable signal for revenue teams
Build and maintain integrations across the GTM stack (e.g., Salesforce, ZoomInfo, Outreach, Gong, Spiff, Omni) via APIs, MCPs, native connectors, or iPaaS platforms to create a high-fidelity, connected data ecosystem
Document system configurations, workflow logic, and integration architecture to ensure operational continuity and enable self-service for end users and business stakeholders and also enable AI automations and agents. Document first and use that context layer to build.
Partner with RevOps leadership and GTM stakeholders to translate business requirements into scalable technical solutions, proactively flagging risks and surfacing opportunities before they become problems