About HopSkipDrive

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 20states. 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.

How we work

We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.

Who We Are

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:

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
You’ll report directly to the Director of Revenue Operations and work closely with senior team members and cross-functional GTM leaders.

Who You Are

You are a systems thinker and hands-on builder who moves fluidly between technical configurations and strategic context. You don’t just maintain tools — you make them smarter. With the following skills, you’ll make a tangible and immediate impact:

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 WorkatoA 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 auto

GTM Engineer at HopSkipDrive