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'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.

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 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

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role is 120,000-130,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

* This role will be fully remote in one of the following states AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI, PA**

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