Job Description
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 120000-130000. 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**
Skills Required
- 5+ years experience in GTM Engineering RevOps Systems or Salesforce Admin within high-growth B2B SaaS or marketplace environments
- Salesforce Administrator certification or equivalent hands-on expertise
- Deep proficiency with Salesforce flows validation rules permission sets custom objects and reporting
- Demonstrated experience incorporating LLMs automation agents or AI-assisted enrichment tools (e.g. Clay n8n Gemini Claude) into GTM workflows
- Hands-on experience managing a SaaS GTM tool stack including renewal tracking vendor evaluation and ROI analysis (ZoomInfo Outreach Gong Spiff)
- Experience connecting tools via REST APIs MCPs native connectors or iPaaS platforms (Zapier Make Workato)
- Comfortable building automations debugging integrations and working with APIs (able to read docs and use AI coding tools)
- Ability to document system configurations workflow logic and integration architecture to enable operational continuity
What the Team is Saying









HopSkipDrive Compensation & Benefits Highlights
- Healthcare Strength—Corporate W‑2 employees are offered medical dental and vision coverage plus HSA/FSA options mental‑health resources/EAP and short‑ and long‑term disability. These components are explicitly listed on the company’s benefits materials for corporate roles.
- Leave & Time Off Breadth—Corporate roles include flexible PTO paid holidays and a company‑wide end‑of‑year closure with some materials also noting Summer Fridays and volunteer time. This time‑off design aligns with a remote‑first setup intended to support flexibility.
- Equity Value & Accessibility—Company ownership/equity is provided to full‑time corporate employees in addition to salary and a 401(k). This adds a long‑term compensation element to the package.
HopSkipDrive Insights
What We Do
We help get students to their destinations safely and on time. Our technology connects school partners to a network of highly vetted drivers with small vehicles and wheelchair-accessible vehicles complementing the yellow bus filling in gaps and enabling schools to support student transportation needs. Our partnerships with school districts child welfare agencies and nonprofits ensure equitable educational access for our most vulnerable populations including youth in foster care youth experiencing homelessness and youth with special needs.
Why Work With Us
HopSkipDrive exists to create opportunity for all through mobility. As the leader in innovative supplemental school transportation we’re taking a different approach to addressing inequities in educational access that are affecting millions of kids each day. We’re paving the way for a future where every student has the chance to succeed.
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HopSkipDrive Offices
Remote Workspace
Employees work remotely.
HopSkipDrive’s headquarters is located in Los Angeles’ Little Tokyo district and we love this space! However we believe strongly that most roles allow for a remote-first approach to work and most of our employees work remotely.
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Date Posted
07/08/2026
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