Who You Are

Our Data Science and Analytics team is a fast-moving, AI-forward group, that utilizes a modern data stack including SQL, dbt, and Snowflake to deliver accurate data across the company. This analyst role will provide a direct, embedded partnership to the Revenue Operations (RevOps) group. You will:

• Support quota and attainment reporting, giving RevOps leadership real-time visibility into performance versus targets.
• Analyze funnel conversion, win/loss rates, and revenue trends to surface growth opportunities and churn risks for RevOps to act on.
• Contribute to dynamic, scenario-contingent models for revenue forecasting and pricing analysis using Excel, Google Sheets, and/or modern BI tools.
• Partner with Sales leadership on forecasting by providing growth metrics and forward-looking projections to inform planning decisions.
• Maintain and improve Snowflake and dbt data models to ensure accurate, consistent reporting in the source data.
• Version-control all data products in GitHub and build automations to eliminate recurring manual tasks.
• Translate complex data findings into clear, decision-driving language for Sales and RevOps stakeholders.
• Develop self-serve reporting tools that allow business leaders to answer day-to-day questions independently.

Who You Are: 

You are a proactive, technically-grounded analyst who moves fast and understands the intricacies of the sales motion and revenue operations. You are inherently curious love to think critically about the details and the big picture.  You are an expert at interpreting business requests and translating them into rigorous, reproducible analysis while utilizing AI tools to enhance your workflow. You excel at building strong cross-functional relationships to drive alignment on key business objectives. You have excellent communication skills and can translate findings for both technical and non-technical audiences.

5+ years of experience in a data-intensive analyst role at a technology company, specifically within Sales or Revenue Operations.

• Advanced, production-grade SQL skills with the ability to build reliable models and debug complex data issues independently.
• Proven expertise building sophisticated, dynamic models in Excel or Google Sheets for scenario planning and revenue forecasting.
• Direct experience working with dbt for data modeling and transformation within a cloud data warehouse like Snowflake.
• Technical proficiency with Salesforce CRM data models, reporting structures, and data hygiene practices.
• Experience using modern BI tools (such as Tableau, Looker, or Omni) to build reports and self-serve analytics.
• Demonstrated ability to use GitHub for version control, documentation, and maintaining reproducible data pipelines.
• Experience integrating AI systems like Claude into your analytical workflow to increase speed and accuracy.

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 $95,000 - $110,000. 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**

Who We Are

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.

As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility — while making a meaningful difference for those who need it most.  

The Role

The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management, the RAM sets and executes account strategy and provides recommendations to senior staff for required resources, collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account.

This is a revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires strong client communication skills, demonstrated commercial acumen, high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders.

To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:

• In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Who You Are

Required

• 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
• Proven ownership of retention and expansion revenue.
• Strong executive communication and presentation skills.
• Demonstrated success managing complex, multi-stakeholder accounts.
• Advanced CRM discipline and data fluency (Salesforce or equivalent).
• Experience leading cross-functional account execution.
• Comfort operating in ambiguity with accountability for outcomes.
• High operational rigor and the ability to leverage AI into daily workflows 
• Experience in education, government, or regulated markets.
• Familiarity with Challenger or similar insight-led sales methodologies.
• Background in transportation, logistics, or marketplace platforms.

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 committed to fair and equitable compensation practices. The salary range for this role is an $85,000-90,000 base with an OTE of $130,000 - $140,000. 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.

NOTE* This role will be remote but candidates must be based in (Northern CA / Bay Area) . There will be travel required.  The role will require 2-3 days on-site client visits every week.

Who we are

This role will provide exceptional, proactive support for our clients throughout the operational lifecycle. This position bridges the gap between Implementation, Customer Success, and ongoing Operations to streamline service delivery and ensure a premium client experience.

The Metro Service Manager will take ownership of ongoing client operations and issue resolution. This new role will work closely with cross-functional teams to proactively address client needs, improve service quality, and optimize ride experiences. We are looking for creative problem-solvers who, like us, believe that challenges require innovative approaches, unique perspectives, and new ways of thinking.

• Serve as the primary point of contact for assigned clients, ensuring needs are addressed and solutions delivered with urgency and professionalism.
• Respond to and resolve complex client inquiries, leveraging internal resources and collaboration to provide swift resolutions.
• Lead and manage the implementation of new business from contract signed through launch, ensuring a successful implementation process and maintaining communication with clients throughout the implementation 
• Act as a trusted advisor by continuously learning about HopSkipDrive's evolving products and services to best support clients.
• Gather and analyze feedback on ride experiences to identify improvement opportunities and implement service enhancements.
• Collaborate with cross-functional teams to address systemic issues affecting client satisfaction and advocate for impactful changes.
• Partner with Customer Support Specialists to resolve real-time ride and account issues while delivering weekly optimization reports.
• Conduct virtual and in-person client meetings to strengthen relationships, align on goals, and ensure adoption of best practices.
• Drive the strategic planning and execution of business reviews to align ongoing service strategies with client objectives.

Who You Are

You’re a proactive and strategic customer success professional who excels at building strong client relationships, solving complex challenges, and driving measurable results. You thrive in fast-paced environments and are passionate about enhancing client experiences through data-driven insights and collaboration.

• 5+ years of experience in Customer Success, Account Management, or Implementation roles, preferably in a high-pressure or start-up environment.
• Willingness to travel (10%-20%) to strengthen client relationships and support service strategies.
• Proven ability to manage client relationships, resolve issues swiftly, and deliver exceptional customer service.
• Strong communication skills, both written and verbal, with the ability to present insights and solutions effectively in meetings and reports.
• Expertise in analyzing data, identifying trends, and implementing actionable solutions to improve client outcomes.
• Experience collaborating across teams to address root causes of recurring challenges and enhance service delivery.
• Proficiency with CRM tools such as Salesforce or Kustomer, and advanced Excel skills are preferred.
• A proactive, problem-solving mindset with the initiative to drive continuous improvement and innovation.
• You are tech-forward and committed to operational excellence. You actively leverage AI tools (such as Gemini) to streamline workflows, summarize complex client issues, refine communication, and derive insights from data sets, and you are eager to apply this expertise to enhance client outcomes

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 committed to fair and equitable compensation practices. The base salary range for this role is $80,000 - $90,000. 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.

*NOTE* This role will be remote but candidates must be based in the Arizona metro. There will be occasional (10-20%) travel required as well.  

Who We Are

The New Markets team is a fast-moving, high-impact group focused on launching and scaling operations in new regions. We are looking for an analytical, adaptable, and proactive operator to join our team and own the end-to-end success of our marketplace performance.

• Own near-term supply and demand forecasts for launch markets by designing and maintaining predictive models aligned to company directives.
• Operate and optimize marketplace configurations, including zip code mapping and cluster assignments, to maximize supply-demand matching efficiency.
• Design, build, and ship targeted productivity promotions to address fill rate gaps, manage market spend, and drive operational efficiency.
• Evaluate market health by monitoring net revenue and contribution margin, recommending cross-functional remediation for struggling markets.
• Monitor performance trends proactively, identifying root causes of off-track metrics and bringing forward data-backed recommendations.
• Own end-to-end project workstreams by defining scope, identifying owners, tracking progress, and ensuring cross-functional execution.
• Leverage AI-assisted workflows to accelerate research, monitor territory performance, and pressure-test strategic recommendations.

Who You Are

You are a high-agency operator who thrives in ambiguous environments and possesses a relentless drive to solve complex operational challenges. You have a proven track record of managing stakeholders, utilizing data to influence outcomes, and building scalable processes from the ground up.

• 3+ years of experience driving superior results in analytical, cross-functional, or operations roles, ideally in marketplace, logistics, or high-growth environments.
• Excel/Google Sheets power user capable of building complex, elegant models with advanced formulas and dashboards that work for non-technical stakeholders.
• Demonstrated ability to make nuanced business decisions based on imperfect information while remaining accountable for the outcomes.
• Proven ability to lead projects involving stakeholders who do not report to you, aligning teams and resolving friction to drive closure.
• Strong communication skills with the ability to translate complexity for different functions and levels without losing precision.
• High agency in identifying necessary actions and executing them independently in a fast-moving environment.
• Experience independently pulling and structuring data, with comfort using SQL or other data querying tools.
• Working knowledge of Tableau; expected to grow in report-building and contribute to team dashboards
• Demonstrated comfort using AI tools (such as Claude, ChatGPT, Perplexity, or equivalent) as an integral part of your actual daily workflow.
• You’ll flex across the full lifecycle of a launch — from infrastructure setup to cross-functional coordination to performance monitoring — doing whatever it takes to get a city operational and on a path to contribution margin positive. 
• This is not a role for people who wait for direction. It’s for operators who identify gaps, build the tools to close them, and hold themselves accountable to outcomes.

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 95,000 - 110,000.  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**  Prioritizing candidates in Eastern and Southeast states based on business needs. 

Who We Are:

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact.  Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions. 

As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what's possible in mobility-while making a meaningful difference for those who need it most. 

The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.

This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.

To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:

• In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions.
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Who You Are:

Required

• 8+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
• Proven ownership of retention and expansion revenue.
• Strong executive communication and presentation skills.
• Demonstrated success managing complex, multi-stakeholder accounts.
• Advanced CRM discipline and data fluency (Salesforce or equivalent).
• Experience leading cross-functional account execution.
• Comfort operating in ambiguity with accountability for outcomes.
• Experience in education, government, or regulated markets highly preferred 
• Familiarity with Challenger or similar insight-led sales methodologies highly preferred 
• Background in transportation, logistics, or marketplace platforms highly preferred
• High operational rigor and the ability to leverage AI into daily workflows 

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 committed to fair and equitable compensation practices. The salary range for this role is an $90,000-100,000 base with an OTE of $150,000 - $170,000. 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.

NOTE* This role will be based in MN, WI, MI, PA, VA, MD, DC. There will be travel required.  The role will require 2-3 days on-site client visits every week.

Who We Are

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.

As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility — while making a meaningful difference for those who need it most.  

The Role

The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management, the RAM sets and executes account strategy and provides recommendations to senior staff for required resources, collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account.

This is a revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires strong client communication skills, demonstrated commercial acumen, high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders.

To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:

• In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Who You Are

Required

• 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
• Proven ownership of retention and expansion revenue.
• Strong executive communication and presentation skills.
• Demonstrated success managing complex, multi-stakeholder accounts.
• Advanced CRM discipline and data fluency (Salesforce or equivalent).
• Experience leading cross-functional account execution.
• Comfort operating in ambiguity with accountability for outcomes.
• High operational rigor and the ability to leverage AI into daily workflows 
• Experience in education, government, or regulated markets.
• Familiarity with Challenger or similar insight-led sales methodologies.
• Background in transportation, logistics, or marketplace platforms.

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 committed to fair and equitable compensation practices. The salary range for this role is an $85,000-90,000 base with an OTE of $130,000 - $140,000. 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.

NOTE* This role will be remote but candidates must be based in (WI, MN, VA, MI, PA) . There will be travel required.  The role will require 2-3 days on-site client visits every week.

Who We Are

We are a team of advocacy and legislative professionals working to drive change through rulemaking, community organizing, and coalition building to support our policy priorities. Our small but impactful team is composed of creative problem-solvers dedicated to advancing transportation equity through strategic government relations.

• Monitor, analyze, and track legislative and regulatory activity across assigned markets to identify business risks and opportunities.

• Build and maintain working relationships with policymakers, agency staff, legislative aides, and third-party advocates.

• Draft high-impact position papers, testimony, comment letters, and internal policy memos.

• Support the coordination of external lobbyists and advocacy consultants in assigned jurisdictions.

• Partner with cross-functional teams, including Legal and Operations, to translate policy developments into actionable business guidance.

• Represent HopSkipDrive in stakeholder meetings, coalition convenings, and public forums.

• Contribute to internal reporting on legislative status, hearing calendars, and advocacy progress.

• Utilize AI tools to support research, drafting, and workflow efficiency consistent with team standards.

Who You Are

You are a highly organized, detail-oriented strategist with a proven track record in developing and overseeing results-driven policy campaigns. You are a skilled communicator who can navigate complex regulatory language and serve as a key advisor on all matters related to government affairs.

• At least 5-6 years of combined experience in government relations, regulatory agencies, or public policy roles.

• Proven ability to research and analyze statutes and regulations with high attention to detail.

• Demonstrated experience with the legislative process and managing relationships with external lobbyists.

• Strong ability to translate complex policy impacts into clear guidance for business stakeholders.

• Exceptional communication skills with experience serving as a public face to policymakers and governmental contacts.

• Proven track record of building relationships with diverse stakeholders to further organizational missions.

• Highly organized with the ability to manage and advance several policy initiatives simultaneously.

• Strategic mindset with the ability to identify policy-related opportunities in rapidly shifting markets.

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 - $135,000. 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*

Who We Are:

The Operations Excellence team is the engine behind how HopSkipDrive scales its processes, systems, and operational workflows. In 2026, this role is uniquely focused on leading the team through a pivotal transformation: shifting from manual, people-intensive operations to AI-enabled, automated workflows — all while maintaining the safety and compliance rigor our platform demands. You will be responsible for the following:

• Lead the AI & Automation transformation, owning the strategic roadmap to move Operations Excellence from manual oversight to intelligent, exception-based processing using Agentic AI workflows, and LLM-integrated tooling.
• Manage and develop the Ops Excellence team, including a manager and three direct reports, fostering growth during technical transitions. 
• Identify, prioritize, and execute automation opportunities across central operations, supply activation, marketplace workflows, and compliance processes — working cross-functionally with Product and Engineering to build and iterate.
• Drive measurable improvements in throughput, yield, and cycle time, hitting or exceeding the efficiency benchmarks set for the 2026 fiscal year.
• Leverage 2026-standard automation tools (Agentic AI workflows, advanced OCR, automated identity verification, and internal AI orchestration platforms) to evolve process capabilities and eliminate manual friction.
• Synthesize complex data insights from our analytics suite to proactively identify and resolve funnel drop-off points, process bottlenecks, and operational risk areas in real-time.
• Partner with Product and Engineering to define the technical roadmap for intelligent process automation, including zero-touch onboarding and automated re-certification journeys.
• Build the AI/Automation KPI framework, establishing metrics for automation impact — time saved, error reduction, cost efficiency, and team engagement lift.
• Manage hybrid workforces, ensuring that onshore teams and offshore partners are up-skilled and effectively utilizing our latest AI orchestration tools.

Who You Are:

You're a strategic leader who thrives on the challenge of evolving operations through cutting-edge technology. You have a proven track record of managing high-volume processes and leading teams through the cultural and operational shifts that automation demands. You bring:

•  Change Management Leader with experience guiding teams through technical transitions and fostering an "AI-first" mindset across the organization.
•  Operations Transformation Experience — you've led at least one major shift from manual to automated workflows in a high-growth or technology-driven environment.
•  Technical Problem-Solver proficient in leveraging modern AI/ML tools, Agentic workflows, and LLM-integrated processing to scale operations.
•  Data-Driven Strategist who uses advanced visualization and predictive metrics to analyze funnel health and drive continuous improvement.
•  Strong Cross-Functional Collaborator skilled at partnering with Product and Engineering to build and iterate on internal technical tools.
•  People-First Manager with 5+ years of management experience, including experience developing mid-level managers. You know how to build trust, address engagement gaps, and develop talent — especially through periods of significant change.
•  Strategic Project Leader with advanced project management expertise, leveraging ROI-driven analysis to prioritize process intake, optimize resource allocation, and maximize impact.
•  Results-Oriented Operator with a deep focus on targeted outputs, yield optimization, and reducing cycle times in a high-growth environment.

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 in is 105,000 - 150,000 per year. 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, CT, 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*