Go-to-Market (GTM) Engineer

Our goal is to create opportunity for all through mobility.

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

Our Information Technology teams take pride in advising and enabling our go-to-market (GTM) functions, ultimately driving growth by delivering scalable systems, automation, and data driven insights.

As a GTM Engineer, with consumption-based “pay as you go” business model experience, you will support the business through the following responsibilities:

• Configure and optimize Salesforce and connected GTM tools (CPQ, marketing automation, customer success platforms, etc.) to ensure seamless data flow and operational efficiency.
• Apply AI-powered tools for forecasting, intelligent prospecting, and automated outreach.
• Integrate applications via APIs and automation platforms to ensure seamless data flow.
• Design and implement automations to eliminate manual work and improve GTM efficiency.
• Partner with Sales Ops, Marketing Ops, and Customer Success to identify bottlenecks and design scalable processes.
• Develop reporting, dashboards, and analytics to measure pipeline, revenue, and team performance.
• Gather requirements from GTM stakeholders, translate them into technical designs, and deliver scalable solutions.
• Document processes, systems, and configurations; deliver user training and best practices.
• Build workflows that capture, score, and route leads from web traffic, signups, and campaigns.
• Work cross-functionally with Sales, Marketing, Product, Finance, and IT to align on GTM initiatives.

Who You Are

You are a visionary GTM engineer who will be a “force multiplier”, passionate about leveraging automation and AI to build scalable systems that empower high-performing GTM teams. With the following skills, you will make a tangible and immediate impact, propelling our Revenue team's growth:

• Hands-on scripting, coding, and prototyping skills (Python, JavaScript) for integrations and automations.
• Experience with APIs, webhooks, and automation platforms (Workato, Zapier, n8n).
• Technical expertise with Prospecting, Lead Management, Sales Engagement, and Sales Enablement and Deal Management platform integrations (e.g., Outreach,Seismic, HubSpot,ZoomInfo).
• Applied AI knowledge: Designing AI-driven scoring models that combine CRM, product usage, and external data to prioritize accounts.
• Familiarity with various AI tool and platform implementations (LLMs, conversational AI, RevOps AI tools such as Gong, Fireflies, Intercom, Drift, or LangChain).
• Familiarity with custom Competitive Intelligence tools and integrations.
• Proficiency with data analysis and BI tools (SQL, Snowflake, Tableau, or equivalent).
• Strong understanding of GTM and Revenue Operations principles and best practices.
• Effective communicator with the ability to translate complex needs into actionable solutions.

Nice to have experience:

• Applying machine learning forecasting models (e.g., Vertex AI) to predict pipeline health and revenue 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 base salary range for this role is $145,000 - $165,000. 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 in which we hire in: 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