Senior Learning & Development Facilitator

Position Overview

At HopSkipDrive, 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.

Our small but mighty Learning & Development team is dedicated to fostering a culture of continuous growth and excellence at HopSkipDrive. We are a two-person team passionate about designing and delivering impactful learning experiences that empower our employees and leaders. The Senior Learning & Development Facilitator will be instrumental in bringing best practices, upleveling our existing programs, and spearheading new initiatives to support our rapidly scaling organization. By aligning learning initiatives with business priorities, we do, and you will, support the business.

Responsibilities

• Design and develop comprehensive learning experiences, including instructor-led content (virtual and in-person), eLearning modules, job aids, and multimedia assets, applying adult learning principles and instructional design methodologies.
• Facilitate engaging and impactful training sessions on a variety of topics, with a strong emphasis on leadership development, team development, and change management.
• Conduct thorough needs assessments and analyze skill gaps to identify appropriate training solutions and lead the development of blended learning programs.
• Manage multiple instructional development projects simultaneously, ensuring timely delivery, stakeholder alignment, and effective collaboration with cross-functional teams and external vendors.
• Evaluate the effectiveness of training programs using data, learner feedback, and performance outcomes, continuously iterating to improve impact and demonstrate ROI.
• Stay current with industry trends and innovations in learning technology and leadership development, integrating modern learning approaches (microlearning, social learning, LXPs, mobile learning) into program design.
• Partner with subject matter experts (SMEs) and business leaders to translate complex information into clear, concise, and actionable learning content.
• Proactively identify opportunities for new programming and methodologies, creating repeatable resources and frameworks to support organizational scalability.

Requirements

• 7+ years of experience in a Learning & Development role, with a strong focus on instructional design, learning experience design, and program development.
• Proven expertise in facilitating and coaching both virtually and in-person, with a track record of attracting and engaging participants.
• Demonstrated experience in leadership development, including building, facilitating, and assessing the influence of change management and leadership development for various organizational levels.
• Strong practical knowledge of learning technologies.

Application Instructions

• [Application instructions not provided]

Company Information

• Company: HopSkipDrive
• Mission: To create opportunity for all through mobility.
• Industry: Technology, Transportation
• Funding: Series D, $100M raised
• Recognition: Inc. 5000 (4x), Deloitte 500 Fast-Growing Technology list
• Team: Small but mighty Learning & Development team (2 people)