Full-Time

New Business Sales Manager

Posted on 11/14/2025

HopSkipDrive

HopSkipDrive

501-1,000 employees

Safe child transportation via vetted drivers

Compensation Overview

$150k/yr

+ OTE + Equity Stock Options

Remote in USA

Remote

Category
Sales & Account Management (1)
Requirements
  • B2B Strategic Sales Experience: 10+ years as an individual contributor with a track record of prospecting, managing a pipeline, pitching, effective negotiation, and closing. Specific experience focused on hunting and closing new enterprise accounts with complex, medium to long sales cycles (12+ months)
  • Effective Leadership: 5+ years leading sales teams of 5 reps or more to meet or exceed targets through repeatable and scalable methods.
  • Growth Mindset: You believe that you and your team can always improve, and you are motivated to ask challenging questions and do the research to identify and continuously refine your approach. You have a high degree of resilience, intellectual curiosity, and a growth mindset necessary to navigate the ambiguity and complexities of a dynamic market
  • Scaling Teams: Proven experience scaling a sales team through predictable and repeatable methods that we will allow the organization to measure and coach individuals' performance.
  • Demonstrated Trust: Commitment to building trust, credibility, and collaboration with both internal and external audiences through clear and effective communication while working in a remote environment. Demonstrating success in consistently hitting and/or exceeding sales goals and quotas.
  • Startup Mentality: The ability to work independently in a fast-paced, deadline-driven environment with minimal direction and high visibility while remaining flexible to change.
  • Tech Stack Familiarity: Experience with CRM tools and sales analytics platforms, for example, Salesforce, Seismic, and Outreach along with the G Suite(Docs, Sheets, Slides).
Responsibilities
  • New Business Focus: Lead the team to aggressively prospect and close new accounts, consistently meeting or exceeding quarterly and annual new business revenue targets.
  • Forecasting and Pipeline Management: Own and manage the accurate weekly, monthly, and quarterly sales forecasting process, ensuring pipeline health and data integrity through deep pipeline reviews.
  • Strategic Planning: Ensure all Account Executives develop and execute comprehensive territory plans and strategic account plans, focusing on high-potential targets and market penetration.
  • Deal Support & Executive Engagement: Provide expert deal support for high-value opportunities. Lead and facilitate executive engagement to accelerate sales cycles, drive multithreading, and secure key deals.
  • Target Prospecting: Implement and coach AEs on high-impact prospecting strategies and best practices.
  • Account Executive Management: Directly manage, mentor, and motivate a team of Account Executives to maximize their individual and team performance.
  • Coaching & Development: Serve as a dedicated coach, providing constructive feedback on deal strategy, negotiation, presentation skills, and overall sales execution. Conduct regular one-on-one sessions and field shadowing.
  • Talent Development: Identify individual strengths and weaknesses, developing personalized growth plans and necessary training to enhance sales acumen and professional development.
  • Accountable Leadership: Set clear performance expectations and hold team members accountable for targets, activity metrics, and process adherence, celebrating success and managing underperformance effectively.
  • Sales Acumen: Demonstrated expertise in understanding complex sales cycles, market dynamics, and customer business challenges, coupled with exceptional ability to recruit, lead, and inspire a high-performing sales team.
  • Problem Solving and Analytics: Utilize strong problem-solving and analytical skills to interpret sales data, identify performance gaps, and quickly adjust strategies to capitalize on market opportunities.
  • Communication Skills: Possess superior communication skills (written and verbal) to articulate complex value propositions, manage internal stakeholders, and engage credibly with senior-level customers.
  • Embrace Resilience: Foster a culture of resilience within the team, navigating setbacks and market challenges with a positive, proactive, and determined attitude.
Desired Qualifications
  • None, since after filtering the text for non-trivial items, the job posting does not list any "desirable" or "preferred" qualifications.

HopSkipDrive provides specialized transportation for children, connecting families, schools, and social service agencies with vetted CareDrivers who ensure safe and reliable rides to school, activities, and essential appointments. How it works: CareDrivers set their own hours and undergo extensive background checks and training, with technology and logistics coordinating pickups, routes, and on-time arrivals. The company earns service fees from families and partner institutions, focusing on safety and dependability rather than general ride-hailing. What sets HopSkipDrive apart is its mission-driven model: a focus on child safety, formal partnerships with school districts and counties, and a rigorous driver vetting process that enables scheduled, organized transportation for youth. The goal is to make sure children reach their destinations safely, on time, and with trusted adults supervising the ride while offering flexible earning opportunities for CareDrivers.

Company Size

501-1,000

Company Stage

Series D

Total Funding

$107M

Headquarters

Los Angeles, California

Founded

2014

Simplify Jobs

Simplify's Take

What believers are saying

  • School bus driver shortage persists, increasing district demand for supplemental transportation services.
  • Flexible Invoice Groups automates complex billing across multiple funding sources, reducing administrative burden.
  • Ride Recording: In-App and Track My Ride enhance safety positioning, strengthening district contract retention.

What critics are saying

  • School district budget cuts reduce supplemental transportation spending as districts prioritize core services.
  • Established logistics firms enter market with lower-cost fleet infrastructure, undercutting HopSkipDrive pricing.
  • Gig-economy reclassification forces CareDriver employment status change, eliminating flexible cost model advantage.

What makes HopSkipDrive unique

  • Direct CareDriver relationships eliminate middleman markups and fragmented data versus unregulated brokers.
  • Specialized focus on McKinney-Vento, foster care, and IEP students addresses underserved market segments.
  • RouteWise AI platform provides multimodal routing and budget alignment automation for districts.

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Your Connections

People at HopSkipDrive who can refer or advise you

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

401(k) Retirement Plan

401(k) Company Match

Unlimited Paid Time Off

Company Equity

Stock Options

Health Savings Account/Flexible Spending Account

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

2%

2 year growth

5%
The AI Journal Ltd
Mar 12th, 2026
HopSkipDrive Elevates Student Safety Standards with Launch of Ride Recording: In-App

HopSkipDrive elevates student safety standards with launch of Ride Recording: In-App. Additional features empower students to track their own rides in real-time for added peace of mind, while ensuring transparency for school districts LOS ANGELES-(BUSINESS WIRE)-HopSkipDrive, the leader in safe, fast, and simple supplemental student transportation, today announced the launch of Ride Recording: In-App. This major safety milestone enhances the company's existing ride recording capabilities, bringing school districts an even more affordable, flexible, and secure recording option than dashcams. This launch joins the new "Track My Ride" web interface designed to increase visibility and transparency. The introduction of Ride Recording: In App represents a significant development in HopSkipDrive's leadership on safety. Available network-wide across all HopSkipDrive markets, 100% of rides this Fall will feature Ride Recording: In-App. This enhances the company's existing dashcam recording solution by utilizing the native camera capabilities of the driver's smartphone. To ensure The AI Journal Ltd. meet the unique needs of every district partner, HopSkipDrive will continue to offer in-ride dashcams for districts that require them. By integrating directly into the device drivers already use for real-time navigation and ride management, Ride Recording: In App enables HopSkipDrive to consistently improve the software while preventing driver intervention or access. To ensure total security and privacy, drivers have zero access to the files, and all footage is automatically wiped from the device after the ride. This software-based innovation also allows the company to scale this feature across all districts effortlessly, meeting interior recording requirements for students of all needs without the high expense or time-consuming process of retrofitting an entire fleet with physical hardware. Captured via a direct system that ensures total security and student privacy while extending visibility and transparency to school districts and HopSkipDrive's Safe Ride Support(R) team, which helps provide human eyes on every ride. In addition to Ride Recording: In-App, HopSkipDrive is proud to announce Track My Ride, which gives riders access to a link to track their journey in real-time. While many riders use the HopSkipDrive app today to see their driver and ride details, the company recognizes that some students rely on wearables, smartwatches, or school- or government-issued devices that do not allow app installs. Track My Ride fosters digital equity by providing secure, masked SMS links that open in a standard web view. This removes the friction of app downloads and eliminates the need for manual staff coordination, creating a simpler, less stressful pickup experience for riders, caregivers, and school staff alike. By providing real-time visibility to every student regardless of their device, HopSkipDrive gives riders the peace of mind they need to feel confident on their way to school while ensuring caregivers no longer need to share access to their account credentials and the caregiver-specific permissions within that app. "At the end of the day, student transportation is built on trust," said Joanna McFarland, Co-founder and CEO of HopSkipDrive. "By introducing Ride Recording: In-App and Track My Ride, we are reinforcing that trust with even greater real-time visibility and a clear record of every journey. We want our partners to have the most reliable safety features available, along with the administrative tools that actually make their jobs easier." About HopSkipDrive HopSkipDrive is a leading technology company partnering with school districts to get kids to school more quickly, safely, and easily than anyone else. The company is modernizing the $30 billion school transportation industry through two core solutions: a care-centered transportation marketplace and an industry-leading transportation intelligence platform, RouteWise AI(TM). HopSkipDrive's marketplace supplements school buses and existing transportation options by connecting kids to highly-vetted caregivers on wheels, such as grandparents, babysitters, and nurses in local communities. RouteWise AI helps schools and districts address critical challenges, including budget cuts, bus driver shortages, and reaching climate goals. HopSkipDrive has supported over 13,500 schools across 21 states, with nearly 1,300 school districts, government agencies, and nonprofit partners. More than five million rides over 95 million miles have been completed through HopSkipDrive since the company was founded in 2014 by three working mothers.

Business Wire
Mar 12th, 2026
HopSkipDrive launches in-app ride recording for student transport safety across all US markets

HopSkipDrive, a student transportation company, has launched Ride Recording: In-App, a software-based safety feature that uses drivers' smartphone cameras to record all rides. The system will be available across all markets this autumn, with 100% of rides featuring the technology. The in-app recording solution enhances HopSkipDrive's existing dashcam capabilities whilst offering a more affordable and flexible alternative. Drivers cannot access recorded footage, which is automatically deleted from devices after rides. The company will continue offering physical dashcams for districts requiring them. HopSkipDrive also introduced Track My Ride, a web-based interface allowing students to track journeys in real-time via SMS links, eliminating app download requirements. Founded in 2014, the company has completed over five million rides across 21 states, serving nearly 1,300 school districts and partners.

Remote Source
Dec 15th, 2025
Alpaca your bags

Alpaca your bags. Inside: Alpaca has team members in almost every time zone, and they're hiring. Plus: Honor and HopSkipDrive, two remote-first companies in the caregiver space, are hiring as well. Really feels like we're in the home stretch for the year now. After this week we're into Christmas and New Years! Still trying to wrap my head around using the date "2026" but I suppose I can save that battle for a few weeks from now. Alpaca, Honor, and HopSkipDrive are featured this week, collectively hiring for almost 60 remote jobs. Best of luck in your search! Companies hiring remotely. * Alpaca builds financial services APIs and bridges the gap between those who can access financial services and those who cannot. * From their Careers page: "Our teams are not just global, we're also 100% remote and have team members in almost every time zone and continent (except Antarctica). By joining Alpaca you'll be part of a multicultural, international organization." * See their job openings here. * Honor is a technology-enabled home care company that partners with local agencies and health systems to provide in-home care for older adults by matching them with professional caregivers and coordinating care through a centralized platform. * From their Careers page: "A remote-first work model lets you work from anywhere in the U.S. or occasionally pop into a satellite office." * See their job openings here. * HopSkipDrive is a transportation platform that provides safe, reliable rides for children and seniors, using vetted caregivers and drivers to support families, schools, and care organizations. * From their Careers page: "we believe strongly that most roles allow for a remote-first approach to work. We support employment across the U.S. and employee flexibility to accommodate personal commitments, which we believe ultimately leads to a more inclusive and diverse workforce." * See their job openings here. 20,000+ remote jobs. Remote-First focus. * Remote Source is the only remote job board with a certified Remote-First filter - these companies aren't about to force you back into an office. * We guarantee no scams because we hand-pick each employer featured on the job board. * All of our company feeds are updated multiple times per day, so you can be the first to apply to your favorite jobs. * With a free account, you can view all jobs on the job board. That's already more than what most remote job boards can say! * For less than $1/week, | Pro users get even more: * Remote-First Company search filter * Leadership Roles search filter * Daily custom email alerts * Unlimited saved jobs * Unlimited saved searches If you're serious about finding a remote job ASAP, or you don't have time to search for new remote jobs every single day, the | Pro plan was built for you. Try it out today: Helpful links. The Remote Source job board has 20,000+ open remote jobs, all from hand-picked, established companies. It's updated daily, and it's completely free to access all jobs, unlike most major remote job boards. PRO users can filter for remote-first companies and Leadership Roles, get unlimited saved jobs and searches, AND get daily email alerts for jobs matching their search criteria. If you'd like to get more updates from us throughout the week, you can find us on Instagram, X, LinkedIn, Facebook, and Threads. I'll ship your choice of a Remote Source Yeti or Stanley mug to the first person who can guess where this was taken

School Transportation News
Nov 12th, 2025
HopSkipDrive Elevates Safety Standards with New CareDriver Education Programs and Enhanced Certification Process

HopSkipDrive elevates safety standards with new CareDriver Education Programs and enhanced certification process. New Initiative Deepens Commitment to Safety Acrossthe Entire CareDriver Lifecycle, from Pre-Certification to On-Platform Education LOS ANGELES, Calif. - HopSkipDrive, a technology company solving complex transportation challenges for more than 13,500 schools, today announced key enhancements to its industry-leading safety program. The company has launched a strengthened educational curriculum for CareDrivers, developed in partnership with child development experts, and will be rolling out a more sophisticated, skills-based CareDriver certification process to offer enhanced support for all students, including those with diverse needs and Individualized Education Programs (IEPs). This dual investment raises the industry bar by shifting from fixed quantitative requirements to a more thoughtful, qualitative assessment of a candidate's caregiving capabilities. As part of the HopSkipDrive 15-point certification process, this skills-based video screening moves beyond fixed requirements to a more meaningful evaluation of a candidate's situational judgment, empathy, and readiness to work with children. Because HopSkipDrive maintains a direct relationship with the CareDriver community, the company is uniquely positioned to implement these higher standards for screening and ongoing education, contributing to its industry-leading safety and compliance record. In parallel, HopSkipDrive has launched new educational modules designed to provide CareDrivers with leading-edge skills to support neurodivergent riders. The curriculum was developed in partnership with Jenifer Eaton, MA, BCBA and Timothy Humphrey, M.S.Ed., BCBA, of Rooted in Play, as well as Steve Nederveld, former Director of Mental Health for Cherry Creek Schools. Eaton and Nederveld also recently joined HopSkipDrive's Safety Advisory Council. The program focuses on understanding sensory sensitivities, de-escalation techniques, and communication strategies. "Safety and trust are the foundation of everything we do, and this evolution of our programs represents a deeper commitment to those values. We know that being a great caregiver starts with prior experience, and is further developed with the resources and education HopSkipDrive provides once CareDrivers are on the platform," said Jen Brandenburger, SVP of Safety at HopSkipDrive. "By pairing a more intelligent, skills-based certification process with expert-led continuing education, we can help ensure CareDrivers are exceptionally prepared to support every child. This holistic approach raises the standard for the entire student transportation industry and reinforces our commitment to being the most trusted partner for schools and families." The new initiative reflects HopSkipDrive's dedication to providing the most empathetic and effective specialized transportation solutions, built upon a foundation that includes trauma-informed care education, Child Abuse and Neglect screenings, and three types of rigorous background checks. "A safe, positive ride to school plays a crucial role in a student's overall success and that begins with a prepared, empathetic adult behind the wheel," said Jenifer Eaton. "HopSkipDrive's commitment to helping CareDrivers better understand trauma-informed practices and the unique needs of neurodivergent students is truly invaluable. By equipping CareDrivers with these insights and strategies, we're building a more compassionate and responsive system, one that ensures every student is supported with the patience, understanding, and respect they deserve." The new education modules are now available to all CareDrivers on the platform, and the enhanced certification process will begin rolling out to new applicants over the coming weeks. About HopSkipDrive HopSkipDrive is a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. HopSkipDrive is modernizing the $30 billion school transportation industry through two core solutions: a care-centered transportation marketplace and an industry-leading transportation intelligence platform, RouteWise AI. HopSkipDrive's marketplace supplements school buses and existing transportation options by connecting kids to highly-vetted caregivers on wheels, such as grandparents, babysitters, and nurses in local communities. RouteWise AI helps schools and districts address critical challenges, including budget cuts, bus driver shortages, and reaching climate goals. HopSkipDrive has supported over 13,500 schools across 17 states, with nearly 1,300 school districts, government agencies, and nonprofit partners. More than five million rides over 95 million miles have been completed through HopSkipDrive since the company was founded in 2014 by three working mothers.

Travel And Tour World
Sep 17th, 2025
HopSkipDrive's New Model Enhances School Bus Systems Amid Driver Shortages

School districts such as Tolleson Union High School District in Arizona have already partnered with HopSkipDrive to optimise their transportation networks.

INACTIVE