New Business Sales Manager

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. We are seeking a highly motivated and results-oriented New Business Sales Manager to lead our team of Account Executives (AEs) with a singular focus on driving all new revenue acquisition. The ideal candidate is a dynamic leader with exceptional sales acumen and people management skills, a proven ability to forecast accurately, and a passion for coaching and developing top sales talent. This role is critical to the company's growth strategy and requires a leader who demonstrates accountable leadership and an embrace of resilience in a competitive market. .

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

Revenue Generation & Strategy

• 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.

Team Leadership & Development

• 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.

Who You Are

You're passionate about scaling and mentoring a world-class sales team that will drive sales growth, and deliver impactful solutions to prospective clients. With personal expertise in pitching, negotiation, and closing, you can confidently coach your team to sell the value propositions of HopSkipDrive to prospective clients and convert them into active paying clients. You’re motivated by results and thrive in dynamic environments where our contributions directly drive to success.

With the required qualifications and necessary experience listed below, your impact will be tangible and immediate:

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).

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 a $150,000 base with an OTE of $230,000-$250,000. 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**