New Business Sales Manager

HopSkipDrive

5d•Remote

About The Position

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. 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:

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.