About PrePass PrePass® is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates—creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building scalable systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling through seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day.   That’s why people join us: our solutions operate in real time on highways and interstates across the nation, helping fleets go farther, faster. This work is high-impact and complex, requiring thoughtful leadership, strong execution, and a deep understanding of customer and business needs. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation. Position Summary As a Mid Market Account Executive, you will own the full sales cycle for fleets operating between 200 and 1,000 vehicles. You will serve as a consultative partner to mid-sized for-hire and private carriers, demonstrating how PrePass’s weigh station bypass, toll management, and safety solutions reduce operational costs and improve fleet efficiency. This role requires strong discovery skills, multi-stakeholder relationship management, and a proven ability to close new business in competitive mid-market segments. Essential Responsibilities Revenue Growth & Pipeline Development - Drive net-new revenue by sourcing, qualifying, and closing mid-market fleet customers - Partner with marketing to convert inbound demand and execute targeted outbound efforts across the 200–1,000 vehicle fleet segment - Consistently prospect, secure meetings, and advance opportunities through the sales pipeline Sales Execution & Deal Management - Own the full sales cycle, including discovery, product demonstrations, business case development, pricing, and contract execution - Lead contract negotiations that balance customer value with strong commercial outcomes for PrePass - Maintain accurate forecasting and pipeline hygiene using PrePass sales technologies and processes Customer Engagement & Consultative Selling - Navigate complex fleet organizational structures and engage stakeholders across safety, operations, maintenance, finance, and executive leadership - Deliver consultative value by understanding fleet workflows and aligning PrePass solutions to operational and financial objectives - Serve as a knowledgeable advisor on bypass, tolling, and compliance trends impacting mid-market fleets Cross-Functional Collaboration - Leverage internal resources including solutions consulting, marketing, analytics, and revenue operations to accelerate deal cycles - Collaborate cross-functionally to support customer success and inform go-to-market improvements   What Success Looks Like - Develop a deep understanding of how PrePass solutions improve fleet efficiency, safety performance, and cost savings - Build credibility as a trusted advisor to mid-market fleets through expertise in operations, compliance requirements, toll program dynamics, and technology adoption - Consistently generate pipeline, secure meetings with decision-makers, and deliver effective product demonstrations - Thrive in a fast-paced, growth-oriented environment and contribute to the development of repeatable Mid Market AE playbooks and best practices

• Drive top-line revenue growth through new customer acquisition. • Sell Skillsoft Content, Platform and Services solutions directly to corporate decision makers. • Partner with Specialist reps on cross-sell opportunities for new customers. • Collaborate and partner with Growth reps on upsell opportunities in a land-and-expand sales motion. • Influence prospects at the senior leadership level. • Develop a thorough understanding of Skillsoft sales plays. • Win by representing a solution line with key competitive differentiators. • Partner with related sales, marketing, and support resources in the successful advancement of critical opportunities and market penetration. • Responsible for meeting prep with research, agendas agreed on by prospect and a tailored presentation coupled with impeccable follow-up. • Outline measurable and defined business objectives and goals with timelines, (related to revenue and growth of whitespace). • Document sales data for accurate pipeline management and provide management, feedback and recommendations on pipeline health, risk, opportunity, and progress. • Operate with a sense of urgency, be competitive, and demonstrate a positive, winning attitude.

• You will develop sales plans to effectively and efficiently the accounts within an assigned territory. • You must be able proactively prospect, identify, qualify and develop a robust sales pipeline with minimal supervision. • Meet and exceed your monthly, quarterly and annual sales goals. • Utilize your outstanding communication skills, and sales savvy combined with industry and company knowledge to close deals • Build and maintain close relationships with key decision makers and stakeholders internally, and externally • Understand market trends and interpret data relevant to our initiatives.

• Making daily cold calls & sending emails/text to connect with prospects • Converting prospects & leads into Bobtail clients • Collaborating as a team to accomplish individual, team, and company-wide goals • Maintaining a pipeline of leads and opportunities using our CRM (Salesforce) • Effectively using other sales tools to track progress and improve your performance • Learning about each client’s needs, industry, and competitors. • Building long-lasting, mutually beneficial relationships with prospects and clients to create a better customer experience. • Following up with prospects throughout the sales cycle to continue nurturing them. • Presenting the value of Bobtail products and services to prospects • Staying current on company offerings and industry trends.