About the Company

Pathwise (formerly TransAct) is a leading provider of cloud-based operational solutions built for the K–12 education community. With more than 30 years of experience and a team that includes former district administrators and transportation directors, we build software that solves the real challenges of running school operations. Serving more than 3,000 school districts and charter organizations—along with 25+ state departments of education—Pathwise delivers expertise driven tools across student transportation, after-school program management, McKinney-Vento coordination, parent communication, and board governance.

About the Role

We are seeking an experienced K–12 Account Executive to drive new business growth within the education market. This is not an entry-level sales role. Direct experience selling to K–12 schools, school districts, or state education agencies is required. Candidates should also have demonstrated experience carrying a quota and closing complex, multi-stakeholder sales opportunities. You will own opportunities through the full sales cycle—from prospecting and discovery through demonstrations, procurement, negotiation, and close. Success requires an understanding of how school districts buy, the ability to navigate lengthy and sometimes complex procurement processes, and the discipline to consistently build and advance pipeline. Experience selling technology to K–12 transportation departments or transportation leadership is strongly preferred.

Responsibilities

• Own the Full Sales Cycle
• Develop and execute a territory and prospecting strategy that consistently creates qualified pipeline.
• Identify and engage district decision-makers, operational leaders, executive stakeholders, and other buying influences.
• Lead discovery to understand district needs, workflows, challenges, priorities, budget, decision criteria, and timing.
• Manage opportunities from initial engagement through proposal, procurement, negotiation, and contract execution.
• Consistently achieve or exceed assigned revenue and sales targets.
• Navigate Complex K–12 Sales
• Build relationships across multiple stakeholders within school districts and education organizations.
• Navigate K–12 purchasing processes, including RFPs, formal bids, purchasing cooperatives, budget cycles, security reviews, legal review, and other approval requirements.
• Manage longer sales cycles with clear next steps, strong follow-through, and effective deal strategy.
• Develop compelling business cases that connect Pathwise solutions to district operational and strategic priorities.
• Sell Consultatively
• Become knowledgeable about Pathwise products and the operational challenges they solve.
• Conduct compelling presentations and demonstrations tailored to district executives, transportation leaders, operational teams, and other stakeholders.
• Partner with Solutions Engineering when technical validation, solution design, or deeper product expertise is required.
• Clearly articulate value, differentiation, ROI, and customer outcomes.
• Build and Manage Pipeline
• Maintain sufficient pipeline coverage to achieve revenue targets.
• Prospect through outbound outreach, referrals, conferences, industry relationships, partnerships, and inbound opportunities.
• Maintain accurate opportunity stages, close dates, next steps, deal risks, and forecasts in CRM.
• Use data and pipeline metrics to prioritize activity and improve sales performance.
• Collaborate Across Pathwise
• Partner closely with Sales Development, Solutions Engineering, Customer Success, Marketing, Product, and other internal teams.
• Share market intelligence, competitive insights, and customer feedback.
• Ensure a strong transition from Sales to implementation and Customer Success following contract execution.

Qualifications

• Direct professional experience selling products or services to K–12 schools, school districts, or state education agencies.
• At least 2 years of experience carrying an individual sales quota in a closing sales role.
• Demonstrated success meeting or exceeding revenue targets.
• Experience selling software, technology, or another complex solution involving multiple decision-makers and stakeholders.
• Experience managing longer sales cycles, including opportunities lasting approximately 90 days or longer.
• Strong prospecting and pipeline-generation capabilities; this role requires proactive business development in addition to closing inbound opportunities.
• Demonstrated consultative selling, negotiation, and relationship-building skills.
• Strong verbal, written, presentation, and executive communication skills.
• Ability to independently manage multiple active opportunities and competing priorities.
• Experience working within a CRM and maintaining disciplined pipeline and forecasting practices.
• Ability and willingness to travel regularly, up to approximately 30%, for customer meetings, conferences, industry events, and territory development.

Preferred Skills

• Experience selling directly to K–12 student transportation departments, transportation directors, or district operations leadership.
• Experience selling recurring-revenue SaaS or subscription-based technology.
• Experience with public-sector or K–12 procurement processes, including RFPs, formal bids, purchasing cooperatives, and structured approval processes.
• Existing knowledge of K–12 transportation, school operations, or education technology.
• Established relationships within the K–12 education or student transportation community.

Pay range and compensation package

Pathwise offers a competitive compensation and benefits package, including medical, dental, and vision insurance, a 401(k) with company match, paid time off and holidays, and a flexible remote work environment. This position offers a base salary range of $85,000–$95,000, plus approximately $65,000 in target variable compensation, based on achievement of applicable sales goals. Actual compensation may vary based on experience, qualifications, and other job-related factors.

Equal Opportunity Statement

Pathwise is an equal opportunity employer committed to building a diverse and inclusive team. We consider all qualified applicants without regard to any protected status under applicable law and provide reasonable accommodation for the application process, interviews, and essential job functions.