Enterprise Account Executive - Future Opportunity

About the role

As an Enterprise Account Executive at Frontline Education, you will lead the most significant and strategically important partnerships with large school districts, state systems, and multi-entity education organizations. This role focuses on leading Frontline’s most complex, enterprise-wide opportunities, where success depends on navigating large-scale systems, aligning diverse stakeholders, and driving long-term organizational impact.

Responsibilities

• Own the full lifecycle of enterprise partnerships, driving a land-and-expand approach that supports retention, adoption, and long-term customer value
• Grow enterprise partnerships by identifying and activating expansion opportunities across departments, schools, and systems
• Own and lead Frontline’s largest and most complex enterprise opportunities from strategy through close, including multi-year, multi-solution agreements often spanning significant organizational investment
• Develop and execute comprehensive account strategies that align to long-term customer priorities, driving both new growth and expansion across districts, states, and education systems
• Build and sustain trusted relationships with executive stakeholders, including superintendents, cabinet leaders, and state decision-makers, serving as a strategic advisor
• Navigate complex buying environments, aligning diverse stakeholder groups around shared goals, measurable outcomes, and long-term value
• Design and position enterprise-wide solutions that connect Frontline’s capabilities to customer priorities, enabling operational transformation at scale
• Articulate and quantify the value of Frontline’s solutions, linking investment to measurable operational and educational outcomes
• Lead and align cross-functional deal teams, bringing together Solutions Consulting, Product, Marketing, Legal, Finance, and Customer Experience to deliver cohesive, high-impact outcomes
• Structure and negotiate complex agreements in partnership with internal teams, balancing customer needs with sustainable business outcomes
• Maintain clear, accurate forecasting and pipeline visibility while confidently managing long, multi-threaded sales cycles
• Contribute market insights and competitive intelligence to internal teams, helping shape product direction and go-to-market strategy
• Mentor and elevate peers by sharing enterprise selling approaches, insights, and best practices across the organization
• Represent Frontline externally as a trusted voice in the education and edtech community

Requirements

• Significant experience leading large-scale enterprise sales in SaaS, edtech, or similarly complex environments
• A track record of closing and expanding multi-year, high-value agreements across large, distributed organizations
• A consultative, customer-centered approach that prioritizes outcomes, builds trust, and fosters long-term partnerships
• A strong executive presence, with the ability to engage, influence, and guide senior leaders through complex decisions
• Experience navigating complex procurement processes, stakeholder groups, and organizational dynamics
• Strong business acumen, with the ability to connect solutions to strategic, financial, and operational outcomes
• Curiosity and openness to leveraging AI and emerging technologies to enhance planning, insight generation, and engagement

Qualifications

• A deep sense of ownership, taking accountability for outcomes and leading with clarity in high-impact, high-visibility situations
• The ability to balance long-term strategic thinking with disciplined execution across extended sales cycles
• Comfort using AI-enabled tools to strengthen forecasting, account planning, and decision-making
• Adaptability in navigating evolving customer needs, shifting priorities, and complex environments
• A collaborative mindset that values shared success, open communication, and continuous learning
• A commitment to understanding customer goals deeply and making decisions with their long-term success in mind
• A willingness and ability to travel up to 33% of the time, with travel varying by deal stage, customer needs, seasonality, territory priorities, team meetings, events, and other business needs

Skills

• Strategic thinking and execution
• Customer relationship management
• Complex negotiation and agreement structuring
• Market research and competitive analysis
• Collaboration and teamwork
• Leadership and mentorship
• Communication and presentation skills
• Use of AI and emerging technologies

Benefits

Frontline Education offers a competitive compensation package designed to recognize and reward high performance. This role carries total on-target earnings of $280,000, comprised of a base salary of $140,000 and on-target commission of $140,000. The compensation structure, including territory alignment, quota, and performance metrics, will be confirmed as part of role scoping.

Pay

Total on-target earnings: $280,000

Schedule

Up to 33% travel, based on customer, territory, and business needs