Enterprise Account Executive

Frontline Education; United States; On-site; USD 140,000 - 150,000; Full time

Benefits offered by this job

Volunteer Time Off

Ten Paid Holidays

Personalized Time Off

Paid Sick Time

Wellness initiatives

Job summary

Frontline Education seeks an Enterprise Account Executive to lead strategically important partnerships across large school districts and state systems. You will drive land-and-expand opportunities, align stakeholders, and deliver long-term value in a remote United States setting.

You’ll partner with executives to design AI-enabled, scalable solutions that transform education operations, while navigating complex procurement and multi-team collaboration across the country.

Qualifications

• Five+ years selling enterprise SaaS/education tech or similar complex solutions.
• Track record closing multi-year, high-value agreements across large organizations.
• Consultative, customer-centered approach prioritizing outcomes and partnerships.
• Strong executive presence to influence senior leaders through complex decisions.
• Experience navigating procurement processes and stakeholder dynamics.
• Strong business acumen linking solutions to strategic outcomes.
• Curiosity and openness to AI-enabled planning and insights.

Responsibilities

• Own the full lifecycle of enterprise partnerships from strategy to close.
• Identify and activate expansion opportunities across departments and districts.
• Lead multi-year, multi-solution deals with cross-functional teams.
• Develop account strategies aligned to long-term customer priorities.
• Build trusted relationships with executive stakeholders and state decision-makers.
• Navigate complex buying environments with diverse stakeholder groups.
• Quantify and articulate the value of Frontline’s solutions to customers.

Skills

Enterprise SaaS sales

Executive stakeholder engagement

Consultative selling

Procurement navigation

Business acumen

AI and emerging tech

Job description

Location: Remote within the United States. Regular travel up to 33% of the time required based on customer, territory, and business needs.

How You'll Contribute to Our Mission

At Frontline Education, our mission is to transform how schools work, so every educator and student succeeds. Our vision is every school thriving. Every community stronger. As an Enterprise Account Executive, you will lead Frontline’s most significant and strategically important partnerships, working with the largest school districts, state systems, and multi-entity education organizations across the country. 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.

You’ll partner closely with customer executive level leaders to understand their most pressing challenges and help design solutions that transform how their organizations operate. By aligning strategy, stakeholders, and outcomes, you’ll play a critical role in advancing our mission to transform how schools work, so every educator and student succeeds.

How You'll Drive Success

• 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.

What You Bring to Help Us Grow

• Five or more years of demonstrated success selling enterprise SaaS, education technology, or similarly complex solutions.
• 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.
• 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.

What You'll Need to Thrive

• 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.
• 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.

Our Mission, Our People, Our Purpose

At Frontline Education, we’re reimagining what’s possible by becoming an AI-first organization, transforming how we think, work, and serve the educators who shape our schools every day. By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most — their students.

As part of our team, you’ll be expected and empowered to build and apply AI skillsets that grow with you, because at Frontline Education, technology amplifies what matters most: the human drive to learn, improve, and make a difference.

How We Support Growth, Balance, and Well-Being

• Personalized Time Off: Take time when it’s needed most — whether that’s a family vacation, a reset day, or simply time to rest and refocus.
• Paid Sick Time: Separate, dedicated sick leave to care for yourself or loved ones.
• Volunteer Time Off: Paid time to give back and support causes that matter to you.
• Ten Paid Holidays: Enjoy meaningful moments and traditions throughout the year.
• Our Philosophy: We believe time away from work helps you bring your best self to it.

Continuous Learning and Growth

• World-Class Learning Access: Explore thousands of on-demand courses through platforms like LinkedIn Learning.
• Leadership & Technical Skill Building: Develop new capabilities and chart your own professional path.
• AI Empowerment: Use OpenAI tools to build fluency with emerging technology and harness AI as a creative partner for innovation and problem-solving.
• Tuition Reimbursement: Invest in formal education to advance your skills and career.
• Ongoing Learning Culture: Participate in company-led webinars on AI, inclusion, and industry trends—designed to inspire curiosity and continuous improvement.

Health, Happiness, and Purpose

• Wellness Initiatives: Company-sponsored programs that support physical, mental, and emotional well-being.
• Employee Assistance Program (EAP): Confidential support for you and your family’s needs.
• Comprehensive Benefits: Health and financial benefits that support your happiness and future.
• A Culture That Cares: At Frontline Education, we want every team member to learn, grow, and thrive—personally, professionally, and purposefully.

The full base compensation range for this position is $140,000 - 150,000, with On Target Earnings up to $290,000. Compensation for this role may include a base salary and performance-based incentive opportunity. Actual compensation will be determined according to the approved range for the position and may consider relevant experience, skills, geographic location, internal equity, and other applicable factors.

Eligible employees may have access to:

• A performance-based sales incentive plan.
• A 401(k) plan with company match.
• Employee stock purchase opportunities.
• Comprehensive health and financial benefits.
• Personalized paid time off and dedicated sick leave.
• Tuition reimbursement and professional-development resources.
• Wellness initiatives and confidential employee-assistance support.

Frontline Education is an equal opportunity/affirmative action employer. We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.

Interview Process & Data Privacy

As part of our interview process, Frontline uses video conferencing tools that may include photo capture and automated transcription features. A screenshot or photo may be taken at the start of the interview for internal identification and record-keeping purposes only. Transcription tools may be used to support consistent note-taking and evaluation.

These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside of the hiring process. Candidates may opt out of transcription by notifying their recruiter in advance. Frontline processes candidate information in accordance with applicable data privacy laws and only for legitimate recruitment purposes.

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