Vice President, Enterprise Accounts

Vice President, Enterprise Accounts

Location: Remote, United States

Travel: Up to 40% of time, based on customer, team, and business needs

How you’ll contribute to our mission

As Vice President, Enterprise Accounts, you will lead the team of Enterprise Account Executives responsible for Frontline’s most significant and strategically important partnerships, spanning the largest school districts, state systems, and multi-entity education organizations across the country. Reporting to the Chief Sales Officer, you will be a key member of the sales leadership team, owning the strategy, performance, and growth of Frontline’s enterprise segment, where success depends on navigating large-scale systems, aligning diverse stakeholders, and driving long-term organizational impact.

You’ll build and lead a high-performing team of enterprise sellers, partner with executive leaders inside Frontline and across our customer base and help shape how we win and expand in our most complex opportunities. By aligning strategy, people, and outcomes, you’ll play a critical role in advancing our mission to transform how schools work, so every educator and student succeeds — and our vision of every school thriving, every community stronger.

How you’ll drive success

• Lead, coach, and develop a team of Enterprise Account Executives, setting a clear vision, high standards, and a culture of accountability, engagement, and ownership
• Own the enterprise revenue plan, delivering against new business, expansion, and retention targets across Frontline’s largest districts, state systems, and multi-entity organizations
• Define and execute the enterprise go-to-market strategy, including market segmentation, prioritization of high-potential markets based on TAM, product fit, and funding dynamics in K–12 education
• Lead annual planning, territory and account design, and quota-setting for the enterprise segment in coordination with Sales Operations and Finance
• Develop scalable playbooks and sales motions for enterprise new business, account expansion, and multi-solution selling
• Drive a land-and-expand approach across the enterprise portfolio, ensuring each account has a comprehensive strategy that supports adoption, retention, and expansion across departments, schools, and systems
• Partner with sellers on the largest and most complex enterprise opportunities, including RFPs, multi-year contracts, and consortium or statewide agreements, guiding opportunity strategy, competitive positioning, and deal structuring from strategy through close
• Serve as an executive sponsor for top-tier district and state clients, building trusted relationships with superintendents, cabinet leaders, CFOs, CIOs, and state decisionmakers
• Partner with Customer Experience on engagement plans, quarterly business reviews, and renewal strategies for strategic accounts, monitoring account health and guiding recovery for at-risk relationships
• Monitor key performance indicators such as win rate, sales cycle length, average selling price, and pipeline coverage, and lead regular performance reviews to inform coaching, resource allocation, and strategic adjustments
• Deliver accurate, transparent forecasting and pipeline visibility to executive leadership, aligning CRM usage, forecast methodology, and pipeline hygiene, and using data and AI-enabled tools to identify risk and opportunity early
• Partner across Solutions Consulting, Product, Marketing, Legal, Finance, Procurement, Customer Experience, and Revenue Operations to deliver cohesive, high-impact outcomes for enterprise customers
• Guide the structuring and negotiation of complex agreements and joint go-to-market initiatives, balancing customer needs with sustainable business outcomes
• Partner with the revenue leaders to align process, messaging, and handoffs, and to share best practices across the sales organization
• Recruit, hire, onboard, and retain top enterprise sales talent, building a deep bench, low regrettable attrition, and a clear path for career growth
• Bring market intelligence, win/loss insights, and customer feedback to Product and executive leadership to help shape product direction and go-to-market strategy
• Build customer reference and advocacy programs, and represent Frontline externally as a trusted voice in the education and edtech community

What you bring to help us grow

• Fifteen or more years’ experience in sales leadership in SaaS, edtech, or education services, including leading national or enterprise sales teams
• A track record of building, scaling, and consistently exceeding revenue targets, including double-digit revenue growth, for teams closing and expanding multi-year, high-value agreements across large, distributed organizations
• Demonstrated success recruiting, coaching, and developing enterprise sellers and sales leaders, including leaders of sellers
• Strong executive presence, with the ability to engage, influence, and guide senior leaders, both internally and within customer organizations, through complex decisions
• Deep understanding of the K–12 education market, including sales cycles, decision-making structures, funding models, and school district procurement
• Experience navigating complex procurement processes, stakeholder groups, and organizational dynamics, including public sector and multi-stakeholder environments
• Strong business acumen, with the ability to connect solutions to strategic, financial, and operational outcomes and to manage a forecast with rigor
• Experience scaling sales organizations during periods of transformation or product expansion
• Familiarity with the sales technology stack, such as Salesforce, Gong, and Clari, and a data-driven mindset with comfort in forecasting, pipeline analytics, and sales KPIs
• Curiosity and openness to leveraging AI and emerging technologies to enhance planning, insight generation, coaching, and engagement
• Advanced understanding of SaaS deal structures, revenue recognition, and compliance rules

What you’ll need to thrive

• A deep sense of ownership, taking accountability for team and company 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
• A coaching mindset that raises the performance of individuals and teams, and builds trust through candor, consistency, and care
• Comfort using AI-enabled tools to strengthen forecasting, account planning, pipeline inspection, 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 40% of the time, with travel varying by deal stage, customer needs, seasonality, 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.

Compensation & Benefits

Frontline Education offers a competitive compensation package designed to recognize and reward high performance. This role carries total on-target earnings of $400,000, comprised of a base salary of $200,000 and on-target commission of $200,000.

Inclusion, Belonging & Equal Opportunity

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.

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