Strategic Account Executive - MA

Description Location Remote: Massachusetts, United States. Greater Boston area preferred. Regular travel up to 33% of the time 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. Reporting to the Regional Sales Director, you will lead some of Frontline's largest and most complex expansion and new-customer opportunities. You will help school districts and state-level education organizations connect their priorities with solutions that simplify operations, support educators, and create lasting value for their communities. This is a senior individual-contributor sales role. You will shape long-range territory strategy, guide sophisticated enterprise pursuits, and serve as a trusted advisor to senior education leaders. You will also influence how our broader regional sales team learns, collaborates, and succeeds. You will take ownership of outcomes from early account planning through long-term customer partnerships. By learning what matters most to each customer, bringing the right people together, and making decisions with the customer’s goals in view, you will help Frontline earn trust and build relationships that extend well beyond a single transaction. How You’ll Drive Success Develop and execute long-range account and territory strategies aligned with customer priorities, market opportunities, and Frontline's growth objectives. Identify and prioritize high-potential school district, regional, and state-level opportunities using data, customer insight, and thoughtful market analysis. Lead complex expansion and new-customer pursuits involving multiple stakeholders, solutions, funding considerations, and decision-making processes. Build compelling business cases, return-on-investment analyses, and multiyear proposals that connect Frontline’s capabilities to measurable customer outcomes. Serve as a trusted advisor to superintendents, cabinet members, state leaders, and other senior stakeholders by listening closely and understanding the outcomes they are working to achieve. Coordinate internal resources across Solutions Consulting, Product, Marketing, Client Experience, Legal, Finance, and other teams to deliver a unified customer experience. Take ownership of opportunity strategy, next steps, risks, and commitments throughout the sales cycle. Maintain accurate, timely forecasts and a disciplined view of pipeline health, deal progression, and territory performance. Meet or exceed revenue goals while building sustainable customer relationships and protecting long-term value. Use AI-enabled tools thoughtfully to strengthen account research, scenario planning, strategic modeling, meeting preparation, and opportunity analysis. Review AI-assisted work for accuracy, context, confidentiality, and relevance before using it in customer or business decisions. Mentor Account Executives across experience levels by sharing approaches, providing coaching, and helping colleagues navigate complex opportunities. Contribute insights from customers and the market to improve Frontline’s sales strategies, messaging, products, and customer experience. Represent Frontline at conferences, customer meetings, and industry events with credibility, curiosity, and a clear understanding of the challenges facing education leaders. What You Bring to Help Us Grow Five or more years of demonstrated success selling enterprise SaaS, education technology, or similarly complex solutions. Experience leading large, multistakeholder sales cycles involving executive decision-makers and extended evaluation processes. A strong record of expanding accounts, developing new business, and meeting or exceeding revenue expectations. Advanced consultative and value-based selling capabilities, including discovery, business-case development, negotiation, and executive communication. Experience developing multiyear account strategies and navigating complex organizational, procurement, funding, or regulatory environments. The ability to build trusted relationships and communicate credibly with senior district, state, and internal leaders. Strong financial and analytical judgment, including experience developing return-on-investment models and strategic proposals. Consistent forecasting discipline and confidence using CRM, pipeline-management, and sales-productivity tools. Experience partnering across functions to move complex opportunities forward and deliver strong customer outcomes. A willingness to share knowledge, coach colleagues, and contribute to the success of the broader sales organization. What You’ll Need to Thrive An ownership mindset and the discipline to carry strategic commitments from planning through execution. The ability to balance ambitious growth goals with the long-term interests of customers and Frontline. Curiosity about how school systems operate and a commitment to understanding each customer’s priorities, challenges, and measures of success. Sound judgment when navigating sensitive customer information, complex negotiations, and competing priorities. A collaborative approach that brings together different perspectives and creates shared accountability across teams. Comfort working independently in a remote environment while remaining connected to colleagues, customers, and regional priorities. Adaptability when customer needs, market conditions, technology, or business strategies change. A practical learning mindset and an interest in using AI and emerging tools to improve preparation, analysis, and decision-making. The ability to coach others through questions, examples, and shared learning rather than relying solely on direction. A commitment to representing Frontline with integrity and strengthening trust in every customer interaction. 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. Compensation & Benefits The full base compensation range for this position is $105,000 - 110,000, with On Target Earnings up to $220,000. 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. Paid volunteer time. Tuition reimbursement and professional-development resources. Wellness initiatives and confidential employee-assistance support. 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. 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. Our Privacy Policy: Your privacy is important to us. Click here to read our general Privacy Statement, and click here to read our Applicant Privacy Statement. #J-18808-Ljbffr