Regional Sales Manager

Description

Location: Naperville, IL

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 Regional Sales Manager, you’ll play a critical role in bringing that mission to life by leading and developing a team of Account Executives (AEs) and Associate Account Executives (AAEs) focused on helping school districts solve meaningful operational challenges.

This role combines strategic leadership, coaching, and customer partnership. You’ll help your team build trusted relationships with district leaders, navigate complex sales cycles, and deliver solutions that create measurable impact for educators and students. You’ll also foster a culture where accountability, collaboration, curiosity, and continuous improvement thrive.

You’ll work closely with Regional Sales Directors and cross-functional partners across Marketing, Sales Operations, Client Success, and Product teams to drive growth while ensuring the customer remains at the center of every decision.

How You’ll Drive Success

• Lead, coach, and develop a team of AEs and AAEs to achieve regional revenue

  goals and deliver consistent customer value.

• Create a high-performing culture grounded in accountability, collaboration,

  inclusion, and continuous learning.

• Support team members through coaching, pipeline strategy, deal progression,

  forecasting, and territory planning.

• Partner with Regional Sales Directors to execute go-to-market strategies aligned

  to company growth priorities.

• Help sellers deepen customer relationships by understanding district priorities

  and aligning solutions to meaningful outcomes.

• Use Salesforce and AI-enabled tools to improve forecasting accuracy, pipeline

  visibility, productivity, and sales effectiveness.

• Foster thoughtful adoption of new technologies and data-driven practices that

  help teams work smarter and serve customers more effectively.

• Collaborate cross-functionally with Marketing, Sales Operations, Client Success,

  Legal, and Product teams to improve the customer experience and accelerate

  growth.

• Hire, onboard, and develop talent while building strong succession pipelines

  across the sales organization.

• Monitor performance metrics and proactively identify opportunities for

  coaching, operational improvements, and market expansion.

• Lead with integrity and transparency while helping teams navigate change with

  confidence and resilience.

What You Bring to Help Us Grow

• 5+ years of SaaS or EdTech sales experience, including experience leading or

  mentoring customer-facing sales teams.

• Experience managing or coaching Account Executives, Associate Account

  Executives, or similar quota-carrying roles.

• Proven ability to consistently achieve or exceed revenue targets within a

  consultative sales environment.

• Strong leadership, communication, and relationship-building skills across all

  levels of an organization.

• Experience managing sales pipelines, forecasting, and territory planning within

  CRM platforms such as Salesforce.

• Ability to analyze sales data and translate insights into actionable coaching and

  business strategies.

• Demonstrated success building collaborative, customer-focused team cultures.

• Comfort navigating evolving technology and leveraging AI-enabled tools to

  improve productivity and decision making.

• Bachelor’s degree or equivalent combination of education and relevant

  experience preferred.

What You’ll Need to Thrive

• Lead with Ownership: Takes accountability for team success, customer

  outcomes, and continuous improvement.

• Build Stronger Teams Together: Creates trust, encourages collaboration, and

  helps others grow through coaching and support.

• Obsess Over Customer Success: Understands what matters most to customers

  and leads teams to solve for long-term outcomes, not just short-term wins.

• Embrace Innovation Thoughtfully: Explores new technologies and AI-enabled

  tools with curiosity, responsibility, and practical business focus.

• Adapt Through Change: Maintains focus, resilience, and optimism in a fast-

  moving environment.

• Communicate with Clarity and Empathy: Builds alignment across teams while

  fostering an inclusive and respectful environment.

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 includes a base salary of $120,000 - 130,000, and performance-based incentive opportunity with On Target Earnings up to $240,000. 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.

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