Remote Senior Enterprise Sales Executive – Education Tech

Frontline Education Group; United States; Remote; USD 105,000 - 110,000; Full time

Benefits offered by this job

401(k) plan with company match

Tuition reimbursement

Paid time off

Wellness initiatives

Volunteer time off

Job summary

Frontline Education Group is seeking a senior, enterprise-focused sales leader to drive large expansions and new-customer opportunities within the United States, remotely with MA territory preference. You’ll guide multi-stakeholder pursuits, craft ROI-driven proposals, and partner across functions to deliver measurable outcomes for school districts and state education bodies.

You will own account planning end-to-end, build trusted relationships with senior leaders, and ensure accurate

Qualifications

• 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.

Responsibilities

• Lead complex expansion and new-customer pursuits involving multiple stakeholders, solutions, funding considerations, and decision-making processes.
• Build compelling business cases, ROI analyses, and multiyear proposals that connect Frontline’s capabilities to measurable customer outcomes.
• Serve as a trusted advisor to senior education leaders 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.

Skills

Enterprise SaaS sales

Education technology

Multistakeholder sales

Executive-level communication

Forecasting & CRM usage

Strategic account planning

Revenue growth

Investment/ROI modeling

Cross-functional collaboration

Coaching and mentoring

Tools

CRM systems

Pipeline management tools

Sales productivity tools

Job description

Frontline Education Group is seeking a senior, enterprise-focused sales leader to drive large expansions and new-customer opportunities within the United States, remotely with MA territory preference. You’ll guide multi-stakeholder pursuits, craft ROI-driven proposals, and partner across functions to deliver measurable outcomes for school districts and state education bodies.

You will own account planning end-to-end, build trusted relationships with senior leaders, and ensure accurate