Boston, Massachusetts, United States · Remote OK
$90k–$125k/yr
Role Overview The Account Executive is a quota-carrying, territory-owning revenue leader responsible for driving annual bookings growth across an assigned K–12 region. This role owns the full sales lifecycle &mdash…
Skills: B2B SaaS Sales, Consultative Selling, Pipeline Generation, Outbound Prospecting, CRM Management
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The Account Executive is responsible for driving annual bookings growth and managing the full sales lifecycle within an assigned K-12 region. This includes generating a self-sourced pipeline, managing complex multi-stakeholder deals, and utilizing AI tools to optimize outreach and research.
Candidates need 3+ years of B2B SaaS sales experience, preferably in the K-12 education sector, and a proven track record of managing public-sector sales cycles. Proficiency in AI productivity tools and the ability to communicate ROI to cabinet-level district leaders are essential.
The Account Executive is a quota-carrying, territory-owning revenue leader responsible for driving annual bookings growth across an assigned K–12 region.
This role owns the full sales lifecycle — from outbound demand generation through district close — positioning Level Data’s solutions (ROI, Grow, Brolly) as essential systems for strategic planning, compliance management, and measurable district impact.
The Account Executive is accountable for consistent quota attainment, predictable pipeline generation, new district acquisition, account expansion, and serves as a key driver of Level Data’s national growth strategy.
This is not a transactional sale. It is a strategic, multi-stakeholder district sale.
AEs at Level Data are expected to operate as AI-native sellers, using AI tools to accelerate research, sharpen prospecting, and improve the quality and speed of every customer interaction.
• Own a regional revenue quota in annual new and expansion bookings
• Maintain 2–3x pipeline coverage to ensure forecast predictability
• Prioritize net-new district acquisition while expanding existing accounts
• Achieve >100% annual quota attainment
• Execute structured deal plans for all opportunities
• Source a majority of pipeline through self-generated outbound prospecting
• Execute structured cadences targeting Superintendents, CFOs, Directors of Special Education, Federal Programs, and Curriculum leaders, etc.
• Generate consistent qualified meetings and new pipeline each quarter
• Qualify opportunities based on authority, funding source, timeline, compliance urgency, and measurable impact
• Maintain disciplined opportunity progression with strong stage conversion rates
• Leverage AI tools (e.g., Claude, or comparable platforms) to research districts, identify trigger events, personalize outreach at scale, and prioritize territory coverage intelligently
• Build and maintain executive-level relationships across assigned strategic districts
• Multi-thread opportunities across district cabinets and department leaders
• Position Level Data solutions around strategic plan execution, CIP tracking, compliance risk mitigation, special education accountability, funding alignment, and ROI measurement
• Partner with product and implementation teams to close complex, compliance-driven opportunities
• Independently manage discovery, demos, pricing strategy, proposals, and procurement navigation
• Navigate RFP processes and district contracting cycles
• Drive urgency in sales cycles
• Close ARR opportunities with disciplined follow-up
• Maintain CRM accuracy >95%
• Deliver accurate weekly and quarterly forecasts
• Track and improve stage-to-stage conversion rates, sales cycle length, win/loss ratios, and average deal size growth
• Maintain disciplined CRM hygiene at all times
• Partner closely with SDRs, Marketing, and Customer Success
• Serve as the voice of the customer internally
• Ensure smooth handoff to implementation to protect renewals and expansion
• 3+ years of B2B SaaS sales experience, with strong preference for K–12 education
• Experience managing complex, multi-stakeholder, public-sector sales cycles
• Strong discovery and consultative selling skills
• Ability to speak fluently about ROI, funding pathways (ESSER, IDEA, Title programs), compliance, and measurable district outcomes
• Comfortable selling to cabinet-level district leaders
• Proficiency in CRM systems and structured deal management
• Executive-level communication and presentation skills
• Demonstrated AI literacy: actively uses AI tools to research accounts, draft outreach, prepare for calls, and improve productivity — not as a novelty but as a standard operating practice
• Actively uses AI tools (e.g., Claude or equivalent) for district research, stakeholder mapping, outreach personalization, and meeting preparation
• Uses AI to synthesize public data sources (state report cards, budget documents, strategic plans, board minutes) to build high-quality account intelligence before first contact
• Applies AI-assisted writing tools to produce first drafts of emails, proposals, and follow-up communications, then edits for accuracy, voice, and district-specific context
• Understands the limits of AI output: verifies facts, avoids AI-generated errors in customer-facing materials, and does not substitute AI research for genuine discovery
• Stays current on AI tools relevant to the sales workflow and proactively shares best practices with the team
• Remote role
• 40% travel within assigned region
• Requires consistent outbound activity and weekly meeting targets
• Competitive base salary + uncapped commission
• OTE aligned with quota and performance
• Benefits package including health, PTO, and retirement
Data you can trust. Outcomes you can measure.
In K–12, data is everywhere but it's not always accurate, connected, or actionable. We give leadership teams and administrators data they can trust: Standardized, validated, and seamlessly aligned across systems. By connecting every point of information—from enrollment and attendance to IEP service minutes and districtwide purchases—to strategic goals, we equip leadership teams with the insights they need to measure progress, align stakeholders, and maximize student impact. With our tools, educators gain not only visibility, but the confidence to make informed decisions that drive meaningful, measurable outcomes.
Offices: 6850 Stadium Dr, Kalamazoo, Michigan 49009, US
Data you can trust. Outcomes you can measure.
In K–12, data is everywhere but it's not always accurate, connected, or actionable. We give leadership teams and administrators data they can trust: Standardized, validated, and seamlessly aligned across systems. By connecting every point of information—from enrollment and attendance to IEP service minutes and districtwide purchases—to strategic goals, we equip leadership teams with the insights they need to measure progress, align stakeholders, and maximize student impact. With our tools, educators gain not only visibility, but the confidence to make informed decisions that drive meaningful, measurable outcomes.
Offices: 6850 Stadium Dr, Kalamazoo, Michigan 49009, US
