Account Executive

Level Data LLC•Boston, MA

10d•$90,000 - $125,000•Remote

About The Position

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.

Requirements

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

Responsibilities

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