LR Squared · 5 days ago
Enterprise Account Executive
United States
Full-time
Remote
Senior Level
5+ years expLR Squared is seeking a seasoned Enterprise Account Executive with deep experience selling enterprise software solutions into U.S. public school districts. This role focuses on complex, consultative sales cycles and requires strong relationships with key stakeholders in K-12 education to drive the full enterprise sales cycle.
Staffing & Recruiting
Hiring Manager
Lynne Rutkowski
Responsibilities
Own and drive the full enterprise sales cycle for assigned U.S. public school districts (K-12), from prospecting through close and renewal
Prioritize and focus on progressive, forward-thinking school districts that:
Maintain strong, well-developed relationships with their State Board of Education
Are willing to actively advocate for their needs and funding at the state level
Explore innovative educational delivery models, including options for stay-at-home, homeschooled, and hybrid students
Build trusted relationships with savvy, politically astute, and innovative school superintendents who are passionate about student outcomes and teacher support
Build trusted relationships with key decision-makers and influencers, including:
School Superintendents
Assistant Superintendents
CIOs, CTOs, and Directors of Technology
School Boards, School Committees, and procurement teams
Develop a deep understanding of each district’s technology environment, budget realities, compliance requirements, and instructional priorities
Navigate and manage complex procurement processes, including RFPs, RFIs, bid responses, and board presentations
Accurately forecast pipeline and revenue, aligning sales activities with district budget cycles and approval timelines
Deliver compelling executive-level presentations and product demonstrations tailored to non-technical and technical audiences
Collaborate closely with sales engineering, customer success, and leadership teams to ensure successful evaluations, implementations, and long-term adoption
Maintain expertise in K–12 digital learning and online program trends, with a strong understanding of data protection and other regulatory considerations relevant to district decision-making
Represent the company professionally at conferences, regional meetings, and education-focused events
Position Braintree as a long-term district partner, not just a vendor, by prioritizing transparency, responsiveness, and shared success
Provide market insights and feedback to internal leadership to inform program development, pricing, and go-to-market strategy
Collaborate with marketing and leadership to refine district-facing messaging that reflects evolving K-12 needs and policy shifts
Qualification
Required
Experience or working knowledge of the homeschooling movement and its impact on public school districts, including how districts provide resources, services, technology access, and funding support to homeschooled and hybrid-enrolled students
5–10 years of enterprise software sales experience specifically selling into U.S. public school districts (K-12)
Demonstrated experience navigating long, multi-stakeholder sales cycles in public-sector/K-12 environments
Strong understanding of school district budgeting cycles and fiscal-year constraints
Strong understanding of board approval processes and public-meeting requirements
Strong understanding of procurement rules and compliance in public education
Exceptional presentation, communication, and interpersonal skills
Ability to translate technical solutions into clear business and educational value
Strong organizational skills with disciplined pipeline and account management
Willingness to travel as required
Preferred
Existing relationships within K-12 school districts or regional education networks
Experience working with value-added resellers (VARs), system integrators, or education-focused partners
Familiarity with E-Rate funding and other education grant programs
Experience digital learning solutions in regulated environments
Company
LR Squared
Recruiting & Connecting Two Generations of Sales Executives, Sales Engineers & Cloud Architects for the Data, Protection, Cloud Services & AI Automation Community.
2-10 employees
Funding
Current Stage
Early StageLeadership Team
Leon Rutkowski
Partner
Lynne Rutkowski
Partner
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