Mid-Market Account Executive

Mid-Market Account Executive itopia · Chicago, IL or Miami, FL preferred (Remote considered for the right candidate) · Full-Time

itopia is hiring a Mid-Market Account Executive to own the new logo motion across the 10,000 to 30,000 student enrollment band — approximately 660 K-12 school districts nationwide. These districts are large enough to have real instructional programs, functioning IT departments, and established procurement processes, but agile enough to move in 60 to 120 days when the right solution appears at the right time. This is itopia's highest-volume direct sales opportunity and it is largely untapped.

This is a founding seat. You will be building upon a repeatable and expanding playbook — identifying the highest-priority districts, developing outbound sequences that resonate with IT and Curriculum Directors, and setting the template that future Mid-Market AEs will follow as the team grows.

This is a pure new logo hunting role. Your quota is built entirely around new ARR closed. You own the full sales cycle end to end — discovery, demo, proposal, negotiation, and close — with no handoffs and no SDR or BDR support. Pipeline is self-sourced through outbound prospecting, conference attendance, inbound partner deal registrations, and channel referrals.

You will not be starting from zero. itopia is carrying open opportunities in the mid-market band that will transfer to you immediately.

About itopia

itopia is a K-12 cloud computing platform that gives districts a single place to deliver and control Windows applications, SaaS tools, AI tools, YouTube, and browser extensions — all under a unified policy and visibility engine. Our buyers are IT and Curriculum directors at large K-12 districts, and we're focused on becoming the platform of record for the top 100 districts nationally.

We serve districts including Houston ISD, NYC Public Schools, Miami-Dade County, and Cy-Fair ISD, and operate 100% through a channel-first model with CDW, Trafera, Howard Technology Solutions, Vivacity Tech, and other leading education resellers.

We're a lean, high-output team. We move fast, we don't overthink, and we build things that actually get used in schools.

Responsibilities

• Self-source 100% of your own pipeline through outbound prospecting, conference attendance, partner referrals, and inbound follow-up — there is no BDR or SDR support in this role
• Build and maintain a structured prospecting list of high-priority districts within the 10k–30k enrollment band, prioritizing those with active instructional technology initiatives, recent device refresh cycles, or expiring lab infrastructure
• Execute multi-touch outbound sequences via HubSpot targeting IT Directors, CTOs, Curriculum Directors, Instructional Technology leads, and Procurement contacts
• Develop and own relationships with CDW, Trafera, Howard Technology Solutions, and Vivacity Tech regional reps to generate partner-sourced pipeline and co-sell on active opportunities
• Attend EdTech conferences and K-12 events as a primary pipeline generation channel — CoSN, ISTE, FETC, ACTE and state-level technology director conferences are core to this motion
• Run the full sales cycle end to end — discovery, demo, proposal, negotiation, and close — with no handoffs
• Lead all customer-facing activity: discovery calls, product demonstrations, proposal presentations, and contract discussions
• Position itopia against the real problems mid-market districts are trying to solve — fragmented governance across SaaS, AI, and browser tools; expensive on-prem labs; constrained device fleets; and overworked IT teams
• Manage all deal registration, partner communication, and channel coordination for opportunities in your territory
• Navigate district procurement processes including state contracts, cooperative purchasing agreements, and CDW education procurement vehicles
• Own accurate deal stage management and weekly forecast submission in HubSpot — the Director of Sales should never have a surprise from your pipeline
• Audit and re-engage the 50–60 inherited open opportunities in month one, then build new pipeline alongside progressing them
• Maintain 3x pipeline coverage against quota at all times and create a minimum of 10 new qualified opportunities per month from self-sourced prospecting and partner referrals

Qualifications

• 3+ years in a closing AE role — SaaS, EdTech, or technology sales strongly preferred
• Demonstrated track record of self-sourcing pipeline and closing net new logos — this is not a role where leads are handed to you
• Experience selling into K-12 school districts is a significant advantage; experience selling into state and local government, higher education, or other public sector institutions is relevant
• Familiarity with the K-12 procurement landscape — state contracts, cooperative purchasing, CDW Education — is a meaningful plus
• Comfortable running a full sales cycle end to end with deal sizes in the $15K to $75K ACV range
• Experience co-selling with channel partners, specifically CDW or regional education technology resellers, is strongly preferred
• HubSpot proficiency or strong CRM discipline in a comparable platform
• Exceptional discovery skills — the ability to uncover the real problem behind a district's stated needs and connect itopia's solution to that problem in a way that creates urgency
• Self-directed and comfortable building structure in ambiguity — you are the first person in this seat and you will be setting the standard
• Chicago-based preferred; remote considered for the right candidate

Our Sales Culture

itopia operates a 100% channel-first sales model. Our partners — CDW, Trafera, Howard Technology Solutions, Lenovo, Google, and Microsoft — are central to how we go to market. We move fast, we hold each other to high standards, and we believe that clarity and accountability are acts of respect. We are building the team that will take itopia from a strong early footprint to becoming the platform of record for the top 100 K-12 districts nationally, and every hire matters. The Mid-Market AE is a cornerstone of that plan.