District Development Representative

District Development Representative itopia · Chicago, IL (Hybrid, 2–3 days in office) · Full-Timeitopia is hiring three District Development Representatives (DDRs) to own the inside sales motion within our most strategic K-12 accounts — the largest school districts in the United States, all with 30,000+ student enrollment. In every case, itopia already has central office support, an active pilot, or a live paid engagement. The district relationship is established. Your job is to go school by school, build pipeline, book meetings, and close deals.This is a sales role, not a scheduling role. DDRs at itopia are empowered to close. When a school-level contact is ready to move, we expect you to move with them — no internal process should slow down a deal that's ready. For complex, multi-stakeholder opportunities, the Key Account Executive (KAE) leads and the DDR supports. The best DDRs will blur the line between inside sales and closing AE over time, and we expect career growth to reflect that.About itopiaitopia 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, 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.Open Territories (please indicate your preference when you apply)Large 30k+ Enrollment K-12 District — East: One of the largest districts in the U.S., 1,800+ schools. Central office support and marketplace access in place. The highest-volume inside selling opportunity in the portfolio.Large 30k+ Enrollment K-12 District — Central/West: A major Midwest district, 500+ schools. Active pilot with central office support and clear intent to expand district-wide.Strategic Accounts — Strategic: A portfolio of itopia's most important paid customers across Florida, Texas, Maryland, and California. Active ARR with significant room to grow school by school.ResponsibilitiesOwn outbound prospecting within your assigned territory — identifying and reaching principals, assistant principals, CTE coordinators, department heads, IT directors, curriculum leaders, and other school- and district-level decision-makersLeverage existing district relationships, active pilots, and central office support as warm credibility in all outreach — you are expanding within committed accounts, not selling coldExecute high-volume, personalized multi-touch outreach via HubSpot (email, phone, LinkedIn) tailored to school context, program type, and instructional focusClose school-level deals independently when a site contact is ready to move — when a principal is ready to sign, you close it, log it, and move to the next oneBook a minimum of 16 qualified school-level meetings per month for the KAE (ramp: 8 in month one, 12 in month two, 16 by month three)Maintain an active prospecting list of 150+ target contacts at all times within your territoryIdentify and flag expansion signals — inbound interest from new schools, over-utilization, new program launches, or device refresh cyclesDeliver a written pre-call brief to the KAE at least 24 hours before every meeting, covering stakeholders, the hook that generated the meeting, school context, and recommended discovery angleOwn HubSpot contact records, activity logging, and day-to-day pipeline hygiene within your territory; ensure every open opportunity has a future-dated next stepParticipate in a weekly 30-minute pod sync with your KAE to review pipeline, align on prospecting focus, and reconcile HubSpot dataManage scheduling and calendar coordination for KAE-facing meetings, and support proposal and quote coordination for KAE reviewQualifications2+ years in an inside sales, SDR, BDR, or similar pipeline generation roleDemonstrated track record of high-volume outbound prospecting — email sequences, cold calling, LinkedIn outreachExperience with HubSpot or a comparable CRM; strong pipeline hygiene and activity logging disciplineExceptional written communication — capable of crafting outreach that earns a reply from a busy school principal without reading as templatedOrganized, self-directed, and comfortable managing a high volume of simultaneous outreach threads without losing quality or follow-throughGenuine interest in education technology required; familiarity with K-12 or EdTech strongly preferredExperience navigating large, decentralized institutions — school systems, municipalities, healthcare networks, or similar — is a meaningful advantagePrior knowledge of or relationships within large 30k+ enrollment K-12 school systems relevant to your territory of interest is a significant plusBased in Chicago and able to work hybrid (2–3 days per week in office)Our Sales CultureWe 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. We have a product that wins — Houston ISD, NYC Public Schools, Miami-Dade County, Montgomery County, and Chicago Public Schools are proof. We believe winning is engineered, not accidental — built rep by rep, call by call, deal by deal. You will always know exactly what a strong month looks like and how your performance connects to the company's growth. Accountability goes both ways: we expect a lot from our team and we are equally accountable to them.If you are driven by a big market that hasn't been fully taken, a product you can genuinely believe in, and a culture where your contribution is visible and valued — this is the right place to build your career.