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AwardSpring is a Chicago-based, established SaaS company partnering with colleges, universities, and foundations across the US and Canada to manage donor programs. The Head of Marketing and SDRs leads top-of-funnel efforts, builds the inbound engine, and scales the Fund Platform in a hybrid Chicago setting.
You will coach SDRs, run campaigns, and drive category creation while leveraging an AI stack and an attribution-focused mindset to grow pipeline and revenue.
AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.
Full-Time
Chicago, West Loop, hybrid three days a week, with travel to the conferences we attend
$140,000 - $160,000 base
$175,000 - $200,000 OTE
~$35,000 - $40,000 variable target
plus equity
You run the top of the funnel at AwardSpring: marketing and the SDR team, as one function with one number. That number is pipeline dollars created. Demand is the single biggest constraint on the business, and this seat exists to remove it.
We sell scholarship and donor management software to colleges, universities and community foundations. After ten years we have about 300 of the 1,300 two-year colleges, and most of the rest run on older tools that haven't kept up. Two-year colleges do not search for this category. They ask a peer, read a publication, hear a podcast. Four-year universities buy through a committee of about five people. Foundations find us on their own, and the work there is speed and disqualification. Today most of our pipeline is outbound that our sellers source by hand.
You inherit a paid-media agency, marketing contractors, an SDR team that books first meetings for our Account Executives by phone, and an AI stack that removes most of the production and research work. The SDRs and the marketing contractors report to you. You coach the SDRs, build the inbound engine, and build the category for our Fund Platform. Attribution between marketing and sales does not matter here. The total going up does.
Three more numbers come up every week: speed to first touch on an inbound lead, paid spend with a read on lift, and inbound pipeline created per month.
Agents research, draft and produce. You and your team decide what ships and what gets said on the phone. You should arrive having built campaign or prospecting systems with AI, not just written captions with it, and you will be expected to take work off the SDRs’ plates by automating it rather than hiring for it. We check this at day 30 and in every quarterly review. If you don't instinctively reach for AI before doing things manually, this role will be a hard adjustment.
Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.
Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.
Take pride in the process. Fast is the standard and thoughtfulness is non‑negotiable. Eyes on the work you control, not the scoreboard.
Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.
Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week, with travel to the conferences we attend.
AwardSpring is an equal opportunity employer and hires without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. We're committed to an inclusive, harassment‑free workplace.