When Jackie Kroeger-Donovan (Stern '20) joined the Summer Launchpad (SLP) as a founder of Theatre Galleria — an online marketplace connecting theatre designers with materials — she left with more than an MVP. A decade later, she came back to campus to teach this year's SLP cohort what she wishes someone had taught her about hiring.
Since Theatre Galleria, Kroeger-Donovan has built teams at nearly every stage of company growth. Before her first startup, she bought and ran a restaurant at 22 — eight years, roughly 20 staff, zero turnover in the kitchen the entire time. After Theatre Galleria, she joined the early team at Aktiv Learning, where she built out operations, HR, and customer success before taking on sales leadership for the first time and scaling the company through its acquisition by Top Hat. From there she moved to Richardson, a leadership coaching and sales performance firm, and today, nine months into building the CS team at Loop AI, none of what she's about to share is theoretical.
The team wasn't wrong. It was the wrong fit.
Kroeger-Donovan opened with the hire that changed how she thinks about hiring. At Aktiv Learning, she inherited a 6-person sales team that was a genuine fit mismatch — experienced people who were built for the structure and resources of a larger organization, dropped into a scrappy startup environment. She had no budget and no time to fix it once she identified the problem. Rather than compete for the same experienced sales candidates every other company was chasing, she asked a different question: who would value what a scrappy, performance-driven startup could offer?
Her answer: theatre grads auditioning during the day, who needed flexible hours and were comfortable performing under pressure. She posted the role on Playbill.com. Her first hire had zero sales experience. In his first week, he outperformed all six existing reps' previous three months combined.
The lesson she draws from it isn't "hire theatre kids." It's that the hire worked because his skills matched what the job actually required, the goals were crystal clear from day one, and he was fully bought into the culture and constraints of the role. When resources are limited, she said, map out what you can actually offer a candidate. Then, go find who values exactly that.
Build the worksheet before the job description.
Kroeger-Donovan's framework starts before scheduling a single interview. For every role, she fills out a worksheet mapping required skills and experience, then separates true must-haves from skills a candidate could coach into. Her test: is this requirement actually mission-critical to the role, or is it a proxy for an underlying skill that's coachable? She pressure-tests this with her co-founders so everyone aligns on what's non-negotiable before the search begins.
She evaluates every candidate across four dimensions: skills and experience, incentive alignment, culture fit, and behaviors and desires. Of the four, she was clearest about which one is most expensive to get wrong. Missing on experience means you teach someone — costly, but fixable. Missing on incentives means you adjust compensation or structure. Missing on culture fit is different. High performers will still try, but if they don't believe in what they're being asked to do, every task becomes a drain on their energy and yours.
Design one interview question per must-have — then push past the first answer.
For each must-have on her worksheet, Kroeger-Donovan writes a matching interview question, then scores candidates against those must-haves after every interview rather than going on overall impression. Her go-to technique: ask for two or three examples of the same thing, not just one. The first answer tends to be polished and rehearsed. The third is where real motivation shows up.
She's also candid that her worksheet isn't gospel. If a candidate makes her question one of her own must-haves, she treats that as useful signal. Sometimes it means she got the requirement wrong, and she'll rewrite the worksheet before moving forward.
Managing people well means clarity isn't optional.
On the people-management side, Kroeger-Donovan's approach centers on removing surprises. A difficult conversation about performance, she said, should never come as a shock to the person on the receiving end. If you're being clear and consistent along the way, it starts to feel like a collaborative decision rather than an ambush.
Her feedback framework moves in three steps: situation, behavior, impact. Ask an open question first ("How do you think that went?"), and only after hearing the other person's take, offer your own view. She's also built a values rubric for her current team. It defines what a "1" and a "5" look like for each core value, used quarterly for self-assessment and coaching conversations. Her advice for early-stage founders: don't try to build an 11-page version of this. Two or three behaviors that actually matter is enough.
On retention, she pointed out that even in a strong hiring market, founders can't out-resource bigger companies. She’s fielded seven cold outreach messages for team members in the last two weeks alone. What keeps people, in her experience, isn't compensation parity. It's transparency about where the business is headed and genuine investment in a person's growth. Inertia favors staying when people feel connected to the mission.
On AI in hiring: use it to sharpen your judgment, not replace it.
Kroeger-Donovan uses AI heavily for the operational load of hiring — note-taking, scorecards, and tracking candidates across a high volume of interviews, including one month where she did 45. But she was direct about one boundary: never let it generate feedback that goes straight to a team member. She said that's the fastest way to break trust with the people you manage. Use it to keep yourself honest and organized, not to do the human part of the job for you.
