The One About Pam and Archer Career
Plus, a brand new website, upcoming events, and more!
I’m excited to announce the launch of our brand new website! www.edtechchicago.com
We also have a new member database and intake process. All new and existing members, please fill out this form (also on the website) to update your info in our database. You will receive an email with links for each tool in our tech stack.
Founder Spotlight
Meet Dr. Pam Schilling, this month’s featured founder. Pam is CEO and Chief Learning Officer at Archer Career, a career and professional development platform for students, recent graduates, and post-docs. Continue reading to learn more about Pam’s story!
Windy City EdTech (WCE): What does your company do? What big problem are you trying to solve?
Pam: At Archer, we empower early-career professionals—students, recent graduates, and post-docs—by curating targeted e-learning courses that build the skills and confidence needed to excel in the workforce. We focus on career readiness and confidence to address the widespread issue of underemployment and job market challenges by providing a carefully curated library of courses with practical insights, expert guidance, and career-focused learning to ensure a real return on educational investment.
Windy City EdTech (WCE): What inspired you to start Archer Career?
Pam: After working in strategy consulting, I took a sabbatical and returned to Chicago Booth to coach full-time MBAs. It was the summer of 2008 and soon thereafter the financial markets collapsed. It was brutal. I saw the most confident and competent students struggle. Many came to my office in tears. I also saw how the “structures” relied more on person-to-person knowledge rather than systems. The tools were either missing or overwhelming. When I left Booth to start my first company, a coaching firm, I saw the same issues across many campuses, student populations, working professionals, and career paths.
It is cliche, but I drew an app on a napkin. I started showing it to my coaching clients and students in my workshops. Everyone said, “We need that!” So, I built it. Like many founders, I saw a need and I was arrogant enough to know I had a different approach and that I was the one to tackle this problem—and no one else was.
Windy City EdTech (WCE): What sets your product apart from others?
Pam: Archer has a combination of domain knowledge, user-centric design, and tech-enablement. First is domain knowledge. My team and I have been students who sought highly selective jobs and were successful in getting them. We worked in higher education, as faculty, staff, administrators, and in career offices. We have also been employers on the hiring side. Few other companies in our specialized area of EdTech have this combination.
Like most start-ups, we listen to our users. We do not over-build or add things that are fancy. All of our courses are quality reviewed by students and other learner audiences. We prioritize and say no to things based on listening to this feedback.
Finally, the tech-enablement is critical. We’ve built with MINIMUM necessary technology. We use multiple advanced AI tools to build our courses. We are licensing a best-in-class platform, always cautious not to over build. Individuals within higher education are often skeptical of new technologies and slow to adopt.
Windy City EdTech (WCE): How can we help you?
Our best business development is word of mouth. Introductions are powerful. We benefit from introductions to career offices, alumni offices, faculty, and other individuals in higher education who want to tackle this challenge of early career readiness and confidence, and to collaborate with us to innovate.
Absolutely download our app and try a course! Here is a login to our Demo Coursepack.
If you know individuals with expertise in content relevant to early career learners, please send them my way—same with motivated and talented students. We do have internships.
Windy City EdTech (WCE): Why are you building in Chicago?
Pam: Chicago is my home and the place that took my career to new heights. I attended two universities here: University of Chicago (Booth MBA) and DePaul University (Doctorate in Business Administration). Both are customers, strategic partners, and testing grounds for much of our R&D.
More importantly, I’ve worked on both coasts and have extensive ties through my network and discussions with the VC community. We are builders and have a very specific purpose to serve as a business. Chicago is the best place to do what we do, drive our growth, and generate the impact we are obsessed with in career readiness.
Windy City EdTech (WCE): Do you have any co-founders?
Pam: This is one of the more challenging parts of our startup journey. I’ve had two co-founders over the years. Both of them exited Archer at different points. My first co-founder was a long-time colleague. We worked together in the early 2000s in consulting. Her superpowers were technology and project management. Together we launched our MVP, secured angel funding which proved critical during our first two years, and built the Archer brand.
My second co-founder met me in a workshop at UChicago. He then hired me for coaching. We decided to do a trade—my coaching for his project management skills. He helped us launch our second product (during covid). His superpower was relationship management. We built our GTM strategy from scratch and developed key relationships with multiple graduate and medical schools. That trust has been critical in our growth.
Both co-founders exited at different points for different reasons. The lesson is that the startup journey is not easy. Beyond 2-3 years is very very very hard, even for the most motivated and resilient people. Launching is easy. Building, growing, and selling is much more difficult.
Windy City EdTech (WCE): What are some of the challenges you’ve faced while building your company?
Pam: Much could be said here, but I’ll reflect on the three biggest things.
Don’t forget your why. When you are building, trying to get funding, going to visit customers and doing pilots, hiring people, getting awards, getting users, and the like, things are great. Then, hard stuff happens. Contracts don’t happen. People depart. Pilots don’t convert. Investors say no. You get negative feedback. Through all of that you must stay motivated and focus on your why.
To build or not to build, and for whom. We began Archer by creating our own platform. A proprietary micro-LMS. It was fantastic. We had a third-party developer. That was very hard and very expensive, and there were fragile elements, along with some mistrust. I changed CTOs and that relationship went south, so we hired our own developer. That created pros and cons. Without large funding, I could not take our platform to the next level. I had to make a tough choice to license our platform and do a conversion of our courses. That was hard, expensive, and slowed us down. It was absolutely the right decision, but was painful at the time.
Market evolution and change. We were ahead of the higher education market—no one had heard of micro-learning. Trying to educate the market is difficult to nearly impossible. Then, AI came and created a lot of noise. We are not an “AI-product”—we are AI-enabled. It shutdown all investor conversations and for a while created conflict in our business development as our buyer was flooded with “save-the-day” AI products. Over time, this has settled. We remained focus and gave attention to our outcomes, testimonials, and building a brand that people know and trust which is very important in sales. Plus, AI-generated resumes are still crappy, so that helps!
Windy City EdTech (WCE): What are you most proud of with your startup?
Pam: We are still here. We have amazing customers. We have a product that is valued and getting better. We are financially strong and continue to find ways to bootstrap successfully and source non-dilutive funding. A few weeks ago, I received an email from a potential customer who wanted to meet and discuss using our platform. This was a person I have known a while who runs a career office. They had heard from colleagues what we were doing and felt our solution was what they need.
I wanted to build a company. To create a brand externally and internally that served a mission and followed first principles. That is Archer Career and I am extremely proud of it, and that makes me excited for what the future holds for us!
Check out our previous founder spotlights!
Upcoming Events
EdTech Institute of Chicago February Happy Hour
Thurs., Feb. 20 from 5:30-7:30 pm CT
RSVP (Luma)
2025 Chicago EdTech Extravaganza Event Presented by Startup Grind
Weds., Feb. 26 from 6:00-9:00 pm CT
A night showcasing the top Edtech startups in Chicagoland! See who wins Midwest All-Edtech 2025 honors, hear their pitches, and sit in on a fireside chat with former LearnCore Cofounder (exited to Showpad) and current Screencastify CEO Vishal Shah.
EdTech Institute Members can receive $10 off GA and last-minute tickets. Use promo code INSTITUTE at check-out!