ScaleUp Chicago 2021 Recap

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On May 12, we joined our presenting sponsor Wipfli in welcoming business professionals and entrepreneurs to ScaleUp Chicago 2021! This year’s virtual event brought together the full 1871 community for a day of learning, networking, and sharing stories of success for scaling companies across Chicago and beyond. Together, our presenters tackled some of the most pressing topics in the business world, including the lessons we’ve learned from the pandemic and how we can better negotiate in-person and virtual flexibility in the workplace.

We started our day off with a strong brew at our coffee connect, where Brewpoint Head Cafe Manager Alex Corsi guided our attendees through Coffee 101. From there, we were caffeinated, connected, and ready to learn!

In our opening panel, we welcomed back a few familiar faces in 1871 CEO Betsy Ziegler, The Forge: Lemont Quarries Co-Founder & CEO Jeremie Bacon, and Jellyvision CEO Amanda Lannert. When these three leaders met last year at ScaleUp, the reality of the COVID-19 pandemic and its effects on business had fully set in. This year, they discussed the lessons they learned from their shift from the physical to virtual workplace and spoke with optimism about the future. Calling in from a tent in the woods, Jeremie explained the need for a new sense of balance in our lives by finding a way to reinforce employee and customer bonds. Amanda also spoke candidly about her company’s vision of the post-pandemic office, which includes an indefinite optional in-person experience, bench and cafe style seating that emphasizes collaboration, and the incorporation of Zoom spaces to better accommodate a hybrid workspace. 

The panel quickly established an important theme that many presenters reiterated: as companies prepare for the possibility of a coming “tsunami of resignations,” or as some have termed the “Great Resignation,” we must renegotiate the employee/employer contract to better care for the whole person, not just the whole employee. 

From here, we jumped into our morning sessions, where participants learned leading insights on a variety of important topics. In “Doing Well and Doing Good: Community Engagement and Impact at Any Stage,” Relativity Head of Social Impact Colleen Costello discussed ways companies can promote community engagement and social impact at a time when doing good in the community is just as important as doing well in our business endeavors. 

Next, we talked about organizational design for growth with our lineup of experts, which included ParkerGale Principal Jimmy Holloran, Hazel Technologies VP of People Michelle Mesina, Pangea Money Transfer VP of People Carolyn Kwon Montgomery, and XSELL Technologies Head of People Elles Skony. Panelists explained that HR needs to work closely with each team to gain clarity and alignment in a company’s hiring goals and needs, which will allow a company to slow down or speed up the recruitment process or readjust their priorities as needed. On the topic of the hybrid workplace, they argued that business leaders need to learn now how to lead hybrid teams in a way that removes in-person bias. Jimmy also reiterated the hybrid is most likely the way of the future, noting that “companies that are flexible and get it right will win the war for talent,” because ultimately “younger Gen-Z employees will end up making the decisions for companies.”

Before we breaked for lunch, our participants were treated to a fascinating lesson on the growing role of machine learning and AI from Enova Chief Technology and Analytics Officer Joe DeCosmo. During the session, Joe explored how the pandemic has accelerated the shift toward machine learning as consumers have begun to gravitate towards AI assistance, including personalized shopping, customer service bots, and more. Joe proposed a new, human-focused approach to AI, in which this innovative technology can replace repetitive, low value tasks and improve the customer experience to free up staff to focus on customer-facing, value-added activities. 

While our morning was packed with enlightening information, our participants were still hungry for more after lunch! In our first afternoon session, we discussed OKRs and Transitional Roadmaps with Kin+Carta Principal Product Carla Pajak, Zebra VP of Portfolio & Strategy, Products and Solutions Group James Poulton, Groupon Global Head of Technical Program Management Christine Stone, and Wipfli Technology Industry Leader Girish Ramachandra. The panel agreed that companies should reframe their view of KPIs away from a checklist to a roadmap leading them where they want to go. 

In our last session, Sales Assembly President Christina Brady and Salesforce Regional Vice President, Enterprise Corporate Sales Jaron Kent talked about how businesses can impact their bottom line with company culture. Jaron reiterated how important it is to stay proactive when leading a team virtually, and advocated for leaders to incorporate options for office hours and virtual happy hours in order to over communicate as necessary while also giving your employees your undivided attention over the video camera. 

Finally, we finished ScaleUp strong with a closing fireside chat between Betsy Ziegler and Relativity CEO Mike Gamson. Mike spoke about his deep connection to Chicago, how that love for his home guided him throughout his career, and how entrepreneurs can access coastal VC funding without ever leaving the Midwest. Mike also reiterated many of the insights provided in the opening panel, and reminded participants that in addition to investing in re-envisioning the physical office space and video skills, we must commit to inclusive leadership—not just in regards to race, gender, and age, but also time zones and location. 

Thank you again to everyone who joined us for this year’s ScaleUp Chicago and to everyone who made this event possible, including our panelists, presenting sponsor Wipfli, and gold sponsors Invest Northern Ireland, Okta, Ramsay Innovations, Salesforce, and The Wall Street Journal!