Shradha Agarwal, Co-founder, ContextMedia; David Fisher, CEO, Enova International; and Amanda Lannert, CFO, Jellyvision Lab, along with moderator Bradley Serot, SVP, CBRE, talk about their experiences in running tech companies in Chicago. They share about similar and contrasting challenges that they have had to face at their startup, midsized, and veteran companies.

Some of our key takeaways from the conversation:

  1. Growing Pains:
    As a company grows, a lot of time goes into managing and restructuring the organization. The job descriptions of the employees get more narrowed and focused; thus, expanding its workforce gets more and more difficult.
  2. The Secret to Attracting Talent:
    Creating jobs that offer a learning curve and continually challenge employees is the lucrative way of attracting the top tech talent in the market. It is important for companies to strike the right balance between structure and freedom to create a work culture that acquires and retains great talent.
  3. People Matter:
    For companies to motivate and inspire its employees, instilling a sense of complete ownership for their work is pivotal. Employers must show respect for their employees’ work, appreciate their talents and skills, and consider the ideas put forth by them. Complete transparency throughout the organization is crucial so that the goals of the company are communicated across all levels.

Below are some of the key points and moments from the conversation:

  • 1:24 –Shradha, David, and Amanda give a brief introduction of their respective organizations
  • 4:08 – Efficiently managing an organization, creating a positive work culture, prioritizing products, and hiring talent in larger numbers are some of the challenges faced by companies
  • 7:52 – Quality work and providing a positive work culture attract tech talent
  • 11:21 – A favorable workspace helps boost collaboration and fosters good office culture
  • 19:24 – Giving employees a sense of ownership, listening to their ideas, communication across all levels, and respecting talent helps motivate and inspire employees
  • 23:59 – Chicago can sustain growing businesses because it has a lot of trained talent and a strong sense of community
  • 27:50 – Q&A: Is there anything that you wish you had done and has anything gotten better, from a community standpoint, while growing as a company?


Co-founder, ContextMedia
CEO, Enova International
CFO, Jellyvision Lab