Dawn Lepore - Former CIO, Charles Schwab

Comparing Large and Small Companies

Dawn Lepore is on the advisory Board of Lead Edge Capital. Dawn was the CEO of drugstore.com, which was acquired by Walgreens. Prior to joining drugstore.com, Dawn was a senior executive at Charles Schwab, where she served as vice chairman of technology, operations, administration, strategy and active trader, and was the Chief Information Officer. Currently Dawn serves on the Board of Directors at AOL, and more. She previously served on the Board of eBay, Wal-Mart Stores and the New York Times.

Comparing large and small companies

Differences between large and small companies

  • Large companies have vast resources but do not move as quickly as small companies
  • Large companies make it harder to see beyond individual business silos
  • Small companies provide a greater sense of purpose and ownership than large companies, but smaller companies have to be much more frugal

Advice for transitioning between large and small companies

  • When transitioning to a small company, must be cognizant that resources will be much more limited and that you will have to perform more tasks outside of your main role
  • When transitioning to a large company, you will have more resources, but it will be harder to get things done
  • When transitioning to a large company, it’s key to identify and build relationships with influencers in the organization

Personal examples of company differences

  • When Dawn started as CEO at drugstore.com, she immediately drove the vision of the company and applied strategies that she had learned over the course of her career
  • Given drugstore.com was initially a much smaller company compared with previous companies that she had managed, she had to do much more work outside of her main role all the way down to basic logistics and admin tasks