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Keys to Digital Transformation & What Motivates You to Work Hard [Episode 662]

Chris Aarons, a Partner at Inc.Digital and co-author of The Digital Helix: Transforming Your Organization’s DNA to Thrive in the Digital Age, and Bridget Gleason, VP of Sales for Logz.io and my regular partner, join me on this episode.


First guest: Chris Aarons

  • Organizations that want the promise and rewards of digital business need to change how they think, act and behave. ‘Digital wrapping’ is not it. Chris compares transformation to steamships replacing sailing ships.
  • Amazon knows what you want before you want it. Target knows your wife is pregnant before you do. Data is changing our lives. Companies need to understand the value of insights to keep pace with their customers.
  • Chris talks about themes of information and streams of data available to any business. Stores build profiles on you starting with your Zip Code and your online behavior.
  • A company needs to be digital at their core to transform what they do and how they partner with their customers.
  • People are not naturally data savvy. Look for the moments that matter to your customers. Chris explains ways customers make a big purchase. Digital companies can be at the right place at the right time to serve them.
  • Chris gives a case study of a business learning how to spot the right moment to cold call a prospect. It is critical to see the signal through the data noise.
  • Digital transformation is an economic transformation. What are the keys to transformation? One in six companies sees themselves as digitally transformed to get a real ROI on their transformational efforts.
  • Digital transformation creates new possibilities, new markets, and new things that company can do. Chris notes Amazon’s AWS as an example.
  • A digital mindset is the starting point of transformation. How is data connected to the company? How can everybody work cooperatively, not in silos?
  • A two-person company today can function as large companies did years ago, using a digital architecture. Start by understanding the data you have and getting closer to your customers. Look at their social profiles.
  • Chris tells what AT&T should have done to save him as a customer but they missed the signals in the data.
  • Chris explores drivers of digital opportunity: near-instant fulfillment, customization, unlimited experimentation, new markets, competition against big companies, more ability at less expense, and innovation.


Second Guest: Bridget Gleason

  • Being in a startup, you end up wearing a lot of hats and working long hours.
  • In the last 10 years, the percent of women in sales leadership roles has not increased, by one study. Andy is astonished but Bridget is not. When Bridget was raising her children she deliberately avoided leader roles.
  • Bridget started to work longer when her children were in college. She had owned a business, with hours that met her needs. She sold the business to consult. Then, a client talked her into working full-time to build a team.
  • Bridget considered it a full-time consulting engagement. It lasted five years. Now at Logz.io, she is not interested in a Chief Revenue Officer role. If she wanted it, she would go for it. She has the experience, but others find barriers.
  • Bridget finds that where she really thrives and what she enjoys is creating a culture and a dynamic and getting the right people. She has done this before. She would rather do that than pore through sales reports and territories.
  • The bigger title is not always where you will find the biggest reward. The point is to continue to challenge yourself in the role you have. Never become complacent. Know who you are and what makes you tick.
  • Bridget does not think most women crave the pace of leadership in a startup. And some men consider that women are not ambitious. Bridget says the bias is definitely there.
  • We sell into a world with diverse stakeholders and buyers. The sales organization’s diversity at a minimum should match the diversity of their market. The salesperson needs to meet the market in their mental neighborhood.