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How to Relieve the Seller’s Burden with Bridget Gleason & David Kerr [Episode 601]

Bridget Gleason is VP of Sales for Logz.io and my regular partner on Front Line Fridays. We’re joined on this episode by David Kerr, CEO of Octiv.


  • Bridget and Andy welcome special guest, David Kerr. They discuss liberal arts schools. Andy studied History. Bridget studied English, Business, and Math. David studied Politics. David says critical thinking is now a missing skill.
  • There is more pressure these days to get the best grades and go to the best schools and choose your degree before you start.
  • Octiv focuses on the sales enablement and productivity space. They look at solving the problem of seller’s burden through automated document generation for all sales documents to drive the efficiency across sales teams.
  • Seller’s burden includes internal complexity (approvals, pricing), product complexity (SKUs, configurations), and external complexity (a number of decision makers and influencers in the client space). Sales was always complex.
  • Part of today’s complexity is the volume of investigation and discovery to be managed. Back to the school dialog, people used to apply to three schools; now they apply to 15-20 because of the automation and common apps.
  • Customers do the same, getting multiple free demos. There are greater volume and demand for detail. Bridget sees the number of SaaS deals a team manages increasing with increased onboarding from rep turnover.
  • Octiv used to be called TinderBox, but Tinder became a popular product and it was distracting, so they renamed to Octiv. Andy says distraction is a fourth burden on the seller. David talks about Millennials distracted by Slack.
  • With the large stacks, it is difficult to untangle the knot of what is effective. David suggests that automation can streamline the distractions. Technology, applied correctly, gives the reps more time to focus on selling.
  • Unattended automation does not bring the rep closer to the customer. Personalized social selling, augmented by AI can make connections — until it looks automated. We need humanization at scale (not mail-merge).
  • Person-to-person communications are most relevant. Prospects don’t want phone calls all the time. Bridget encourages reps to look for connections in common, a person, place, or thing, and include it in a contact.
  • It doesn’t take an archeological dig to find a connection. Five minutes of searching can often find something of interest to the contact that connects the rep to them. In a high-value deal, it may be worth doing more research.
  • David gravitates toward enterprise sales because of the human connection. People buy from people they know like and trust. David talks about a very relevant and pleasant gift he received from a vendor.