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Delve Into The Details To Make Every Sale With Josh McKenty

Deals die in the details...so pay attention



Professional Sales Tips you'll learn today on The Sales Podcast...

  • Why Josh?
    • Led the first Cloud migration project of the US government as Cloud Architect;
    • Founder/CTO of Piston (acquired)
    • Early Team Lead at Netscape;
    • Team Lead at NASA;
    • Founder of Delving.

Related episodes and posts

  • Dual citizen: USA and Canada.
  • 2007 at NASA, helping with cloud computing.
  • Started writing software at age six and selling at age seven.
  • He always enjoyed getting in front of customers.
  • Was a sickly child, so he couldn't do a lot of sports around 1983, and his mom had a computer, so he was able to learn early on.
  • Learned to type and learned to spell at the same time.
  • Sales and Sales Ops see each other as a necessary evil.
  • But Sales Ops needs to know what the play is.
  • "CTC Selling" Change the Conversation.
  • Become a trusted advisor from a product salesperson.
  • Subscription models make you earn your sale every month.
  • Help your customer prove they got value.
  • CTC Selling becomes personal.
  • All business is personal.
  • Help your champion.
  • Application Owner, Business Owner, CIO—ABC.
  • His parents sold vacuum cleaners door-to-door.
  • He did training quarterly when he had a global role.
  • The fundamentals don't change.


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  • Be honest.
  • Drive the details.
  • BANT (Budget, Authority, Needs, Timing), MEDDIC (Metrics, Economic buyer, Decision criteria, Decision process, Identify pain, Champion).
Deals die in the details."
  • Delivery, when, and where?
  • Do you get over-commitment of resources?
  • CRMs end up being dumped into spreadsheets.
  • All of this ERP data goes into spreadsheets.
  • Delving into the data.
  • Data science was big in the work he was doing.
  • None of this was working.


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  • They were tracking every touch and using BI tools, but it was hectic and inefficient.
  • The data is always changing.
  • Then COVID and the Suez Canal and the supply chain issue hit.
None of this was working."
  • The auto industry was hit really hard.
  • Vendors were logging into Ford's portal.
  • The downside was the cost of stopping the entire production line.
We have a pile of spreadsheets, and we're trying to make sense of it."
  • Dates, dollars, details...most sales reps don't want to talk about.
  • 800 million people use Excel monthly.
  • He's just pragmatic about it.
  • The spreadsheet is what is passed back and forth.
  • You need a sense of traceability.
  • The board uses it for presentations.
  • It's not just embarrassing if you get it wrong, but it hurts relationships.
  • He had a great team at Pivotal that wanted to continue working with him.
  • The reason people never dealt with this problem is that it is stupidly hard in a boring way.
  • Comparing two spreadsheets is hard.
  • It's not like tracking changes in Word.
  • He spent a full year working this out.
  • He did a lot of hard math work to know they had a viable solution.
  • Then they got feedback from customers.
  • He raised money from VCs with whom he had relationships.
  • Don't leave the boring details to be your customer's problem.
  • He loves Challenge Selling, but you have to be right and have a track record and be humble about it.
  • He was covering Gap at one point, and they were suffering, and he showed up to a conference sponsored by the CIO. Here's the QRM (quantitative risk management). You're losing, and here's why.
  • Let's turn your challenge into the plan.
  • There are no magic bullets, but there are bullets.
  • Bill Cook and James Watters at Pivotal.
  • You can't wait until the of the quarter.
  • Pace of change is key.
  • Paul Maritz was their CEO, and he had a vision.
  • He knew the value the first three customers were receiving.
  • Just rinse and repeat.
  • JP Morgan Chase knew what they wanted to do with Pivotal.
  • His learning loop got faster.
  • Learn from patterns.
  • (Batch your sales calls.)
  • If you have a Monday meeting, check out Delving.

Sales Growth Tools Mentioned In The Sales Podcast

  • Hire The Best Speaker for your sales meeting or marketing conference
  • Take The CRM Quiz: get a free consultation with me
  • Donate: Just because you like the show, the no-bullshit approach, and don't want to buy a book, software, or The Make Every Sale Program.
  • The Sales Agenda: take control of every sales opportunity like a pro.
  • Leadferno: Turn lurkers into leads
  • Founders Card: Get $20,000 in free processing from Stripe, save 15% on Bose, and save on hotels, travel, car rentals, you name it.
  • Send Drunk Emails: ...that get opened and get you paid!
  • Phone Burner: work the phone like a machine so you can be a human when you connect.
  • Sendspark: Send video emails that make an impact so you can stand out from the noise. Use promo code SALESWHISPERER to get 33% off for three months


  • Guest Site: https://app.delving.com/
  • Guest LinkedIn: https://www.linkedin.com/in/joshuamckenty/


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