Udai Kanukolanu (ex-Motorola, Dell, Ericsson; at Rakuten at the time of recording) has spent two and a half decades in the industry. He started in R&D and moved through product and program management into sales. He tells Isaac T Cohen on The Buying Decision that sales used to be "about wining and dining", that salespeople "were measured on the Rolodex", and that this no longer survives: "trust is built on ability these days." His advice if he were starting over: "first let's deeply understand the business that our customers are in." He also tells the story of a deal to migrate millions of subscribers from one platform to another, where six months in the team was ready to give up.

In this episode:

• (00:32) Sales in four parts: understand your customer, represent them inside your own company, stay true to your numbers, and be strategic
• (02:37) Why the human side of a big transformation, like on-prem to cloud, is harder than the technology, and why "70, 80% of CTOs don't survive these transformations"
• (10:18) The three-legged stool for complex deals: the sales lead as quarterback, solution people, and the execution arm that "generally tends to get missed"
• (12:25) From wining, dining and the Rolodex to second- and third-level conversations, because "trust is built on ability these days"
• (17:26) If he were starting over: immerse yourself in the customer's industry first, because a couple of ChatGPT questions "doesn't get you there"

Guest: Udai Kanukolanu
Host: Isaac T Cohen
A ManyMangoes / MangoMagic production

Watch: https://mangomagic.live/episode/live-recording-the-buying-decision-podcast-series-udai-ex-dell-ex-motorola-ex-ericsson-now-rakuten-m1x2d1
Hub: https://mangomagic.live/p/the-buying-decision

One question. Twenty minutes. Thirty years of quota.

Chris Lee (ex-Siebel Systems, ex-Salesforce twice, ex-DocuSign, now back at Salesforce) tells Isaac T Cohen on The Buying Decision about his first big win at Siebel Systems: a financial institution, a deal of "a little over $35 million in revenue", and a campus where meeting executives in each building meant the front desk and a sign-in. His route was the fire escape, into the basement and up into the main executive offices. He also shares what he took from the CEOs he worked with: Tom Siebel and Marc Benioff pre-IPO, Keith Krach at DocuSign, and Bill McDermott at Siebel Systems. Plus his rule for selling with your CEO, and why "the sale is about people buying from people." His definition of sales: "the one thing that you're really passionate about that you want somebody else to also have."

In this episode:

• (02:06) How he got into sales: his grandmother's walnut magnets, door to door at eight, reading people's faces
• (05:33) What he took from Siebel, Benioff, Krach and McDermott, and why McDermott made everyone "feel so special"
• (09:47) "Rule number 32": follow the CEO's steps, but "not give up on the meeting"
• (14:21) The $35M deal: traditional software, not subscription, at a financial institution
• (15:06) The fire escape: under the campus and up into the executive offices, "for almost two years"
• (19:39) Why great sellers don't need to be "the big showman"
• (22:48) AI fatigue, and why people buy from people

Guest: Chris Lee

Host: Isaac T Cohen

A ManyMangoes / MangoMagic production

Watch: https://mangomagic.live/episode/chris-lee

Hub: https://mangomagic.live/p/the-buying-decision

One question. Twenty minutes. Thirty years of quota.

Gerard Grassi (ex-Oracle, Genesys, Skuid, SAP, Verizon, AWS) joins Isaac T Cohen on The Buying Decision to unpack the human side of enterprise sales — trust, buying committees, and judgment when the number has nine figures.

In this episode: • Why human connection still wins enterprise deals • How trust shapes high-stakes decisions • What a $250M buying committee really cares about

Guest: Gerard Grassi Host: Isaac T Cohen A ManyMangoes production

Watch: https://mangomagic.live/episode/gerard-the-buying-decision-ex-oracle-ex-genesys-ex-skuid-ex-sap-ex-verizon-ex-aws-i0gps6
Hub: https://mangomagic.live/p/the-buying-decision

One question. Twenty minutes. Thirty years of quota.