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The Customer UnSuccess Podcast

Hosted by Joe Di Grande

Tired of Customer Success conversations that sound like they were written by a vendor's PR team? The Customer [Un]Success Podcast cuts through the noise to expose what’s actually broken in Customer Success, and other GTM roles, and what to do about it.

29 episodes · publishes weekly · latest 2026-04-06

Rank

#99

Substance

42.3

/ 100

Why it scores where it does

The Customer UnSuccess Podcast ranks #99 on The B2B Podcast Index with a substance score of 42.3 out of 100, scored across 3 recent episodes. It scores highest on guest caliber and insight density. Genuinely senior and relevant practitioner: a Chief Customer Officer with 20+ years spanning a $40B+ regulated enterprise and multiple tech startups, giving her credible perspective on both worlds.

The five-dimension breakdown

Averaged across 3 recently scored episodes, with cited evidence.

Insight Density

9.3 / 20

A few useful concepts (anti-goals framing, the structured prioritization interview test, the EBR knowledge tell) but heavily diluted by generic career advice, agreement filler, and small talk about Christmas sweaters and LinkedIn Lunatics.

“maybe starting out with writing out things that you absolutely do not want”

“I give a list of five things and I want them to prioritize it”

Originality

8.3 / 20

The anti-goals concept and the deliberately-ambiguous interview exercise are reasonably fresh, but much of the episode recycles common career advice ('know thyself,' 'do your research,' 'use ChatGPT') without contrarian or first-principles thinking.

“it's easier for folks to think in anti-coals”

“be willing to take a step back in title if everything else matches up”

Guest Caliber

11.3 / 20

Genuinely senior and relevant practitioner: a Chief Customer Officer with 20+ years spanning a $40B+ regulated enterprise and multiple tech startups, giving her credible perspective on both worlds.

“I'm joined by Miranda Dekonsky. She's the chief customer officer at FEXA”

“at a company that was a very large $40 plus billion dollar a year company. I spent nine years there managing a portfolio of accounts”

Specificity & Evidence

7.0 / 20

Some concrete texture - named enterprise logos, a detailed walk-through of two contrasting candidate responses, the seven-day EBR trap - but the bulk is hypothetical scenarios rather than real outcomes, dollar figures, or measurable results.

“just GM, Toyota, AstraZeneca, Bosch, Ford”

“you have a EBR that is due in seven days, and you have uh 10 Zendesk tickets”

Conversational Craft

6.3 / 20

The host asks relevant follow-ups and steers the conversation, but defaults to constant agreement ('100%', 'I love it') and never challenges or pressure-tests any claim, including the contrarian title-downgrade advice.

“100%. Yeah, I love it”

“No, it's too, it's super interesting”

Standout episodes

  • Chaos Threshold: Startup CS Vs Enterprise w/ Maranda Dziekonski Chief Customer Officer at Fexa

    2026-03-09

    49
  • How To Win Over The C‑Suite and Turn Champions Into Heroes w/ Rachel Provan CEO of Provan Success

    2026-04-06

    46
  • Stop People-Pleasing, Start Outcome-Pleasing w/ Jess Szivos VP of Customer Success at Invisory

    2026-03-23

    32

Rank over time

First period on the Index - history builds from here.

Episodes

3 scored on substance · 29 tracked in total.

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