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#657True Confessions of a Sales Leader75.0 / 100Get badge
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True Confessions of a Sales Leader

Hosted by The Olsen Group

Listed under Business

True Confessions of a Sales Leader is a podcast where sales leaders share the secrets of their successes and failures, while offering hard won guidance along the way. We’re here to help you transform your sales organization by developing the skills, system and culture that lead to sustainable and significant results.

25 episodes · publishes monthly · latest 2024-07-16 · ~35 min/episode

Rank

#657

Substance

75.0

/ 100

Breakdown

Scored 2026-07
Updated monthly

Sales rank

#21 of 279

Best B2B Sales Podcasts →

Across the index

#657 of 6182

Substance

Top 11%

outscores 89% of the index

Why it scores where it does

True Confessions of a Sales Leader ranks #657 on The B2B Podcast Index with a substance score of 75.0 out of 100, scored across 1 recent episode. It scores highest on guest caliber and insight density. Lee Blakemore (CEO with 30+ years in sales, IBM experience, Anthology/Blackboard background) and Justin Picciano (VP Sales & CS, Accenture background) are credible operators with real execution experience at scale. However, they are primarily discussing their own relatively early-stage product (Introhive) and lack the heavyweight brand names or breakthrough results that would push them into the 17+ range. Both are solid practitioners but not transformational figures in the broader industry.

The five-dimension breakdown

Averaged across 1 recently scored episode, with cited evidence.

Insight Density

15.0 / 20

The episode contains some useful framework-based insights - particularly around ICP definition, bottoms-up/top-down planning, and relationship-driven selling - but much of the content rehashes familiar B2B playbook concepts (forecast accuracy, discovery importance, data quality). The discussion lacks novel data points, specific metrics, or counterintuitive claims that would elevate it beyond standard sales leadership wisdom.

“we really took a step back and put a real solid level of focus on what our ICP or our ideal, uh, client profile is”

“you have to do it both the bottoms up and sort of the top down if you will”

Originality

13.0 / 20

The episode leans heavily on established B2B sales frameworks and widely circulated concepts: relationship-based selling, forecast control, alignment between product and go-to-market, and the dangers of over-relying on data/AI. While the speakers are experienced practitioners, the core ideas presented - including the Moneyball analogy and the pitch about warm introductions - are conventional and recycled across many sales podcasts.

“people buy from people. I say it all the time”

“garbage in, garbage out”

Guest Caliber

19.0 / 20

Lee Blakemore (CEO with 30+ years in sales, IBM experience, Anthology/Blackboard background) and Justin Picciano (VP Sales & CS, Accenture background) are credible operators with real execution experience at scale. However, they are primarily discussing their own relatively early-stage product (Introhive) and lack the heavyweight brand names or breakthrough results that would push them into the 17+ range. Both are solid practitioners but not transformational figures in the broader industry.

“I've been in sales for my entire career, so, which has been just a little over 30 years now”

“I began my career at Accenture and has since worked with numerous leading organizations specializing in transforming companies to handle growth at scale”

Specificity & Evidence

14.0 / 20

The episode largely avoids concrete numbers, timelines, and named customer examples. While Lee references IBM experience and market pivots, he deliberately declines to name specific countries or provides few details on outcomes. The discussion of Introhive's ICP work and go-to-market strategy is generic and lacks the granular metrics (contract values, win rates, sales cycle length, CAC/LTV) that would substantiate claims. The guest offers anecdotes rather than evidence.

“There's several examples. So we've had examples of going to certain markets. I uh, won't name countries”

“the market dynamics were such that uh, even though the market was large and attractive, there's other, there's other factors to play”

Conversational Craft

14.0 / 20

The host (Scott Olson) asks reasonably structured questions and occasionally invites depth (e.g., requesting specific IBM examples), but rarely pushes back or challenges the guests' claims. When Lee intentionally withholds specifics ('I won't name countries'), the host moves on without pressing. There is little evidence of the host stress-testing assumptions, highlighting gaps, or introducing friction that would deepen insights. The conversation flows smoothly but remains largely in agreement mode rather than pursuing tough follow-ups.

“Lee, could you share specifically a little bit more specific on here was the go to market strategy”

“Lee, I wanted to see if we can go back to the IBM examples”

Standout episodes

  • Unlocking B2B Sales Success

    2024-07-16

    75

Rank over time

First period on the Index - history builds from here.

Episodes

1 scored on substance · 25 tracked in total.

  • Unlocking B2B Sales Success

    2024-07-16 · 50 min

    75 / 100

Frequently asked

What is True Confessions of a Sales Leader's substance score?
True Confessions of a Sales Leader scores 75.0 out of 100 for substance and ranks #657 on The B2B Podcast Index. That puts it ahead of 89% of the B2B podcasts we rank and #21 of 279 in Sales. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is True Confessions of a Sales Leader worth listening to?
Yes - True Confessions of a Sales Leader outscores 89% of the B2B sales podcasts and shows we rank on substance, so a sales operator is likely to come away with something useful.
Who hosts True Confessions of a Sales Leader?
True Confessions of a Sales Leader is hosted by The Olsen Group.
How often does True Confessions of a Sales Leader publish?
True Confessions of a Sales Leader publishes monthly, has 25 episodes, released its most recent episode on 2024-07-16.
Which True Confessions of a Sales Leader episode should I start with?
Our highest-scoring recent episode is "Unlocking B2B Sales Success" (75/100) - a good place to start.

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Guests who've appeared

Lee BlakemoreJustin PiccianoRyan George

Topics this show covers

The themes that come up most across this show's episodes.

Sales training · 25CRO · 25revenue growth · 25sales manager · 25sales director · 21sales leadership · 4Customer intelligence platformIntrohiveRelationship intelligenceSaaS SalesMulti-stakeholder buying committeeswarm introductionsSales Pipeline AnalyticsForecasting ToolsDiscovery in SalesCybersecurity Concerns in SalesCRM platformsDigital marketing

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