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#2113Definitely, Maybe Agile66.8 / 100Get badge
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Definitely, Maybe Agile

Hosted by Peter Maddison and Dave Sharrock

Adopting new ways of working like Agile and DevOps often falters further up the organization. Even in smaller organizations, it can be hard to get right. In this podcast, we are discussing the art and science of definitely, maybe achieving business agility in your organization.

226 episodes · publishes weekly · latest 2026-07-02 · ~27 min/episode

Rank

#2113

Substance

66.8

/ 100

Breakdown

Scored 2026-07
Updated monthly

Engineering & DevTools rank

#141 of 289

Best B2B Engineering & DevTools Podcasts →

Across the index

#2113 of 6183

Substance

Top 34%

outscores 66% of the index

Why it scores where it does

Definitely, Maybe Agile ranks #2113 on The B2B Podcast Index with a substance score of 66.8 out of 100, scored across 5 recent episodes. It scores highest on insight density and conversational craft. The episode offers moderate substance with some concrete learnings around data quality, human-in-the-loop validation, and AI adoption patterns, but relies heavily on exploratory discussion and surface-level observations rather than novel frameworks or deep analysis. Several points (nimbleness, compliance as market signal, MCP workflows) feel underdeveloped or speculative rather than backed by operational depth.

The five-dimension breakdown

Averaged across 5 recently scored episodes, with cited evidence.

Insight Density

14.8 / 20

The episode offers moderate substance with some concrete learnings around data quality, human-in-the-loop validation, and AI adoption patterns, but relies heavily on exploratory discussion and surface-level observations rather than novel frameworks or deep analysis. Several points (nimbleness, compliance as market signal, MCP workflows) feel underdeveloped or speculative rather than backed by operational depth.

“Data quality is important. An example I'm seeing now is with our conference call transcripts endpoint. We recently created a product that transcribes earnings conference calls, and it utilizes AI under the hood to transcribe speaker names, but the AI is just looking at the audio and it doesn't have a great enrichment engine to properly transcribe those names.”

“My biggest learning is that so much changes so quickly with AI, and every week there's a new advancement. So my biggest learning is just to be nimble and adaptive.”

Originality

13.6 / 20

The core ideas - humans in the loop for quality assurance, compliance as competitive signal, adaptability in AI adoption - are increasingly standard in B2B tech discourse circa 2024-2025. The specific application to financial data is useful but not contrarian. The MCP discussion is forward-looking but vague and not distinctively original thinking.

“I think having a human in the loop nowadays is as important as ever.”

“If you've done the work to invest in your security posture, both from a time and money standpoint, you're a legitimate business.”

Guest Caliber

11.6 / 20

Tommy Cotter is a relevant operator with real responsibility for data products at a 15-year-old financial platform processing significant volume and complexity. He speaks from lived experience scaling AI and data infrastructure. However, he is not a founder or C-level executive with broader strategic mandate, which limits the seniority bar; his role is specialized (director of data products) rather than broadly applicable to diverse B2B operators.

“My name's Tommy Cotter. I'm a director of data products at Benzinga.”

“I'm mostly focused on the licensing side of our business. All of the news content and data within Benzinga, all that outbound flow to other businesses where they may use that data and white label it within their platforms.”

Specificity & Evidence

12.8 / 20

The episode includes some concrete examples (earnings call transcription, SEC releases, SOC2/GDPR compliance, speaker name enrichment), but lacks quantitative metrics, timelines, business impact figures, or detailed failure/success stories. The financial arbitrage example is illustrative but anecdotal. Most claims remain at the level of 'we're doing X' rather than 'X generated Y% improvement' or 'we had Z problem that cost us.'

“A lot of times the official SEC document for an earnings release will come out at say 4 p.m. And investors maybe buy based on what's in that official document. And then an hour or two later, the official conference call happens where the executive is speaking about how the company performed. And a lot of times investors will find one nugget of information in that earnings call that contradicts what they just previously read in the SEC release.”

“We're focusing on our SOC2 and GDPR compliance.”

Conversational Craft

14.0 / 20

The hosts ask reasonable follow-up questions and show domain familiarity, but the conversation rarely pushes back, challenges claims, or explores contradictions. Questions are often open-ended and exploratory rather than sharp. The hosts occasionally offer their own takes (e.g., Peter on orchestration engines) but don't use them to pressure the guest or test his thinking. The exchange feels collegial but lacks productive tension.

“Can I just... what has changed in 15 years?”

“Can you describe what nimble looks like?”

Standout episodes

  • Data, AI, and Knowing When to Let Go - with Tommy Cotter

    2026-06-18

    81
  • AI Adoption Starts With How People Think, Not Which Tools They Pick - with Royce Sin

    2026-06-11

    81
  • Organizational Honesty in Agile Teams

    2026-07-02

    66

Rank over time

First period on the Index - history builds from here.

Episodes

10 scored on substance · 61 tracked in total.

  • Organizational Honesty in Agile Teams

    2026-07-02 · 18 min

    66 / 100
  • AI Is Speeding Up Delivery. Are You Building the Right Thing?

    2026-06-25 · 18 min

    51 / 100
  • Data, AI, and Knowing When to Let Go - with Tommy Cotter

    2026-06-18 · 26 min

    81 / 100
  • AI Adoption Starts With How People Think, Not Which Tools They Pick - with Royce Sin

    2026-06-11 · 34 min

    81 / 100
  • What Organizations Get Wrong About Junior Engineers and AI

    2026-06-04 · 15 min

    55 / 100
  • AI in the room, helping non-technical teams actually use it

    2026-05-28 · 17 min

    80 / 100
  • Why Your SDLC Is Broken with Andre Kaminski

    2026-05-14 · 46 min

    94 / 100
  • Intent Is Not Enough

    2026-05-07 · 14 min

    77 / 100
  • Why AI and PowerPoints Are Quietly Killing Your Product Intent

    2026-04-30 · 17 min

    73 / 100
  • Do You Actually Have a Capacity Problem?

    2026-04-23 · 20 min

    79 / 100

Frequently asked

What is Definitely, Maybe Agile's substance score?
Definitely, Maybe Agile scores 66.8 out of 100 for substance and ranks #2113 on The B2B Podcast Index. That puts it ahead of 66% of the B2B podcasts we rank and #141 of 289 in Engineering & DevTools. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is Definitely, Maybe Agile worth listening to?
Yes - Definitely, Maybe Agile outscores 66% of the B2B engineering & devtools podcasts and shows we rank on substance, so a engineering & devtools operator is likely to come away with something useful.
Who hosts Definitely, Maybe Agile?
Definitely, Maybe Agile is hosted by Peter Maddison and Dave Sharrock.
How often does Definitely, Maybe Agile publish?
Definitely, Maybe Agile publishes weekly, has 226 episodes, released its most recent episode on 2026-07-02.
Which Definitely, Maybe Agile episode should I start with?
Our highest-scoring recent episode is "Data, AI, and Knowing When to Let Go - with Tommy Cotter" (81/100) - a good place to start.

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Guests who've appeared

Dave Sharrock · 2Tommy CotterRoyce SinAndre KaminskiDavid Sharrock

Topics this show covers

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

Context engineering · 2Psychological safetyRisk managementOrganizational transparencyCapacity planningvisual management systemsburn-down chartsburn-up chartsrelease boardswork management systemsproject delivery deadlinesFeature prioritizationProduct delivery vs. project deliveryAI augmentation and feature commoditizationIterative and incremental developmentCustomer validation and feedback loopsBig upfront design (BUFD)Business risk vs. delivery risk

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