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Episode 29: Retiring into the Next Chapter of Impact.

Beer Stories for Private Equity · 2026-08-25 · 27 min

0:00--:--

Key moments - from our scoring

Substance score

51 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality9 / 20
Guest Caliber13 / 20
Specificity & Evidence8 / 20
Conversational Craft10 / 20

Harry Moseley brings a distinctive perspective to private equity conversations: unlike typical PE insiders, he's built a career across corporate technology, financial services, and advisory roles rather than within PE partnerships. Trained as an engineer-turned-software developer, he emigrated to the US in 1979, founded an early fintech platform for derivatives and risk management in 1981, spent 14 years at UBS and later Credit Suisse in banking technology, then unretired to join Zoom as an advisor where he worked directly with CEO Eric Yuan. Moseley's selection criteria for advisory roles centers on three filters: the people and leadership team he'll work with, a distinctive platform or challenge (not "me too" companies), and his genuine ability to add value. He emphasizes agility in strategic planning cycles, warning that AI adoption requires companies to redesign processes from scratch rather than retrofitting technology into existing workflows. He also highlights emerging macro risks: AI-driven cybersecurity threats, supply chain unpredictability amid geopolitical instability, and the need for organizational resilience. For PE operators and portfolio company leaders, Moseley offers hard-won lessons about making yourself dispensable for promotion, the importance of peripheral vision in competitive landscapes, and the necessity of rapid organizational pivots when market conditions shift.

Key takeaways

  • →Make yourself redundant in your current role to enable promotion; organizations promote from within only when backfill is possible.
  • →AI implementation requires redesigning entire processes from a blank slate rather than retrofitting AI into existing workflows.
  • →Companies must shorten strategic review cycles and embrace agility to adapt to unpredictable shifts in geopolitics, supply chains, and competitive dynamics.
  • →Cybersecurity has evolved from a technology issue to a business-critical issue as bad actors increasingly use AI to find system vulnerabilities.
  • →Advisory role selection should be filtered on three criteria: genuine affinity with the leadership team, a distinctive/differentiated platform, and demonstrated ability to add value.

Guests

Harry Moseley

Topics in this episode

KPMGZoomUBSsupply chain resilienceCybersecurity threatsEric YuanDerivatives and options tradingCredit Suisse First BostonFintech platformsAI adoption and process redesign

Questions this episode answers

What made Zoom fundamentally different from competitors like WebEx, Skype, and GoToMeeting?

According to Eric Yuan, while competitors' platforms worked, they didn't work reliably, were not easy to use, and lacked consistent quality and stability. Zoom's radically different technology architecture solved these problems, which is why Yuan built the platform.

How should companies approach AI adoption to maximize benefits rather than disappointing returns?

Companies should not retrofit AI into existing processes; instead, they need to redesign processes from scratch on a blank slate, identifying the start and end states first, then embedding AI as a core part of the redesigned workflow.

What are the top macro risks business leaders should prioritize beyond AI and geopolitics?

Supply chain unpredictability (due to shifting suppliers, price volatility, and geopolitical disruption), cybersecurity threats amplified by AI-enabled bad actors finding system vulnerabilities, and the need for organizational resilience to handle rapid, constant change.

What criteria does Harry Moseley use to decide which company advisory roles to accept?

He evaluates three factors: the people and leadership team (must genuinely like and want to spend time with them), the platform (must be distinctive, not a me-too company), and his demonstrated ability to help solve their specific challenges.

How has the nature of corporate strategy cycles changed in response to AI and market volatility?

Strategic review and planning cycles need to become shorter and more evolutionary; executives must be willing to reassess and redirect resources frequently, even mid-cycle, rather than adhering to rigid annual or semi-annual planning cadences.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some useful operational lessons (making yourself redundant for promotion, process redesign for AI integration, agility in strategic planning) mixed with substantial biographical storytelling and general observations about AI, cyber security, and supply chain volatility. However, much of the substance is either broadly known (AI hype cycle, need for agility) or vague enough to limit actionable takeaway. The specific tactical advice is sparse relative to runtime.

make yourself redundant because if you don't, you'll never get promoted
companies need to sort of take it back to basics...redesign the process leveraging AI as opposed to trying to get AI to fit into your existing process

Originality

9 / 20

Most frameworks and observations are recycled: AI disappointment after hype, supply chain unpredictability, cyber risk, need for agility. The Zoom origin story (reliability vs. competitor mediocrity) is personal but not particularly contrarian. The advice to redesign processes from scratch for AI is sensible but not novel. No first-principles challenges to conventional wisdom or truly counterintuitive claims emerge.

do they work well? Do they work reliable? Are they easy to use?
throw it all out, take a white sheet of paper, build the process from scratch with AI

Guest Caliber

13 / 20

Harry has legitimate scale experience (UBS, Credit Suisse, Zoom advisory) and senior-level exposure across finance and enterprise SaaS, making him materially credible on technology and organizational issues. However, he is primarily an advisor and board member rather than an operating executive currently running a business at scale. His perspective is informed but not from the sharp end of current execution risk.

longtime senior executive in the world's leading technology companies, management consultancies, and private equity firms
I was working for UBS for about 14 years

Specificity & Evidence

8 / 20

The transcript relies heavily on anecdotes and broad observations with minimal concrete data. The Zoom conversation with Eric Yuan and the story of the CEO firing product management are narrative-driven but lack measurable outcomes, timelines, or impact metrics. No financial figures, adoption rates, or quantified business results anchor the claims. Cyber risk and supply chain commentary remain abstract.

I remember Eric looked at me and said, I have two questions in response to your one question
a friend of mine who runs a search firm there and he was telling me how the CEO woke up one day and you know, and fired the entire product management team

Conversational Craft

10 / 20

Scott asks reasonable setup questions but rarely pushes back, challenges assumptions, or pursues uncomfortable follow-ups. When Harry makes broad claims (e.g., 'AI is going to cause more hiring'), Scott does not press for evidence or examples. The interview reads more as a friendly biographical conversation than a probing deep-dive. Few moments of productive tension or skeptical challenge.

So Harry, you are from where? Born and raised where?
what brought you to the U.S. uh, and what kept you here?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B68%
  • Speaker A32%

Most-used words

private10equity10today10harry10back10zoom10beer9world9interesting9first8technology7remember7nail7role7call6bank6

Episode notes

This podcast is powered by MonogramGroup ( - Welcome to Beer Stories for Private Equity! In our 29th episode, we are joined by Harry Moseley, a retired (sort of) senior executive across many notable corporate and PE positions. Among their beer stories, Scott and Harry discuss his origin story in Dublin, Ireland, his long and distinguished career as a tech leader, and what PE executives should be focused on today. We know you’ll enjoy their convo. - We are receiving great responses to our podcast, and have several guests scheduled for upcoming episodes. If you would like to be considered as a guest in our lineup, please email smarkman@monogramgroup.com. - Follow Harry Moseley, on LinkedIn (

Full transcript

27 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome to Beer Stories for Private Equity. Join us for our weekly happy hour, tapping into 27 years of PE experience one pint at a time. Beer Stories for Private Equity is powered by Monogram Group. On today's show, we're excited to be joined by Harry Moseley, longtime senior executive in the world's leading technology companies, management consultancies, and private equity firms, as well as a current board member, investor, and advisor to several companies. And for Monogram Group, here's your host, Scott Markman. Please fasten your seatbelts. Welcome to the latest episode of Beer Stores for a Private Equity. I'm your host, Scott Markman. And joining me today is, uh, Harry Mosley, who was based in New York. Um, I've gotten to know Harry over the last year or so, and, um, have found him to be one of the most kind of interesting, diverse, uh, dynamic folks that I've met in a long time and thought he would be an excellent guest, uh, for the podcast. And so, Harry, welcome to Beer Stories.

Speaker B: Thank you, Scott. A pleasure to be here. I think we need to find a way to have you meet more people. If I'm one of the most interesting that you've met, let's let our listeners

Speaker A: be the judge of that. Um, so before we get into our conversation, um, as we always do on Beer Stories, um, we bring out early and often, as we say in Chicago, our beer. And so my beer du jour Today, it is 3:10, by the way, so it's not a crazy thing. Uh, Central time is, uh, Smithick's Red Ale, made by our good friends in Guinness. At Guinness. I'm sorry. Um, and so I'm a huge red ale fan, and I've had this many times, and it's outstanding. And what is your year?

Speaker B: That was a great call. I'm not as creative as that. I'm, uh, Sierra Nevada.

Speaker A: All right, so we're both drinking ales, and so there's something pale ale.

Speaker B: I'm very fond of pale ale.

Speaker A: All right, so the best sound in town. And I even have a pilsner glass, so, um, gonna be official here. All right, cheers. Ooh.

Speaker B: Awfully good.

Speaker A: Awfully good. All right, so we always start our conversation with a little bit of background. Um, I am going to tip my hand here a little bit about Harry, Um, which is, um, unlike a vast majority of our guests, he is not in and of and immersed in the world of private equity. He is related to, understands, and involved with private equity, and we can talk about that, but he's not a Partner at a firm. He's not a portfolio company CEO. He has a very interesting diverse background, but I'd say more on the corporate side and has been involved in private equity related activities over the last five years. Ish or so, something like that. So there is a correlation. But, um, I really thought that that was an interesting angle to bring to the table. Um, so with that bit of background. So Harry, you are from where? Born and raised where?

Speaker B: I was born and raised in Dublin, Ireland.

Speaker A: Oh. And so that's why I had the Smithics here, because it was made down the street.

Speaker B: That was no accident. That was delivered.

Speaker A: Shikaboom. Thank you very much. What did your dad do?

Speaker B: So, uh, initially he was manufacturing beds. Uh, and bed manufacturing back then was all by hand. So you'd stuff the mattresses by hand. The bed frames were made out of wood. Um, and the wood had to be cut and the wood had to be nailed like physically with nails. And there was no pneumatic guns for. It was like, you know, I mean, the workers had a, had a big canvas sort of apron. I remember this like yesterday. I was probably like eight or nine at the time. And this is how I spend my summer. And uh, it's like these. So these men had these canvas aprons stuffed full of nails and they would take a nail out and they would hammer the nail in. Sometimes they drop a nail, sometimes the nail would bend. And of course, you know, the idea of picking up a nail off the floor, that's not happening. Why should I pick a nail up off the floor when I can just take another nail out of my apron? And my father explained to me that those nails cost money. And so, uh, so my first job ever was actually dragging a magnet on a rope around the factory to pick up the nails. The straight ones went back in the box and then the bent ones I had to straighten out and put back in the box. So that was my earliest start of my working career.

Speaker A: Was. Was this your father's company?

Speaker B: Yes. Yeah.

Speaker A: Okay, so we have something else in common. I mean, I, I'm, I'm sure a much smaller company, but my parents own a business. They started the year I was born and I, I, um, grew up going there. And I worked there as a kid, probably off and on through high school, you know, winter vacations or vacation, whatever. And I did that. The equivalency of, you know, taking the magnet and walking across. My parents, um, did, uh, trophies and plaques and document laminations and a bunch of hodgepodge of stuff. But one of My jobs was to take the boxes that came in from the manufacturers of the wooden plaque board boards and the metal plates, like the brushed brass plates and the figurines of the trophies and stick them in the bins and all of that stuff. So like you, I kind of learned the business from the ground up. So I certainly you know, did my homework and looked at your sort of, you know, listings in, in LinkedIn and you know, for anybody who looks at Paris background, it's about you know, six feet long. Um, so what brought you to the U.S. it looks like maybe your first U.S. job was credit Suisse First Boston and Blackstone, KPMG and Final Zoom. So what brought you to the U.S. uh, and what kept you here?

Speaker B: Yeah, um, so as I explained I transitioned from engineering to computer science working for the software company in London. In um. There's um, there's the, the long version and the short version of what happened in June of 1979. June, July of 1979. The short version is I um, got transferred uh, for. By the. I got transferred to New York working for the same software company that I was working for in London. Uh, there's a more interesting story that I can tell you over a beer about what actually transpired. But the outcome was my wife and I were, my wife at the time and I were sent uh, to New York for six months. And um, that's how I got to New York, worked uh, for the work for that company until the fall of 19 uh 81, so call it broadly speaking over two years. And then um. And then in uh fall of 1981 I started my own company, uh, which today you call it a fintech company. It was a company focused on um, uh we built a platform for doing accounting, risk management and trading, uh, off balance sheet transactions, essentially futures and options derivatives, um, uh, back in 1981 and then in 1984 uh, for a variety of reasons I decided I uh, would leave my own company and uh, I joined UBS. Uh so I worked for UBS for about 14 years. Um, and then they merged with Swiss Bank Corporation. I decided I didn't want to be part of that merged organization, took my risks and ended up with Credit Suisse. Uh so a lot of people say that's interesting. You work for one Swiss bank, then you went to work for another Swiss bank and your wife uh, is Swiss. All those things, you know, sort of were independent uh, uh, transactions if you will. Not that my wife was a transaction that far from it. But um, uh they just sort of uh, they were just coincidental.

Speaker A: Um, so as you kind of again, you sort of worked for the titans of, you know, finance and, and you know, leadership and whatnot, what were you seeking with each new position? Knowing you were sort of staying in technology as software?

Speaker B: Yeah. You know, sort of all boils down to the same things I said earlier, which was, um, nice people, people I like, people I could enjoy working with, breaking bread with, having fun with, uh, and that there was a purpose behind it and a challenge. Um, uh, you know, if there, if there was no challenge, you know, earlier, you know, when I was very early in my career, uh, uh, one of my, uh, advisors, and we can come back to that in a moment, one of my advisors said the best thing you could do, Harry, is make yourself redundant. Mhm. Because if you don't, you'll never get promoted. Because when, you know, and I learned that, uh, you know, and I saw that sort of from the other side as I sort of climbed the ranks of, you know, organizations, you know, you're looking around, you know, you have a great opportunity and the first thing you want to do is you want to promote from within. Right. So you look around your organization. Who, who can we put into this role? And then you, you know, you see some, somebody, Jim or Laura, who would be great for the role, but there's no one to backfill them. So you can't promote them into the role. And if you do, you're taking a risk and then you have to backfill them and it becomes difficult. But if you, if that person has made themselves, uh, dispensable, um, uh, such that they can take on a new role, that's terrific. So that was one of my early lessons in my career.

Speaker A: So one of the first things I learned about you is that you had retired, maybe started your career as one like a board member, advisor kind of person. Then you unretired and worked for, I think Zoom was your last corporate job and then have retired again. So what led to the unretiring? And so just talk for a minute about sort of your role at Zoom.

Speaker B: Yeah, absolutely. So, yes, I retired back in, uh, December, uh, of 2017, um, with, with no intention of, you know, working in the, you know, working for a company ever again. Um, hadn't really figured out what I was going to do with my time. And I, I, I do remember sort of that time, uh, very well where I was, you know, sort of, um, uh, getting up early, still doing breakfast at 7am in the city, doing dinners, taking every call, et cetera, and um, so, as my wife said, it's like, you know, yes, you were retired back then in December of 17, but didn't seem like you were retired because you were still burning the candle at both ends of the wick. Um, I got called soon after I retired from kpmg, uh, to join Zoom. And I remember talking to Eric Yuan, uh, back in those early days. And, uh, I remember saying to Eric, much like on a call like this, it's like, eric, you know, explain to me why Zoom when you have all these other platforms out there. You had WebEx, you had Skype at the time, you had GoToMeeting. Log me in. You had blue jeans, another one that sort of gone. Um, you had facetime, uh, those others, I can't remember them now. Um, and I remember Eric looked at me and said, I have two questions in response to your one question. The first question is, Harry, do they work? Sorry, go on. And I remember my answer extraordinarily well. And, uh, I said, yes, they do. And his second question was, do they work well? Do they work reliable? Are they easy to use? Is there great quality, reliability and stability? No. That's why I'm building Zun. And, uh, then we got into talking about the technology and the architecture of the Zoom platform, which was radically different to everything else that's out there. Uh, Eric is brilliant. In a word, brilliant. Absolutely brilliant. And he has built a fabulous company,

Speaker A: um,

Speaker B: uh, which is, you know, sort of still. It's like whenever I get invited to a meeting on a different video platform other than Zoom, it's like, I still shake. Um, and it still just doesn't work. Nothing works quite as good as Zoom.

Speaker A: So broader question about your, you know, your advisory, you know, sort of role. How do you decide which firms or companies to say yes to, and you'll sort of become involved in and try and help them? And then a subset of that is especially the world of private equity. Which firms. What are you looking for? How do you approach how you think you can help them? Because private equity firms have lots of folks that have an advisory capacity or operating partners or something on the side. And so, given the broad context of what you've been talking about, especially about sort of the people side and sort of the looking, uh, for something distinctive. What's your filter on efsa?

Speaker B: Yeah, it's those three. Three things. It's the. It's the people, the platform, and, um, my ability to help. So I gotta love the people. Gotta be, you know, gotta, you know, in almost every case, the. You Know, the CEO of the company has become like a personal friend. We, you know, break bread together several, uh, of them. We do it with our spouses. Uh, we spend time together. We have. It's like, it's fun. It's like, gotta really, really like the people. It's, um. You know, there was, uh, one organization that approached me about being an advisor. And I found that, uh, the CEO and his leadership team were a little bit egotistical. And, um, they didn't have, uh, any peripheral vision as to what was going on in their specific industry that they were targeting. Uh, and when asked about competition, they were. They discounted the competition. They said that this competition doesn't exist because. Because we said so type of thing. Which, uh. Anyway, um, so it's one is the people, the leadership got to really like them. 2 is. Can't be a me too. Like, what's different about you? Uh, what are you trying to do? It's got to be a really interesting challenge. Um, you know, one of the. One of the companies I advise is the Israel Discount bank of New York. Uh, and, um, Abner Mendelssohn is the CEO. He's a terrific guy. He's got great vision, really, really nice. Uh, he got a great leadership team and he's rebuilding the bank. And, um, uh. And uh, that's kind of like fun. It's where I started my career back in the late 70s. I was building banking systems. So the idea of sort of helping Avner and his team build a bank today is kind of, you know, sort of really fun and interesting opportunity given all of the technology advances that we have now.

Speaker A: So with that context of a broader question, if you were to identify one or two macro business topics that you think business leaders should stop what they're doing and pay attention to. I don't mean something like, how is AI going to affect the world? So that's broadly being debated and understood. Or I make this up. Iraq, Iran, war or something. But things that make you think that anybody who's listening to this is not aware of or paying attention to that based on your, you know, perch that you think they should be.

Speaker B: Uh, well, uh, you know, you. You hit a couple of them. You know, first of all, you know, AI is like, you know, I think we've had. We've gone through sort of the, uh. Uh, the, you know, sort of the. We've, you know, we've seen the innovation from an AI perspective. You know, we've got all sorts of expectations of what AI can do. You know, you. You Read about how companies laid off thousands of people as a consequence of AI. And then most recently in the Wall Street Journal this past week, CEOs are actually saying, well, guess what? It's like AI is actually going to be, you know, as ah, a consequence of AI, we're going to be actually hiring more people. Uh, so they're, they're recruiting as opposed to laying people off. So I think that's kind of interesting. Um, I think some CEOs are sort of now experiencing the disillusionment, uh, if you will, uh, quote the Valley of Despair, uh, uh, from AI because they are spending all this money, they've put AI in the hands of employees and it's like, well, where's all the benefits coming? It's like, I don't see the benefits. I don't see, you know, sort of, we don't, we don't see the uplift. And I think that with respect to AI, what companies need to do is they can't just try to leverage AI into existing processes. You need, they need to sort of take it back to basics. What's the start, what's the end? And how do we, how do we um, how does AI fit into that process and re. So redesign the process leveraging AI as opposed to trying to get AI to fit into your existing process. So it's like throw it all out, take a white sheet of paper, build the process from scratch with AI as part of it now. So I think that's, that's really important. I think the world is um, structurally changing. You know, the uh. We've got a lot of things that are unpredictable, out of our control. Whether it's you know, wars or tariffs or uh, politics, what have you. And I, uh, think that companies need to sort of be thinking about sort of uh, uh, how to, how are they going to roll with all of these unpredictabilities, uh, things that are out of their, um. One of the things that it, you know, sort of um, comes to mind that I think companies need to sort of think about is like uh, the, their whole supply chain, because that supply chain is changing all the time. And so your supplier can come from one part of the country or one part of the world today, and maybe it's going to change tomorrow and maybe they'll be in business, maybe they'll be out of business. Prices go up, prices go down. Uh, it's like, you know, it's so, so from a CEO's perspective, from an executive perspective, unpredictability, things constantly changing. What I Thought today is not what I'm thinking tomorrow. What I'm thinking tomorrow is not what I thought today. It's like, it's very difficult. It's very, very difficult. Um, and then, you know, and then cyber, um, you know, cyber security has always been top of mind, but it was seen as a sort of, as a technology issue, not as a business issue. And cyber security I think now has be. Is much more of a business issue than it ever was before in terms. Because, you know, whilst we see all the benefits coming from AI in terms of operations, in terms of service management, in terms of sales and what have you, uh, AI is also being leveraged, uh, to be the bad guy. And we read or read about how, you know, some of these AI models have run away with, you know, because they have the ability to authenticate and find holes in other systems. You know, the bad guys are leveraging AI. And so this has become a real critical issue for I think every, uh, company out there. It's like, how do they, how do they combat this cyber. Um, and it's, uh. I would recommend that CEOs of companies sort of exercise their ability to be resilient in a, From a cyber perspective.

Speaker A: So along those lines, you think about sort of the cadence of strategic review and planning and turning it into investments in people and uh, processes and whatever the cadence of that is every six months, a year or something like that. Do you think that that should be getting shorter and more like, you know, be evolutionary? Because that's how AI is impacting business and companies need to be reassessing things faster and be more nimble, broadly speaking. Because they don't have a choice.

Speaker B: Yes, I think that, uh, the ability to be agile and to be able to redirect resources, change things on the fly and, and not to be, um, uh, not to be afraid to call it out and say, I think this is, you know, I think we need to reevaluate, you know, this process or reevaluate this business unit, how it functions, how it operates. You know, I was talking to somebody fairly recently, oh, when I was in Israel, um, uh, I was talking to a friend of mine who runs a search firm there and he was telling me how the CEO woke, uh, up one day and you know, and fired the entire product management team. And the reason he did that was because he didn't believe that they were still working in the analog world as opposed to the digital world. He couldn't get them to work in the digital world. He couldn't get them to leverage the technology and the tools. So he decided that he was just going to wipe the slate clean and start that whole function in his company again from scratch. Very, you know, sort of very, uh. I'm trying to think of a more professional way to think, say what I'm thinking, but it was a very, uh, courageous. That's probably the best way to put a very courageous, uh, way to deal with the issue.

Speaker A: Sounds like move fast and break things.

Speaker B: Yeah, yeah. It's, uh, you know, it's, um. You know, when people, you know, when. When AI first came out, which I think it was probably a little over three years ago now, everybody said, like, experiment with AI. Um, and. But, you know, the. And if. And if the experiment works, then harness it, leverage it, and run with it. But, um. But don't be frightened and don't be worried if it. If it. If it doesn't work, because then you learn. That's also a learning opportunity. Right? To learn what doesn't work is just as important to learn what works.

Speaker A: Harry, thank you so much for being on the podcast today. This was a brilliant conversation. I hope that our listeners get as much out of it as I did. But I have one last question for you. How on earth have you accumulated 16,257 followers on LinkedIn, which I think is a land record?

Speaker B: There's many more people, many more than me. Um, uh, you know, it's, uh, you know, given. Given the role that I had at Zoom, uh, you know, I was connecting with an awful lot of people in an awful lot of companies in an awful lot of geographies, and so, you know, that was because I. I love talking about Zoom and the technology and the architecture and the platform and how and why it was different. And, um, um, people wanted to hear, so. Yep.

Speaker A: Awesome, Harry, thank you so much. This was incredible, and I look forward to seeing our long, uh, conversations. From all of us at Monogram Group, thanks for tuning in to Beer Stories for Private Equity. Don't forget to hit the subscribe button and you'll be notified as we release new episodes, Please check out the show notes in the description from today's episode. Our email is podcast@monogram group.com Feel free to email us with any comments or questions, and we'll try to answer them in our next episode.

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