As an experienced product leader considering a VP or CPO role, I want to understand the skills, trade-offs, and mindset shifts required at the executive level so that I can build a clear, practical plan for what to develop next in my career.
Ever feel torn between wanting the impact and scope of a VP or CPO role and worrying about what you might lose along the way? If you’ve been reading job descriptions, Reddit threads, or career advice that all seem to contradict each other, you’re not alone. In part two of our product management career progression series, we get honest about what actually changes as you start aiming for executive product leadership.
We welcome back special guest David Nash to unpack the real work behind VP and CPO titles, and the parts no one puts on the career ladder diagram. We dig into how success gets measured differently, why influence matters more than authority, and what it really means to trade hands-on product work for organizational, financial, and people decisions. We also talk about how to prepare without rushing. What skills matter, how to spot roles that are set up to succeed, and how to stay grounded when the politics and ambiguity show up.
If you’re considering the VP or CPO path and want clarity instead of hype, pull up a chair on the porch. Learn from the scars, shortcut some hard lessons, and leave with a clearer sense of what to build toward next and whether this path is truly right for you.
Introduction and Episode Overview
[00:00] framing part two of the product management career progression series
[01:30] why moving up is less about leveling up mindset and more about changing orientation and scope
Guest Introduction and Personal Context
[02:37] David Nash’s background as a multi-time CPO and why lived experience matters at this level
[03:50] personal milestones and rapport that ground the conversation in real leadership journeys
Transitioning from Director to VP
[04:26] the myth of empowerment and why more senior titles do not remove constraints
[06:46] the three Ps framework: product, practice, and people, with people becoming the dominant focus
[07:41] staying close enough to the work without drowning as the scope expands
Challenges and Strategies in Executive Product Leadership
[08:53] legacy products, uncomfortable trade-offs, and why old platforms often fund innovation
[10:40] unwritten strategy, executive subtext, and navigating ambiguity that is never documented
[17:41] balancing short-term delivery with long-term outcomes that executives and boards care about
[19:33] building alliances across the executive team to survive competing priorities
Leadership Trade-offs and Organizational Reality
[21:58] sacrificing product purity without losing intent as responsibility shifts toward the business
[26:49] the CPO mindset shift from product-first thinking to business-first accountability
[29:51] dysfunction at the executive level and why maturity does not magically appear with title
Personal Growth, Mentorship, and Meaning
[41:10] why mentoring and developing people becomes the most fulfilling part of leadership
[43:59] reflections on impact, legacy, and staying connected to why the work matters
Closing Reflections and Takeaways
[46:11] one-word takeaways capturing growth, trust, discomfort, and people
[47:26] final thoughts on preparation, clarity, and choosing the VP or CPO path intentionally
Todd Blaquiere (Co-Host) (00:00):
Hey, thanks for listening. Please subscribe to our newsletter at theproductporch.com for notifications on the latest episodes and exclusive content.
David Nash (Guest) (00:07):
I'm finally going to be empowered. I'm going to be on chain and they're going to let my awesomeness flow unabated. And you know what? That did not happen when I became a vice president. It also did not happen when I was senior vice president, and it certainly did not happen when I was chief product officer a few times.
Ryan Cantwell (Co-Host) (00:30):
[00:00:30] Welcome to the Product Porch with Todd Blaquiere, Joe Ghali, and me, Ryan Cantwell. Today on the porch, we're joined by David Nash for part two of our career ladder discussion, to have a candid conversation about life as a CPO and what it really takes to succeed in product leadership. Now settle in folks, because on the product porch, every topic is a product topic. I miss this, but I like how it specifically is mentioned, the countdown in the last episode.
Joe Ghali (Co-Host) (00:58):
Wayne's World will forever live on [00:01:00] in my brain.
Ryan Cantwell (Co-Host) (01:00):
Through Joe.
Joe Ghali (Co-Host) (01:02):
Yeah. Through Joe.
Ryan Cantwell (Co-Host) (01:03):
Through Joe.
Todd Blaquiere (Co-Host) (01:04):
Well, I'm glad we're together to take on part two of this series. So in part one, we've been talking about the product management career ladder. Covering each step of that ladder. In part one, we talked about product manager and director of product management. Anyone can go back, listen to that first episode, but just as a quick reminder, some things we talked about there. No mindset is better. We're not talking about upskilling your mindset as much as we're saying have the right orientation for your seat. [00:01:30] Altitude and horizons shift. PMs are close to the ground, more time with customers. Near term trade-offs, directors zoom out. Start looking at systems, processes, portfolios, longer planning cycles. Talk about how hard it is to let go as you make that transition from individual contributor to director. You get less direct contact with customers. You can't be the here all the time because you're moving from shipping work and you're getting all the attention for the workkeepship to, "Oh, now I'm leading people and systems and I got to get respect and credit in a different way." [00:02:00] And the big mistake we called out was being too tactical as a director.
(02:04):
You got to step back and let some mistakes be made. And some decisions just don't make sense until you're in that chair. I think some of those themes are going to continue on as we move up the ladder into VP and CPO. We have our good friend David Nash here joining us. Thank goodness, because apparently our pod gets a bump every time David joins. David is a multi-time chief product officer. He has an extensive background in B2B SaaS. He's an American expat [00:02:30] living in Portugal, now doing investment advising, fractional interim CPO work and coaching. David Nash, welcome.
David Nash (Guest) (02:37):
Hey guys, it's awesome to be back again on the porch. Happy Friday or whenever this thing airs. Great to see you all. And welcome back to Joe.
Joe Ghali (Co-Host) (02:45):
Thank you, David. I felt bad, David, that I couldn't make it the last time. So I'm glad I get to go back on the porch with everyone with an extra large cup of sweet tea. It's the morning and it is, yes, it is my birthday. [00:03:00] I'm 39 for the 10th year in a row. Forever.
David Nash (Guest) (03:03):
And holding.
Todd Blaquiere (Co-Host) (03:04):
A new contract, Joe only comes on his birthday. So we'll see him again 2027. I'll see you in 12 months.
David Nash (Guest) (03:12):
Joe's got the job we all want.
Ryan Cantwell (Co-Host) (03:13):
That's right. And David, I'm excited to welcome you here again onto the porch because it's very personal for me too. I'm interested in learning about some of your experiences as you've kind of progressed through the product [00:03:30] management career ladder. And I think it'll be really interesting because selfishly, I'm going through an early part of that progression, getting some leadership responsibilities and I want to know what to look out for and that kind of stuff. So I can't wait to dig in.
Joe Ghali (Co-Host) (03:49):
Congratulations, Ryan. A well-deserved promotion, by the way. So well done. Absolutely.
David Nash (Guest) (03:54):
Yeah. Congrats, Ryan. You're going to kill it. And I think I know enough about the environment you're in to know it's [00:04:00] a place where you're going to be able to really open your wings and really grow and have a lot of impact.
Ryan Cantwell (Co-Host) (04:06):
Awesome. Well, thank you guys. I appreciate it.
Todd Blaquiere (Co-Host) (04:08):
So one thing Ryan said is learning from your experience. That's Ryan, you have a question?
Ryan Cantwell (Co-Host) (04:11):
I want to know from looking back as you've taken on leadership responsibilities and such, going from that director to more of a vice president style role, what felt different to you?
David Nash (Guest) (04:26):
Well, it's really funny. I'm going to start with a big myth [00:04:30] that you've all experienced. Remember when you were back as kind of a entry level or mid-level product manager, individual contributor, and you were really frustrated by those idiots above you making those decisions and, oh my God, what were they thinking? And you thought to yourself, "Man, when I finally get that next promotion, when I'm finally director, I'm finally going to be empowered. I'm going to be on chain and they're going to let my [00:05:00] awesomeness flow unabated and I'll be able to correct all those injustices, fix all the wrongs in the world, and I'll finally be empowered." And you know what? That did not happen when I became a director of product. It also did not happen when I became a vice president. I think you know where this is going, so I'll speed up the next two.
(05:22):
It also did not happen when I was senior vice president, and it certainly did not happen when I was chief product officer a few times. [00:05:30] Yes, you become more empowered to do things, but you're solving a very different set of problems and you're learning all and over again. So it's like the Rubik's Cube goes from three by three to nine by nine, and you're still learning, you're still growing, you're still making mistakes. And everything that got you here that got you to today will not get you into the future unless you are really self-aware, you're open to coaching, you're open to [00:06:00] learning. And that's just a whole new set of problems. So when I finally get that promotion where I can do whatever I want, you guys will be the first people-
Todd Blaquiere (Co-Host) (06:08):
Oh, got to let us know. Got to let us know how you get that.
Joe Ghali (Co-Host) (06:12):
Absolutely. David, if I can, I think let's start. I want to start simple then. The first thing you said is you're solving a different set of problems when you move from director to VP level. Can you just give us a couple of examples of different sets of problems that [00:06:30] you solve for when you move in from that director role to that VP role? Just like level set. It can be agnostic across products and across industries. What are some of those different set of problems that one may encounter like in Ryan's particular scenario?
David Nash (Guest) (06:46):
Sure. Well, I break them down into the three Ps because everybody needs a framework. So I'm going to use my age old one. The three Ps are of course product. What do you do with your product, family, your roadmap, if you have a portfolio of products, [00:07:00] the second P is for practice, right? How do you make the sausage? And the third of course is people. And arguably the third P is the most important, right? Because as you move up, you inherit people, right? Presumably you haven't hired everybody yourself and presuming that you're going to hire people who I hope are better than you, at least that's what I've always tried to do, people who are stronger than I ever was. You're going to inherit people who may be great contributors, but might be in the wrong role. [00:07:30] So people, if I had to draw a pyramid, I think Joe, as you get higher, the hiring and the organizational development becomes a lot more important, both being clear in expectations.
(07:41):
And we'll probably come back to this later in our discussion, not just getting clear on what to expect, but how to inspect in a way where you're staying close to the work because it's also very easy to drift away and lose touch with what's happening in the trenches. And it's a balancing act because [00:08:00] if you get too close for it, of course, you will dive exhaustion because there aren't enough hours in the day and you can't do the other parts of the job. But if you get too far away, I believe you're just as useless if you don't know what's going on. So anyway, those are the three Ps. They become a little broader and you have to zoom out a little bit, but you absolutely cannot and must not lose touch with what's happening in the trenches.
Ryan Cantwell (Co-Host) (08:25):
David, you said four words that my spidey sense started [00:08:30] tingling. You said, "What were they thinking?" Now you have an opportunity to address that. Did you have a moment of realization that popped up where you said, "Oh, what were they thinking? Now I see. Now that I have that perspective, I'm in this role, I see why that decision was made where before it wasn't something that I was aware of.
David Nash (Guest) (08:53):
" Sure. I think there's a very popular example that I've seen. Oh my God, maybe four times [00:09:00] in B2B SaaS, so many companies go through the, particularly if they're not digital native companies, if they're older than a decade or two, they have a bunch of on- prem stuff. And these are old, creaky systems and everybody of course has SaaS fever before we had generative AI fever. Everybody wants to move that stuff to the cloud. And in a lot of these old products, you wonder as a product manager or even as a product director who's kind of fairly siloed on one product, why don't we just move this? And [00:09:30] oh my God, this is your dad's product platform.
(09:34):
As you see the financials, the ugly truth or the inconvenient truth is that some of those products that you've divested years ago or you've stopped investing in rather are printing money. They're incredibly profitable, these so- called long tail products. And I've gone through this several different times where you want to be really thoughtful about blowing up a business which is basically printing money. And so it goes against everything we're taught as [00:10:00] everything our engineering colleagues and architects and CTOs want, which is to be on the latest and greatest stuff. That's one example with the old stuff, the creaky stuff, the stuff that gets no respect has fiercely loyal customers who pay every month and who you're not investing in maybe other than information security vulnerabilities and those kinds of things. So that's one. That's probably a good one, Ryan. There's others, of course.
Ryan Cantwell (Co-Host) (10:24):
I like that. Now you also talked, Joe had a really [00:10:30] good question about the new problems that you're exposed to. If you were to look back and give your past self advice, is there anything you would do differently to prepare for those problems?
David Nash (Guest) (10:40):
I think one of the key things I've learned in the last several assignments was when you're a little lower in the organization, things are handed to you. Even if you don't understand them, you're told to do this, do that, and then do the other thing. And they're more execution focused. When you talk about strategy, you're often told our strategy is we're going [00:11:00] to invest in X, we're going to milk Y and we're going to maybe try Z for some new greenfield thing. When you're actually forming strategy, a lot of stuff is not written down, right? There's tribal knowledge, there's what's in the CEO's head, what came out last night over cocktails that isn't in the roadmap, what was the discussion at the last board meeting? And so what's kind of percolating? And so there's a lot [00:11:30] more ambiguity or there's things that are known, but maybe aren't written down and aren't shared.
(11:36):
And again, culturally and behaviorally, different CEOs and different executive teams operate very different in terms of transparency, in terms of, shouldn't the whole organization know this versus going to keep this a secret? And I've been on that continuum from one end to the other and back. So those are some of the things that I had had to learn going through that journey.
Ryan Cantwell (Co-Host) (11:59):
Oh, cool. [00:12:00] And Todd, you probably weren't expecting this. I'm going to ambush you. Okay. Yeah. So Todd is a CPO, relatively recent, right?
Todd Blaquiere (Co-Host) (12:10):
Yep.
Ryan Cantwell (Co-Host) (12:12):
Same question. What would you have told your past self as you prepare for these leadership positions?
Todd Blaquiere (Co-Host) (12:18):
Oh, that's a great question. First off, as we talk about that change from director to VP, I think what really actually prepared me and helped me for being a VP was [00:12:30] the time that I spent as a consultant.
(12:32):
I would love if I was saying I was playing chess and I had, that was part of the plan like, "Hey, I'm going to go get some consulting work that's going to help me learn exactly how to be a more effective VP." But that wasn't exactly how it was designed. But the reason I say that helped is because when I became VP was the first time when I had to really take ownership of the organization. Up until that time, I led teams and I think that was one of the first key differences. And so leveraging my consulting [00:13:00] experience of, okay, how do you evaluate a product organization? We're always evaluating the organization, but from our own perspective as a product manager or director, it could be better for just to this. It's completely different to be a consultant and look externally. And so as a brand new VP, I just played consultant at first.
(13:17):
Let me just step back, evaluate this, and that helped me game plan strategically. So I think learning those skills, again, accidental, but I think that was really advantageous. Have the skills to be able to evaluate [00:13:30] an organization and start there when you come on new. If
Joe Ghali (Co-Host) (13:34):
I can interrupt,
(13:35):
Todd,
(13:36):
I really, really liked the phrase taking ownership in the organization. And you mentioned the skills. Can we take you just a moment, maybe just call out a couple of key skills and maybe even elaborating because when I hear taking ownership of the organization, I think there's a lot of different ways to interpret what that means. Can you just peel that back a little bit?
Todd Blaquiere (Co-Host) (13:57):
Yes. David mentioned something. I think we can [00:14:00] connect the dots here
Joe Ghali (Co-Host) (14:01):
And
Todd Blaquiere (Co-Host) (14:01):
Expound upon something David just said as part of taking ownership because David mentioned three different categories, product, practice, and people, and said that the last one was most important. That's the first, I think, a fundamental difference as you take on leading the organization and you move into that VP role is your role in relation to people and the people category changes. So I'd love to hear from David, what becomes the focus in that people [00:14:30] category in your new role as a VP? How's your relation to in that category change in regards to people?
David Nash (Guest) (14:37):
Oh, it's a great question, Todd. So I think it goes back to fundamentals. We're coached as we're growing hopefully to not just manage down or lead people, but manage sideways and manage up. In fact, I often say, and I'll steal this shamelessly from somebody though, I forget the original source, that you don't manage people, right? You manage budgets, you manage schedules, you manage inanimate objects, you [00:15:00] lead people, and that means gaining their trust. And that means when you ask them to do things that may be uncomfortable, where they don't understand the root cause for doing it, that they're going to trust, they're going to trust you. So with people, building alliances and trustworthy alliances becomes more important than ever because when I'm sitting in executive staff, forget my team and my direct reports for the moment. When I'm sitting in executive staff, there's drama in there, right?
(15:29):
There's alliances, [00:15:30] there's the founding team, the new guys, the center of the tree versus the new rings that were added later, and there can be us versus them. And it's not that it's deliberate or that people are evil, it's just people, right? It's people at a different level and you really have to enroll alliances, particularly when you want to do hard things, figuring out, are they in the right role? And I've inherited so many people, especially when we did acquisitions, [00:16:00] we did more than 20 acquisitions in a couple of years. Oh my goodness. And so I had people, when I first came in, I was given a spreadsheet at company X with 70 rows on it of people who were product manager in title. Many of them were great people, but man, they weren't anything that anybody in this group would recognize as a product manager.
(16:20):
They were subject matter experts. They were excels people, marketing people, customer success people, strong people in the wrong role, right? So driving an organization at [00:16:30] scale. Now in a smaller company, Ryan, like your company, again, the problems are not nearly as manifest, but they're still there and you need to help get people in the right roles where they can be successful, coach the people up who are coachable and for the people who aren't coachable, you have to coach them out or find another role for them. And that's really hard.
Ryan Cantwell (Co-Host) (16:52):
Right. If I may move the conversation beyond people for a second, I know that's the most important part. I couldn't agree more, but [00:17:00] there's a perspective difference too, I expect. And I'm curious for your insights here because both time and aperture of what you're looking at, what should I anticipate assuming these new responsibilities, does the definition of long-term, short-term change for me?
David Nash (Guest) (17:25):
Oh man, Ryan, thank you. That's a breaking ball that I know how [00:17:30] to hit.
Joe Ghali (Co-Host) (17:32):
Todd loves baseball analogies, by the way. That one was for you, Joe. David. The other one that puts baseball in.
David Nash (Guest) (17:41):
If we go back to RP for practice, one of the biggest things, again, aside from people is managing expectations on timing,
(17:49):
Right? Because when you're in the board meeting and you sign up for X revenue and Y EBITDA or margin, these things are going to take time in a lot of cases, particularly [00:18:00] when you use the dreaded transformation word. I now have a serious full allergic reaction when I hear the word transformation because it is the most often misused perverted word, well-intentioned, which is almost meaningless. So I have led a number of transformations, some of them successfully. And the biggest challenge is setting expectations on what's reasonable versus what's aggressive. So Ryan, to go back to your, does your definition [00:18:30] of long-term versus short-term change, no, you have to do both. Sorry,
(18:35):
Right? But you have to deliver improved earnings, improve top line revenue, improve retention, right? Whatever the unit economics are that your business and your investors care about, but you also got to deliver the meat and potatoes every quarter, right? Because when I walk into the boardroom or the executive staff room, everybody around that table wants something from product that they're not going to get. They're not going to get, because it was a single most important thing to them, [00:19:00] right? The chief revenue officer is telling the CEO and the CFO that, well, they can't deliver that next big fish or that next big whale or retain them because they're not going to get the thing in the roadmap they want. The CFO is not getting the margin savings from changing the cloud service provider. The marketing team isn't seeing enough value coming they can put into the next go to market.
(19:25):
So building those alliances, and it doesn't just happen at roadmap time [00:19:30] once a year, then you put it back in the closet and lock it for a year. It happens every week because you have to bring those people along with you so they will cover you so that when they're not getting the thing that they think is most important, they understand why
(19:44):
That they're going to defer to what's best for the business, not just what's best for their individual function, and they're going to have your back and you'll do it with them too. So when I mentioned before, the building alliances at the executive staff is the most important thing [00:20:00] because they can smile at you and they can kill you behind your back without realizing it. And I've made some great alliances and I've struggled with others in the role. And if you don't have alliances around that table, you're a dead man walking.
Todd Blaquiere (Co-Host) (20:16):
I'd love to dig into that. I know Joe has a question. I just want to add something really quick here. I think, David, though, you just highlighted how short-term and long-term does change, because especially once you get to the CPO level, a quarter, two-quarters [00:20:30] is short-term. At the IC level, two-quarters was long-term. It really was. As much as we won our product management befoward thinking, their short-term is literally the sprint.That's where they're at. We have forgotten about the sprint. Our short-term is one, two-quarters, our long-term is five years, three to five years. And so I do think that changes a little
Joe Ghali (Co-Host) (20:53):
Bit. So David, I learned this when I was in a previous role. Being a product practitioner, [00:21:00] we try to live by the who, the why, the outcomes. We try to bring those practices and techniques to the team and we want leadership to do it. And it's a slog in many cases. Do you feel like when you get to a chief product officer level, just even talking about some of the challenges you're dealing with, do you feel like you have to sacrifice some of the purity of the product fundamentals that you've [00:21:30] been raised on? Because it's like, let's deal with reality. I got to appease my stakeholders. Let's deal with reality. I have to make sure that I have to get alliances with the chief revenue officer or the chief financial officer. So even in my own experiences, the higher we get, we have to make trade-offs on, yes, I want to really apply the product mindset.
(21:58):
Use some of those buzzwords, [00:22:00] but I think you have to make some trade-offs or some compromises where you still have the intent, but maybe you have to relent on some of the things you feel like you've been pushing as a product leader in the organization because I think it's a little easier when you're at a director or senior product level. But as you move up, I think having those conversations gets harder. What's your reaction to that?
David Nash (Guest) (22:28):
Oh, an affirmative. Big affirmative, [00:22:30] yes, Joe. But I don't look at it as selling out or losing your soul. It's trade-offs. And if you're particularly ... So again, there's some situational difference here because a small or early stage company will be very different than a public multinational company.
New Speaker (22:47):
Sure.
David Nash (Guest) (22:47):
So putting that aside for the moment, although not to diminish that, it's all trade-off. So when I'm at a town hall, a global town hall and there's people in the room and on the Zoom meeting from [00:23:00] four continents, and you have to package things up in soundbites to bring people along, they're all second guessing you. They're all like, again, who is this idiot and why isn't my child the fairest hair of all of them? So you have to bring people along. And the way you do that is by not waiting till you have the town hall and the big tent, right? You need to be in constant dialogue. You have to make sure that at least your leadership team, again, whatever your direct reports are who are also people managers [00:23:30] and people leaders that they know what's going on so they can filter it, adapt it situationally for their team so that when they hear the thing in the big tent, it's not like, "Oh my God, the sky is falling." And that takes a lot of work.
(23:44):
It took a lot of my energy to bring your leadership team along. And here again, the transparency and the culture of the company will limit or enable your ability to do that. But that's what I found. So the people understand that he didn't sell out, [00:24:00] he still cares about all the product things and delivering value and all that stuff,
(24:06):
But we know that every product manager knows that we're doing this big deal for the big customer because that customer really is worth several million bucks and they're important to the business. They have to understand the why so that they can process the what. So understanding the why, got Simon Sinek said it years ago, right? Oh yeah. Yes. Getting people to understand the why, [00:24:30] which is easier in a small company and a hell of a lot harder in a large company because of all the telephone game that people play and half interpreting things. That takes a lot of energy, but if you do it right, then you can lead cross-functionally, cross geographically and cross-culturally.
Todd Blaquiere (Co-Host) (24:49):
David, I think you're saying some of my own experience, lived experience, and I want to test here, does this apply even when you get to larger companies? But what I found is you're always making trade-offs [00:25:00] no matter what your level is. It's just the size of those trade-offs changes. So when you were a product manager, it was like, "I'm going to make the support team happy. Do this one ticket really
Joe Ghali (Co-Host) (25:10):
Quick."
Todd Blaquiere (Co-Host) (25:11):
Yeah, not the most meaningful thing. It'll make them happy. I'll appease them, I'll move on. Those trade-offs at the CPO level still exist. They're just much bigger in terms of scale, investment, timeframe. And to your point, I think then requires even that much more, I don't know for lack of a better word, politicking or communication [00:25:30] influence around it. There's just a lot more communication you have to have because the blast radius gets so much wider, but you're still making similar trade-offs.
David Nash (Guest) (25:40):
100%, Todd. And just flashing back to our last time together on the porch, we spoke about the need to do very unsexy product work sometime
(25:49):
Because it moves a needle on the business. I think any career-minded product manager should be exposed to that stuff as early in their career as possible so [00:26:00] they understand that sometimes you got to sweep up after the elephants because the back of the parade is the part that's passing by you at that moment. You're still throwing a parade, but you got to shovel yada, yada, yada because the business needs it. And when the business is making money, by the way, then you can do all the other things, right? When the business is stressed about revenue, retention, operating margin, meeting investor expectations, [00:26:30] everything in product becomes a lot harder. So that's the way I sell it. When I say sell it, I don't mean disingenuously, but you sell it to the team by we have to do these things so that we can do the other things as well.
Todd Blaquiere (Co-Host) (26:43):
That's so critical. My key paradigm shift moving from VP to CPO,
Ryan Cantwell (Co-Host) (26:48):
Because
Todd Blaquiere (Co-Host) (26:49):
I think you just highlighted. Through my entire career and even as a VP, it was still all about product and products impact on the business, [00:27:00] just changing what are we releasing to what's the next investment to what's the ROI and how do we do that continually? But then getting to the CPO level was I had an aha moment in the room talking to my CEO when I realized I'm actually not focused on product anymore. As a CPO, I'm focused on the business. And if [00:27:30] I have a good, healthy leadership dynamic, we're doing that all together and making those decisions together on the leadership team, but I'm not focused on product anymore, even though that's the organization I influence to achieve the business goals. And so it changed my whole perspective. I mean, we talked about in that last podcast with you, Nash, we talked about using language, getting away from product language.
(27:52):
I found as a CPO, I mean, I just abandoned that language altogether. There's no value in it. I'm completely talking about [00:28:00] the business to where the business should go. I'm only talking product language when I'm turning around to the product team. Anyway, that was a big aha moment for me. It probably seems obvious, but walking away from a call, realizing that my key customer was no longer my customer, I'll explain that, was huge because as a smaller company looking for the next sale and exit to the next investor, my customer is the next [00:28:30] investor,
(28:32):
Which is the buyer of our company, which is a really weird thing to think. So I'm not worried that ... I mean, I am worried, of course, about our customers and clients and I am, but the primary persona for me is the person who will buy our company. That was a big paradigm shift for me.
David Nash (Guest) (28:50):
Oh, 100%. We're on different teams, right? You have to translate. Todd, you said it perfectly. Translate the language of one to the language of the other without losing the intention.
Joe Ghali (Co-Host) (29:00):
[00:29:00] Todd, you've said so many great things, especially about ... I love your perspective changes and you get away from using product language and we've been talking a lot about how to prepare, what to expect. I would imagine, David, in your experience, there's been a lot of dysfunctions you've encountered as you've moved along in your career, right? I think the word you used is a litter box. What are some [00:29:30] of those ... I know David always brings a new set of phrases to the porch, which I really appreciate. David, what are some of those dysfunctions to be aware of or to look out for as one moves from a director to VP, VP, the chief product officer?
David Nash (Guest) (29:51):
I think we all have an idealized version of what a high function team looks like, right? Because we've seen all the Simon Sinek videos and [00:30:00] Listen to various leadership gurus and all. I worked for a guy named Andy Grove years ago who wrote some of the seminal books on management of leadership. And yet you walk into these rooms and look, people are imperfect. I know I certainly am. And we all come in with our biases. I worked for a CEO once of a very, very large company who was pretty immature as a leader goes. And [00:30:30] I don't want to say too much more about it to protect the innocent or the guilty. But this guy made me promise when he hired me, you're not going to believe this. I'm going to say it slowly if I have to. He said, no matter what you do, you have to promise me you're not going to change the product roadmap.
(30:50):
And let that sink in for a second. I know. Todd, too bad people can't see your facial reaction when you publish it because I heard that and I gave him [00:31:00] a blank stare like, did I just hear you correctly? I was making sure my ears were working. And because he had in his mind what the product roadmap ought to be. And here I am being hired as the chief product officer, the first a company ever had, by the way. So in his mind, he was hiring a general and he was just going to say, "I decided we're going to take those three hills, put the troops in those hills and take them." And so I took the job anyway because I really wanted the job. I overrode every red flag [00:31:30] that went off in my mind at that moment. And I did the manual override.
(31:35):
I know the core is melting down, but I'm going to take the job anyway. And I turned the alarm off. And it came back to roost months later where, again, as the chief product officer of a large multinational organization, really constrained on the degrees of freedom that I had to do what many rational people realized needed to be done.
Joe Ghali (Co-Host) (31:56):
Because you can't avoid some things you just can't avoid, but maybe it's in [00:32:00] how you interview the leadership to know to probe at some of these so that you're at least eyes wide open going into this new role.
David Nash (Guest) (32:09):
Well, that was one that expectations of constraint that you try to probe for before you hire. And the other is, again, expectations on timing. I think Ryan asked about it a short while ago.
Ryan Cantwell (Co-Host) (32:26):
Yeah.
David Nash (Guest) (32:27):
What is long-term or what is short-term? I turned down a [00:32:30] role when I was still in the UK to lead the transformation of this particular company. And I mean, I really wanted to stay in the UK. They were going to sponsor me. But again, this time, I was a little bit older and a little bit smarter. And I ran from that job because I knew from having interviewed the entire leadership team and the chairman of the board and one of the investors that it was a completely unrealistic set of expectations
(33:00):
[00:33:00] For transformation. And I may be a slow learner, but I'm capable of learning. And I knew that there was absolutely going to be, it was going to be a death march, unrealistic. And so the best thing I could have done for my own sanity is to not take that role. So expectations on timing, expectations on people sometimes. I often ask when I'm interviewing a CEO, even for a fractional interim role, who are the all- stars on your product team and why? [00:33:30] What makes them a good product leader? And who are the people who you think have gaps and why? What's the impact? And sometime they're on the money, often they're wrong, right? But it's really important to know the biases that you're walking into.
Todd Blaquiere (Co-Host) (33:44):
I think we should expound. You mentioned it, you teased it a couple times. I'd love to dig into it. The most important thing is to have those relationships of influence with your peers at the executive level. So the other chiefs, if you have a C-level title. I found that to be true. In fact, [00:34:00] your team is always your peers, not the people who report to you. So when I think of my team, I think of the executive team, I don't think of the product team, but let's dig into that. You mentioned some of the headwinds you're automatically facing. If you're coming onto a team that's already established, there's already norms there. There's politics there that you maybe are aware of, maybe not aware of.
(34:23):
If you're coming in a promotion role, they may already have a preexisting relationship with you and see you a certain way. And so you mentioned [00:34:30] you implied some of these headwinds that you're already facing. What have you found to be effective? What are some things? I mean, if you have like a, "Hey, let's just be honest here. Let's get some real on the table." Give us some of that real. What should we expect? What's the one expect as they're coming into that now executive role, understanding the most important thing is to influence and have those relationships with their peers?
David Nash (Guest) (34:55):
What I've done is I've taken maybe the first month, first, [00:35:00] sometimes longer, is to just interview everybody. It's the people I want to interview. This is after I've started, by the way. So this is part of my ... And I write my own 30, 60, 90, 100 day onboarding plan. I interview people that I need to kind of get the pulse because the reality is their reality that you're walking into. And then there's also people who find you. There's always people who find you. And that's [00:35:30] going to take a good month or so. I'm going to write it all down. I'm going to digest it. I'm going to get a lot of insights from that. And I'm going to get some bad data in that as well because people bring all their opinions and all the antecedent action that happened before you got there, but that's trying to get a reality.
(35:48):
And checking in with your boss about, here's what I'm hearing. This is kind of like what you told me. This is very different than what you told me. Do you have any other insights? [00:36:00] Like you said X and I'm hearing Y. Help me understand this in a way that's not too threatening to them. And so that's what I've done. And then I keep those away. And again, some of those are early signals that you'll use to navigate organizational development later. Sometimes you meet some diamonds in the rough who have been just kind of stuck in the organization [00:36:30] and they can contribute so much more, but they haven't had a champion. I found this in every company I've worked in, somebody who was so strong and so undervalued and underutilized in the organization. And I found some of those in my first 30 days. And so you try not to break too many things until you know how the hell it works.
(36:54):
Once you know how it works, you're going to break things. You're going to want to break things and rewire things. But oh my God, [00:37:00] you walk into a new power plant, you probably shouldn't throw that big red switch because you have no idea what the hell it does. And again, managing the guy who hired you or the lady who hired you, that you're going to learn before you do anything and get their agreement that you can't come in to completely reconfigure the ship until you know how the hell the steering connects to the rudder.
(37:26):
So I think that's really precious time that you negotiate coming in and [00:37:30] you make your onboarding plan all about your learnings, but you start from getting your data set together and the body of evidence that will inform everything you do from that point forward.
Todd Blaquiere (Co-Host) (37:42):
I'd love to hear, David, if you've had this experience, I had an assumption coming in that I realized might highlight a myth. And that was my assumption was, hey, at a certain level, you don't have to deal with any immature problems, right? You get to a [00:38:00] certain level and you just have a certain level of maturity and understanding. Now I will say, I'm lucky to work with a very mature team who doesn't feel like toddlers in a room. Also, I think I believe that everyone will just get it. In other words, I have fought my entire career trying to explain it being product, trying to just explain it. But once I'm at the highest level, everyone will get it, everyone's mature, and we can now just do business. [00:38:30] David, same thing, you
David Nash (Guest) (38:31):
Experienced that? Oh, it happens exactly like that, Todd. Everyone gets it. Everyone's mature. I've been in meetings.
Joe Ghali (Co-Host) (38:39):
It's like you become a Jedi. Everyone's material.
Ryan Cantwell (Co-Host) (38:43):
These aren't the roads you're looking for. Yeah. You will listen.
David Nash (Guest) (38:46):
Yeah. No, I've been in executive staff meetings where some members were made to cry.
Todd Blaquiere (Co-Host) (38:53):
Oh, no. I
David Nash (Guest) (38:53):
Mean, deeply personal people stuff. Well, when I talked [00:39:00] about dysfunction again, there are some great teams. I'm sure there must be, right? It's like there must be life in other planets. I have yet to find one, which was anything like what Simon Sinek said it would be like. So I think it's a good aspiration, but you read the books, the seven dysfunctions of a team, a Patrick-
Ryan Cantwell (Co-Host) (39:21):
Great book. Let's hear
David Nash (Guest) (39:22):
It. Yeah,
Ryan Cantwell (Co-Host) (39:23):
Let's see.
David Nash (Guest) (39:24):
Yeah, those books, and we've experienced all of them. So yeah, it's a myth because you [00:39:30] know what? We're still people. We're still people. We're all, even the best of us are imperfect and we bring our baggage into that room and you leave that room and you have to explain things that you still don't agree with, but you have to be on board. You've got to salute the flag. And so integrity, our integrity is put to the test more than ever when you're sitting in that executive staff meeting or around the boardroom [00:40:00] and you have to lead with integrity and the higher you get, while that should become easy, as you said, sometimes it becomes harder. And that's been a big takeaway for me.
Joe Ghali (Co-Host) (40:16):
Ryan, we haven't scared you off yet, have we? I mean, you're hearing all the horror stories or all the ...
Ryan Cantwell (Co-Host) (40:22):
No, I mean, I go ... So if any of you are familiar with the Muppets, one of my natural states is [00:40:30] Beaker just waiting for danger to before me at every turn. So I think you guys are just validating what I already felt is all. So I'm not scared, Joe. I'm just ... All right. Now, I know it's not going to be different than what I expected.
Todd Blaquiere (Co-Host) (40:48):
All right, David, give us your vast wisdom here. Outside of money and power, why would someone want to do this? Maybe the answer is there is no reason, but why would someone [00:41:00] want to do this?
David Nash (Guest) (41:01):
Well, the first thing that comes to mind is I wasn't qualified to do anything else.
Joe Ghali (Co-Host) (41:08):
My career- That community titled a podcast, by the
David Nash (Guest) (41:10):
Way. My career as a singer/songwriter never panned out. So I do that. I do that for therapy. On a more serious note, I have been blessed to have been mentored by some great people in my career, and I felt it was my calling, my life mission, really, not to be overdramatic, [00:41:30] to pay that back, and to be in a position where I could lead people, try to show them at least my version of what good looks like, and plant a seed, which would help them in their career. And I'm really happy to say over the years, I've been in touch with many people who have reported to me over the years, who've become lifelong friends. We haven't worked together in 25 years, some of these people, but we certainly know we were in the trenches together, and whether it was [00:42:00] the Great War or that XYZ B2B SaaS company, we bonded and they told me I helped them, and that's worth more than any paycheck or stock option or bonus at the end of the year is that I left a little bit of myself and them.
(42:17):
They went on to do great things, great chief product officers or senior executives in some way, and I'm so fulfilled knowing that I had a little part, just a little part to nudge them in the right direction. [00:42:30] You can all think back to great teachers you've had when you were in school, and you can probably count them on the fingers of one hand, right? Because there were just a few that rise. So I wanted to be one of those people that someone would think had a really helpful nudge in the right moment where they could do something. So that's why I still do this job. I'm working part-time now. I'm failing retirement, I suppose you could say, but I'm working just enough, just enough. And that's what still draws me back [00:43:00] to the flame. I'm still the aspiring singer/songwriter and meanwhile here I am in a product podcast so you can see how my singer-songwriting career is coming along.
Ryan Cantwell (Co-Host) (43:09):
Yeah. David, I usually just drop the mic. That answer was magic. So my head went to the same place immediately because I think it's true of a lot of product people. They get into product because they love it. They love that style of work. And then you find yourself migrating away from it as you climb [00:43:30] through the corporate ladder. But what fills the void, and this is true of me, you're speaking to my heart, David, is I love the people aspect of things. I really do enjoy that. Todd, I saw you responding as David was going through too. And Joe, I don't think Joe has a label on him that doesn't say, work with people, get the most out of people, that kind of thing. Now we're just in an affirmation circle. I feel like I brought us into that position.
Todd Blaquiere (Co-Host) (43:59):
Absolutely. [00:44:00] I was also thinking, David, I hope you count me in that list of people who has grown because of you. That's right. So you've given me a lot of help in my career as well.
David Nash (Guest) (44:09):
Yeah. Well, you're very kind in the checks and the mail.
Joe Ghali (Co-Host) (44:14):
I'll say this, just working with even working with Todd and Ryan and seeing Todd's journey as he's kind of moved along in the last few years, Todd is happier. He is excited. It's like the idea that he gets to [00:44:30] share all these great techniques and he gets to teach and mentor. It's like he may not say it, but every time we get on these podcast calls or time we get on a call, just the three of us and he shares a story about something he's been able to implement at BetterRx, I think that's what we all aspire to have. It's like that fulfillment of like, "Hey, we've made somebody's life better." Whether it be the person at the end of the food chain at BetterRx [00:45:00] or it's how he's resolved, created better internal alignment across the organization, how he's gotten everyone to march in the same direction.
(45:12):
You can't put a price on that. You go to bed tonight, you feel like you can conquer the world. And I think that's the dopamine hit that comes with getting to that next level is knowing that I've made a difference. And Todd never [00:45:30] says it. You can just hear it in his excitement. And I think anyone that's listening to this, I think that's why we do it. That's why we take the step into the black abyss of some of these leadership roles because that opportunity doesn't come often.
(45:49):
I think that's ultimately what we're trying to get to.
David Nash (Guest) (45:51):
And so is it selfish? Maybe it's a little selfish, but that's okay.
Todd Blaquiere (Co-Host) (45:55):
Well, Joey Tribiani would argue that there are no unselfish good deeds. So [00:46:00] that's a Fred's reference. Because it makes you feel good, so it's not unselfish. In interest of time, I'm going to try something different. Let's do one word takeaways.
Ryan Cantwell (Co-Host) (46:11):
Oh, I love this. Discomfort.
Todd Blaquiere (Co-Host) (46:14):
Ooh,
David Nash (Guest) (46:16):
Good word. Everything boils into growth.
Todd Blaquiere (Co-Host) (46:20):
Growth. People. Oh. And I'm going to say trust. Put it in a blender.
Joe Ghali (Co-Host) (46:27):
Put it in a blender. We got it. [00:46:30] Well, this has been awesome guys. David, it is always so good to have you on the porch. And this was like a good bookend to the first part. I wish I made the first part of it, but David is always so great to have you on. Thank you again just for your passion, your excitement. And I think Todd even said it just for your mentorship over the years. I think all of us are where we are today because you took a chance on the three of us when we were brand new consultants just a few years ago. Well,
David Nash (Guest) (46:58):
It's my pleasure. Like I said, [00:47:00] I'm really enriched by the people that I try to surround myself with and you guys all do that for me. So I'm better because I know you guys. So thanks for inviting me on the porch again.
Ryan Cantwell (Co-Host) (47:10):
Oh, so great seeing you all again. It always is, guys. This has been so valuable to me. Thank you for the time.
Joe Ghali (Co-Host) (47:16):
Excellent. Until next time, David, don't be a stranger.
David Nash (Guest) (47:20):
Back at your brother, wishing you guys all a super successful 2026. And Ryan, congrats again on your promotion.
Todd Blaquiere (Co-Host) (47:26):
Thank you. Thank you. I appreciate it. Thank you for joining [00:47:30] us on The Product Porch. We release new episodes every two weeks. You can also find us on LinkedIn for more content. We offer a special thank you to AJ and Jack Blaquiere for the music. The views and opinions expressed by the hosts of this podcast are their own and do not represent nor necessarily reflect those of their employer.