Advancing your career, with Shelley Perry

Speaker A: Uh, uh, hey everyone and welcome to for the Love of Product, brought to you by the product led alliance. I'll be your host, Tiama Hansen Drury, chief product officer at Mina Technologies, an all around passionate product aficionado. Each episode we'll be looking at the head and the heart behind product led growth, the passion and the practice of product. And we'll be picking the brains of seasoned CPOs and heads of products, as well as visionary founders and investors getting their inside stories. Enjoy. Okay. Ah, hello and welcome to another episode of for the Love of Product. I am really excited to have a fantastic guest with us today. Her name is Shelley Perry. Um, if you are not aware of Shelley, ah, she today acts as an investor, a board director and advisor. Um, she specializes in a very specific and unique kind of set of, uh, businesses, which is the SaaS scale up stage. So has a lot of operator experience in that space, um, and was a former software and SaaS operator, also a former CPO. She's a huge advocate for good product leaders. Um, we'll get into that later. Who has now turned into an investor and she specializes in helping accelerate growth in the shortest period of time for the least risk, resulting in exponential enterprise value, um, increase. So I know that this is going to be a great interview for our audience and, um, let's kick off. Shelley, where are you zooming in from?

Speaker B: I am zooming in from San Francisco this morning. So, uh, zooming in. Super happy to that. You've accommodated the time zone for me, so thank you.

Speaker A: Well worth it. Well worth it. And we are here. We were just talking about how it's actually your favorite time of year. It's spring. Um, and you were saying a little bit about why spring, uh, is that favorite time of year for you. What is that reason? I think it's a nice one.

Speaker B: Yeah. Spring is just the rebirth, it's growth. I think the days are longer. So for kind of Type A personalities, you can kind of maximize the day. You know, we have a lot of daylight and the mornings are just full of energy because there is so much more daylight. And I think in general people are just in a better mood. So it's just my favorite time of year.

Speaker A: I'm with you as a former resident of Seattle who now lives in London. Uh, spring, uh, is the light, the physical and actual, uh, proverbial light every year.

Speaker B: So I'm happy. Yeah. I have to say though, that my love of spring is not from residing in San Francisco. I actually grew up in the east coast, the northeast coast of the US and upstate New York. And so spring in San Francisco is actually kind of what they call, you know, leading to June gloom. So the feeling is probably from my childhood, not necessarily where I reside right now, but I just carry it forward.

Speaker A: Absolutely, absolutely. Um, okay, so Shelley, uh, let's jump into introducing our listeners to, you know, give us an elevator pitch on you and who you are, you know, what, what your history has been, um, and where you're at today.

Speaker B: So I have really specialized in software since the beginning of my career. I actually started out as an accountant and knew really quickly that I liked automating it way more than actually doing the accounting work. But it's a background that I very much enjoy. And So I spent 25 years as a software operator, strictly as an operator, starting from kind of accountant to developer to VP of engineering engineering through to cpo, uh, to CEO and board member. I did spend five years with Insight Partners. Actually when I joined Insight Partners, it was Insight Venture Partners. So I went through the venture to operator or to partner transition. So I spent five years also with uh, Insight from the investor kind of operating partner perspective. And today I work with scale up CEOs specifically. I have a fondness for founders who are, want to stay with the business as it scales and want to go from kind of growing from founder CEO to CEO of a scale up. And I very specifically put the CEO in two different spots there, if you could kind of catch that. And the reason I like specializing in that stage is because I have so much reverence for people who can start a company and get it to a skill stage. Because many of them fail. They learn quickly, they have a lot of grit. Right. They're very direct. Right. It's how they got to the stage. There are, and a whole lot of luck as well. And there are things that they just need to be more aware of that they didn't take the time to learn because they were scaling their company to where it is. And I think that, um, providing more access to that information will kind of help the entire ecosystem.

Speaker A: I love that. Do you think that there are certain characteristics that make it so that. Because oftentimes you hear about people, you know, selling their company and they are on an earnout and then they leave. So it's a unique group of people that want to go in and they want to scale up with that.

Speaker B: What, what are the. I think that like I did, I think with sometime at SAS Doc, I think I did a session on kind of what's really important for that CEO is for to decide what you want. Do you want to scale? And it's not you, it's just that that CEO role changes as uh, the company scales. That role is different and person want that role and it's not good or bad, it's not negative or positive. It's more of when they don't want to change with the role and then it gets changed for them. So I think it's just kind of deciding that you want to, that you want the role and it's not personal because it is very different as you scale. And I think what makes someone very good, starting from zero, going to uh, that early stage scale up is very different to what is successful in scaling. And it's just, just the energy is just different and how you spend your time is different. And so I just think it's important that the CEOs really do it with purpose and decide and then they can create that transition and more value for the company, whichever direction they want to go.

Speaker A: Absolutely. So um, going back to kind of some of your early C level roles, you spent some time at Ticketmaster, some time at Hewlett Packard, um, uh, then into Newegg, right. Ntt when did you make the decision and why that you wanted to transition into the venture side of things.

Speaker B: So I think that when you look at my career I think you pull out some of the names that are more recognizable but in the early stage of startup and scale up those names aren't quite as recognizable. So I started working um, in the startup community and there is a difference between startup and scale up. But I started working in the startup community pretty early on in my career. I'm not sure I knew that that was what it was called because I didn't grow up, you know, kind of talking about it all the time. I grew up in a tiny small town in New York and no one was talking about startups, they were talking about Kodak. So I'm not sure that I was able to identify it early on that that's what it was. But I, I realized that one of the things that I like to do is really take things from ideation and they are just starting to get that scale and guide it to the next level. So I worked on, you know, one of my early, I think my early roles was take in health care, was working with a hospital and an insurance company to kind of create this incentive which is now similar to the Kaiser model in the US And I just, I like taking old business models with new or uh, old business processes with the new models. And kind of bringing them uh, to uh, to scale and larger companies. While they do that, they tend to do it in innovations. And you see me at NTT innovation, right? You saw a little, I did some of that at Hewlett Packard as well. So I've always been interested in that stage. But I think what you have to realize is if you're successful in that stage, it grows up, right? It doesn't stay, it grows up. And I think that when you're with a company and you take it through those stages, you inevitably are uh, with then a name that people recognize. And I was with Chargebee early on at 4 million. No one knew what charge me was. And now everyone in the scale up community or even in the finance finance community knows who charge me is but they didn't know who they were at 4 million. And so I think it's really understanding that if you're successful it is going to get to that big stage and where do you exit out? And as I was reflecting on what do I like to do, uh, what am I good at? You know I'm really good at all of the stages because I have a financial background. I can do turnarounds, I can do all of these different things. But then what am I passionate about? What when I get up in the morning, it's not work. It's like you want to dig into it and, and pattern that I recognize where I really enjoyed the scale up stage. The startup stage is too early for me just in terms of probably younger. I would have been good at it but it wasn't available to me. I just wasn't uh, I didn't know that much about it. But the scale up stage is when there is not a lot of clay, but there is some clay and the trajectory is going up um, before it kind of gets into that, that public stage which I also enjoy financially. But it is very different in terms of the roles in the day to day. So I narrowed in on what am I good at and what do I like to do and I found that intersection and it really is in the scale of stage of growth.

Speaker A: Was it a choosing uh, first to pick more operator roles that were in that space before then going into kind of advising um, and kind of ventures or was it just did it happen naturally? Right? Was it just kind of natural?

Speaker B: I don't know about anything kind of happening naturally. What I think is important for everyone in their career is that you have a trajectory of where you want to go and you might not know every single step that's there, but you kind of have that long term path of, of what you see in your future now. It can change, right? But, but knowing what it is allows you in all of our roles to prioritize some of those things that are going to stretch you to the next thing and also to take advantage of opportunities when they hit because you don't necessarily know where they are. Uh, Insight, for example. I'll give you an example. I never had on my radar ever that I would go work for an investment firm as a software operator. I was never going to work for an investment firm. Or I mean, it wasn't never. It was just I didn't have it on my radar at all. But what I did have on my radar is that I knew in the end of my career, which I was hoping to retire much earlier than others because I worked a lot. So I had planned for semi early retirement and I knew that I was going to want to be on board, do some challenging things, but not necessarily work full time because I, uh, like this space. So while I knew that that's where I was going, I was collecting the experience that I needed. And I had experience, you know, big companies, small companies, startups, scale ups, M and A integration. I've had experience with big companies having investment firms and doing investments, but from a big company perspective. And what I didn't have was really understanding how do investment pure investment firms decide which companies they're going to invest in, how do they make those choices and how do they get their money? And part of it is I just love to learn. And so I was also like, how do I round out that? Because I knew it was going to be important to what I wanted to do eventually. And the opportunity with Insight came up, I wasn't looking for it. In fact, the reason it came up was I had worked with Insight in various ways as a networking experience, you know, for the past several decades. And the Newegg, uh, on my CV was actually an Insight portfolio company at the time. And they asked me to come in and I got that through my connections with Ticketmaster and Insight. And so it came up opportunistically and because I knew that that was the one area that I wanted to, I was able to take advantage of the opportunity because it was like, oh, I never had that on my radar. Let me put it into context of where I wanted to go.

Speaker A: Yeah, okay, so two questions on that. And then I want to get it back to the networking piece because I think that's, uh, interesting. Um, the first is you Know, you said that you, you kind of had an idea about later in your career, what you were looking for on some boards, maybe doing some advising and things. Today in this day and age, you know, this whole concept of a portfolio career, it's become pretty common. But I'm curious, did you have somebody who you saw or looked to that was doing something like this that you thought, I want to do something like that or was it something that you were like, I want this type of a creative, uh, both impact.

Speaker B: My answer is going to be, I don't like to be negative, but my answer is going to be somewhat negative, but through a positive. And, and that is, um, I, I follow patterns, I study patterns, right? It's, I can't help it. I have finance background. I was an engineer. And it's just partially I was drawn to those things. And even as an investor is, you see patterns. And so I studied patterns and I grew up in, you know, uh, right outside of Rochester, New York, tiny, tiny town. And everybody worked for Kodak. No one thought Kodak wasn't going to be there. No one thought, you know, Blockbuster wasn't going to be there. And I learned pretty early on that no one's going to manage your career for you. You need to really know where you want to go. No one's going to do it for you. There's probably a little bit of trust issues going on there as well. But I learned early on that each stop along the way has to be something where I am m providing value, but I'm getting value for my next thing. And I just, there wasn't anyone, unfortunately. I wish I would have networked earlier. I wish I would have reached out earlier in my life, but it was just a pattern that I recognized. Uh, just in general, looking at, you know, friends or family kind of being, oh my gosh, where did my role go? And I never wanted to be there. I also am a change junkie. I love messes and I, once they get cleaned up and once things get rolling and I don't, it's, you know, so I also knew that, you know, it typically takes three years or so to kind of come clean things up. And I also knew that because I am, that I, I'm not good in steady state businesses which tend to be some of the bigger businesses. And so I just found that along the way. But the key to it is to understand no one is going to write your career for you. No one. And I think one of my pet peeves, if I had one, it was someone says can you mentor me or what should I do next? And I just, I, I have no patience for that because it's. You can look at other people, you can plan it, and then you can ask me, how can you achieve that? Or how can you achieve the next thing and then unfold. But no one can do that for you because you have to look at what you know, what you're good at and what you're passionate about, and then take the time to do the research and then people can help you along the way.

Speaker A: Okay, excellent. The other thing I'm curious about is that you, and you talked about it a little bit just now. But for people who don't have maybe, uh, the natural inclination to get perspective, uh, on themselves and notice those patterns, do you have any tips on ways to, to kind of take a look at like, what is the pattern of your life? What is the thing that's driving you? You know, because it's not natural to everyone.

Speaker B: Yeah. So I think the first thing, and I, I tell this to a lot of the C suites that I work with, the scale up C suites is the very first thing, is in times of stress, and stress can be good stress and, uh, stress can be bad stress. In times of stress, what is the first thing you do? And this is in your professional life, this is not, I go eat a gallon of ice cream. This is like in times of stress in your business and things are going really well or things are going bad, what do you hunker down in, right. And notice what that is because, or ask someone else to notice what that is, or tell you what that is and recognize that is not good or bad. Because we all have aspirations and we say we're going to work out every day, we're going to do these things, but in times of stress, you know, maybe we'll eat the ice cream. So what is that? Because that is what your natural tendency is. And then what you want to do is find out how to exploit that. Not say, it's bad, I got to stop doing it, but exploit it. Because you want to exploit your, uh, strengths and whatever that is. I promise you it's a strength. It's just you might not be in the right role or the right trajectory to exploit that strength. That's number one. One. Number two is to look at other people who are in the role that you're in today. And, and it's important that you take your title and your stage of company, because those titles don't always mean the same thing. And then they have progressed to what you think you want your title to be. And then we'll tie this back into networking and go reach out to those people and ask them, um, what is your day to day like today? What is different to what you thought you wanted? Because half those people, I promise you, that role is not what they wanted. Right. And, and it's important to kind of know those things and you're not picking on them or doing anything, you're just asking them specifically. And if you do that and you ask them very pointed questions, that doesn't take them a long time to return. And it's not something that you're sharing. You know, in social media, people will be genuinely honest with you about those things, the pros and the consultation. And then if you like what they're saying and you understand what the surprises were or what was different about it, or how they would have interviewed differently for a different role at the same title, you can then plan your path against that. And I think that that is, that's a perfect way. It's exploit your strengths. And if you don't know what your strengths are, ask someone else around you to tell you what they are, and specifically not in good times, bad times. And then follow the path of the titles and go not to the people who are aspiring to get to the title, which is naturally what we try to do, go to the people who've already achieved that level and ask them how different it was to what they thought.

Speaker A: One of the questions that we, um, had for you from, um, the audience that knew you were coming, was, is there a point where it's too late to try and start this process? I think the question was related to maybe starting to make a change into more of a portfolio career or trying to network up and change roles. But I think it applies here as well. So I'd be curious, is there a point where that outreach is going to be not appropriate? Talk us through your thoughts.

Speaker B: I don't believe that there is any time that there's something that you want to do that you just truly are passionate about. And this is why, I mean, people say it all the time, as Simon Sinek says it, but know your why. Like, if you're just doing it because it's great and you want to make more money or there's no more jobs left in the title you have is never going to work right, so hang that up. But if you have a reason for the why that you're doing it, it's never too late. It may be that it's going to take you two or three years to do it because you don't have, you know, some of the network built up or the credibility built up. But you can get that along the way while you're earning money, you're kind of providing and building that network. So, you know, this is in context of professionalism in product and SaaS and software and tech. I think if you want to go be a, uh, surgeon and there's 10 years of school, you could probably still do it, but your eyesight starts to go. So you have to put a little bit of reasonable. But anything in the world with which most of us live in, I think that are watching this, the professional world, there isn't anything you can't do. It's just you may have to start talking to different people, expand your network to the group of people of where you want to go, not the people that you're with. And you have to ignore the noise of people telling you you can't do it big time.

Speaker A: Absolutely. And I think that'll be an inspiring answer for people. So thank you for that. So to your point, it can take 10 years maybe to retrain as a medical professional. But also, I think, um, one of the things you shared with me is, you know, you were in contact with insight for 10 years, you know, roughly before you had anything. So let's talk about what that, that relationship looked like prior versus you coming on and what that tells other people about how to leverage networking. Um, because I think you have some very clear lessons from that that you would share.

Speaker B: I have clear lessons from it because I didn't grow up with money. I didn't grow up with kind of, you know, a name, you know, a family name. That kind of opened doors for me. I'm an introvert, naturally. Uh, you know, so I think that I just never understood. You read about networking. You did, but I never understood the power of networking. And I probably also never understood what it really meant. Because most people, I think, that don't know what it means is that, well, I've just lost my job. Now I have to network and I go have to go reach out to people and say, hey, do you have a job for me? And, you know, that's humbling and scary and all of those things. That's not what networking is. Networking is building a community of people who trust you and know that you're going to answer the bat phone when they call about something specific. We all have friends or family that when something happens, we call this person, but not this person. Right. We call this person for this. So I think we can kind of relate to that in our own life. And I think that you have to be that expert for someone, right, that they're going to call. They correspondingly have an expertise most of the time. Sometimes it's not even reciprocity in that individual, it's someone they know.

Speaker A: Right.

Speaker B: And so when you start thinking about networking, as I want to share my unique expertise to people who need it, when they need it in a community that then helps me when I need it. And that's not to get a role or anything else. Sometimes it's just, hey, I'm trying to do this. What's the latest? And early in my career as a, as a cto, I would have to do that because there was no way I could stay current on the tech, right? So I had to do it with, with simmers, uh, up and coming developers because they were staying on top of things. So how does that relate to uh, things that I did with Insight prior to working with them? And that is they would sometimes be doing due diligence on a, uh, deal and it was maybe more scale or something that they knew I had expertise in and they would call me and they weren't calling me saying, you know, is A$500 an hour, you know, thing. It was like, hey, can you take a look at this and can you give feedback? And it's with deals they're uh, very time specific. And so you, you do it, you answer it a. Because you have expertise in it. Maybe at that point in my, you know, HP career or at uh, ntt, I was a little bit bored because those companies tend to be big. So it was interesting to me to kind of do something different but you're building credits along the way. And then, you know, as Insight started to expand and they needed more expertise with what I know how to do, which is kind of scale companies. And specifically I had an area in terms of product, tech and finance that they needed in terms of scaling that you know, there became a win win. So I think it's, it's understanding that you've gotta help people understand what your unique offering is and then offer it up for free. Uh, and you know, you can't always say no or uh, sorry, you can't always say yes. You have to learn how to say no because you will never have any time. But you have to selectively start to build your network and you have to have people know what your unique expertise is and there's no better way to do that today. Than through sharing content, like rich content of something that you're an expert in or your unique, uh, insight. I've used insight too much. But your unique perspective or analogy or some way that you've kind of mastered something new and you're relating it to something that you know before that's going to relate to other people so they can master the concept that much faster. So you have to be known as an expert in something. Generalists, you know, even as you go up in leadership, generalists don't have that opportunity. There's, there's roles for that, but it's much harder for people to do that. And you have to make yourself available when they need it, not when you need it, which is not, uh, always

Speaker A: the same time you, you maybe got into something there. That, um, is one answer for my question. But what I was going to ask is what is, you know, what are misconceptions about networking or what do people get wrong about networking? Um, maybe one is like thinking you only do it on your time, for example.

Speaker B: But I, I think that, you know, I, I posted a something on LinkedIn recently and I was traveling with a friend and again, Adam Sandler was accepting a, uh, lifetime comedy, uh, award. And there was this show and it was all of his friends that if you watched anything with Adam Sandler, he has kind of the same group of people in a lot of his movies. And there is friends. And the next day, one of my close friends, we were at the beach when we were watching it and she said, oh yeah, all of his best, you know, his buddies. And, and the, the thing is, is like you only get jobs or they get, they got this role because, um, because they know someone. And that's true right? As you go up in your career, by the time you get to be a director or vp, you know your craft. If you don't know your craft, you probably shouldn't be in that role. Right? And it's no longer like refining your craft because you know it. I mean there's small tweaks, but now part of your net worth or part of your worth to a company and part of your net professional worth is the number of people in your network. And that means they know your name and they will answer your call. And that doesn't have to. That's for deals, that's for introductions. Sometimes it's back channel references. Sometimes it's the difference between someone taking a role at your company because your name is there and they want to kind of be in your orbit, whatever that is. There's such a negative connotation about kind of like, oh, they got that because they know people. And I'm just like, yes, they did. And I think there's a connotation that only like, it's, it's, especially in tech, it's a broad network and all of that. Does that exist? It absolutely exists. However, I think that if you embrace networking and you build your community from early on because it's like compound interest, it, you know, accumulates. A lot of the people that you started out, you know, in, you know, your first job, they're going to end up being CEOs, they're going to end up being, you know, in these different C level roles at different times. And it's that group of people that are going to help you and it's because they know you and they trust you and they're going to make introductions. And again, the higher up you go in your career, it's not a should I do it yet? It's part of the selection criteria for you taking that role. So I think the misconception is that it's just something I need to do later or it's a negative when in fact, fact it's not. And uh, I'll give you one more point on that. And just to kind of help people. This. The reason it's so important the higher up you go is because as you rise up in your career, you are at the top of the whatever functional expertise you have and it carries on for CEO and it carries on for board. And that is there's no one in your organization who, number one, you can be sharing or asking that question to because sometimes it's confidential that you're actually asking it. And number two, there's no one as high as you. And so if you actually want to get information quickly about ways to do something or people to hire, you've got to use that network. So they're not just hiring you because you're good at what you do, they're hiring your network, which gives them a force multiplier of your effectiveness.

Speaker A: I love the idea that networking is like compound interest. I think that's great, we'll take that away.

Speaker B: It absolutely is, because that's my finance background and everything. But it is compound interest. It's, it's something that again, um, whenever someone loses their job unexpectedly, I have empathy for them and if they just reach out to me for the first time, I try to help people. Because you do have empathy for them, but you have no idea how badly I want to Say to them, please, when you get your next role, don't stop networking, right? Just keep going. And so many people stop. And it's just detrimental too, I think, quality of life kind of, because it makes things easier when other people can help you and you help. Help other people. But it certainly is really critical to your career as you get higher up.

Speaker A: Okay, action item for everyone listening. If you're not spending regular time networking, now's your time. And follow the, uh, masterclass Shelley just gave us on how to do that. Okay, let's switch gears into the world of product. So you know that we've got a lot of people listening to this that are chief product officers or they have ambitions to be chief product officers. And one of the things that. Things that you and I spoke about, um, is a pretty pivotal moment for you, um, in your career, right, where, um, you got some feedback that shaped, I think, you and how you act. But it also. There's some real lessons for CPOs and aspiring CPOs. So can you tell us a little bit about the. That, that experience? The, uh. If I wanted to know all that shit, I wouldn't have you.

Speaker B: Uh, yeah, I'll try not to share, uh, swear, I guess, though.

Speaker A: No, it's fine on this topic.

Speaker B: Yeah, there you go. So, um, I tried not to too much, but I think. So I was thinking a lot about this, you know, after our pre. Discussion, just to kind of hone in on some of the important points. But the critical moment in my career is I was. It, uh, was my first SVP role at, uh, Hewlett Packard, which was a very large company, so all titles are different. And I was preparing this, uh, update for the. Basically CEO of the business division of. This is about $10 billion business division. And I had recently taken on that role to take on a very, uh, massive investment in a lot of the SaaS solutions at HP at the time. And I meticulously created this report. I mean, it was, you know, this Word document, Microsoft at the time. And I meticulously created this update of just things that. I think it took me days to create this report. And I give it to my, um, my leader at the time. And he looks at it and he's like, throws it at me. I think I even printed it, which is ridiculous, but I printed it because it was the time. And he says, he literally threw it at me. The pages went flying. And he's like, I don't want to know all this shit, Shelley. I want to know the summary. I want to know, um, any Risks. I want to know if I go into a meeting, if I'm going to get hit from behind, where I need to have your back, what's going off track. That's all I want to know. Right? And, uh, it was one of those things where you're just a little bit crestfallen because you've spent so much time, but you so appreciate the feedback. And for me, I, I just appreciate feedback. I don't need to tell you it's much better for me than someone like, meticulously articulating what I didn't do well. Like, I just. That's all I needed. Right. And so I started studying kind of like, what does it mean? You know, one, you have to understand, I didn't know at the time that he came from a consulting background. And if you understand people with consulting, they do a management consulting, they do a lot of rolling up of things, right? And so I had to go deep into my career and be like, when did I do this? And I did it with the Feld Group when we were exiting eds that ultimately got acquired by hp. But I had to dig into my background to try to be like, how can I do this? But I had to look at his background, I had to look at what he's used to. I had to reach out to people that report to him because this was not a world I lived in. I came from scaling up, uh, tech businesses or finance. And those leaders wanted the detail because they, you know, they had grown up and they needed the detail because maybe they were in my role prior and they wanted it. So it's when I started learning that you have to understand different stakeholders, you have to understand how they want to consume information. And it's not necessarily how you want to prepare it or you've prepared it before and it's different. And yes, there's templates out there and there's all these articles. This is how you create a strategy. You've got to adjust it for the situation you're in with the leaders that you're dealing with or the board that you're dealing with or whatever that is. And I think that product people specifically, um, and technology people are not great at it because they don't really like to summarize things for leadership anyway. And so product people helping to summarize these things in business context for the way that stakeholders, not your customers, but stakeholders, which include board members, which include other C suites, which include, uh, acquisitions people who are going to acquire you, it's very different to how you want to Present it and you've got to take those stakeholders into account. And it was just a pivotal moment for me because then I started studying that not everyone is from tech backgrounds and they want to know all this stuff because that was interesting to them and, and earlier in my career it gave you credibility. If you didn't have that detail in there, you were not considered credible. But that's because I was also working for kind of startups and venture and those, and it was a sign of credibility. So I think it's really mastering understanding your audience, which can be different because sometimes when I work with early stage companies, I've got to go backwards and realize that that's the level they need it. But then, uh, my role is to try to help them level it up, up in their context. So it was super pivotal for me. But it was, you know, it was, yeah, having that, that paper kind of flown at you and you're just, I don't need this. You're just kind of like this. Uh, the other thing that it did for me was I was always extremely interested in data. Having a financial background, you have mass amounts of data. I, and I knew at that point that it was just entirely critical that, uh, because you have so many stakeholders that you needed to find ways to kind of roll up that information. And me creating this very manual report that just got thrown into my face. You know, I didn't want to have to spend that time, but I knew I needed to spend probably the same amount of time figuring out what was important to the audience. But the three days I used wasn't figuring out what's important to him, it was me gathering the data. And so I didn't really want to be in that situation. So I got very interested early, early, early on with um, uh, data like product operations. But that also has to do with the fact that I worked in consumer with Ticketmaster and everything we did was data related. So I then applied it to B2B.

Speaker A: So you do a lot of advising, uh, of companies now. Um, and one of the things that you help them with is their product hires. Right. And what are the right hires? And it's different based on obviously to the point you're saying who that individual is is like, right. But also the stage of the company that they are in. Um, can you talk to us a little bit about, you know, how founders should be interviewing for their, their product hires and um, what are the considerations that you try to remind them to take into account in that process?

Speaker B: Yeah, so I, I'm going to Rephrase and say that uh, I help hire the lead product role. I don't help hire multiple product people but the lead product role, their first one. And the reason is, is because the right lead product person should be hiring the rest. And in fact uh, if it is the right individual, they're going to be able to do that. I think that uh, it depends if, if that CEO has come from a product background that discussion is different than if that they've come from a CFO background. So if CFO becoming a CEO, uh, and then hiring product, if they've come from a sales background, it's different. So I try to make sure again this is me putting it in the context of where they came from. Right. So that we're grounding and then expanding on what is the right role? What does the right profile look like for your company? And I can't go into it in all of the detail today, but I will just say that they have to look at stage of their company. You have to look at um, the how stage of your company, just where you are in maturity, where you are in ARR growth for SaaS, most of us, recurring revenue. So ARR and what your other C suite looks like. So if you have a really strong finance person who's strong enough P and a, you know, your product leader maybe could be a little bit weaker in finance. But if you're, if you don't have a strong accounting leader or not accounting, FP&A finance leader, your product person needs to have financial acumen. And that's because they have to kind of look at pricing and packaging and they have to kind of look at unit costs because if you only have kind of a controller there, which is perfectly fine, none of this is good or bad. It's just you have to look at your entire C suite and the stage of your company and your propensity of what you do in times of stress you as the CEO and kind of hone in on that right profile. There is not a single right profile of product person or a scale up. Let me tell you why every scale up is unique because otherwise you would not be in the scale up stage. You went from being startup to scale up. Over 50% of startups fail and what allowed you to get there. And the trade offs that you made as a CEO along the way to get there are different than another CEO made. Some of them are super data oriented, some of them are super sales oriented. Whatever it is, however you got to that early stage of scale, you made trade offs and when you're hiring your first C suite and I, I define C suite as anyone reporting directly to you. So sometimes the title is vp, sometimes it's easy, but it's the first hire. Reporting directly to you is your kind of C suite. And I always say you have to look at, in scale up, uh, what are you going to be doing over the next next 18 months because that's the profile you need. And more than likely if that person is, does not have, has not mastered their craft and is ambitious that they're seeking growth during that time period, more than likely in 18 to 24 months, you're going to have to replace them. And it's not because they are bad, it's because they didn't grow fast enough because you're in the scale up stage of growth. And it's the, it's a very uh, a lot of change happens. It's kind of like the teenage years. A lot of change happens during that and sometimes people just can't grow fast enough. There are a few that do but it's because they're personally ambitious so they know where they want to go and they're providing value and they're also growing. Most people don't. And so you end up having to replace most of your initial C, uh suite hires in, in an 18 to 24 to 36 month time period. Not because they're bad, it's just they can't grow as fast. And if you're a first time founder, if you're a founder of first time CEO, you can't coach them nor is it your job. They have to have a big enough network to be growing outside of your company. It's actually, it's impossible for you because you're actually growing into the CEO. So you, it's not your job or could you to kind of grow them in those roles. You just have to accept the fact that you're going to have turnover in the C suite and just make sure that you're hiring for what you're facing in the next 18 to 24 months.

Speaker A: Nice. Okay, very clear. Um, one of the questions I wanted to have you try and give some guidance to our listeners on is if you are a product person considering taking a role in a scale up and you haven't worked in a scale up before, you know what, what should they know? Uh, it's a different beast as you said. And can they be successful in a scale up if they haven't gotten that experience before? If they're in a product leadership role?

Speaker B: So I Think that uh, for me I think that ah, scale up stage companies are a fantastic way to break through for product leaders to break through to the next level. Because it is if you have hit kind of that director or VP level where you're still hands on, you still know your craft like you, you can still do it. You haven't kind of, you're not in this big company where you know, you have all of these people below you and all you're doing is rolling up reports and I'm not saying that that's all you're doing but I have worked in those big companies so there's a big percentage of time doing that. But if you're still at that level, I think scale up is a great early stage. Scale up is a great transition for you to accelerate your career because you get much more exposed to things around the strategy of the business, around the other C suite pain points and you really have an impact on, on the whole company. And in bigger companies you just, and I don't even bigger companies, even later stage scale ups as a VP versus not a C suite you don't have as much. You, you, you, you contribute but you don't have as much to this strategic direction and valuation of the company. So it's important to understand that uh, it's not your job and this is the biggest thing, it is not your job job or desire for you to train everybody else on what product does and what product is. It is your job to run the departments, do those things and not tell anyone else because I'm sure the leaders wouldn't throw the paper in your face because you wouldn't even be printing it. But they don't want to learn and nor do they need to. It is your job to put the context of what you're doing in terms of everyone else so that you can get the business outcome outcomes. So I think it's important to know that you are at the top, that you're going to spend time, you know, all the way at the bottom. Like hands on keyboards doing things maybe you haven't done in 10 years but there's no one else to do it until you figure out where the holes are. Because as I said, every startup made different choices before they got there. And so you've got to figure out where the holes are or where the assumptions your create a plan that's built on assumptions of things being there that may not be there and that will faul like fold like a house of cards. So it's knowing that every day in Kind of the first six months you're going to go from all the way down here, hands on keyboard to all the way up here strategically. And um, then you're going to figure out where you can apply things and what team you need to hire. And that's why I clarified in the beginning of this to say I don't help with product hires, I help with the top product hire because it's really the devil is in the detail to understand what that team needs to look. And I think most leaders that go into first time C suite roles in scale up is they try to do more of the same. They take their toolkit from the last role and they say this is going to work. They make all kinds of assumptions based on their experience bias. They don't actually say, you know, sales doesn't have enablement so they're maybe selling the wrong things. Maybe for the first four months you actually have to work on helping them with enablement. You can't say I'm helping them with enablement. You just have to go help them with enablement and then start building your team. So it's, I think that if you want to go into scale up and I strongly encourage it because I do think that it will accelerate your career faster than anything else if you're kind of at that, uh, you know, director to first time VP in a little bit bigger company. It's, it's a career accelerator is talk to as many money scale up CPOs, right. CPOs or VPs that are about to be CPOs.

Speaker A: Right.

Speaker B: They're on that track and ask them what they're doing day to day because it will be very different to any other. Even if you talk to a CPO that works for a very big company, you don't need to talk to them. You need to talk to CPOs that are in scale up, uh, companies ideally in, if they've been there for two or three years, figure out what their ARR was and then find those people and ask them their three year trajectory. Yeah. Against what you're taking. But it's a very different, it's a very different stage of a company. It is a career accelerator. And the first year. I guess the other thing that I would say is we all go through different seasons in our personal life and there's never kind of this balance of like work life balance 100% of the time. You tend to, sometimes you go through a season that it's, you know, you're focused on work and then uh, you kind of like oh my friends and my family needs some things or my family needs this. And it's not like you ever drop your family, but there are times when sometimes your family life is like kind of, you know, a little bit, it's calm. Right. If you are hitting one of those times in your life where it is, you know, it's like particularly volatile. I would not take a C suite scale up role until you pass through that. That. Because the first year is all consuming. And if the second year is all consuming, you didn't do a good job in the first year. Yeah.

Speaker A: Okay, one last question before we start to wrap up. Um, you were mentioning about how people, you know, can't just come in with a set of, you know, I've done this this way before and I'm going to just kind of go from the, read from the lines and I guess it comes down to like. Do you think there's lots of people who talk about, oh, we've got a playbook for X, Y and Z. Is there a playbook for a scale up? Uh, or is it really going to be quite different? Like talk about that.

Speaker B: So I think that there is not a single playbook for uh, the order in which you do things from the time if you go to an early stage scale up. And I'm just going to say early stage scale up is somewhere between kind of 1 and 5 million ARR. And the difference has to do with, with how much your product is, you know, what the price is, right. So it's repeatability to repeatedly selling a small portion of what you have to the same cohort that you can repeatedly sell is really what it is. And then you can use that nugget to start to scale. So if you look at the playbook from what do you have to do to go from that to a hundred million, right. It's clear what the steps are. There are, I mean it's clear what needs to be done. Done. The critical part of early to mid stage scale up is there are so many things that need to be done. You can't do them all. There's not enough resources, both in terms of um, financial but experience resource.

Speaker A: Right.

Speaker B: Because a lot of times in that early stage scale up you have your C suite who's very experienced and then you have much more junior people and you have to spend time kind of teaching those junior people some of the basics.

Speaker A: Right.

Speaker B: And then as you grow you can kind of start filling in the middle management. It's the how to get there or what needs to be done. That's a Playbook, I could tell you what that is and you know, ad nauseam. It's, it's not about that. It's the order in which you do it. And that order is unique to your company. And what happens most of the time is that especially for first time uh, founders that are just going to scale is they think I've hired all these experienced people, I should be going in the right direction. But what happens is the product person decides what the right direction is because it's what worked with them before. The marketing person decides what their right direction is because it's worked with them before. Uh, the finance person, you name it like this. C Suites. Unless they've worked together before, which in early stage scale up, most of the time it's first time C suite and they haven't worked together before. There is nothing wrong with what the product person thought was the first thing to do or the CFO or that. What matters is they're all going in different directions and they're all making assumptions without knowing it that when they came into that last company or when they, when that playbook worked in that order, that many things were already in place. Right. Like I, well I'll give you a perfect example. Um, I was talking to a new first time cmo. So use a different role but a first time CMO who had come from a high velocity business, uh, that well established. Two high velocity businesses are really experienced demand generation cmo. First time C suite. And she came in and made this great plan about like what needs to be done to kind of get to what she knows you need at 100 million. And the whole plan was predicated on the fact that uh, the hired SDRs had a script that worked and they didn't. Right. And so she spent all of that time creating this. Now there's nothing wrong with the plan. All of those things need to be done, done. But what does it matter if you create a bunch of demand when you're handing it off to a team that's getting the first call that doesn't have a script, it's these little things that matter a lot. And you've lost at that point, you've lost two or three months because that person spent 90 days versus kind of. It's not just your area that you have to take into account, it's kind of understanding where the company is and then, and what order of things you do, your department or what you're responsible for. And sometimes that's very different because sometimes the resources need to go toward another area for your area to be more effective. So I think the biggest thing is is to understand that as you're at the highest level of a role in your company you can't go around saying I'm going to look at everything. But you have to look at everything without saying it.

Speaker A: Yeah. And I mean not only look at everything but find a way to, to gain that alignment and test those assumptions before going too far right down the path. And that's, that's hard because you're right it can be seen as you're sticking your nose into something else. You're trying to own everything but really it's about exactly.

Speaker B: But that it's not you. You know that the order that you're doing things and sometimes people don't know because if you've spent so much time. I think, I think if we go back to the last. The question you asked me prior which was what are some of the mistakes that you know first time scale up. People going to scale up in leadership roles and product do is that they. When you're in uh, non the top role in a product position you don't have as much reverence or understanding. Some people do but most don't and it's usually people who come from other disciplines into product. But if you've only been in product product and you're so focused just on product in SaaS businesses like product touches everything. Right. And so it's not your job to say product touches everything and you should listen to me. It's your job to kind of sleuth around and then suggest an influence to kind of get to the right next action. I kind of equate it to jury duty.

Speaker A: Right.

Speaker B: Like you go into jury duty and sometimes you have to kind of like control like the evidence and kind of get everybody aligned so you can actually really uh get to, to a conclusion. And I think that first time founders being scale up CEOs they're also not good at the coaching of that because what got them to where they are is the doing and you have to kind of transition to being a coach to facilitate the conversations. And and that's hard for founders because they're doers and uh, so the C suite needs to self regulate and facilitate those conversations between them. And often what they're doing is kind of they're all going to the CEO because that's what they're used to. And I'm saying like no, you gotta like self team regulated. So scale upping is a team sport.

Speaker A: But anyway and leveraging your network for that as well as you were saying.

Speaker B: And your network, right, Your network is critical because, I mean, you use it all the time. You sit there and go, hey, uh, you talk to a CMO or you talk to a cfo. What, What. Why might this person be thinking of this, us? Because it's not about you getting across what you're trying to do. It's about you changing what you're trying to say in words they can create, that they can understand. And often it's just leveraging your network to say, hey, I tried it this way. Can you give me another way? I might get, uh, a CFO to understand that? And often it's someone you've worked with before. And so they had an aha moment when you were working with them and say, hey, can you give me an idea of how to say this to someone else? Network is critical for that.

Speaker A: Great.

Speaker B: Another way to use your network.

Speaker A: That's ah. Right. Okay, Shelly, this has been so great. I am really excited to get this out to everyone. Um, we are at the time of the show where I'm going to ask you my favorite question, which is if there was a museum dedicated to the world's most important products, not the most successful, the most important, what would you say should be in there and why?

Speaker B: So just one. You can go with more. Um, okay, so I'm gonna go with, um. I'm gonna go with two, and then I'll have another. So the first one. And I always think it's important to say why. And one of them is successful, one of them isn't. But my first one is, um, I was. Is. Is a Kindle. And I'm gonna tell you why I think that. And that I was the early adopter. 2007 was when they first came out. I had one of the first candles. I still have it. It's like 3G network to update it. And it was. But when I started to travel, I only wanted to bring one bag because of the Europe, you know, I was American and I had to like, get down to the one bag for carrying. And I stopped reading until that as much because I didn't want to take the books with me. And Kindle was so pivotal in my life in terms of being able to carry hundreds of books and just start reading. You know, we now read them on our phone. But Kindle, uh, was. Or we have Kindles. I took one to the beach. But it was just so pivotal in terms of reading. And so I, I think, think that, uh, it was influential and should be and probably is in the hall of fame. But the second one is, is when I discovered this product, which is somewhat of a service product, and that is a fractional personal assistant. And I don't mean personal assistant like at work, an, um, EA or a va. I mean a personal assistant to help me with my personal life. And as, uh, anyone who might be, you know, the primary organizer in their household, I'm saying this politically corre. Right. Sometimes you have to carry a lot of things and you don't necessarily do things for yourself. And when I discovered there was this concept of a personal assistant who could, you know, send birthday cards for me, make my birthday, or make my doctor's appointments, uh, make sure that the physical mail. Not as much of that anymore. But at the time, many years ago, it was important that all the physical mail was open before I came home home when I was traveling, so I wouldn't have to spend the weekend opening it, making sure I was scheduling girls weekends, you know, just. Just different things. When I discovered that, it changed my life because it helped me to have someone who could stay with me from job to job. So as you have kind of this portfolio career, if you will, or kind of moving from job to job, having this consistency in your life, and it's not very expensive, and people who do that, that like to help you, and it creates an economy for. At the time, it was before the sharing economy was as big as it is, and it created roles for, um, mostly women who wanted to stay at home with their kids and have a flexible job. And I didn't care when it was done. I just needed someone who could come to where I lived, you know, a little bit and then do a lot of the stuff virtually because I traveled. And so for me, if there was anything I think that had a super big impact on my life, life, uh, it was that. And so virtual personal assistant. I thank people who do that, who do want to do it for a living and who created platforms to connect people.

Speaker A: Awesome. Uh, I'm excited for that one. I think it's a great suggestion. And since you told me that, I have invested in myself, so thank you for that.

Speaker B: So there you go. I'll give you some other tips offline of different things you can do with it that I've refined over the years.

Speaker A: So. Amazing. Okay, well, Shelly, thank you so much for your time today, sharing your wisdom and your passion. Um, we appreciate you.

Speaker B: All right, thank you. Thanks for having me. Bye.

Speaker A: Thanks for listening to the podcast, guys. Be sure to share the word of product led growth far and wide and let your colleagues, friends, family, neighbors and anyone you think who would like to know that there's a kick ass product podcast on offer from the Product Led Alliance. If you haven't already, don't forget to sign up to the Slack community and check out all our other great content, upcoming events and other ways to get involved@productledalliance.com and let's come back again next time to talk more about the Head, the heart of product with it.