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Podcast

The Path to Tech Executive Roles

The Cloudcast

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  • Shifting to Strategic Thinking
    • Moving to senior roles requires a shift from execution to strategic thinking.
    • Executives must consider the system itself, resource allocation, and organizational structure. Transcript: Drew Saur Yeah, no, it’s a great question. And it’s the place that, that I sort of got stuck myself. And so just kind of origin story, right? So I was, for me, it was, it was director to, we had called it executive director, which is, which was kind of like a vice president type role. And I was, you know, classic technologist. I was focused on delivery. I would try to be really good at my job and I got stuff done and I was really, you know, well-regarded and well-rewarded. And they said, I did a great job and I was all set to get promoted. And for the first time in my career, I didn’t. Right. And so what did I do? I buckled down, I worked harder, I did even more hours and more projects, I actually got a bigger bonus, and I still didn’t get promoted. And that was kind of the aha moment for me when it was, it’s not just work harder, do more. There’s actually a different sort of scale, a different set of things that people look for in the more senior roles. And that was really eye-opening for me. And in hindsight, like once you kind of get past it and you kind of see it, it’s much easier to kind of recognize. But ultimately, we’re all trained to deliver, right? And so for most of your career, you’re rewarded for getting the job done. But when you think of the more senior executive roles, it’s no longer about execution. It’s about what should we do? Where should we go? How should we allocate our resources? And that’s really why, you know, you have to start to think about, you’re no longer working in the system, right? As an execution person, but you’re starting to think about the system itself. How is the organization structured? How are these teams built? How is the money allocated? And it’s just a very different set of things that you need to learn kind of in addition to the execution stuff, that’s always going to be important. (Time 0:06:55)
  • Defining Work-Life Balance
    • Define work-life balance specifics, like family dinners, to guide job choices.
    • Increase your value to shape your role and achieve desired flexibility. Transcript: Drew Saur Yeah. And there, there are kind of two halves to that equation that I find. So the first is really exactly to your point. Like what, what do you want? Right. If you, if you had the magic wand, that kind of question, which you could, you could design the job, the job that you want, you know, my, I always encourage people to actually write it down. Like the more detail you can, you can put to it, the easier it is to actually figure out whether or not you’re going to actually find it. Right. So when people say work-life balance, that’s great. But then what exactly does that mean? Right. So I’ll just give you my own example. Like, so for me, it was really important, you know, dinner with the family, right. That was just kind of one of those things that I put out there and said, okay, I want, you know, it can’t be a hundred percent of the time. That’s really difficult, but like 90 plus percent of the time, I want to be home and have dinner with my kids. And I want to be able to, you know, no, I can’t, I probably can’t pick them up at school every day, but whenever they have an event, I want to be able to go to it. Right. And those are of put that on paper and say, what exactly does it mean for you? That’s really step one is, do you actually know what it means? Because once you have that, then you can start to look at the opportunities. You can start to look at your own job and say, how do I basically craft that myself? How do I set up my own role and shape it to the point that I can still do the things that are really important to me? And what you find is that if you’re stuck doing a lot of things you don’t want to do, one way to sort of really change that is to make sure, back to what we talked earlier, the value that you’re Offering is that much more, right? So if I need you at the office all the time, it’s probably because basically I don’t think you’re being productive enough or I need you to do something that I think requires you to be in The office. And so my job is if I want to go home and eat dinner with my family, I have to come up with something that’s just as valuable, if not more valuable in terms of delivery or ideas or something. So you don’t honestly care that I go home and have dinner, right? That’s not the criteria you’re using, but nobody’s going to do that except you. Right. And that’s kind of the first thing I always try to tell people is unfortunately, it’s great to have sponsors. It’s great to have mentors, but nobody cares as much as you do about your own life. (Time 0:10:51)
  • Aaron’s Job Search Journey
    • Aaron Delp initially cast a wide net in his job search, considering startups and larger vendors.
    • Through coaching conversations, he refined his focus, finding a middle ground aligning with his values. Transcript: Aaron Delp And I’ll, I’ll share a little bit of my experience too. And this goes back to conversations you and I had last summer, uh, when I was starting to look for roles and, and I kind of had this path and I have a background in startups and I have a background At big vendors. And so I’ve done a little bit of both, right. And we’ll get to unique value prop here in a little while, but, but, you know, I was going out and I was doing interviews and some of them were at startups and some of them were at larger traditional Vendors. I knew I wanted to stay in the vendor space. Like I didn’t want to go back to the customer area. Um, but I had to like sit down and it was interesting because at first I was like, Oh, I just, you know, I’m just looking for a challenging girl. So I’m going to kind of cast a wide net. And I remember you and I kind of having conversations as I was going through the interview process. And there was, you know, a couple startups actually, where it was like, hey, I could go run, you know, marketing at this startup. And it’s like, man, that’s going to be a lot of work. And don’t get me wrong, it sounded fun. It sounded engaging. And when I first was interested in all of this, I’m like, yes, that’s what I want. But I think you and I had some conversations around that of like, hey, is this really what you want to do? And then we kind of found a middle ground, if you will, in my hiring process that kind of worked where I was last year. And so kind of a word of advice to everyone out there, find what is your happy medium for all of this. And actually, I won’t name names, but I had a conversation with a well-known person in our industry and actually past guest on this podcast. Um, and I, you know, we were just kind of talking a little bit about it and he’s not in Silicon Valley. Um, but it was like a little bit of like, okay, you know, what made you kind of decide where you went with your career path? And he was like, look, he’s like, I’m not in Silicon Valley. I want to spend time with my family, you know, and, and all these other things, it was just a balance thing for him. And he decided, cause I felt like he definitely had the potential to go pretty far in the industry. (Time 0:13:04)
  • Focus on the Hiring Manager’s Problem
    • Focus on the hiring manager’s problem, not just telling your story.
    • Demonstrate how your experience directly addresses their specific needs. Transcript: Drew Saur I mean, it’s, it’s a great question because it’s tricky and it’s non-intuitive in many ways, right? Because when you go to an interview, and even when you think about your value proposition, you think it’s about you, right? They’re asking you all these questions. They’re asking you all this background. Tell me about a time you did this. Tell me about a time you did that. And it sounds like it’s all about you. And, you know, what I always tell people is it’s not about you. It’s about the problem that they’re trying to solve. And interviews are proxies, right? Because what they really want to know is if I hired you in this job, how would you succeed? Right? That’s what they actually want to know. And since they don’t know that, they start asking you questions. And you say, tell me about a time you had a difficult experience with a coworker, you had to do something. Okay, great. But what I always tell people is remember the context of the question, right? And so the idea is, and why do I care about your answer? Like that’s the thing you want to append to every story that you tell is tell me about a time that you had a difficult experience with a coworker. And why would I care about that in the context of hiring this position for this problem at this time, right? Because it is all about, can you solve the hiring manager’s problem? And so if you keep that in mind, right, that sort of takes away, honestly, 80% of the mistakes people make because they tell this really interesting story. And they’re like, that was a great story. And they’re very engaged in the, in it went great. Like we, you know, I hear this all the time, which is, yeah, it was a great interview. Did you get the offer? Well, no. Well, then it wasn’t that great an interview because you didn’t get the one thing that we’re trying to do, right? And oftentimes when people start, it’s because they’re telling quote unquote, a good story. But if you ask yourself, does that solve the problem for this job? There’s a very specific thing that this hiring manager is looking for. And so one of the easiest ways to stand out is always keep that in mind, right? So whenever you’re asked a question, you answer it and you think about it from their perspective. And you say, okay, here’s what we did. But based on my understanding of your company, the research I did, the questions I asked you, does this resonate? It sounds like this could be helpful to you, right? And so always trying to turn it back to how can I help them solve their problem is really the point of the interview. So again, it’s just a slightly counterintuitive way to approach it. (Time 0:17:19)
  • Tailoring Interview Approach
    • Aaron Delp improved his interviewing by researching each person and tailoring his message.
    • He realized not every role is a good fit, despite his experience. Transcript: Aaron Delp Well, and I’ll add this because I think this, so I, you know, I, I was doing some interviews prior to talking to you. And then I think that this was kind of that light bulb moment, like, yeah, okay. I had my unique value prop. But also to the way I felt like I turned around my interview process personally, was so I again, background in marketing, but I would have to do analysts and press interviews. And anytime you did analysts and press interviews, it was, it’s not about you. And it’s not even necessarily about the, you know, the product or the press release or whatever you’re talking about. You were trying to get across a very specific message to that one individual person. And we would have to do a bunch of interview prep, um, you know, for this person or the research that they did, or what is the, you know, super interesting to them. And so like, I never thought of it in the context of when I was interviewing. And so like, I was going through interviews and this was, this was prior to this, this was a couple of years ago. And it was like, I was just going for various like VP of marketing jobs or senior director of marketing jobs. And they would be like, Oh, what, you know, what’s your experience with PLG marketing? And I would try and, you know, stumble through the questions, but I didn’t necessarily have it. And so like, it made me also realize twofold things, like what, what’s in it for them specifically so you had to kind of research not just the role but each person you’re interviewing So that you can really relay that to you’re talking about but also to pick any role in our industry that job title what they’re looking for may be very specific or very unique and you may Not fit it. Like sometimes it’s just not a good match and you just need to, and, and that was really hard for me of like, what do you mean? I’m, I won’t be good at this role. Like it’s, you know, I’ve, I’ve done all these other things. I could do that. That’s no problem. Right. But it, but it, it made me realize how to tailor all of these, um, much more so and, you know, increase my success rate, uh, dramatically with something like that. (Time 0:19:27)
  • Prioritizing Key Areas
    • Focus on two key areas when overwhelmed: targeting your desired role and defining your unique value.
    • Start with these basics before tackling interview skills or other aspects. Transcript: Aaron Delp Yeah. Drew Saur And when I coach people, I mean, in my sort of practice, we have this thing called the executive blueprint, right? And there’s sort of six different areas. And the trick though is, as you said, you can’t work on all six at once. And so for every individual, depending where they are, like there’s one or two things that they need to focus on. And, you know, for somebody starting out there, there are almost two that are all pretty universal in terms of where you can start. And it depends on how well, you know, what you want, right? So one is, I don’t really know what I want. I want to do something different. I want to do something new. That’s where you should focus your time. You should go talk to people, find out what real jobs exist, go talk to those people and figure out, is that actually what you want to do all day? Right. And so that’s sort of setting your target is, is very important. And then the second place is your value, right? Is going through all the stuff you’ve done and saying, what does make me unique? What are the things that if you line 10 people up who want this job, I have something that nine out of 10 other people do not have? Like, what is that thing? And those are usually the two, you know, by far most common places to start is again, it’s either trigger trying to figure out what you want, the targeting, or trying to figure out what It is that you offer. Cause those are the first ingredients before you actually got to figure out, well, then how do I convince somebody to hire me? How do I do interviews? There’s a lot of other stuff that you can add in there, but I always start with the basics, right? What is it that you offer or what is it that you want? (Time 0:22:29)