041: Elevate Your Career: The Power of Executive Search Revealed

00:00 - 00:51 | Sam Wholley:
A lot of what retained search, executive search is advising. I mean, if you've done hundreds of CTO searches, like you kind of know where the corners are, how to see around them. You can kind of feel if a candidate who started out to be the right candidate, maybe becomes not the right candidate and a good search leader will tell the client, look, I don't think this person's right. We should keep going. Or it could be to the candidate, like basically it seems like things have gone a little sideways, maybe this isn't the right thing for you to because retained search folks really want to develop long term relationships with people. This is about a person and their family, right and a company. And so this the stakes are not low, right? You want to make sure that that's right when the fit is there, right? Because it can really have an impact positively or not on a person and their family and the company and call it a family or not, but they're pretty simple.

00:52 - 03:01 | Christopher Nelson:

Welcome to podcast for financially focused technology employees. Are you working for equity? Do you have questions on how your career and money work together? Then welcome. Every week we discuss strategies and tactics for how to grow your career, build wealth and reach your financial and lifestyle goals. Hello and welcome to Tech Careers in Money Talk. I'm your host, Christopher Nelson. Today we want to discuss two important things. How do you work with executive recruiters? And what do executive recruiters think is the future of AI in the workplace? Both of these are critical topics if you want to grow your career, build wealth, and live the life that you want. Executive recruiters, many people don't understand, are incredible advocates and can help you accelerate your career faster. These are also the same people that have a view into how the industry is changing with AI being introduced into the workplace. And we need to understand what is our relationship need to be with this powerful technology, this disrupting a lot of things. How do we need to be in relationship with this so that we can position ourselves for the best role possible? There's no other person to talk about this than an executive recruiter who is working for a premier venture capital company. I want to introduce you to my friend Sam Wholley. Let's go talk to him now. All right, I'm excited to introduce you to Sam Wholley to Tech Careers and Money Talk. He's a partner at Lightspeed Ventures who is responsible for building the product development talent in executives for the portfolio. He started his career as a software engineer and a consultant before getting into executive search. And I think the fun fact about Sam is that he's an avid music aficionado with expansive tastes that include everything from Nas, Dave Matthews, Paul Simon, classical, acapella. I don't know, like that could be a podcast episode in and of itself, right? I would love that.

03:01 - 03:03 | Sam Wholley:

Thank you, Christopher. It's great to be here.

03:03 - 03:38 | Christopher Nelson:

Yeah, thanks so much. So I want to get straight into it. I know, for myself, you came along at a point in my career, when my career was, was moving and developing as an executive, you became this phenomenal consulieri. We were working on some things together. I never got placed with you, but we developed a phenomenal relationship. And I think It has provided and still provides such value to me. I wanted to share with people, number one, defining what executive search is and specialized search. If you could help us understand that, I think that'd be great.

03:39 - 04:57 | Sam Wholley:

Actually, no, that's fantastic. I'm glad you distinct the wish between the two because executive search and specialized search, they can be the same, but they can also be side by side. So executive search is really when you're bringing a leader into an organization, you are changing the DNA. Like there will be someone who has leadership responsibility, many times fiduciary duty, right, to a company. They will be hiring people. Those people will change the course and the trajectory and the topology of the company. And so, there's a process that is related, but not at all the same as when you're building on a team and you're bringing in individual contributors, etc. So executive search is the process of expanding a company's executive team by way of functional leadership or could be CEO, could be board, etc. Specialist search could be executive, but there could also be a person, for example, who specializes in quant researchers for hedge funds. That is specialized search. Unlikely that executive search, but the two can be, the two can be, um, could be in the same Riviera partners. The search firm that I was at for a decade was both was specialized in engineering, product design, data science leadership. Um, so executive search that happened to be specialized. There are certain specialized executive search firms out there that might be go to market or sales specific. Um, Riviera was, was that so.

04:58 - 05:37 | Christopher Nelson:

Right. And generally speaking, these executive and specialized search firms, they will have a specialization and they're going to be hired by, I mean, a venture capital group who wants to seed executive talent in their portfolio or by growing private companies that want private or public companies that want to bring new talent in. And so And they generally speaking, operate as, you know, third party consultancies that are paid for, but they're outside of, you know, normal recruiting that is inside. And so why do companies then usually engage this third party?

05:38 - 07:22 | Sam Wholley:

It's usually for a couple of reasons. Number one, you want to make sure if you have an urgent hire that you have dedicated resources on it. And by just virtue of the name, you're retaining a firm, that firm, that search leader is spending, they're dedicating their time to making sure this role gets filled and filled in the right way. It could be some companies, when they're large enough, may have an executive search group. That group may have their own networks that could potentially fill all roles, but maybe they don't have a specialization in one particular area, or they're also one or two people and they need to fill four. That's just not possible to do it well, right, internally. And so they may just need to bring on a firm to help with one or two roles while they're taking on three or four, depending on the stage of the company. And so other times it's because they just don't necessarily have Either the experience or the confidence in themselves to be able to fill that role. A lot of what you mentioned it's a lot of what. retained search, executive searches advising. I mean, if you've done hundreds of CTO searches, like you kind of know where the corners are, how to see around them. You can kind of feel if a candidate who started out to be the right candidate, maybe becomes not the right candidate. And a good search leader will tell the client, look, I don't think this person's right, we should keep going. Or it could be to the candidate, like, basically, it seems like things have gone a little sideways, maybe this isn't the right thing for you to because retained search folks really want to develop long term relationships with people. This is about a person and their family, right and a company. And so this the stakes are not low, right? You want to make sure that that's right when the fit is there, right? Because it can really have an impact positively or not on a person and their family and the company and call it a family or not, but their group their organization.

07:23 - 08:35 | Christopher Nelson:

Well, and this is why I think it's so important for people to be aware of what Executive Specialized Retained Search is, the, the people who run those organizations, because I have to say for my, my career, when I discovered it, it was magical in the sense that you you, you have this, this third party, whose incentives are twofold, right? You're, yes, you want to find the right talent for the company. So you are employed by the company. But at the same time, you want to cultivate your own network of talent to be able to align and partner with the companies. And so you really are a broker that has both people's interest in minds. And so this is where I think it's so important that people understand that dynamic because, you know, you can be a consultant, you know, in and around finding the right fit for people, the right, you know, companies for people as well. And so I want to just try and explain how, from your perspective, how can mid-level executives really benefit from a relationship with retained search recruiters?

08:36 - 10:58 | Sam Wholley:

So part of it is, there is a bit of a misconception that you have to be an executive to have a relationship with an executive recruiting firm. And that's not the case because ultimately, executive can mean, it really means the function in the company. That could be a 15 person company, it could be a 1500 person company or a 15,000 person company or so forth. Right. If you have aspirations towards being an executive at some point, first of all, you want to understand are those the right aspirations and do you have them for the right reasons? And so talking with someone who works with executives all day, is a great thing. And so my former colleagues in exec search firms and contemporaries, there are lots of people who have great advice because they're doing one thing all day, every day is talking to executives and hearing what makes a great executive. And so they can give back information to the candidates. Like, here's what needs to be done if you're going to do this job well. And generally speaking, I've been very fortunate to work with people who I do think really care about the can, not just at Riviera, by the way, at other firms, But certainly, they really care about giving you the right advice. And on the other side, they really care about how that placement really changes the trajectory of the company. You know, you could cast dispersions on maybe many different professions around, well, people are transactional, but good ones really care. They do want to make sure that you're helping. And so I think that while you're making your way through your career and taking on more managerial responsibility, leadership responsibility, and executive responsibility, those are three distinct things. And so you can be a manager and maybe an okay leader. You can be a great leader and maybe an okay executive, right? And one does not belie the other, nor is necessarily there's not a good or bad answer. And one is not right, nor is one wrong. It's about what's right for you. And so I think just being able to really have almost a coaching conversation with people who are doing these functions, this could be facilities and operations, it could be finance, it could be marketing, whatever it is, there are like you said, specialized executive recruiters who do this. And it really does help to know the people who work in those spaces because they can see what is a CFO in a tech company has very different experience and experiences as well in, let's say, a food or CPG company, right? And so it's really important to talk to the people who know the industries that you're in.

11:00 - 11:40 | Christopher Nelson:

Well, and that, and that is part of the, the relationship is being able to have conversations with, you know, an executive recruiter that can help you understand what's happening in the industry, what are trends, what are things that you need to, to know about, and then also helping you understand. I mean, one of the biggest values I got was in, in partnership with different executive recruiters was understanding where there were holes in my game. Like, okay, you know, from a experience perspective, and then also from a, you know, evaluation and how it was executing perspective, that type of feedback is going to help you grow and is going to help you really get ready for the next role.

11:41 - 12:27 | Sam Wholley:

So yeah, and you know, sorry, sorry, sorry, but you brought up a huge point. It is not easy. I think you would agree. It's not easy as a human to give constructive or let's face it negative feedback. And so right as a candidate, when you're talking to an executive recruiter, tell them, look, I want the God's honest truth. I want you to tell me good, bad, or ugly. What's working? What's not? What do I need to change? What did I do badly or poorly? If you use that relationship to be constructive, it can be extremely powerful. But you need to give the recruiter, I wouldn't say it's permission, but it's also giving the validation that they can tell you what you didn't do well either. Rather than, oh, they're going to go in a different direction. Why? Tell me what I did. Please just, I need that help.

12:29 - 13:06 | Christopher Nelson:

And you're 100% correct that as the candidate, I want to make sure that you realize I'm open. I'm letting you know there's no filter between us. And when people are able to do that, the richness of the data that you get back, the feedback of what executive search team observes, what the client has observed, those are the actual nuggets and the lessons learned that will allow you to accelerate your career a lot faster than if you if you continue with, you know, some things in your blind spot, honestly.

13:09 - 13:26 | Sam Wholley:

Over time, personally, I've found in my own career is you get to learn to be comfortable with your blind spots. And so then you put yourself into better positions where those blind spots aren't blind spots anymore. And so I think that just comes a little bit with age, but it comes also with some self-introspection.

13:28 - 14:15 | Christopher Nelson:

Well, it really it really does. And this is where this is where I think this relationship is so valuable, because I think we're literally just, you know, teasing out, you know, really how these relationships evolve in a real conversation between somebody who was a candidate and who somebody was an executive, you know, search executive, you know, in a relationship where you go in, you give permission, you're going through a process, you're getting feedback. And it's not like done in that moment. I think it's important for people to understand that when the feedback comes, it's not done. Because ultimately, when you're building a very healthy relationship, people realize you're going to have to go back to the lab, you're going to have to then iterate on some things, come back with some different results and get ready for what happens next.

14:15 - 14:56 | Sam Wholley:

Yep. Exactly. And then also be figuring out having an executive recruiter sometimes help you figure out who the right executive coach is, because you're right, there is, it's not a transactional relationship, but we could be once a week, you know, that's fine. But you need to have a programmatic, more structured way for someone. If I'm getting feedback from a recruiter, I need to take that and then put a plan into place. That's what executive coaches are for. And a lot of times executive coaches were executive recruiters because they can understand what the development path of someone who has feedback, how do you instantiate and implement that feedback? Those two things can go really hand in hand for someone who really wants to develop themselves.

14:58 - 15:24 | Christopher Nelson:

And it's so important that you understand that this what we're talking about right here is this is these are growth accelerators when you get into these types of relationships. And so how do people, you know, you're, let's say you're mid level at your career, your senior manager, you're aspiring to direct a role, what is the appropriate way to start, you know, building relationships with executive recruiters? And what's maybe the timing? Yeah.

15:25 - 16:36 | Sam Wholley:

Yeah, if there are people in your organization, I've always been lucky to have super, I have been very lucky. I've never worked in an organization that was sort of top down and didn't want the right things for me. Not everybody I realize is that lucky. But if you're in an organization where your manager, your leader, whatever, someone in the company has those relationships, ask them. Who are the people I should be getting to know now for the next 10 years of my career? Is there a search firm that continues to call you? Who's sending you emails, right? Who are those people? And ultimately, because those recruiters are the ones with the search remits that that person will want, right? And if that person is truly a supportive leader, sometimes they would say, timing's not right for me, or this isn't the right role for me, but you should talk to Christopher, right? If they're helping you along the way in your career. It's harder if someone, a great person on your team leaves, but it's better for them in the long run. And I would always want that for anybody on my team or anyone I work with. Because if some companies that shed talent, it's hard, but it's also a compliment, right? Because you've developed people that other companies want to hire. It's fundamental.

16:37 - 17:21 | Christopher Nelson:

Well, and that's an important point that I think younger managers, managers earlier in their career don't always understand that when you get a reputation for helping talent grow and move to the next level, you will then start attracting people who want to work for you because you're seen as somebody who is, you know, minting the next level. When I was at a point in my career where I figured out a coaching program myself to help people get from senior manager to director, and I was minting a lot of directors, that created a lot of inbound interest, you know, in, you know, IT organizations and tech, because people realized they could come work for me and make that leap that traditionally is pretty hard.

17:22 - 18:09 | Sam Wholley:

Yeah. Two other ideas. Number one of those two is actually how I met you, right? It's talking to people who left the organization and say, look, this was great for now, but I just don't know if there's a road for me over the next five to six years. So maybe they have feedback for you. Maybe they can say to you, I think you could be in that slot in six years, but here's what I think you need to work on. Or they could introduce you to those recruiters. That happens all the time, right? That's how you learn that. But the second idea of two is also LinkedIn. So most executive search firms are doing events. They'll do meetups or dinners, industry professionals. They usually do a hashtag, right? Look on LinkedIn for the firms that are holding these events. If you don't have someone who can make first order connections, look at those firms and then write it.

18:11 - 18:37 | Christopher Nelson:

That is phenomenal. And that actually leads into my next question is, in this era of LinkedIn, and LinkedIn in the last, I'd say, three years has hit this whole new level. When somebody is positioning themselves to get picked up by executive search, how important is LinkedIn? And what are some of the key things they need to do to make themselves professional and ready on that level?

18:37 - 20:05 | Sam Wholley:

LinkedIn is the new resume. It's always been that way for the past or always, but it's been that way for the past seven or eight years, right? I very rarely see a CV or a resume these days. I think LinkedIn, if you can really, it needs to be clean and it needs to tell a succinct story. So for every role that you have, give a sentence or two about what you did and if you can measure it, ideally measurable impact you had on the company, right? Built a product that had 250% growth over eight months, something like that. If you've been progressively promoted, that's good. LinkedIn has its pros and cons. One of the pros it has is that it gives you the tenure of start and finish, but it can also show breakdowns by promotion, right? individual, senior software engineer, software engineering manager, director of software engineering under one company. That shows progression over a short amount of time, hopefully. And then in each of those roles, just continue. If it's three roles in four years, that's great. Have one of those roles have two sentences, not six sentences in total, because that just sort of is a little bit overkill. So short, articulate summaries of what ideally quantifiable metrics that you have provided to the company to accelerate their growth. Make sure it's clean. You don't have to have all of your activities on there, but it should be very clear or as clear as possible from your LinkedIn, what it is you are really good at, what you do and what you want to do.

20:07 - 20:51 | Christopher Nelson:

Well, and so you just brought up something that I think is really important. And I did an episode earlier, where I really broke down that people don't tell their own story well enough. And that to tell your story in the way of quantifiable results, that has the most impact because it's succinct. The numbers really speak for themselves. They're also usually aligned with company objectives that demonstrate a level of business acumen, like it's packaged very neatly. You hit that three or four times. How important is that for you? Like when somebody is transitioning to the executive level and that level of search, how critical is that that they understand how to translate their results quantifiably?

20:52 - 21:30 | Sam Wholley:

I'd say that the more senior, then the more that less is more matters, right? Because at some point you're going, it's going to be quite evident. If you were a VP of engineering in a company for six years, and that company went public three years into your tenure there, it's pretty obvious that you had an impact, right? The other thing too, that a kid, I've never met someone who uses the word visionary in their profile, who is truly visionary. Like don't let people, You shouldn't have to say it if you aren't. And so you're telling your story and your narrative is one thing, trying to make a decision for people is another. And I wouldn't be the latter. I would definitely do the first.

21:32 - 21:51 | Christopher Nelson:

Right. Uh, what I'm hearing is, is nouns, verbs, numbers, you know, you can leave the adjectives to the side because that's, you know, the, the resume, the LinkedIn, that's going to get you the interview. You're going to have plenty of time to tell the stories, have the conversations in the interview, but you know, keeping it succinct and professional, I think is really important.

21:51 - 21:59 | Sam Wholley:

Yeah. I actually love how you phrased it. Leave the adjectives to the reader and also avoid hyperbole. Always avoid hyperbole. See what I did there?

22:00 - 22:23 | Christopher Nelson:

Yeah. I love it. I love it. So then if LinkedIn is so important, we like then what should a resume be like help help tie this together? Because you know, there's obviously people out searching right now we have some layoffs in the industry. You know, LinkedIn, obviously very important. But but then a resume should that just be, you know, like LinkedIn plus a little bit more?

22:25 - 22:51 | Sam Wholley:

What does that look like? You nailed it, exactly that. It's LinkedIn plus a little more, a little more illustrative details. Maybe there was a key project or some project that really was transformational that you led or something that you would probably, you would tell in an interview, but not, you know, LinkedIn, right? So it's probably no more than twice the length. It's a little more illustrative, but not telling your, you know, my story during that time of your life.

22:51 - 22:57 | Christopher Nelson:

Do you see any articles? Are cover letters even a thing anymore?

22:57 - 23:34 | Sam Wholley:

It's a good question. I would say sometimes. It's not typically the case, but where it does help is if it's not a linear move from point A to point B. If someone, a cover letter is saying, I saw this role that was posted or I understand you're looking for this type of role, Here's why I think, it may not be obvious, but here's why I think that I'm the right person for this job. And it may be something that you did in a job you have on LinkedIn. But to do that, to draw the line between the two points would be just too creative, right? That's when prose helps.

23:36 - 23:47 | Christopher Nelson:

What about an executive or a biography? And is that something that goes into your about section in LinkedIn?

23:47 - 24:14 | Sam Wholley:

Not typically. I think, again, less is more. If there is a summary of a sentence or two that tells a little bit about you and what you've done, LinkedIn is a business social network. There are personal social networks. And so I think also distinguishing between the two is totally fine at the very bottom to have hobbies, maybe, you know, or Eagle Scout or whatever, that's great. But I also think just keeping it about what are you ultimately trying to accomplish?

24:14 - 24:24 | Christopher Nelson:

Right, right. So, so it truly is when you think about executive search, you want it to have a very resume, resume type focus to it. Yeah, clear and succinct.

24:24 - 24:27 | Sam Wholley:

What did you do? And why did it matter?

24:27 - 24:49 | Christopher Nelson:

Hmm. Love that. That's a great roll up. So getting back to what you were talking about earlier, looking and following executive search firms and understanding some of their activities, virtual live activities is really important. Is there a protocol for reaching out to create relationships with executive recruiters through LinkedIn?

24:50 - 26:10 | Sam Wholley:

Whether it's a company or an exec search firm, or frankly anything, a warm connection is always best, right? So if you have someone who can make an introduction, a warm introduction, then that is always the preferable method, right? Because there'll be some context. If, you know, someone is introduced cold, that's blind intros, that's no good, that does not work. And so, but reaching out, cold intros are not good. cold reach outs are fine. If someone writes into an exec search firm and says, Hey, I'm a director of engineering at Lyft. I would love to engage with you to look for my next role. That's fine. But someone that you mutually know, just making a cold intro is usually not the best way to do it because you don't have any context. You don't necessarily know if that is the right person at that firm for that individual to speak with. But if you don't have an intro, just write it and that's fine. I would also say too, just If there is someone who has had a positive interaction with multiple search firms, that's totally fine as well. There's no way that one firm can cover the entire world. It just doesn't work that way, right? And so there are relationships. If a firm is a generalist firm and not a specialist firm, they may have put in a CEO or a CFO or whatever and have a relationship and they can execute searches in multiple functions. And those tend to be pretty durable relationships.

26:12 - 27:18 | Christopher Nelson:

And so going back to the first one, what I heard was, and this was actually something that I did, as I know, after we built our relationship, and I got some warm handoffs to some other firms, there were other ones, I think there were some larger ones that had specialized functions, I think there was a corn fairy has a, you know, it executive search area, I went in through the front door, which I think is what you're saying is there's a way that you can go in and And through the front door, there was I remember there was a specialized CIO search firm, same thing where I just went in through the front door. And if you have a resume, and you have a story that lines up with where you're going, they're going to reach out. Like they want to, they're trying to find a talent pool. And this is so important for people to understand that when you get to this level, leverage your relationships to get warm handoffs, number one. Number two is going through the front door, the virtual front door of some of these organizations, because they're looking for people like you and want to build those relationships. So that's, that's important. That's valuable.

27:19 - 27:56 | Sam Wholley:

Yeah. And look, any good search firm is going to, if you're at a point where you are a candidate for a search firm, retained search firm, you have a career history and any good search firm is going to reach out to you and say, Hey, you've shown some interesting trajectory, right? You look like someone I'd like to get to know, right? Not for now necessarily, but also for later, because that next level of leadership, if they're not doing that, then they're not keeping their networks warm. They're always going back. And that's how you get to a less diverse pipeline, a less relevant pipeline, etc. So the good firms are always looking at who are the next level leaders who are going to be the leaders of tomorrow because I want to get to know them now.

27:56 - 29:33 | Christopher Nelson:

And I want to take people down the path a little bit of what it looks like when you have very healthy executive search relationships. My experience was when I would get a role that would be inbound, I would then reach out to you, I would reach out to somebody else who was in, you know, and I had, at one point, I had probably three executive search relationships, and they were my consolieres, right? I would reach out and I would say, I've seen this role, or it would come from one of them. And I might reach out to somebody else to say, you know, get a third party opinion on that. And No. 1, that's OK, right? It's important for people to understand that having mutual relationships, they, the perspective is going to be on you, that you're developing it as a, as an executive, you're getting multiple opinions, you're vetting these ideas, you're getting coaching and guidance from the broader team. And when it's working well, you get a lot of inbound. Like I still, You know, I mean, I, I still I've been retired from the industry for over a year and a half, and I still get inbound because of great relationships. Right. And, and that's my point to people is that when you put in the work up front, you do good work, you build healthy relationships. how it's supposed to work is that you're going to have these teams that are trying to find your next opportunity that's going to help your career ascend in, in the way that you're navigating it.

29:33 - 29:43 | Sam Wholley:

Absolutely. And that's, I mean, now you're, you're in that flywheel and you're saying, Hey, look, I'm, I'm retired from tech, but you should talk to Jenny or Kevin or whatever.

29:43 - 29:44 | Christopher Nelson:

Right?

29:44 - 29:44 | Sam Wholley:

Yeah.

29:45 - 31:14 | Christopher Nelson:

100%. Yeah, exactly. As in people are still coming and they realize, Hey, you have the good relationship, seeing the talent, helping to continue building those relationships. Because once you're inside the circle, I mean, this is where, why I felt this conversation, Sam, is just so, so, so important is because There was not a lot of information when I was coming up. I was lucky to be a part of that CIO networking group in the Bay Area that started introducing us to more people. We started building a relationship. And then I realized this is so valuable that people need to intentionally seek this out as they're growing their career. Well, so we're going to put a pin, this is part one, where we're going to put a pin in this, and then we're going to come back. And in part two, Sam and I, when we were preparing for this call, he has got a passionate idea of how do we need to prepare our careers for the age of generative AI, we're going to take a quick break, we're going to come right back and talk about that. Hold on. All right, and we are back here with Sam Wholley, and we're going to mix it up on talking about AI, the workforce. How do we really prepare ourselves for what's coming? Because it's obviously that it's coming. I think from your vantage point, you're seeing the industry starting to shift. How do you see AI, generative AI, impacting the job landscape in the next three to five years?

31:15 - 33:35 | Sam Wholley:

I mean, it's going to be huge. It's amazing how quickly this all kind of came about, right? So GPT went GA in November of 2022. And so everything we've heard since then has really not been that long a time, but it will have an immense impact over the next three to five years. I think it's going to make people more productive. I think it can make people more creative. But what it will require us all to do is be better at some people call it prompt engineering, but it's around critical thinking and around critical communication. So it's sort of like you're not going to be able to tell an AI engine. give me a list of the five things in my head, because it doesn't know what's in your head. But if you prepare it with the information, you can get some really good info out. But you also have to check that information. I don't know that we're ever going to be at a point where it's ever going to be 100% correct. And so what we then have to do, kind of as a society, but certainly as If you're an information worker, or if you're not, robots are being controlled by AI-based control systems now, and that will only increase. So I think we will all have some part of our lives that are touched by AI in the next five to seven years. Now, Lightspeed's been investing in this stuff for over a decade, and it's kind of come up really quickly, but there's a lot. It's in there, and you probably don't know you've been using it, and you have been. And so I think that the ability for people to understand how do I make AI my friend to make myself more productive is important. The ability to think about if you're using AI as an enabler or as a disruptor, right? So will this, could this help my job? Could this take my job? All of these things are up in the air and it really doesn't do us any good from an anxiety standpoint to worry about, will this take away everyone's jobs? That's not really going to happen in my opinion. I think it will make our jobs different. Let's take executive search. I don't personally think that any time in the near future will an AI bot be able to do an executive search person's job? Can it 100% increase the efficiency of reaching out and sending emails, even engaging in an initial conversation? Yeah, absolutely. So it can make that process much more efficient. Will it change the human touch? No. Personally don't think that's going to happen in our lifetimes.

33:36 - 34:19 | Christopher Nelson:

And when we think right now, I mean, the current state of generative AI, as you mentioned, it helps us synthesize things, it helps us move faster. But there are still so many things, you know, from a creative perspective, it can't create anything new in the imaginary way that we can. It also does need a lot of input. So I think what I'm hearing you say is lean in, understand the technology and how to be more efficient at your job, but also be looking at the unique things that you do that can't be automated, that can't be turned over to AI, and then focus on how do you actually grow and develop those skill sets.

34:20 - 35:25 | Sam Wholley:

Yeah, and I would even start with the end in mind, right? So if you start to think, what is my job? What are they hiring me to do? What am I here to do at work? What does exceptional look like? And then work back from that. What is it that I bring to the table that no one else but me, maybe even only me uniquely as a human or someone who has my skill set. And then what are the things that some AI bot can do? Can artificial intelligence actually do my job or can it make it better? But it can't get exceptional. It might be good enough. but it can't be great, right? And so if you work on what makes you great, you're really taking the information that AI can make much more available to you and then applying critical thinking on it. So there's probably room for critical thinking increase in every job. If there isn't, those are the jobs that will likely, that's where it gets a little dangerous. Those jobs may go away in the longterm, but critical thinking is the key differentiator. Can AGI ever, you know, have critical thinking imbued into it? Who knows? I thought a lot of things were possible, but that's where I get a little bit skeptical. I don't think that's anywhere near term.

35:25 - 36:08 | Christopher Nelson:

It's so important for people to be leaning in and learning about AI and especially understanding their job, how they can leverage it to make it more efficient. From a search perspective, like right now, how can people help communicate that they are leaning into AI? Is there something that when you're looking at somebody's you know, resume, you're looking at what they're doing. Hey, this is a particular role, you know, let's think, you know, marketing, copywriting. If somebody said, I have taken a course on how to, you know, be a leverage AI to ensure that, you know, all my copywriting is brand specific or something like that. What do people have to do to let you know they're learning?

36:08 - 37:35 | Sam Wholley:

I think it's really a great, yeah, it's a great conversation piece because I think ultimately it's going to be a question everyone will be asked. What are you doing to use AI, to learn AI and use AI in your job, right? And I think that is important. In fact, frankly, it's something that I think So I think if you were able to say, I can increase the time from if you're a journalist from the assignment to the ready copy, right? Is there a way that you can and also understanding its limitations? So I was able to get a first draft done really quickly. I edited for style. I didn't, you know, I fact checked it. I did all the things that we can't rely on the editor to do yet. But it was able to increase my time to ready copy by 50%, 60%. Are there things that, you know, taking again, critical thinking, what does my job, what does excellence in my job really mean? And how did I take a step up and back and say, are there things I could be doing better, more efficiently with artificial intelligence? This is something, frankly, I struggle with because I'm trying, I kind of get caught in my old ways, right? I'm just, I do the things I've always been doing. Sometimes I need to step back and think, could I be doing this better in a different way? And I think as we get, again, general availability of this has not been around for that long. The more history we have with AI, I think the more examples people will have, the products will be better, the usage will be better, integrations will be better, trading data will be better and more accurate.

37:37 - 37:56 | Christopher Nelson:

More applicable. Yeah. Do you know of anything, I'm just curious, on the market from your perspective, especially being in venture, are there any courses or certifications or anything that's out there right now that would sort of establish somebody as, you know what, at least you know the 101 or the 201.

37:59 - 39:03 | Sam Wholley:

I couldn't tell you specific courses, but Udemy and Coursera have some stuff out there. The one good thing about, not the one, but one of the best things about the internet is that stuff is generally available. I mean, podcasts, right? You have great information that's out there. And I think that being able to just understand what is it, what does it mean to me? That will also take some of the fear away. I think there's this general thought about AI is that the overboards are coming for us. You know, anytime you have a technological change, there's a lot of fear, right? And there are pros and there are cons. Take the automobile. When the automobile was ready for use and generally available, it increased people's mobility. They were able to move for families and jobs. They were able to commute out of cities. Some argue that's not good, but it gave optionality, right? It also caused people to lose their lives. Anytime there's something transformational, there will be a pro and a con. Right. And so this is one of those situations and we just have to manage the pros and the cons.

39:03 - 39:19 | Christopher Nelson:

Speaking about reducing anxiety, what are some of the overinflated things that you've heard that people just need to calm down about that, you know, maybe, maybe a little too much, you know, or too soon, right?

39:19 - 41:02 | Sam Wholley:

Well, anytime you hear hyperbole, you sort of have to be skeptical. Like this job will go away because of AI. Maybe. Governmental regulation could make any one of us irrelevant tomorrow, right? There are things that could make us irrelevant or unneeded or unnecessary. But it's show me the receipts, tell me where that's going to happen. If that means that maybe you have to actually change your job or your career, possibly, but that could also happen because of other factors as well. So I think because if there isn't a general understanding of what artificial intelligence means to them and their job and what is it being used for, and also thinking a little bit ahead. So there are phenomenal AI assistants out there, right? Is that going to take, I am not seeing an area where an AI assistant can completely replace a human. I have been extremely lucky to have insanely great EAs in my career. And I think that that is something that we're just not there yet. So I don't see, it can be a helpful enabler and maybe that increases the leverage that a phenomenal executive assistant can have with all of the person that he or she supports and works with. But I don't think it's going to take that over. Lawyers in paralegals, they have different jobs. AI will change how they do their jobs in different ways. But those tools aren't out there to completely replace either of them yet. Could that change in the future? Possibly. computers change data entry in the 70s, right, there will be those changes, reflections. And so I don't think we're at a point yet to say that these things are deterministically good, bad or gone. But we're on our way to be able to have some, I think some view into that probably in the next couple

41:04 - 41:50 | Christopher Nelson:

Well, we are. I mean, you think about it. Let's go back to your car model. I mean, when all of a sudden the cars went into mass production, I'm sure blacksmith jobs went away. Does that mean there's no more blacksmiths today? No, but they're a lot rarer and people need to retool and understand what is the job. And I think in this conversation we're having, it's just reminding me that I think the hyperbole of this will go away absolutely is exactly that. And it's important for people to understand that flip side of how can I be better at my role, be much more efficient? How can I turn, leverage this tool to get to the leading edge and not be on the lagging edge? Because that's ultimately where risk is going to be.

41:50 - 43:03 | Sam Wholley:

Yeah. And that's, by the way, a great advice in any part of your life. It's just who we are and what we do are two different axes, right? And so, also, who you are changes as you age. That's just a fact, right? And so, you talked about this, I started my career as a software engineer. I could be a good, I knew I could be a good engineer, but I don't think I could ever be a great engineer. It's just not who I was. I was, my college roommate is a great engineer. What I liked and what I was good at became different over time. So I'm on basically my fifth career. It took me a while to figure out what I was good at. Who I was changed, what I was good at changed, and the world, and jobs changed. That's a third axis. So who we are, what we do is different. What artificial intelligence will, I believe, cause us to have to think about is the why. Why are we good at what we're doing? The what and the how can be the AI piece. The why is the who we are piece, right? That's what makes you exceptional. But how can you be more exceptional, more efficiently? That's where AI can, I think, play a great part in. helping us all be better at what we do. That could be detailing a car. It could be designing a building. It could be recruiting. It could be podcasts. It could be anything.

43:03 - 43:40 | Christopher Nelson:

Right. I don't want to go down that. I was going to get distracted there for a minute. So let's talk about what are the roles, though, that you are seeing? Now let's tap into your view as you are at Lightspeed Ventures. What are opportunities for people to reskill and actually move into AI-level companies? What are some skills that people could be building out there? They say, you know what? I want to get behind this disruption and not just you know, be somebody who leverages it my day to day, but I want to go build the future. What's out there for them?

43:40 - 45:09 | Sam Wholley:

Yeah, I mean, that's a great question. I think the point, the question I would ask that person is what is their functional expertise? If it's not AI research, that's, that's the people building the actual artificial intelligence models and deployment mechanisms, etc. Then it is maybe building a company that is using applied AI. So if you are a finance person, you could be a CFO at an AI company. But you're still a finance or a marketing. I'm still a recruiter at a venture firm. So unless you are a researcher building the AI center, then you are using those skills for good. You're using your powers for good. If you are a functional leader, you can build a company that does change and impact in AI. It could be model training, it could be tools and development tools. I personally think the next five years are going to be, I think, generally speaking, everyone likes to say the same thing, vertical AI for B2B SaaS applications is going to be changed immensely. Legal tech, there's a ton of applications for this. And so I grew just in the early years of that. So if you want to be part of something transformative, there are tons of opportunities. How do you use your functional skills to build companies that make those transformations? And then how do you use them to transform yourself as well? So if you are in marketing, how do you, if you're in marketing or finance, how do you use AI tools to make your job easier, better, faster, quicker?

45:11 - 45:27 | Christopher Nelson:

Right, right. So so we could play that out. Because I mean, in marketing, it's like, do you then use AI tools so that you can you can generate an AI bot so that anybody who's creating copy or product speak can go in there and have it make sure that it's aligned to to company vision, mission, those types.

45:27 - 46:07 | Sam Wholley:

Absolutely. And also understanding what to look for in the companies. If you are a marketing executive, choosing companies that also use AI for good. For example, there's a company, phenomenal company in our portfolio called Typeface. that what they're doing is micro targeting. So you can create campaigns based on the individual level. So the campaign, the video that you get is different from what I get. That's powerful. That's using AI for leverage. So you're using your job and your role as a marketing executive to be able to use a tool that is using AI in the way it was intended. So being aware of what's out there and why that makes a difference is really important.

46:08 - 47:47 | Christopher Nelson:

What you're highlighting here, Sam, is that if you're actually not part of core, let's say, product AI development, there are those people. And if you want to learn those things, that's a whole other podcast. Totally. However, if you're in the, let's say, the normal business functions of marketing, sales, finance, et cetera, that goes into technology, This is interesting because now you need to be focused really on the business use case and the execution and understanding how that product is going to disrupt the market when you're going in to evaluate those particular roles that you're getting into. I mean, the question that's bringing up for me is now, it sounds like people need to be more focused on the business use case and how it's going to be executed. Because, for example, I see right now in the podcasting space, let's just use this as an example, the one thing that I get hit with is, oh, we're the tool that can take your long form podcast and create all the short clips. There is hundreds of those things coming at me. it would take a lot of time to know the difference. But that's where if somebody says, I want to go take my career in that direction, you need to then understand of those swath of companies, which one is really going to transform the true effectiveness of the content creator of the podcast or to really do that. And that's where I think people when they think about building skills and AI, it's almost honing their business acumen.

47:48 - 48:26 | Sam Wholley:

Oh, absolutely. It's never been more important to understand your business mode because it can be eclipsed really quickly now. So if you're an executive looking at a role, then the classic questions of, I always say, what four things need to happen in the next four years for this company to win the space? Those questions have been relevant for decades, right? Now you also have to layer on what advantages can other companies with AI, or if it's not AI native, AI enabled, technologies or products, how can they catch up quickly? Or better said, what's your unfair advantage? Because that that moat can go away quickly if you're not careful.

48:26 - 49:15 | Christopher Nelson:

Wow. Wow. Yeah. I mean, this well, and I'm glad that we tease this out, because that that to me is the the golden lesson that I think comes out of this. This section of the podcast is people really need to double down on their business acumen and business use case, because that's, as I see this picking up speed from my vantage point, you know, now as a as an LP, on the investment side, it, you know, in thinking about, okay, where do I want to place dollars, it's so important that you you truly are understanding these business fundamentals, because I think companies can, you know, the cycle from start to, okay, this is no longer a leading advantage, let's shut this down. I think that's going to get a lot shorter.

49:15 - 50:20 | Sam Wholley:

Yeah. And look, all of these opinions are mine, not Lightspeed's, but I personally think we're at the end of a hype cycle. And now we're at the beginning where we've already started to be in an AI use cycle where it's now a great AI is out there. People know it. They can spell it. But what does it actually mean and how do you apply it? Right. There will no doubt be huge innovations in the language models and the applications, the training data, the training procedures, et cetera, and all the underlying tools. But we know what it is. We just don't know what it does yet. Right. And so that application of it, what can it do for me is I think where we are. And that's exciting. But you said it exactly right. People need to understand ultimately you're joining a business. So you mentioned, you said the normal business functions of marketing and finance. They are also extremely critical business functions because a technology without a business to sell it. You know, there's a reason that we all had VHS tapes, not Betamax tapes. right? Better technology, not a better business. And so it's a system and it's an organism that all has to work together.

50:20 - 50:37 | Christopher Nelson:

As you were speaking about, you know, this, this evolution to now AI, very core use cases, you know, are there some industries or sectors that, that people should have their eyes open to, you know, in the next, you know, two to three years or, or I don't know, six months?

50:37 - 52:11 | Sam Wholley:

Yeah, that's a great question. I don't, I couldn't point to one particular one. I think it is so pervasive that if you are a consumer creator podcast, there are tons of tools, there are tons of options. If you're on the B2B side, you are the tools and the options, and there are tons of them. I think that Vertical SaaS applications usage of AI is going to be exciting. That's also where we're going to see the biggest difference in profit margins and even companies from an investment perspective, because you could just be much more efficient. If you talk to engineering leaders, they'll tell you simply the advent of co-pilots in coding. I mean, it's pretty wild what they can do. So even if it saves you half the time that it used to take you to perform a job, that's still half the time. And if you extrapolate that among 200 engineers, five days a week, that's great, right? So I think a lot of this is going to, for each of these functions, how do we manage productivity and output? Which I think this is, again, as another podcast, but you talk about remote work and people return to office or people productive. It's a deep and fraught conversation, but I think the measurement of output and what are you actually getting becomes more important because if they do that in half the time, if one person does it in half the time, because they were using AI the right way. then it's going to be incumbent upon that person if they want to overperform to take on more. But ultimately, you're going to see that work itself out.

52:11 - 52:30 | Christopher Nelson:

Right. People are going to have a lot more. I think that's an interesting, you know, conversation, too, at some point of, you know, what's going is that going to provide more flexibility as people can now have these tools, be much more efficient, you know, focus on on getting results in less time? You know, what is what is that? What opportunity does that create?

52:31 - 53:12 | Sam Wholley:

I also, what I worry about is if you, let's say that you had two people who are interacting in a job, and now their AI alter egos are interacting, those people are no longer interacting. And so there is something to be said for being in an office, whether you, you know, you were a remote work zealot or in office zealot or somewhere in between. What I, what I do think we should be aware of is the impact of fewer conversations between humans on those humans. That's a whole different conversation. And I'm not qualified to opine on that from a sociological standpoint, but it's something I think we should be mindful of.

53:14 - 53:53 | Christopher Nelson:

We should, but this goes back to there is a core fundamental that we brought up just a minute ago, which is regardless of the technology, you're running a business. And business involves people. Commerce does involve people. And the greatest businesses that I've seen that I've had the privilege to be a part of have a phenomenal culture that involves touch, communication, understanding, And I think that's going to be a huge differentiator going forward as well, too, is the business. And this has been the trend for many, many years or maybe forever, which is the companies that create the best cultures will continue to grow.

53:54 - 55:04 | Sam Wholley:

Yeah, and we can actually converge to the things we talked about, the automobile and manufacturing. So there was a time when there were no robots in the assembly lines. There were people. And people got worried that robots would take all the jobs. Turns out that didn't happen either. The jobs changed, right? But there were still people, and now there are robots, and they were assembling things. It will probably be a layer upon that. But the good companies that cared about the people and their product, because good people and good technology make good products. They're doing well, and they're utilizing these innovations and technologies to do good things. But the people are also taking care of the people. And you could see an enterprise value. Those things do work itself out, like in the numbers, the companies that do that. Are there companies who don't do that, who also have phenomenal enterprise values? Sure, but that's There'll be that everywhere. Personally, I think what we talked about, converging those two threads is what's going to happen. AI will be just another invention of robots, right, where we can use it for good as long as we just watch out and are mindful of the impacts that they have on existing people, societies, infrastructures, and organizations.

55:05 - 55:27 | Christopher Nelson:

That's great. Well, I'm going to put a bow in that side right there. I want to get us to the fire round. But thank you so much. I think we left a lot of good information for people that they can leverage in their careers to date. But let's get to the fire rounds. Five questions. I know you're a fast talker, Sam, so we're going to get through these. What is the worst career advice you ever received?

55:27 - 56:10 | Sam Wholley:

Undoubtedly. I'm not going to tell you which job. I'm not going to tell you which manager, because I still am in touch with most people I work with. Someone told me when I was resigning from one job and going to another, and this is one career to another, what will your friends think of you when you tell them you did this? And I think looking back, at some point, I think, you know, I cared about that, as maybe we all do. But yes, you know, they say that in your 20s, You try to get people to think well of you in your 30s. You figure out which people are thinking well of you in your 40s. You really don't care who's thinking. In your 50s, you realize no one's thinking of you. And so this was in my 20s. But that was by far the worst bias. If you're taking a job based on what your friends will say, then they're not really your friends, and you shouldn't care.

56:10 - 56:17 | Christopher Nelson:

That's right. That's solid. So in this age of AI and all these changes, how do you keep learning?

56:18 - 57:00 | Sam Wholley:

I'm fortunate, and this was actually one of the things I loved about search, was every new client was something new to learn. And it was kind of being forced on you, right? You had to learn the company, what they're doing, how to pitch it. That's kind of the same thing here as we're seeing all these companies coming in, in various industries, you're learning about them, you're figuring out what makes them tick, what's going to make them excel. So part of that learning is foisted upon me, which I think is important for me, because I can sometimes sit back a little too much and wait for it to come to me. I would like to be better at figuring out one of my goals for this year is to figure out what are the two things that I want to learn that I don't know now and to actually do them. Because I have this list every year and I don't think I ever check it.

57:00 - 57:04 | Christopher Nelson:

That's good. What do you do to recharge?

57:04 - 57:47 | Sam Wholley:

A couple of years ago, I had my meniscus taken out and I used to like to run. But my doctor said, you really shouldn't be running anymore. And I said, I need something I need something to keep my mental clarity and sanity. Like, what do I do for exercise now? And he said, well, you live in California now, why don't you cycle? And so I started cycling. And for the first year, I hated it. But my ex-partners at Riviera were doing it, and they really got me into it. And I started riding with them. And now I love it. And I'm fortunate to be able to go on a couple of trips a year with those guys. It's getting on the bike, getting on the bike in the morning, even if it's just in the garage. It's just mental clarity. And I just need that in my life. So that's been the thing that's I think been the most impactful.

57:47 - 57:52 | Christopher Nelson:

I love that. What's advice that you give your younger self working in tech?

57:52 - 58:31 | Sam Wholley:

Don't take yourself so seriously. I mean, someone also said to me, like, if you don't, they use the word hate, but I think that's what's wrong. If you don't hate the person you were five years ago, you're not growing. I do think that's true. And I'm not sure I love the person I was six weeks ago, but certainly if I look at myself back in my postgraduate career, I really took everything so seriously. And now with the benefit of perspective, I realized it didn't really matter. Just focus on doing the best of what you can do and things will work out. Make the right decisions, do the best you can do, and things will work out. Until they don't. And when they don't, you just chip away.

58:31 - 58:40 | Christopher Nelson:

Yeah, just chip away. And then go back, look at some of those things that didn't work out, turn those into lessons learned. And OK, now what do I have to do different to get a different result?

58:40 - 58:59 | Sam Wholley:

Yeah. And stop making excuses. That's another, I would make a lot of excuses for my earlier self. And I think that's something that we can all I think we can all fall prey to. I certainly did. And so being able to be radically truthful with yourself about the hard things you should and need to hear. I'm much better at that.

58:59 - 59:16 | Christopher Nelson:

That's sort of how we started the podcast. Letting people know, I am open to transparent feedback. It's so important. And we may have answered this in the last section, but what skills should people be building today to be competitive in the next three years?

59:16 - 01:01:06 | Sam Wholley:

I don't know what tools. It's different for each function and each role. But I think that figuring out what tools can be used for good to make your life, ideally, they'll probably be agile, to make your life more productive, efficient, and effective, that's one. The second one is critical thinking, the why. Like what does great look like in my job, in my role, in my company, in my life, in my personal life, right? Because those things are integrally entwined. And so I think that's another thing is how do you make your personal life, because you can make your professional life more efficient. But work will kind of expand to the container that you give it. And so there will be more work right in there. And you can forget about your personal life. So how do you use those tools to think about your job more critically so that you can then see around corners? Because if you can't see why you are indispensable, then you're dispensable. And the third thing, too, I think, is also understanding a little more broadly, and you mentioned this, It's not just about me, it's the business. What risks can my business have that I should be aware of simply so I get caught in my back foot, right? Because where we are in the US, you need to be employed to have healthcare, generally speaking, right? And so family healthcare, retirement, all the other benefits that are necessary for family life, that's important. Whether it's family or individual, that's just tied to employment right now. And so I think understanding like, where, where, where is my job going to be affected? But how can my company be affected? Where's the boat? Just so that you're always, and to your point, like, how do you then get those relationships going so that they're there when you need them? Because when you need them, so will a lot of other people you're competing for resources at that time.

01:01:06 - 01:01:19 | Christopher Nelson:

Oh, and that's so important. Yeah. Well, thank you so much for your time, Sam. We really appreciate you. And I don't know, I think we may we may have another episode in here somewhere, but I just want to thank you so much for your time.

01:01:19 - 01:01:22 | Sam Wholley:

I appreciate it, Christopher. It's great to see you. Thanks for having me. This was fun.

01:01:22 - 01:01:44 | Christopher Nelson:

My pleasure. Thank you so much for joining today's episode. We hope that you enjoy that. Our ask is one thing, please leave us a review. If you like what you hear, please give us a five-star review on Apple, Spotify, or you can go to our webpage. We appreciate you. Thank you so much.