Anne Dwane (Co-founder Village Global, ex CBO at Chegg)

Hey everyone, this is Erik Torenberg and you're listening to Execs by On Deck. Execs is a show for founders, operators, and leaders who want to understand the playbooks, frameworks, and tactics that leading tech companies today have used to scale. Our guests are tech execs in key roles at top tech companies who share their hard-won, earned secrets on how to scale faster.

Today's guest is Anne Duane. Anne is currently co-founder and partner of Village Global, an early-stage venture fund that I co-founded with her. Previously, Anne started Military.com, Zinch, and was Chief Business Officer at Chegg, which she took public. In this episode, we discussed how to do annual planning, how to do comp models, the role of CBO as an allocative role, and much more. Here's Anne. So Anne, let's go through your career a little bit. Obviously, you started Military.com, you sold that to Monster, you, I believe, became CEO at Zinch, you were then CBO at Chegg. How have you thought about how your roles have evolved in your career and how you've sort of of evolved as, as an executive?

Sure. And I'll even go back further, which was I started my career as in market research, in consumer research. And it was actually using scanner data from like products that are scanned at retail. And it was a key learning for my career because I was very junior, but I had the data, I had the truth, and it let me have influence and impact in the organization. And that's a lesson I've taken with me. And then another funny one is I was a brand manager at Nabisco on Planters peanuts. And again, very young, I've been to nut school. And very early in my career, I got the opportunity to be a cross-functional coordination point, right? That's really what a brand manager does. And it is, it can be really valuable to think about not your position in the organization, but the mission And how you're providing clarity and alignment such that everyone can do their jobs better.

Yeah.

And that's been kind of the themes of my career. And I really think if I had to define leadership, it's about how do you help people be more and do more? And that could be an individual or team.

Totally.

So were you on the almond side or the cashew side or the—

We did all. And Yeah, full stack. And, um, the funny part is, in some years, you could make as much money commodity trading as you could actually selling products at retail.

Wow.

Yeah. And, um, be careful a little bit of some of those, um, luxury nuts on, uh, first class and business class. And, uh, because I can tell you that some of them are not the freshest, uh, in the supply chain.

Yeah, kind of makes me reevaluate what I'm doing with my life. Just reflect. Say more of what you said, whoever has the data has the truth, and you've taken that in your career. Like, what are other examples of how you've taken that?

Well, at Chegg, we were very fortunate to have a great data science team, people like Mike Osher, who had come from Netflix, and Ben Van Roo. And with Chegg, we were trying to rent over 100,000 books. And in order to make money when you do that, you have to buy the right books and you have to price them right, especially when you're competing with companies like Amazon and things like that.

Yeah.

It's easy to lose your shirt. And we didn't have every team with their own data. We had one centralized data science team as the source of truth, and they were constantly Driving not to have an agenda, but to have real data. And that made decisions without— throughout the organization really much easier because everyone's entitled to their own opinion, but not their own facts.

Right. Yeah, makes sense. Let's skip ahead and talk about the Chief Business Officer role at Chegg. Talk a little bit about how that role works and how we should think about that role within the context of an executive org because, yeah, my understanding is that Chegg didn't have a COO role.

Correct. And part of that was because Dan Rosenzweig, the great CEO of Chegg, had been COO of a company called Yahoo. And there's something interesting called the Peanut Butter Manifesto, which was written at Yahoo, which said, hey, are we not optimizing the different elements of our business? And Dan always worried that if a COO is responsible for both long-term and short-term, especially in a public company or about-to-go-public company, short-term will win. Short-term and measurable will win over innovation, long-term potential. And so we divided the organization, and it was the— each functional leader, marketing, CTO, whatever, had the responsibility to do things right. And the chief business officer's responsibility was to ensure we do the right things. And so basically, it's an allocative role. Right? Where do resources get stacked up? And then it's a P&L management role. And it is complicated because it's a matrix. But the benefits were, it really, I think, did unleash more from each functional unit, and then kept a good balance on how are we going to make sure we never miss a quarter. And we're still thinking about the future.

Is it something you recommend when you talk about startups that we advise, or that we've invested in, and they're growing and looking to hire a COO? Is the Chegg path one you potentially recommend to them, or how should startups be thinking about that?

I think startups should start very simple and small. And I do think that there is no right org structure. It's really about the— what do you— strategy should drive structure, and personality should also drive structure. So, I have come to believe that most CEOs should have a chief of staff, which is how do they get leverage with them. Many CEOs may benefit from a COO who keeps trains running on time. And the key, and this is, I think, the best lesson of management, is clarity. What is each person responsible for? And run with that.

Yeah. Chegg, you know, you were there, you know, as it went public. Obviously, it's a very big org. You were in charge of, you know, allocation decisions, you know, P&L. What were your frameworks for kind of making those decisions? Or how do those decisions even get done at an org like Chegg?

Well, so one thing that's kind of enlightening, we did an exercise. We read The Five Dysfunctions of a Team, and we might have read The Thin Book of Trust, which is my favorite thing. And we realized that most of the executives were coming to the executive meeting and they would say, well, I'm head of marketing, or I'm head of product, or I'm head of technology, and my team is the technology team or the marketing team. And what we realized is we had to create an executive team of peers that was a high-performance team. And, you know, maybe we think about that at Village too, because we're trying to be a partnership, and partnerships are tricky. So think about— the best advice is think about how do you create a highly functional team of peers at every level? And then how do you also create a highly effective team within projects, right? And as fast as you can scale that up. And trust is actually the hardest thing to scale. So using some of those frameworks, reading those books together, talking about them, having a common vernacular is helpful. Okay. But let's talk about decisioning. So ideally, and I think about this as a founder, you want to devolve decision-making to its most proximate level, right? And within reason, too many CEOs are trying to make too many decisions. And if I could go back and do my career over again, my first startups or something, I would exert less control and more clarity of missions so that the person closest to the problem makes the call and then sets up the metrics by which that decision will be metric— will be measured. And then I think if you can think about setting the event horizon for when you will evaluate the decision, so you could continue, you could stop, or you could go, and you're making an explicit decision, the organization unleashes its potential. And if, as long as those targets are near enough in, you cannot mess with the organization too much.

Yeah. And the challenge at a big org, of course, is that the people that are closest to the problem or closest to the customer sometimes are the most are junior people. There's a lot of, like, mid-level management in between executive or leadership and the people closest to the problem. So, how do you navigate that?

Well, okay, so I'm a big believer that experience doesn't always make better decisions. And if you give people context, they can make better decisions. Because I could argue that the person sitting in the ivory tower is not gonna make a good decision. And actually, I learned this from people at military.com. Because they talked about, in the Marine Corps, the strategic corporal. So in combat, when there's a lot of chaos, right, and things are moving very fast, right, um, you can't always rely on the chain of command, and the person on the ground has the best facts.

Yeah.

So for example, they used to be able to say, um, the mission of this Marine Corps unit or this individual Marine corporal is, do not let people come across that bridge. And the reality is, often Marines who are trained to improvise, adapt, and overcome would actually make the right decision. And sometimes that decision was to blow up that bridge.

Yeah.

Or it was to, you know, do something a lot less drastic. But the facts on the ground are important. And I think it's culture, values and metrics that can ensure norming of good decisions throughout the organization. And if you could master that without a lot of consequences, right? Meaning, you know, maybe they can't move the company's treasury around or something like that. You can unleash enormous potential. And more importantly, you can keep people who will stay with you over time, which today is like a crisis in companies. People wanna move a lot. Yeah.

You know, when people ask, hey, you know, you're doing these budget decisions and enormous budgets, and it was like, hey, why is marketing this and BD that and eng this? Like, how do you sort of think about the percentages or even just frameworks in terms of, you know, why this versus why not that?

So, there's a lot of different ways to handle this. The funniest I saw was at Nabisco, and we had something called consensus budgeting. So, the marketing team would come up with a forecast for the next year, right? And it would be very high because marketing has money and then they have a lot of confidence. And then the sales team would come up with a number and they would sandbag because guess what? Their compensation was aligned to that.

Yeah.

And what we would have, we would haggle for months and get what we called the consensus forecast. And frankly, nobody was happy with it. But I think the best is to put everyone on the same side of the table. and do a bottoms-up exercise. And then as many people as possible have ownership of the whole. So, for example, what is the company's overall revenue target? What's its overall profit or cash flow or whatever target? And then it has to cascade through the organization. And I felt like once people had the same facts, they often make the same decision.

Yeah.

And the other is, accountability to those interim milestones that we talked about. So if the Chegg Study business, which was a digital subscription business, wasn't hitting their numbers in Q1, there would be a revisiting of, are we going to put more in there to make them hit their number? Or do we reallocate to another group that's outperforming? Yeah.

What else is key in just creating really excellent annual plans and making them be successful?

I would say, Making your assumptions clear. And then my favorite thing is thinking about a financial model. And you might say, well, that's for the finance people. And not really. What are the drivers of the business? And it should be so simple. If there's more than like 10 drivers, it's probably not right. It's not that there aren't more exogenous factors that can come in, but like number of leads, Number of customers, average revenue per customer, whatever. And also, the more that you can socialize those king metrics throughout the organization, actually, the more creativity you unleash. And I will never forget that some of the best ideas for increasing conversion or changing user flows or changing the pricing actually came from somebody who had nothing to do with any of those functional areas, but just said, look, if we're trying to maximize conversion, why don't we just eliminate that whole step? Why don't we put, you know, credit card at the end? Or why are we catching first name first when we really need email first, or, you know, text number or something like that?

Yeah, that makes sense. Talk about the CBO role as it relates to a CRO role. Did Chegg also have a CRO? Do you usually have one or the other?

Or— It's a good question. I think that you definitely have a CRO role usually when you have salespeople. So we had, remember, we had direct-to-consumer product-led. Revenue as well as a sales team and things like that.

Yeah, got it.

And can I just make a comment on that? So it's really interesting because I think throughout my career I've seen different groups munge or not munge. So for example, sometimes there's sales and there's marketing, and client success, for example, could live in either group, and even marketing could live in either group. And there's no right way to do this. Sometimes treating sales as a hired gun and saying, you just care about top line, is quite toxic in the organization. Because they won't care about potentially pricing. They won't care about overpromising and all that kind of stuff. So again, for any model, I think it's good to be explicit about what could go right. And then what could go wrong. And then socialize with everyone. So if you have this comp structure, for example, sales team, the way you would game that system is X, Y, and Z. Let's put it on the table, right? And then, okay, so how are we gonna mitigate that? And in some cases, the salespeople that have been working with me would say, I don't care about that. That's your problem, right? If you want me to go get revenue, I'll get revenue. And it's your problem to figure out why the product is not as profitable as it should be. And actually, that's a very healthy conversation. Don't fear difficult conversations in an organization. Tough on the problems. So, you know, very considerate of people, but tough on the problems.

Yeah. Let's build off that. What else is really important to get right when creating a sales org, or what misconceptions or mistakes do you see entrepreneurs making as they're building them out or scaling them?

It's really great to be very simple. And then you mitigate against bad behavior by culture, norms, and leadership. I think too many people are trying to regulate bad behavior out of the system. And so they create these really complicated things that actually just slow everybody down, create animosity in the organization. So for example, I love straight-line commissions that maybe potentially change at different places. I like basically in some cases where you need to really focus on profitability, a commission that's effectively a percentage of gross margin or something like that. But these are all things that should be explicit. And I would say that also, many people in sales organizations, surprisingly, are not as transparent as they should be with the salespeople in terms of, is there a second board sandbagging number? Is there something else that we need to be aware of? And many people are just trying to put blinders on the salespeople, and I don't think that's that helpful.

Yeah. I think that's interesting is that startups, sometimes they might start with, hey, they're a bunch of engineers, a bunch of product people, and now they need to build a sales team. And so they build a sales team, but that kind of brings a different culture because salespeople and engineers and product people are very different. How do you make that work well?

Yeah, it's a great point. And I think founder-led sales are essential because in the beginning, you're still trying to figure out what product to build, right? So founder-led sales, there's no one who sells like a founder. And in some cases, it might be the right move for the founder to continue in sales, even though they have a great product mind. And that's a really tough one for the organization. But again, it all comes down to comparative advantage of each person.

Yeah.

And again, any structure, any role can work as long as there's clarity around it. But at a certain point, when the sales process is repeatable, You definitely should be hiring. And before that, you should have a lot of leverage, like the chief of staff, or maybe there's a utility player that's called head of client success.

Yeah.

But salespeople are tricky to interview because often they interview very well.

Yeah.

Right. And so I would recommend getting really tactical. So give my pitch back to me. How would you pitch the company? I know you don't know everything about the business, but can you come up with a list of 10 people in your network that you would consider introducing as early prospects? Here's our current sales materials. Can you revise them to make them stronger? Can you watch the video recording of an existing rep doing a pitch and provide feedback? Because you're really trying to do that, get that like live-fire exercise, as we say at military.com. And then the most outrageous stuff that I've heard lately is, the person takes vacation from their current job because, you know, all these great salespeople are always gainfully employed. And they come and spend a week, and they set up calls, they are on calls, they're observing calls, they do calls, you know, and you really see if it's a good fit.

Yeah.

And then the other is the more senior salespeople need to take responsibility for setting their own goals.

How important among sales leadership when you're hiring is hiring for people who've done it before at your stage?

I think it's important for somebody who's scaled. I think category is less important. This is what I've learned is I've definitely seen that, you know, the dream company is like a cloud sales company and they're able to hire somebody from another cloud sales company. And it's like, and that's like, wow, they've got both the network and the skills. But good salespeople can sell across categories.

Yeah.

And it's your job to inform them. So get the salespeople. And I think why stage is so important, it's a level of support that they are used to having and the level of interaction with the customer. Because as you all know, like when you have it, like when you're selling for some known brand, right, you get the benefit of the doubt, right? When you're early, you can sell, you have to make it up as you go along. You have to be really interactive. And I'll never forget, a friend of mine was a seller at Oracle and they early on, Years and decades ago. And at the time, you know, Oracle was selling well ahead of their product shipping, you know. And the joke, she said, was Oracle runs perfectly on PowerPoint.

Exactly. Was this in the '60s, or?

Oh, no, it was probably in the '90s.

I'm joking.

Well, you know, when I— my first tablet, you know, I had a chisel for it.

Yeah, exactly. So, experience over category. When you say experience, if you're, you know, hiring your first salesperson at a startup, you want somebody who's been at a startup, not, not just been at a big— so, the same kind of experience.

Yes, because too many people say, wow, I'll hire that person because they have a network of contacts. And in today's world, generally, I will argue access is not the problem. Now, it's a, it's a challenge to get to the head of marketing at You know, some big cloud company. But that's more important is, can you be captivating to them?

Totally. I want to segue. You've been a founder in a bunch of different circumstances, and you've also experienced hypergrowth and scale. And so, you've seen companies evolve via, in terms of peacetime and wartime. Talk a little bit about what that means and what that transition is like and how to do well at both.

Yeah. So, I start... Unfortunately, I started my career in wartime, in the wartime thing. Even when I graduated college, I graduated in a recession, and I took the only job offer that I got, right? So, very easy decision to make. But then later at Military.com, we had raised a lot of money, and things were flying high. And in March of 2000, basically, the capital markets closed. And I'll never forget the board meeting when David Liddell, from USVP said, you thought running a startup was like launching an F-18 off the deck of the aircraft carrier. And in essence, it is actually like driving a Humvee across the desert alone. And we had to cut our team from like 80 to 15. And I think what we did, an exercise, which is really good, Which is kind of— Tim Ferriss has talked about fear setting. But you identify the worst case, right? The worst case is we have to shut this company down. And we actually put a— we drafted a plan for an orderly shutdown. And then we put it in the drawer and we got back to work. And that is psychologically really powerful. The other things— and actually, this is some experience that I shared with founders in March of 2020, which, as you'll remember, for about 2 weeks, it looked a little dicey for, you know, like, how is the economy going to be? And, you know, obviously, there's lots of negative ramifications of COVID But have your fingers on the dials. This is good business advice overall. Where are you spending? And what is essentially the ROI of every dollar you are spending, or let's call it investing, right? And if the economy turns bad, or if there's some competitive action or whatever, you can turn on a dime if If you have your fingers on the dial, you can say, I can stop spending in the least efficient customer acquisition channels. I can stop work on this exploratory project, which is not producing revenue, and we may have to kill it. And that enables you to, I think, just have peace and focus, even when there's a lot of bad stuff going on. And the way Military.com survived, like, and I'll never forget, like, I learned so much from James Currier and the team at Tickle. we had to make customer acquisition a profit center. So, when we spent a dollar on the internet somewhere, you know, back in— this was Web 1.0— or we did even an investment in a viral program or something like that, we would have to have people come in that day and either buy something or take an offer or something like that to offset the cost. But once we figured that out, customers or businesses where customer acquisition is profitable, are growth machines. And so we went from, you know, really dire straits to being a super lean, efficient, profitable, high-growth company. And the other thing I would just say is embrace that pressure creates diamonds. And actually, the hard part of peacetime CEO is creating the urgency and creating the creativity and the resourcefulness that comes from wartime. Right? We didn't have a choice but to figure out how to make customer acquisition profitable. I wish 4 months earlier, before the crash, we had figured that out. Because guess what? We would've been able to maybe raise money or something.

So, how do you do that? How do you have a sense of urgency? Do you sort of invent deadlines? Or, you know, not invent, but you know what I mean?

Yeah. I do think that you gamify.

Yeah.

And you make That's what winning looks like. And always reward what you want to see in the organization. And if people start seeing that certain activities are lauded, then it's human nature, they will generally try to do that.

Yeah. Let's talk about leadership and management. Talk about the difference between the two, or more importantly, what makes great leadership and what makes great management?

So, management, I was trained, is handling complexity. Leadership is inspiring change and that helping people do more and be more. I think that the best organizations today aspire to hire and retain a leader in every seat. Because at the end of the day, if today, if a process or an activity can be described, it's almost one step away from being automated. And that's not a bad thing. I actually think I'm very optimistic that we can elevate jobs even as some are eliminated and keep people on the frontier of doing what humans are really good at. And that analogy, I think, applies to founders too. As a founder, I was always looking for where have we created some stability in a process or a product or something such that it can be handed off to the next person who now manages that little ecosystem. But it's pretty defined, right? Like, it's gamified in the sense of, here's, you know, here's the parameters. But the founders— because founders are especially good at being at the messy frontier, and that keeps the organization just moving. But I think we don't want people who just show up and turn the crank, right? It's how do I make their world better and how does it interact with others? Yeah.

Sam Kushner has called you the best manager he's ever had. And so, for people who are becoming new managers, what's your sort of feedback on whether it's cadence or feedback or just how to become or grow as a manager?

Well, the simple answer is care is a competitive advantage, right? Just, and the Maya Angelou quote was, people People don't care how much you know until they know how much you care. And so care. And I think the first manifestation of care is a great onboarding. And I'm happy to share any specific documents or anything like that. But I have a mutual expectations document, which is what you can expect of me and what I expect of you from day zero. And then I think that the best managers don't have a process that they inflict on people. They're trying to light a fire in that person to realize their potential that they have and work with them on how they want to be managed.

Yeah.

And try to make that process explicit. So, that old Ray Dalio quote, don't just work in the business, work on the business. Work on the relationship that you have with that person.

Totally. You spent a bunch of time at various stages of your career doing acquisitions. I wanna talk about this from both perspectives, but first, let's talk about it from the big From a company perspective, and for heads of corp dev out there, what is the real role in terms of, what are the frameworks that people who lead acquisition at big companies are thinking about, and how do you do that job well?

Okay. Yes. And I think my superpower related to this is having been acquired twice, right? But it should be a build versus buy decision for the company.

And so, when build versus buy? Because right now at On Deck, our instinct is like, oh, that's gonna cost a few million dollars. Let's build it. But when should one be thinking about build versus buy? Like, what is the right criteria?

Okay. One is scanning the environment for the relevant options is always a good idea because they will inform your build scenario, right? Time to market and potentially getting kind of leapfrogged to customers and engagement and stuff like that is really good. Right, if you can do it. And sometimes it's just so clear that an acquisition can be accretive. They have a little machine, and if it was plugged into your distribution machine, it would 10x. And so therefore, there's a lot of value being created. So you can share a lot of that value and the upside with the team that you're acquiring, but still, you know, have a great return for your shareholders. And the public companies, it's the easiest to do this, right? Accretive acquisitions, you can actually see that revenue stream comes through. And the stock price goes up, right? It's really clear. Private company is harder. And the key thing to remember, I think, for the acquirer thinking about this is, are you acquiring the people or the product or the IP or something like that? If it's people, it's a very different decision. And that's 99% of what we do because most acquisitions do not realize their potential. And most great founders, don't stay with the organization. I mean, the fact that the DeepMind team is so active with Google, right? Like, and, and I think actually companies like, uh, in big tech like Facebook actually figured out something very difficult. 10 or 15 years ago, it seemed like 90% of founders would churn out. Not the case today. And, um, if you're going to acquire for people, which is generally, as I said, what's happening, you've got to make sure that you can make And what's changed?

Is it just that Facebook has figured out how to do that or these big companies? Because when they get way bigger than people have imagined, so there's economic upside and then they just kind of leave them alone and let them do their thing even under an independent brand or together. Then you've also seen acquisitions like Periscope at Twitter, which the product itself didn't work, but Kayvon has become such a product executive that it's been a great investment. Maybe it made sense from that angle alone.

Yes. All of the above are true. I do think, though, that in many cases, distribution has become so important that it was— you really unlocked a lot by taking a great product and putting it into a big company. Big companies find it hard to innovate. And that's because there's usually some, you know, big revenue engine, right? Like, this is the innovator's dilemma, right? There's probably some big legacy engine that attracts a lot of attention, And investments and everything like that. And the new people don't get any patience from the organization to go and build, right? Because even as fast as startups move, they're not always perceived as moving fast if they were part of a big organization.

Yeah. So, Series A companies listening, Series B companies listening, maybe they have something like $30 million in the bank or $60 million in the bank, and maybe they see a company that they could buy for, like, 10% or 15% of the money that they have in the bank. What's the advice you typically think about? Like, how should— what framework should they be thinking about?

Okay, so they have cash, and they also may have another currency, which is arguably of a lot of value today, which is equity. And if you believe buying companies with equity is not a bad idea, if you really want to, first of all, incentivize people, but also if you believe that this is going to be very strategic to the company. If it's tactical, use cash. Right. But here's the thing. I think it's tempting sometimes to say, well, we'll preserve the equity for ourselves and we'll give these people like a cash-only offer. And be careful because the best founders don't just want a cash payout. Or basically, you've just given them the seed funding for their next venture. Right? Exactly.

Exactly.

I'm going to segue into topics that relate from the founder perspective. And let's start with acquisitions on the founder side. How should founders be thinking about how to approach corp dev, when to approach corp dev, and how to run that process?

Okay. So, the most important career decisions, including selling your company, require introspection, which is, what do you wanna do? And if you wanna go big and go alone, that really should be part of your calculus, especially in an environment like that. But if you're tired, or if you see that 1 and 1 equals 11, if you sell your company, then do it. The most important thing, like, just of any sales process is create options. So my co-founders and I sold companies always with a venture term sheet in hand. And then you, the acquirer, has to pay what the market has established plus a control premium.

Right.

And what I have always found helpful is to, as the entrepreneur, Put together a plan, which is the 1 and 1 is 11 plan, and says, if we were together, we could go realize this. And so, I do the work, do the work for corp dev. And by the way, I really would recommend work with the CEO, not just corp dev. And the reason for that is too many times corp dev is like spikes the football and says, hey, we did the deal, but they have no ability— To follow up. To make the organization successful. And it is really rare that even when they say you're going to have a standalone division, you won't have significant interactions with the, you know, mothership. And the antibodies can hit hard when you come into a company that doesn't want you.

What are the parallels between running a corp dev process and running a fundraising process?

It is good to have, at a certain stage, you know, you can't waste your time when you're early stage, you don't have product-market fit. But as you get older, you should have But somebody in the organization needs to have great ecosystem relationships, including with the corp dev players at the big potential acquirers, right? And I always thought of the potential acquirers as providing one possibility, which is revenue, then other things like potentially an exit. But I always went into it from the position of, is there something we could do together that would generate revenue for me selfishly or reduce my costs? distribution costs or whatever. And maybe they will— both of us would get to know each other better. But, like, I don't think ever sending a signal to corp dev that you're looking is good unless you're actively looking and running a process.

No. At that point, it looks kind of like a hot seed round process where you're just kind of, like, talking to a few folks, playing off each other.

Yeah.

Yeah.

And then the key advice for founders, I think, is Ask for what you want. So often people focus on like the number, the valuation of something important, but not like, I would want this as a standalone division. I want all these people, whatever, to have this kind of thing. Can I have this? Can I? And the reality is, if you ask nicely, the deals never dry up. They just get— people will be like, that's crazy, you can't have that. But it's worth asking because some of those things are so valuable. Both to you, your team, and to your success. Yeah.

Series A company, Series B company, they're starting to think about acquisitions. What should they look for in a head of corp— in their first corp dev person?

Yeah, that's— it's a really good question because as a CEO, these are the most important hiring decisions. So, as a CEO, I never really wanted to give that up. But depending if you're— and certainly if you're later stage, get a banker who can do these things because, you know, you need to be able to really analyze the business and their forecasts and their things like that. Um, but earlier stage, I think you want a great ecosystem player who's really comfortable knowing everyone, right? Getting the intel about the business, uh, businesses out there and creating preference for your organization. Because many of these, I think, should be partnerships before they're outright acquisitions.

Yeah.

But I have never— well, not never, but really strongly admire, uh, or recommend, um, that you do tests, like, um, before you do pull the trigger on acquisition. You learn a lot by doing a partnership with a company.

Yeah.

The most important is realizing whether there actually is synergy between the two.

Yep, totally. Let's move to other founder-facing topics of advice. Let's talk about hiring. What's really important to get right in hiring in terms of what are the frameworks you find yourself commonly advising founders?

Well, this is the tightest talent market we've ever seen. It's easier to raise money than it is to hire great people. And I think one lens is to think about hire for who someone is becoming. Too many people are hiring for who someone is or has been. Right. And trajectory is everything.

Yeah. As we're talking about this, it makes me think of a specific person that I want to make a more senior offer than I've given them because, yeah, it's just, I could see the lines, you know.

Yeah.

See where she's going. How about on the, earlier you mentioned founder-led sales. We talked to a bunch of technical founders who've never done sales before. What's really important to get right when learning how to make sales for the first time?

Well, my favorite lesson of sales is from George Foreman. You know him with the— and he has one of the best consumer products in the world, which is the George Foreman Grill. And he said, I don't know anything about selling, but I know how to talk passionately about products I believe in. And that is the secret, which is lead with needs, right? And then try to solve somebody's problem and don't try to get more fancy than that. And the problem is when a founder doesn't come from having empathy with the customer, right? But generally today, like, if you have, say, a fintech API or something like that, you're selling to someone who is buying fintech APIs and maybe is dealing with fraud or, you know, whatever. And so you can have a lot of empathy. You know, you don't have sales empathy, but you have empathy with the buyer's needs. Nobody wants to be sold, by the way, too. So it's better to be— I would say better to be compelling than selling.

Yeah. There was a First Round review post that you gave an interview for around being adaptable, an adaptable leader. What have you learned about how to be adaptable?

Okay. So I think actually in that article, I talked about a couple of things I really believe in. So first is the beginner's mindset. Which is regardless of what experiences have scarred you or shaped you, right? How do you try to come at every problem or every investment or whatever from a beginner's mind sense? And it doesn't invalidate experience. It just recognizes that experiences can blind you to some of the bigger issues. The other thing I talked about in there is the gamer's mindset. So gamers, in gaming, learning is the fun. And embrace the joy of figuring things out, because that is startups. And even in big organizations today, I think the pace of everything is accelerating such that figuring things out is actually the job. And keep making that fun and enjoying that fun.

Well, yeah, this is a— that's a great note to wrap on. And for founders who are listening into this podcast, why don't you share a couple of words about Village?

Okay, well, you know this very well, Erik. We're investing at pre-seed and seed, and what we offer founders, uh, hopefully is a game-changing network that includes peers at the same stage or maybe a couple steps ahead in company building, a bunch of operator angels who have really practical networks and advice and, and community, and then Also, our LPs, who are some of the most successful entrepreneurs in the world, they really still have love of the early-stage game. And we've had many of them invest directly or support companies as they grow.

Awesome. Yeah, I haven't found a VC that founders like working with more. So I'm very, like, lucky to partner with you and invest in great companies.

Well, I love working with you, Erik.

Thanks for listening to today's episode. Execs is produced by On Deck, where top talent goes to start companies, find their next roles, or invest in their careers. If you're looking to start a company, uplevel your career, or navigate a career transition, I encourage you to visit beyonddeck.com.

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