Episode 29: Anna Talerico of Corporate Finance Institute on How to Find the Right Human Capital for Bootstrapped Companies
On this episode
Shiv interviews Anna Talerico, CEO at Corporate Finance Institute and Operating Partner at Arthur Ventures.
Learn how capital-efficient companies can make better hiring decisions by focusing on what role they really need to fill. How can companies clearly define those roles and how do they go about finding the best-fit candidates? Plus, when should you invest in cost-center roles like finance and admin, and can/should AI help bridge the gap until your business is ready?
The information contained in this podcast is not intended to constitute, and should not be construed as, investment advice.
Key Takeaways
- Anna’s background and how she perceives business as a former bootstrapped founder (2:42)
- Why being too focused on profitability can limit your business’ growth potential (8:15)
- Why capital-efficient companies might be missing out on the best-fit candidates and how to find those for the stage of your business (11:48)
- How should founders find the right people to take over as the head of each department (18:33)
- Anna’s advice on determining the roles that need to be hired first (21:07)
- Looking at your business with an exit strategy vs keeping the company in-family (22:43)
- An alternative perspective on the risks of expanding too fast (24:46)
- When to invest in cost-center roles like finance and admin (28:17)
- Using AI to help founders find efficiencies and grow or scale your business (31:08)
- How to deal with staffing cuts during uncertain times (35:52)
Resources
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Episode Transcript
Shiv: Alright Anna, welcome to the show, how's it going?
Anna: Fantastic, thanks. I'm happy to be here.
Shiv: Yeah, excited to have you on. We've been friends for many years through LinkedIn and connecting on our approaches to sales and marketing. So super excited to have you on. Why don't we start with an introduction about yourself and your role, and then we'll go from there.
Anna: Yeah, sounds good. So I am a, well, a former founder, so, entrepreneur, and went through a couple of exits as a bootstrap founder, and then joined a venture backed company, Linux Academy, and went through kind of a rocket ship period there for a couple of years, my first venture experience. And when Linux Academy was acquired, I joined Arthur Ventures, our venture partner, as an operating partner. And I've been with Arthur Ventures about four years, but two years ago, took a little bit of a side road and jumped into an operating seat at one of our portfolio companies, Corporate Finance Institute, where I'm the CEO there right now. So yeah, that's a little bit about me.
Shiv: That's awesome. We're actually customers of CFI. We have a couple of courses that we've bought for the team to educate themselves on management consulting and things like that. So yeah, great company, great business. But why don't we talk a little bit about how you perceive businesses and how you got into this world and just your approach overall and how that's kind of affected how you interface with companies or where you see those opportunities.
Anna: Sure. So, you know, I think my being a bootstrap founder for so many years really informs my entire worldview. I was very proud kind of bootstrap founder, just feeling like the honorable path forward was not to buy my way to customers, but to earn them through cash flow and profitability. And so I really, you know, again, I find, I think I always thought the venture world wasn't for me. But then joining Linux Academy, I saw a whole other world, right? That venture was something really different than what I thought and that there are many paths to running a venture funded company and many different types of firms and different ways that firms work with their companies. So it really was eye opening to me. And even I often look back on those times as a bootstrap founder and think, man, I made it so much harder on myself than I needed to. And I saw really what the power of the right partner can do. And so I think that then I really, again, the bootstrapped years will always inform my view, but combining that with what I learned in operating inside of venture backed companies and, and then as my seat as operating partner has definitely expanded my horizons and how I think about things. I think as a Bootstrap founder, you're thinking about enterprise value creation, but for yourself, to try to keep the lights on, to keep payroll going, to hopefully one day have some optionality to have an exit perhaps if that's in your roadmap. But as an operating partner and an operating inside of a venture backed company, you think about it a little bit differently, right? And just have a little bit broader perspective on that. So I don't know if that, yeah.
Shiv: Yeah, it does. And so talk about the bootstrap approach a little bit. And also as an operating partner or venture partner, how you adjust some of those decisions when there is more, I guess, institutional capital at the table.
Anna: Yeah. So, you know, when you're bootstrapped, you really inform so many of your decisions around what the balance sheet looks like and what cash flow’s looking like. And so that's quite limiting in some ways, right? It's honorable and it's healthy, but sometimes it informs decisions and, you know, things that you really would like to take advantage of that you can't. So at Arthur Ventures, we invest in capital-efficient, B2B software companies located outside of the Valley. So when we're investing, typically our companies are usually really capital efficient. And I should say, across the board they are. And so it's interesting. Sometimes right after we invest, I'll be on the phone with the founder and they'll be like, what do I do now? And what should I do with all this cash? And how do I put it to use? And the first thing I would say is do exactly what you've been doing. Right? Like don't let the funding kind of change how you're thinking about your running the business. Think about it as taking advantage of opportunities. And so sometimes that means the company is burning. Sometimes it doesn't, but I think that it's always through that lens of is this sustainable? Right. And how much are we spending to get ARR? And what does that look like? So it's not that you never want to burn or things like that, but it's like looking at how does this play out and how sustainable is this and is it leading to a path to capital efficiency.
Shiv: Right. Totally agree. And walk me through this part that you said, which I find it interesting. You said it's limiting. And the reason I ask about this is I find that a lot of venture backed companies burn too much capital. And it's something that we've talked to past guests on this podcast about as well. But at the same time, I think you're giving like a counterpoint to that, which is that sometimes when you're too focused on being capital efficient or profitable or bootstrapping, you're, you're sometimes going to be holding the business back, I guess, and then would like you to expand on that.
Anna: Yeah, I think so. I think that's exactly right. And that's certainly when I think about my time as a bootstrap founder, I can look at moments where I wasn't able to do something. And if I had had capital or a capital partner, I could have taken advantage of opportunities to move the business forward faster. So I like even in retrospect, personally, I have those moments, but sitting on board seats or working with our companies through these moments, there's oftentimes from outsider perspective, you can really see these moments when perhaps companies are being too limited in how they think, right? Where they, let's say that there's been a vacancy in a really important role that could be, you know, seismic in its impact. Let's say there's a VP engineering role and that the wrong person's been in the seat and now they're gone and that role's vacated. And the founder maybe isn't thinking big enough about, you know, the kind of person or the caliber of person that might really come in and make a huge difference. And so they're, they're being quite restrictive on the budget. Those kinds of things happen all the time and we have to be really careful, right? We don't want to go do that across the board with everything, but sometimes when you kind of see that there's this opportunity to really change the course of the business, if you just think a little bit bigger.
Shiv: And what are some signs of that, right? Because there are characteristics that healthy businesses have. They have good gross margin. They may be profitable. They have cash in the bank. So like, but what are some signs that indicate that this business should be perhaps more aggressive or at least not as conservative with its budget and actually make some bigger bets?
Anna: Yeah, so I think there's so many, it's so company specific, but a good example would be, let's say that a company has just kind of been floating along with, let's say it's driven by leads, right? And so MQLs are kind of just generally going up a bit and they're hitting targets, but the founder has strong conviction around product market fit, around ICP, around, you know, the in just even the predictability of I know if I get 100 leads, I'm going to get 10 opportunities open, they're going to be of this much value. And we're going to close this percentage of them. hen when there's conviction and there's data around that. But then you still see a company kind of throttling, right. But so for example, there might be more audience to get in front of there might be more leads to generate. And you have to be careful that you want to let's say you're going to open up the top of the funnel a bit to drive more leads, you know, as well as I do, you've got to watch, are they following the benchmarks, right? When I open up and now I have 200 leads, am I getting 20 opportunities of the same ACV and closing the same percentage of them? So you have to be mindful at every kind of like step up that you do. But those are examples where you've got data that's starting to get real predictable. You've got founders or an executive team that have a lot of conviction about what they're doing. Those are moments that you really don't want to throttle.
Shiv: Yeah, I think we've seen this with a lot of companies where they'll have great unit economics and good conversion rates or good net revenue retention rates, but they're hesitant to be more aggressive with their sales and marketing efforts. So I think that's one. What are some other signs that you've seen?
Anna: Exactly. Yeah, that's the big one. I would say other signs where are would be where you exactly what I mentioned about the VP engineering example of there's a key role that's that the team feels has been holding them back either the wrong person in seat or not having that role filled. And there's been strong conviction of, if we had the right person, we're certain, right, that we can move the business forward faster. And then they're really limiting the talent pool that they're getting in front of because of whatever it might be, you know, typically budget or equity or things like that. And I say this with caution because obviously we can't go just do that with every role in the leadership team, right? But when you have strong conviction that there's an important role and you need top tier talent, and then you're kind of restricting the candidate pool. So you're not even looking at what could be a really experienced person because you're just not even getting in front of them because of things like budget. I think that that's a missed opportunity, even again, to get in front of them, to get, what does that kind of caliber of talent look like? You know, just even interviewing somebody more experienced or the perfect fit that might be slightly out of your budget range. I think getting in front of those people and having those conversations can really be light bulb moments for teams of like, oh, wow, this is what great looks like. Because often as founders, especially capital efficient founders, you don't know what great looks like until you're in front of it and having those conversations. So I think it's important to have those types of conversations with different types of candidates and to really see what it looks like.
Shiv: Yeah, I think the marketing and sales example is maybe easier to understand in some ways because it's like I put a dollar in, I get maybe a dollar back, or this is my payback period, and it's kind of basic math to some degree. But I think the key role is a little trickier because you kind of have to decide to invest in a significant hire for your business. And it's not inexpensive, right? It's the eight players and key roles can be multi six figure people to hire, right? So at that point, you're kind of making this decision to bring on somebody senior and you don't know exactly what the ROI will be. And there are founders who get in the trap of hiring the wrong person for the wrong role at the wrong time. And, you know, they have false starts or they let go of a new CMO that they may have hired or a VP of sales that they hired. And so it is a big risk that may not pan out. So like, how do you, how do they navigate that? Because that is one of the things that's likely holding them back to get to the next level.
Anna: That's such a good question because we don't always get it right, right? There's not a crystal ball. So we're looking to really define an ideal candidate profile and sticking to that because it's really easy to fall in love with a candidate during the process. And then they're not anything like what you really should be looking for. So I think it's important to start off with who do we need. And sometimes when a founder hasn't ever hired that role, they really don't know. That's quite common. So maybe you have some calls and then you refine who is it that I need. But I think that having a really clear picture of that's important. And then it can be so helpful to have outside perspective of people who have hired these roles before. Even, you know, if I've interviewed a thousand people and placed hundreds of people before, I don't always get it right, but I've got more exposure and experience. So I think getting or other help can be really beneficial. But I think the most important thing is hiring stage appropriately, as I'm sure you agree. And that's the most important thing, right? Getting somebody who took a company from 100 million to 200 million is really different than somebody who operated in a 10 million to 20 million stage. And so I think that's really important to be clear on your stage and what stage you'll be at over just the next 18 months and hiring that person. And I think that I always think about, you know, are you looking for a builder or somebody to run something? So you need somebody to get in and actually build, you know, sales, for example, you know, hire the team processes, playbook, et cetera, or is all that very predictable, well-oiled machine and you'd want just somebody to run it. I think that's another thing where we make a lot of hiring mistakes is not being clear on. Do we need a builder or we need somebody to execute something that's already running and working?
Shiv: Totally. Yeah. We've seen a lot of companies that maybe need a quasi strategy person, but also somebody that knows how to get their hands dirty, try to go to senior. And then that person comes in and is hoping to hire a team underneath them. And that's way too much investment for the business. And then we've also seen the opposite where they need a true executive presence, like board level CMO. And then they're, they have a director of marketing in place instead. And that person can't level up to where the organization needs them to be.
Anna: And both of those things happen so often, right? And I think that a lot of times it can feel more gray than it actually is when you're in the seat, you know, running, you're a founder or CEO and you're wondering, is this the right sales leader? Is this the right marketing person? Are they going to be able to level up? One thing I have found is deep down, you usually know, you just don't want to acknowledge it. If you're asking questions like is this the right person? Can they level up or are they you know overshooting it and they're not you know, they're gonna be too hands off. If you're asking those questions often you do know the answer already and so I find a lot of like founder instincts are spot-on in these moments and it's just having somebody even to talk through it with. Particularly in sales and marketing roles as you probably know It can feel so much more gray than it actually is. These are roles that are very measurable and should be. And obviously we need people to come in and get their feet under them and get ramped. But then it's really black and white if you have the right person in marketing and you have the right person in sales. And I'm a big believer in being really clear about what success looks like. And then it doesn't have to feel quite as gray about if you have the right person or not.
Shiv: Well, what about this concept of founders potentially replacing themselves like you know, it's as you're building a company. The CEO or the founder is kind of the head of every department - marketing sales product finance etc and then slowly they kind of start to replace themselves. Usually a VP of sales is one of the first hires, a head of product maybe one of those first couple of hires as well and then they kind of slowly have to replace those other areas so I Do you think that as you're bootstrapping, founders are kind of holding on to too much and not giving enough away?
Anna: That's such a great question. Oftentimes, they are and oftentimes too, I think founders forget that what they really need to hire first are the areas that they're not strong in, right? Maybe somebody is most strong in product and somehow they're because that's the area of the business they're the most focused on. They're sort of thinking about hiring there, but what they really need is somebody strong in sales or somebody strong in marketing. So I think it's really important to think about where can getting somebody in a role be really additive when you're a founder and you're bootstrapped or you're trying to be really capital efficient. I think too, depending on the stage of the business, you might need that person to come in who is kind of your body double, right? The COO or chief of staff role, so to cover several areas so that you can focus on the areas that you're strongest in.
Shiv: Yeah, totally. I think that that's really good advice is focusing on the thing that you're the best at for the business and bring very unique value in and then replacing the things that are more commoditized that you could hire out saves a ton of time.
Anna: Yeah, I think that's really important. And I think too, oftentimes, your question was really around bootstrap founders, are they holding themselves back sometimes by staying too close and not hiring leaders? I think that's another example of oftentimes we don't know what great looks like, right, in a function. If I'm not comfortable with sales, I don't know how high impact a sales leader might be able to be. And that's why, again, talking to candidates, talking to just your network about these things can be really helpful to help you form a picture of what great looks like.
Shiv: Is there like an order of operations that you prescribe to founders? Because it's hard to invest in all these areas at once, right? Even if you do raise capital or, or, or let's say you're still bootstrap, like you can't go hire all these key positions. So how do you navigate that with founders or what advice would you give them as they're thinking about almost like a crawl, walk, run phase? Like where should they start or which, what are some of the pivotal areas that can make the biggest impact for them?
Anna: Yeah, I think it's pretty simple. It's what's working and what's not. And those things that are working, if we leaned in more, could we get even more out, right? So it's not that you don't want to focus on what's working, but if you've got a predictable lead gen machine and you know that you put a dollar in, you're going to get $2 out, well, you know, do you want to lean in more there perhaps because there's more upside, but then really what is not working? What are the gaps in the organization that need to be filled to help accelerate the business? And that's what's really important.
So you have to look at both, right? There's not an order of operations necessarily, but it's something gapped in the business that's holding you back because you're spread too thin. And if you had others focusing on different areas, you could fill that gap and you could accelerate it, or is it a gap because it's not your strength, right? And you need a partner in that area. So I think it too is specific to who do you have in the business around the founder or the CEO? And then, you know, what does a business need? And every business is a little bit unique.
Shiv: Yeah, I also like to think about this concept of like making your business something that investors value because usually that increases your enterprise value. And one of the things that I think founders miss is that there's a lot of risk across different areas of the business. So one example is that you don't have revenue predictability. And when you don't have revenue predictability, it's far less likely that somebody is actually going to invest in your company. Another is just. It's too founder dependent. And so it's like a key man risk. And so now I got to take on the, the, the headache of making sure that you don't get hit by a bus and at the same time scale this thing to the next level before something like that could possibly happen. So I think removing some of those core risks involves building almost a more healthy or sustainable business. Um, and thinking about it from that lens kind of changes the order of operations that you might do something in. Versus if you were just trying to build it as like it's an owner operated business that you don't ever plan on getting an investor for or exiting one.
Anna: Yeah, so totally two different things, right? Like you're thinking I'm going to be the founder and run this until there's an exit or there's not going to be an accent. There's going to be a succession plan with family or other executives. You do make different decisions in some ways, right? That I think in terms of risk that you're willing to take, or you're not really thinking about necessarily enterprise value or even just pulling back to your point about predictability, you might be, hitting decent revenue numbers every year thinking this is great, I'm paying the bills and I'm paying my team and I'm paying myself. But if you, you know, we as outsiders might come in and say, well, this isn't predictable, this is luck, or this is way too lumpy and it's too erratic or unpredictable. So I think there are different lenses you put on it depending on what some of these goals are.
Shiv: Yeah, do you think there's a risk of trying to expand too fast because Everything takes up more cash flow. And so how does a founder balance those two priorities? You
Anna: I absolutely think that's a risk. And you see that all the time when people just kind of go in and start throwing money at something thinking, well, I've got these unit economics and I've got this, you know, predictable funnel, let's say, and I'm just going to scale it. And then what you find is it becomes less efficient. So I think it's really important to step into those things. And because it might be okay that it gets less efficient because the unit economics are still good or it's still overall efficient enough, but you have to, I think, kind of do that in waves so you really understand what the impact is. Again, the simple example, you get 100 MQLs, you get 10 opportunities that are worth this much and you've got this close rate. What happens then when you open up the faucet, you drive more leads, are you able to maintain that quality, the same audience, are you still attracting your ideal customer profile? There's a lot of things you need to investigate before you go try and get a thousand leads.
Shiv: Right, right. Yeah, I think that's one of the risks where it's like, um, one of the biggest things in business that's underrated, I think it's just, just staying alive and don't run out of cash and just keep going and more and more opportunities come your way as, as you're able to accomplish that. So I think that's the, that's the dance of balancing between being aggressive and at the same time having enough cashflow to just keep going.
Anna: Yeah, I can give you actually another example. I know I've been using a Legion example, but you know, at CFI, we have a software product, Macabacus, that's very product led. You get a trial, you download it and it's a 30 day trial. Some of those trials they can just purchase online. Others become leads, you know, they're evaluating essentially for their enterprise. And we have this very predictable trial to paid conversion rate And we've been increasing our marketing spend over the last year. And the way that we do that is we think in 30 day windows. We think, okay, we increased the spend, we drove more trials. Let's make sure that before we go spend, increase the spend in the next wave, let's make sure that we're maintaining that trial to conversion rate. And so we, that's how we think about it. We kind of think in these like 45 day windows of leveling up the spend to make sure that we're maintaining it because when we decided to increase spend, it's a huge risk that we would get a big false start that we drive a lot of trials. They weren't really ICP and they weren't going to convert. And so taking it in these chunks has been really valuable so that we can make sure the spend remains efficient and those, that trial to conversion rate remains relatively predictable. And we were okay if the trial to paid conversion rate went down, as long as you know, there's certain thresholds that it doesn't make sense anymore. So I think that thinking kind of in waves is really important too.
Shiv: Yeah, I think that's great advice is that way you're more agile with it instead of like just spending significantly more and then you're able to on an ongoing basis measure whether or not you're hitting your projections or you're on target or if you need to make adjustments and that can kind of help you adjust your budgets.
But I guess again, I think on the people side it's a little bit different, right? Because you kind of have to bet ahead of time and then you see a return return much much later on. How do you how do you perceive like cost center roles or investments like places like finance and admin and I guess support can be seen as a revenue generator, but still like areas where you're investing money, but there's not really a direct ROI to that additional investment. But as a founder looking to build the business to a larger entity or even just a more professionalized business, you eventually do have to invest in those areas.
Anna: You do, and this is a tricky balance because in my experience, high growth is super messy. You cannot keep up with it, right? You're never gonna be crossing every T and dotting every I because the train is going down the track too fast and you couldn't even be staffing up those back office roles fast enough to, in true hyper growth. The flip side is, I'm a big believer in institutional readiness, which really comes from a strong back office function, right? That the day that investor comes calling or you're ready to have an acquisition, you've got your T's across and your I's dotted, particularly if you're not in one of those high growth modes where the exit might look a little different. So I think it's really just striking a balance of one of the things I tell my team all the time is like, we're not going for perfection, right? Because at any moment I could add, five more back office roles and there's work to be done, but I'm not going for perfect. So I think that, and a founder who's never been to that before doesn't know what that looks like. So that again goes back to having somebody experienced in -seat with you, whether it's a VP of finance, at some point a CFO, having somebody that's kind of is thinking about the business in terms of things like what percentage of our revenue should these functions be, it can be really helpful.
Shiv: Yeah, I think one of the ways I kind of think about it is as an opportunity costs like the more more effort or time I spend on administrative tasks as a CEO, the less time I'm spending on value creating functions. And so my hourly rate per se for those admin tasks, there's a huge mismatch between what I should be investing that time into versus what versus the time that actually goes into those tasks. So the more I can get that off my plate, I can direct that energy and effort into those things that will actually drive more value for the business.
Anna: I think that's a great way to look at it.
Shiv: Yeah. Well, what do you think about the, the, um, the role of AI as we kind of go here? Because some of these other, and I'm sure you guys are investing in this and usually I don't jump into AI because it's like the buzzy flashy word, but, but I feel like in this conversation, there is some relevance because it can help founders find some efficiencies and kind of scale their processes up a little bit more. And are you investing in that as a focus area?
Anna: Yeah, it's a great question. So as an operator, I can share a couple quick anecdotes. One is at CFI, we recently geared up to turn on AI for our support function. And this is really to us, we think about this as resolving tickets faster and more effectively. So it's a better customer experience. Now, does this mean we're not going to need as many support reps as tickets scale, because support staffing is typically really mathematical. You do it based on ticket volume. And so does this mean now we need fewer headcount as ticket volume goes up? Yes. But the real genesis of this is better customer experience. We believe that AI trying to resolve the tickets, responding more quickly will lead to a better customer experience. So that's something that we're doing at CFI and we're super excited about that. I've done that before in other businesses with really good success. I think another example for us is, I'm sure you're experiencing this too, marketing. I think that you're going to be out marketed if you're not thinking about how can I leverage AI in helping with content creation and content editing and being in a way a creative partner to the marketing team. I think there's just workflows around marketing in particular where AI can be really helpful. Obviously, I'm not a big proponent of using AI to write copy that you just put on the web, but as an editing partner, as a brainstorming partner, AI can be really helpful and speed up the cycles. And then for us at CFI, thinking about how can it accelerate workflows in our course creation and our content creation, our actual training materials, is it that, and we're not doing things like this, but these are certainly conversations we're having, you know, if we train an AI voice on our trainer's voices, can we then put out audio that's faster and better and less prone to errors? Things like that, you know, what internal back behind the scenes. Ways can be accelerated our workflow with AI on our training creation, but maybe some of those things eventually will even be public facing. Right. So yeah.
Shiv: Yeah, I totally see how that's one of the places where I think AI can actually have the biggest impact is these two ideas kind of intersect, which is that the founder is bootstrapping and trying to stay as capital efficient as possible. But then there's this need to staff up to resolve certain problems to make the business more professionalized. And then I think AI's contribution there can be to make the business more efficient without necessarily increasing the number of team members or how much human capital you have and still keeping some of those core business metrics in a good place. Like support is a great example where, you know, one of the core metrics is first call resolution. Or if you think about Google, like zero click searches, like how many support tickets could be avoided by resolving it without even a response or getting the answer just to the customer on demand. So I think, I think those are excellent places that founders should be looking to automate that customer experience and at least a better satisfaction and and Repeat business as well because the customer is getting a better experience at the end of all that.
Anna: Yeah, and it's so measurable, right? If you're afraid that, oh, it won't be a great customer experience, we'll try it. And what's the CSAT like, your satisfaction score and things like that. I think that trying things and being open and being curious and being willing to do that, because it's all measurable and we can see what is the impact for sure. I think if I can resolve a ticket faster, respond to a ticket faster and maintain CSATs, which is what I've seen in my experience doing it in the past, why not? That's a better customer experience. So I think right now it's important for everybody is just to be curious and there's no playbook, right? There's no right or wrong answer. So curiosity and exploring these things and being open about how might they help workflows and processes I think is really important.
Shiv: That's awesome. I have one last question about this train of thought that we're on is just with the current market environment, there's just more uncertainty, right? So we talk about revenue predictability and companies have aggressive growth targets and then a lot of them are missing their projections and then they're cutting back on staff and it's kind of going in the opposite direction. So in an environment like that, how do you balance the uncertainty that's at stake with the revenue along with the need to professionalize the business or invest or be more aggressive with where you want to take the company.
Anna: That's a great question. I think that's I think that there is a swath of businesses that were overbuilt when there were maybe more tailwinds or let's say the absence of headwinds. And the founders that I know and the CEOs that I know that have made some hard decisions to freeze hiring or make some headcount reductions have found that those things have not hurt the business or they've accelerated in some ways and created more agility. This is a sensitive topic, right? For short, because when we're really talking about lack of predictability or some headwinds, we're often talking about human capital, which is usually the largest expense in an organization. And I know a lot of companies have had to make really hard choices around this. But I do think that I don't even know if I'm answering your question, Shiv. I mean, I think that we've had to make a lot of hard choices as company leaders. And through that, when you go through those moments, it certainly informs your plans moving forward, right? If you, let's say, over -hired, you really do in the future think very carefully about adding headcount because you've lived through what it's like to over hire and the pain that can be associated with that and having to right size the organization. I don't know if that answers your question though.
Shiv: No, I think there is a form of an answer there, which is that I think that the market changing revealed that companies had over invested or been almost too aggressive and drifted away from some of those fundamentals that actually made companies great. And waste was kind of allowed. And so that when that shift happens, you almost have to get rid of the excess inside these companies that is actually not adding value. And then I think the flip side is also true, which is that when you remove that excess and you start to really uncover where you want to strategically place your bets to grow the business. And the answer would likely look very different now than it did three years ago when capital was more readily available.
Anna: It would exactly. And I think, you know, when we have to make hiring decisions and headcount plans, I think we have to think about how we pay for this and is this sustainable and is this a role that's going to be additive? I think we saw this so much. I mean, I think we saw this across the board in organizations, but a big one, as you probably know, is the sales organization, right? If you think about 10 years ago, what a sales organization looked like and how many people we had per revenue generated and just over the last five to eight years, it just kind of exploded, the headcount and the role specialization and tool specialization. And we got so far away from just good solid fundamentals. And I think so in many ways, some of the corrections there are going to be far more sustainable and kind of going back to how do we do this sustainably.
Shiv: Yeah, I think that's a great message to close off the episode with. So with that said, like if founders are listing and they want to potentially partner or work with you, what's the best place to find you?
Anna: LinkedIn's probably the best way these days. I'm there and yeah, I'm always happy to connect with people who want to talk shop, that's for sure.
Shiv: All right, and I appreciate it. And we'll definitely link that in the show notes so that the audience has access to that. So with that said, thanks a lot for coming on and sharing that wisdom. I think, especially for founders that are bootstrapping their companies or considering investment, I think there was a ton of great insights on this episode for them to take away and apply to their companies. So I appreciate you doing this.
Anna: Thank you, thanks for the great questions, I appreciate it. It's good to see you.
Shiv: Likewise.
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