Movers & Shakers S2E1: Optimizing SaaS and Cloud Software Companies with Mary D’Onofrio of the Bessemer Venture Partners

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Welcome back to The Room Podcast. Today's conversation is the first episode of our second Movers and Shakers miniseries. In this miniseries, we sit down with on-the-pulse entrepreneurs and venture capitalists to hear about their stories and what they're excited for next. Today, we sit down with Mary Donofrio, a partner at Bessemer. Mary is a growth investor that has led SaaS and cloud investments in companies like Hyperscience, GetInsured, and Finmark. In today's conversation, we chat candidly about growth venture capital and touch on topics such as pivoting from working alongside big tech to getting into venture, growth stage investing and how it differs from early stage, and how the markets are impacting venture today and trends Mary's excited to invest in. Thanks for joining us, and let's open the door.

Mary, thank you so much for joining us here in the room today.

Thank you for having me. It's such a pleasure.

We're really excited to dive into your path into venture at Bessemer, where you are a partner today. But before we go into what you're doing now, we always like to start at the beginning of people's journeys. So curious about where you grew up and how this experience shaped your view of the world.

I am actually born and raised in California, in Los Angeles. My mother still lives at the same house I was brought back to when I was born.

Deep roots in LA.

But I was raised by a single mother, and she is a doctor and went to medical school back at a time when only 5% of medical school classes were female. So starting at a very young age, she was very passionate about education, but then also very passionate about women being whatever they could be and a brave new world in which women could do anything.

I think More so than where I grew up, the person I grew up with probably shaped me most.

And so as I have approached my career and decision-making and educational pursuits, professional pursuits, it's certainly been with the lens that I can achieve anything, certainly as, as a woman.

That's incredible. Our closing question that we ask everyone on our podcast is, who is a woman that has had an impact in your life?

And everyone tries to say their mom, and we've had to start asking people, please don't say your mom. Like, we know, we, we love moms.

It's so So neat to hear about how that relationship with your mom really was the foundation of the confidence and the energy that you've been able to have to step into this world of venture, which kind of, as you alluded to, much like it was for your mom becoming a doctor, is still a space where women are unfortunately underrepresented. And you now get to be that access touchpoint for founders who are looking to have your insight on their board. So a little bit of an allusion there to what you do now, which is working in venture, but did you always think think that was going to be your path?

No, I didn't. Some of the analysts and the college students that ping me asking if they can connect for jobs in venture, I think they're so forward-leaning. I didn't know what venture was when I was in college.

As I mentioned, I grew up with doctor in the household. So it was lawyer, doctor, very straight down the fairway paths is what I was exposed to. So it took me a while.

It really started in college. I was pursuing a degree in politics. And I ended up working at the US Treasury during my summers in college for the Treasurer of the United States at the time. That's where I was actually first exposed to finance. It was at the height of Dodd-Frank regulation in the wake of the global financial crisis. I was there pursuing a career at Morgan Stanley and working there in equity capital markets. I started there to try to see how financial regulation would impact the big banks.

Naturally, as an analyst, you don't see that firsthand, but that was how I first got exposed to the world of finance and then made my way to Morgan Stanley.

At Morgan Stanley, I happened to serendipitously be put into a group doing private capital markets. That was raising money for private technology companies. Effectively, the sell side of what I do today. But I ended up leaving Morgan Stanley to go to business school at Yale. I had worked at Morgan Stanley on transactions for the like of Uber and Airbnb and Zocdoc and Fourscouts, so great tech firms, and I thought, hey, maybe what I'm interested in here is tech. And while at Yale, I worked at Apple doing third-party semiconductors and passives procurement, basically buying semiconductors. And while that job was really interesting, and making those purchasing decisions for Apple was very interesting, what the job ended up being more so was really thinking about the evolution of the semiconductor landscape, and how different semiproducers, Qualcomm, Broadcom, et cetera, AMD, would merge, make strategic moves, et cetera, and how that would impact Apple in terms of pricing.

So it was really learning about a new market, seeing how it would evolve, and then making a bet based on that.

[Speaker] It's kind of cool how you've been able to get exposure of deals like Airbnb and Uber while also understanding kind of how markets move more broadly during your time at Apple. Double-clicking into your time at Morgan Stanley, were there any deal-making lessons learned from seeing transactions with Airbnb and Uber specifically?

They were all very different. And I think the biggest lesson that I was able to take away from it was how to advise companies during really consequential points in their life cycles. For us as bankers, and then even now, for me as a venture capitalist, it happens every day.

That's just what I'm exposed to.

I think it was really about working with those companies, working with the management teams, building relationships, and then laying out the pros and cons and the different decision levers such that they could optimize for their businesses. That's really what I took away. I think that those are skills that I continue to put into practice today.

You are a partner at Bessemer Venture Group, which is an iconic fund in Silicon Valley. What initially brought you to Bessemer in 2018?

After I had this aha moment that venture would combine all of the things that I was interested in doing, I looked for a job, and I was in business school at the time. Trying to think about what stage of venture would be the most apt for me. And given the investment banking background, really decided that growth stage investing was part of a company's journey for me to evaluate the best. And also, a lot of the questions that I would love to help companies to answer if and when I had the opportunity to be on boards— how to scale, what products to add in— versus early on, it's kind of team to ham in finding product market fit. So I reached out to a bunch of Silicon Valley firms and ended up being hired by Bessemer Venture Partners. The man who hired me was a man named Byron Dieter, who ran our cloud practice and originally had the idea for starting a growth stage investing practice at Bessemer. Just to give you a little bit about it, it's a 100-year-old fund actually built with the Carnegie Steel money. Andrew Carnegie Steel, Henry Phipps actually started a Bessemer Trust Investomer Securities out of his fortune from that endeavor. So a very longstanding and storied history, but all in seed and Series A. And I joined to be the first dedicated growth stage investor at the fund. Originally, it was building out a lot of the pipeline, the infrastructure, the frameworks for growth stage investing and thinking through not only net new growth deals, but making good decisions about our existing portfolio. In the past 4 years that I've been at Bessemer, we've made probably 15 or so investments out of 2 dedicated growth funds, Century 1 and Century 2, and we have about $1.3 billion under management for growth.

At Bessemer, in your kind of growth investing practice, you've invested in companies like Hyperscience, GetInsured, Finmark, BigID, LaunchDarkly, amongst others. What were some of the key characteristics you saw in the founders and in the business that made you say, this is the next big thing, we need to help grow this business?

I'll answer that a couple of ways. I think business more broadly was really just a clear why now. I mean, team, TAM, and product are obviously all necessary, and all of those companies had it in spades. But I think the why now imperative is incredibly important as you think about a business being able to scale. I tend to invest as a heuristic around $10 million of some top-line metric. But how is that going to scale to $100 million in the next few years. BigID, which is a data infrastructure company with a data privacy wedge, that was the rise of legislation like GDPR and CCPA. For LaunchDarkly, feature management was consistently cited by a lot of developers I would talk to as a consistent problem when deploying feature changes reliably and scalably. But that combined with the trend of developers and engineers being equipped with purchasing power almost for the first time. And for Netlify, which is my most recent investment, it was the rise of the Jamstack approach to web development, where website presentation and data layers are decoupled. Netlify bakes that into its web development and deployment tool at its core. So I think throughout all the investments, I was able to identify a really clear why now.

I'm happy to also chat through some of the things that I look for in founders as well, but I'll pause there for a second.

I'm just struck by how technical these companies are and how they really are deeper in the tech stack, which is something that oftentimes requires a bit of expertise there. For those listeners who might be thinking, oh, I don't have a technical background, I'm coming from consulting or finance, I've never been an engineer, how did you level up in that way to be able to really effectively evaluate these technical businesses?

Early on in my career at Bessemer, building some reps with these kind of tools. My first investment at Bessemer was in HashiCorp, which is a pretty technical developer platform for DevOps. Terraform, Vault, Consul, Nomad. They're open source projects that HashiCorp commercialized for developers. I think it started with talking to customers. They can obviously help you to get up to speed. And then building somewhat of a network of more technical folks that you can start talking to and relying on. I am not technical. I'm not an engineer by trade.

As I mentioned, I majored in politics and then I went to business school.

I think that was one of the things that I did early on. Also, as you start evaluating some of this more technical tooling, you start figuring out the things that matter to you. If you're evaluating an open source project, what are the heuristics that you're looking to as to whether or not it's gonna be a big one? If you're thinking about something that requires a lot of developer love, like what are good heuristics for developer love and adoption?

What is a DevRel team supposed to look like? What is the evangelism? Where are the places where people are talking about your product?

And I think over time, even being non-technical, especially especially at the growth stage where you have some customer conversations and there are also underlying metrics like customer acquisition velocity and ARR growth and stuff like that. I would call them almost lagging indicators, but you can ascertain whether or not there is material pickup.

You're touching on this delicate balance between founder market fit and customer product market fit, so to speak, which at your stage of investing, which for listeners is quite a bit later than mine. I think most of our companies, we really cap out at Defy at Series A, and you really maybe start at Series A or beyond, is geared towards having actual metrics, actual revenue at scale to be able to evaluate. What is that dance between valuing the company and the team versus the growth and the customer and the metric side?

At the growth stage, it's not that the team, TAM, product roadmap, et cetera, are less important. They're just as important. It's just that the competitive landscape by the growth stage is relatively narrow. So some of those questions about whether or not a market is in fact going to turn into a market— a company is these founders, this executive team has built the company to this scale. Sure, maybe you need to uplevel a sales leader because the person who took you from 1 to 10 is different from the person who took you from 10 to 100. But a lot of those questions are already answered. The question you have to ask is, can this business scale to 100? That question is answered with a lot of financial data. And a lot of it is, especially since I invest in cloud and in SaaS, is whether or not I can invest more dollars into a sales and marketing engine and have it yield actual ARR growth. I look a lot at sales productivity data.

I look at a lot of rep ramp times and sales cycles.

In addition to normal P&L metrics like ARR growth, net retention, gross retention, CAC payback, things like that, because those metrics help to answer the question of can this scale?

So more at the stage in which you're evaluating these businesses, it's around, okay, something is working here. Can we pour gasoline on the fire to continue to scale it profitably such that this company continues to sustain itself? Post our addition of capital here.

Exactly. And the difficulty—

not to put words in your mouth, you're the expert in early stage.

I think one of the difficulties early on is, can I parse through this massive competitive landscape to identify the winner in an interesting market? And for me, it's like, hey, there are 3 or 4 companies in interesting markets that have gotten to my stage. Can I pick the one that's going to make it to be the category-defining company? Yes or no? They're related, but slightly different questions that I'm trying to answer.

It's helpful to unpack the differences there and the different strategies that go into investing at the later stages of growth. You talked about how the partner that you joined under, and then now have grown into a partner yourself, really focused on cloud trends. Curious about your perspective on what will continue to evolve within the cloud ecosystem for enterprise SaaS and software companies.

I do tend to invest in fairly technical tools, as we've talked about. And I think that increasingly developers in particular want choice. Cloud is one infrastructure deployment methodology, but I think the infrastructure continues to grow, whether you're talking about cloud, public or private databases, a bunch of other options. And I think with the rise of security threats and zero trust policies and approaches to security, it'll shape the approaches to accessing infrastructure. So access is a space that I'm looking at pretty deeply as of late, and I think it's going to be increasingly more and more relevant. Another cloud trend in particular that we continue to invest in as a firm at Bessemer is this idea of the globalization of SaaS, where Silicon Valley doesn't have a monopoly on innovation. And you see the rise of massive cloud companies around the world. We have an office in China, and we think that China is an underpenetrated market for cloud. We also have an office a relatively recent office in Europe led by my partner Alex Ferrara. We've had fantastic outcomes come out of there too, like Mambu in Germany, Productboard, Intercom in Ireland. And we think that the globalization of SaaS is going to continue.

And while we do think that SaaS is eating software, it has done so less in other geographies ex-North America.

This idea of access is something that we actually talk a lot about on our show. It's one of our kind of core pillars of thinking through how can we have these conversations to unlock opportunities for all people. What is one company that you have seen recently that is really changing the way for access in the cloud and technical ecosystem?

One company that comes to mind is literally trying to facilitate access to computing resources. It's called Teleport. It operates in a similar space as HashiCorp Boundary, as StrongDM, and then some tangential products from Cloudflare and Okta. But I think the fact that so many companies, both new and old, are going after this problem is exemplary of the fact that access, especially in this new world of distributed and consistently compounding resources and, and infrastructure, is a market that is untapped and has massive potential.

We, we had the pleasure of having Michelle from Cloudflare on a couple seasons back, and she definitely talked about the continued evolution of this space for them and how they're thinking about it. And something that's always struck me is that Cloudflare is a solution that people use in large enterprises, but it's also something that Claudia faced for her startup.

What's been really interesting for me in the founder seat is there's clearly different ways of evaluating businesses from Madison's stage to your stage. And I've had the pleasure of working with many seed stage investors very closely during kind of our early journey. But I think as businesses get to that growth stage, I think founders often have question marks around, like, how does your relationship with your lead investor kind of change as you scale? And so would love to kind of learn more about how you work with the businesses that you invest in, and how is that value-add a little bit different from early-stage investing?

Great question. It relates back to what I was saying about how the questions that I'm trying to ask and answer are a little bit different. And as a consequence, the value-add that I bring is a little bit different. A lot of the help that I provide my companies is on go-to-market and literally scaling, rather than figuring out product-market fit and building early team and TAM. Can we make this into a market leader? What does that mean from a marketing and product marketing perspective? Company evangelism, especially in a more technical tool. Can the product become a platform? From a roadmap perspective, how do you go from single product catering to single use case or user to multi-product, multi-strategy, and what is the right prioritization of how to add products on to what you probably already have as a core. And that extends also to not just product, but different user segments, user profiles, geographies. And I think a lot of that boils down to go-to-market insights combined with some product roadmap. And so one of the things I really love to do is work with go-to-market leaders, helping with customer introductions, doing interviews and candidates, recruiting for go-to-market leadership, advice on sales processes and KPIs, and largely helping companies ramp. And I think as a board member and advisor, that tends to be more my role alongside digging in on finance, digging in on model building and future forecasting, versus some of the leaders of kind of the Series A's, seed stage, which, tend to opine on things that they were opining on since the seed and the Series A. Obviously, they evolve as well. But when it comes to scaling with go-to-market and finance, I tend to plug in there.

That makes a lot of sense.

And I feel like for many deep tech businesses or SaaS businesses, go-to-market is such an interesting part of the business and ultimately its success. Because I think a lot of the talent that you need to bring on in order to scale go-to-market effectively is quite different from the founding team. In your stage of investing, is there a common stumbling block or something that is particularly tricky for growth stage businesses to continue to figure out in order to become that market leader?

The first point you're making is certainly true on investment in go-to-market. Even at maturity, public cloud businesses still spend 50% of their revenue on sales and marketing, so when you think about capital efficiency for a SaaS business, it really is sales efficiency. In terms of a common stumbling block, I don't know if there's one consistent thing that I see. I think it's really the process of experimentation and figuring out what your sales motion is per ACV, per user profile, per product that you're selling. And sometimes the segmentation doesn't happen until too late. And you're trying to sell an enterprise product at an SMB price point, or an SMB bottoms-up product in an enterprise fashion, sales-led. I think my actual answer is, the common pitfall is that people don't do as much experimentation as they should. They rather invest behind a strategy with a thesis that isn't validated by data, rather than trying a bunch of different things and experimenting with a bunch of different go-to-market motions. That are tied to different ACVs, user profiles, geographies, et cetera, before making a really material sales and marketing investment. The difficulty is that once you set the ship and you hire people to do X, it's difficult to have them pivot to Y, because the person who you hire as a sales leader, or even as a salesperson, selling whale hunting deals is a lot different than the person who's doing high-velocity SMB or mid-market deals. But maybe your product's better suited for that than it was to enterprise and large lands. So I think that is a pitfall that I see, and I would very highly encourage any SaaS business that's at the inflection point of its growth to do a lot of experimentation before investing behind one given strategy.

Not necessarily always, like, building the rocket and shooting it, but more along the lines of figuring out various different hypotheses to test before, like, going off and going down one path. That resonates a lot, even though I'm not at that stage. Stage.

I was going to say, Claudia, this feels highly relevant as you figure out your early sales strategy and knowing when to look ahead and be able to say, okay, this has been working, but what else might work as good or if not better as you continue to grow? That's super insightful. Sales is a key part of the founder journey that if you are product-driven growth or you are someone who is technical, it might not be your natural inclination to be a sales leader or a sales iterator. So I love that feedback. One other nugget I heard you share of ways in which someone might be thinking about adding a growth investor to their cap table and why you was around helping on hiring. It's something that has been macro talked about a lot in the market around the great resignation and the conversations of how hard it is to keep great people. At Defy, we totally believe that great people build great companies, and that's just so foundational. And so curious about any founders who might be at this post-Series B level, if they're struggling to retain talent or struggling to hire that go-to-market strategist, what advice would you have and how to think about those emotions today?

First thing is that it's not just you, it's everyone.

There are some specific roles that in particular I think are really difficult to hire for. Every single company in my portfolio seems to want a CMO and a VP People. And I think the VP People or CHRO, however you wanna call it, I think in the context of remote hybrid world and people leaving and great resignation and whatever, that's become an increasingly demanded role.

But I think it's really just pounding the pavement. Use a recruiter, use the VCs in your network to reach as many people as possible.

I ask a lot of CMOs in my portfolio if they have other CMO friends that they might want to tell me about because maybe we can all help each other.

I don't know if I have exactly a trick to make it work, But what I've been seeing is that a lot of these really crucial foundational hires are taking 6 months. And you should budget for it as you think about building your strategy for what fiscal year '22 is going to look like. You should be baking in that timeline. And alternatively, if you think your strategy should change in fiscal year '23, for example, start looking for your new CRO in June so that you have someone who can hit the ground running at the time that you need it. I think the advice is less on—

Hey, here's exactly how you can find a great person, though. Use your networks very wildly.

Make sure you map it to timeline so that you can continue pace and momentum that you want rather than needing to have a stop or lose some of that momentum to find the right person.

You mentioned the year 2022. Let's talk about this year, which has seemingly gone very quickly now that we are in March, and there's been a lot that's happened that has definitely impacted the public markets. Which tends to trickle down a bit quicker to your side of the ecosystem. There's been reports of larger growth-stage investors pulling term sheets through the fluctuating markets, and just generally the contrast of the very accelerated investment pace we all experienced last year. Looking towards what this year might hold, how are you personally thinking about that, and how is Bessemer?

I manage our BVP Nasdaq Emerging Cloud Index, which is a public benchmark of cloud software stocks. it's traded down about a third since November. And as you think about that in terms of market cap, it's gone from almost $3 trillion of market cap to $2 trillion of market cap, which when you think about in terms of market cap turns, it's even more striking. And the average multiple has compressed about 14 times. I think in that context, a lot of investors and growth stage investors in particular are thinking about the fact that you can't underwrite deals, assuming a 50x exit multiple. It just constrains what we think that the pro forma standard multiple will be for a public cloud software business. And as a consequence, it trickles back down into entry prices and our willingness to pay. So for me personally, it makes me think twice, be more conservative, and take a beat before making an investment, particularly at what used to be a market-clearing price. You regularly saw deals at 50x, 100x. And there are some businesses that still can support those valuations. One of the things that I've written about in the past is this idea of growth endurance in cloud software stocks. Cloud software companies tend to grow 80% of their future year as they do this year. So when you think about perpetual growth rates in cloud, it's actually a lot higher than you would think. And for some businesses, if you assume very, very high perpetual growth rates, like, they can still grow into those 50x entry prices.

But not every company can be priced as if it is a top 10 cloud business.

What it's done is, is force more conservatism. We're really looking at large TAM, broadly horizontal solutions, the likes of data infrastructure, security, places where you don't think that there's any kind of artificial constraint on how many customers could adopt it. And being very disciplined about entry price.

There's some fascinating statistics around how the market has shifted so dramatically, even in the past 3 or 4 months. We do believe that there's still going to be great companies that are built no matter what the market looks like. And so I love that final point of yours, and it just makes me want to ask one more question around how you see the market evolving, and specifically at the idea of the trillion-dollar company.

I feel like when we all got started, the unicorn was the thing to build, and now it's, oh my gosh, how about a trillion?

Do you have a bet on who you would say in the next in the next 5 years will be a new trillion-dollar company?

Oh, that's an interesting question.

I don't know if I've thought about it enough. I'm sure one of these will be. I don't know.

Mary, it's been awesome hearing your early journey into venture, your investment thesis, and some of the portfolio companies that you've invested in, and just this broader landscape around cloud, but also the economy and where investments are going market trends there. But as we're coming up on time, what's the future for you as Mary?

That's very kind of you to ask. I think it's more of the same. You know, it's continuing to build the growth practice at Bessemer. Luckily, we've been able to hire some fantastic associates, and we're building the team. And especially as AUM grows, that's more opportunity for more net new investments and more follow-ons into our existing portfolio.

And continuing to help my portfolio companies build and scale, doing all the things I told you that I love to do with them.

So we're the same at Bessemer, but especially as the markets evolve, the great thing about venture is that no day is the same.

And so what it will take to build a category-defining business in 3 years might even be different than it is today.

I know we chatted about how inspirational your mom has been as a figure, but as Madison alluded to earlier in this conversation, we always ask this one hero question to all of our guests, and that is, who's a woman in your life that has had a profound impact on your career?

It was It's the Treasurer of the United States, Rosie Rios, who I spoke about briefly at the very beginning, but she was my first boss, taught me how to be a professional woman in the workplace. She's the consummate networker, always does her best to champion causes that she cares about, at the same time obviously leading government departments. She's been incredibly inspirational, has helped me connect with jobs and opportunities, and the very cool part about it now is that she actually serves on a board that I serve on as well.

So it's all come full circle.

Definitely Rosie, she's amazing and I am very lucky to have her in my corner.

I encourage all of our listeners to find figures like Rosie, especially early in their careers, because it's amazing even now, only a few years out of college, I'm already seeing early mentors from my first year in the working world, like, coming back in my life in many different ways. It's always cool when those relationships do come full circle at many different points in your life and career.

I'm getting dinner with my first boss at Gap this Thursday and I haven't seen her in a while and I'm so excited.

I love this framework of people coming back around.

With that, Mary, thank you so much for taking the time to chat with us. So many interesting insights, and thanks for being on The Room today.

Thank you for having me.

Support for The Room comes from Silicon Valley Bank. Silicon Valley Bank understands these questions can keep founders up at night like Claudia. For over 35 years, Silicon Valley Bank has helped high-growth companies through scalable financial solutions, plus insights and expertise that many other banks just can't, which could be why 50% of US venture-backed tech and life science companies bank with SVB. Learn more at svb.com/next. Silicon Valley Bank, built for what's next.

Cooley is a global law firm built around startups and venture capital. The firm has been devoted to entrepreneurs and investors, partnering with both to transform breakthrough ideas into successful companies. Cooley works with thousands of entrepreneurs and newly formed companies to ensure that they structured for growth and long-term success. Since 2005, Cooley has been ranked the number one most active law firm representing VC-backed companies going public. Learn more at cooley.com and cooleygo.com, Cooley's award-winning free legal resource for startups.

All opinions expressed by Claudia Madison and podcast guests are solely their own opinions and do not reflect the opinion of DefyVC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.