My First Day at Cloudflare Was the Day After the IPO | Heather Orsi
Chapters7
The chapter explains the split between external investor relations duties and internal strategic finance work at Cloudflare, including earnings prep, investor day work, and quarterly benchmarking; it also traces the speaker’s path into Cloudflare and her background in traditional finance before joining.
Heather Orsi shares the exhilaration of joining Cloudflare right after its IPO and explains how she builds investor relations and strategic finance from Lisbon, with a focus on storytelling, analytics, and cross-team collaboration.
Summary
Heather Orsi, Cloudflare’s director of strategic finance and investor relations, recounts starting on Cloudflare’s first public-facing day in 2019 and describes how she balances external investor relations with internal strategic finance. She splits her role between speaking with 30 covering analysts and crafting long-term financial models and competitive benchmarking. Based in Lisbon as part of the Apollo program, she highlights the value of being near developers to deepen technical fluency and her preference for turning complex innovations into clear narratives for investors and the public. Heather also reflects on her varied career path—from investment banking to startups to space and blockchain—sharing the grit and adaptability that helped her build the function from the ground up. She emphasizes mentoring during Women’s Empowerment Month, learning to value the “why” behind requests, and leveraging AI to stay ahead in market analysis and earnings prep. A standout achievement is assembling Cloudflare’s earliest earnings materials and forecasts, then scaling the process to a fully systematized IR/finance function. Her go-to productivity insight? leveraging Lisbon’s time zone to carve out focused mornings for critical work. Closing with a candid look at how AI supports competitive intelligence and earnings preparation, Heather paints a vivid picture of a finance leader who thrives on cross-functional impact and thoughtful leadership.
Key Takeaways
- Cloudflare’s investor relations function began with Heather’s onboarding on the day the company went public in 2019, setting a high-energy baseline for earnings and investor communication.
- Her role spans external investor relations (quarterly earnings, investor days, 30 analysts) and internal strategic finance (long-term modeling, competitive benchmarking for ~100 tech companies).
- Heather moved to Lisbon as part of Cloudflare’s Apollo program, using the time zone to create productive morning windows for US markets.
- She built Cloudflare’s IR/finance function from scratch, including the first earnings materials, which were Word/Excel-based, now fully systematized with a dedicated team.
- Her career path covers traditional finance, private equity, beauty startups, a space tech company, and blockchain—providing a broad foundation for a finance leader in tech.
- Mentorship and Women’s Empowerment Month are important to Heather; she prioritizes sharing knowledge and helping others grow.
- A core insight is the shift from focusing on the “what” to embracing the “why” behind financial questions, enabling more creative and effective solutions.
Who Is This For?
Essential viewing for finance professionals, especially those entering investor relations in fast-growing tech companies, or anyone curious how IR and strategic finance converge in a post-IPO environment.
Notable Quotes
""My job is I I kind of like divide it into like there are like the external facing aspects which is more of the investor relations side and then there are more like internal facing aspects which is more like the strategic finance side.""
—Outlines the dual nature of her role.
""I think I learned a ton. Investment banking is known for being incredibly grueling. I would get in at 9:00 in the morning and I was there till 3:00 or 4""
—Describes the demanding early career environment and resilience building.
""I love that I get to work with so many different people internally... the CFO is phenomenal.""
—Highlights cross-functional collaboration and internal impact.
""Bringing to your question, but… understanding the why allows you to think of more creative solutions.""
—Emphasizes the importance of the underlying reason behind financial requests.
""Moving to Lisbon was pretty incredible because you get this morning window of productivity... while my day has kind of shifted.""
—Explains the productivity benefits of the time zone change.
Questions This Video Answers
- How did Cloudflare’s IPO affect its investor relations strategy in the first year after going public?
- What does a director of strategic finance and investor relations actually do on a day-to-day basis at a fast-growing tech company?
- Why is the ‘why’ behind a financial request more important than the ‘what’ in finance and investor communications?
- How can moving to a different city or time zone impact a finance professional’s productivity and investor outreach?
- What lessons can be learned from Heather Orsi’s career trajectory across banking, private equity, startups, and tech?
CloudflareInvestor RelationsStrategic FinanceIPO 2019Earnings PrepLisbon (Apollo program)Developer relationsAI in financeMentorshipWomen’s Empowerment Month
Full Transcript
And fun fact, my first day at Cloudflare was our first working day as a public company. I'm Heather Orsy. I um based in Lisbon right now. So, I'm part of the Apollo program. Moved to Lisbon in August. Uh prior to that I I was in San Francisco. My role is uh director of strategic finance and investor relations. And fun fact, my first day at Cloudflare was our first working day as a public company back in September 2019. So my job is is I I kind of like divide it into like there are like the external facing aspects which is more of the investor relations side and then there are more like internal facing aspects which is more of like the strategic finance side.
um on the investor relations side. So it's it's essentially being the quarterback of of all things earnings related uh investor day related investor conferences. Uh it's it's a lot of speaking to investors and analysts. So we have 30 analysts that that cover the Cloudflare um story and and so that's really fun. And so based on where we are in the quarter, so actually just uh just on Friday last week, we moved into quiet period um which means I'm no longer talking to investors every day and and and get to spend my time um getting a bunch of work done.
So working on the investor day slides and and and getting ready for earnings prep uh on the on the strategic finance side. So so that's more long-term financial model focused. Uh we do a lot of like competitive and and peer analysis. And so uh kind of tracking when our peer or competitive or like competitor companies are are reporting earnings. Uh we put out like a quarterly benchmarking how Cloudflare is competing against um and and and performing against uh all of the other SAS and and tech companies out there. Um so it's it's a group of about 100 companies.
Um you'll see that uh presented quarterly at the beer at the beer event. Can you explain to us a bit of your path to Clawler? So before joining Clawler? uh before I joined well I've been at Cloudflare for 6 and a half years so it's it's it's it's been a minute time flies when you're having fun but but prior to that out of university I started my career in traditional finance in investment banking doing mergers and acquisitions I then after a couple of years moved to um the buy side so more of the investor side actually and so I joined a private equity firm focused on consumer products in San Francisco um and did that for just shy of 3 years uh before moving over to the operational side and getting some startup experience experience and so um actually worked for a beauty company uh worked for in Hollywood which was an experience and then moved uh over to the tech side of things and joined a space company building the internet in space which which was really really awesome uh and and then moved over to the blockchain world uh for about a year and then you know as a finance person in blockchain back in 2018 uh didn't didn't want to stay there too long it was like the wild wild west and so I I joined Cloudflare in September of 2019.
uh can you give us a a run through on uh what excites you the most for this area uh that uh drive you for the financial sector and investors and what drive you there specifically before Cloudflare I I actually wasn't touching like the market side of of things as much. I was I was more kind of like the head finance person at at at startup companies at at that point. I I'd been doing kind of traditional what I would call like traditional finance for a while and to be totally frank was just starting to feel a little bit of burnout.
Uh and and and so I actually all of the other roles that I was interviewing for were strategy based and so you know strategy at Google, strategy at PaloAlto Networks. Um and Cloudflare was the only one that still touched finance but it was investor relations and it was the only one that was preipo at the time. So I actually thought I was joining for that for the preipo journey. Um it was it was a nice surprise on on my first day to have seen the day before on Friday we had gone public. Um set a high bar for the Monday mornings, you know, coming in seeing balloons everywhere and it was it was it and just everyone was on a high.
It was it was a really fun um exciting time to join. But that market side of of of things was really interesting to me. Um I I had always kind of since university tried to manage my own like stock portfolio and things like that and and and just I was really excited about um about one kind of building the function from the ground up at Cloudflare. I really liked the team uh at at Cloudflare and um and and and also this you know this aspect of of getting to you know interface with analysts and investors and and and investor relations is really neat because it touches so many different I mean it touches every side of the business and so you're you feel like you're you're constantly learning um and and it's and it's it's been really fun.
I'm also curious because you had experience in many different companies. What did you enjoy the most in some of the companies you worked before Cloudflare in terms of lessons learned the things you that surprise you in some of the areas that were quite disperate and different right so in traditional finance what was kind of interesting and and I know this is for women's empowerment month I was always the only female and so that was really interesting like working alongside all you know male colleagues and and especially being so junior in my career um I noticed it you know especially kind at the beginning of of each of those roles like you know I would sit in these meetings and have ideas and I wasn't really speaking up because I I just I felt um intimidated quite frankly and so you know that was a really interesting sort of experience.
I think I learned a ton. You know investment banking is known for being incredibly grueling. I would get in at 9:00 in the morning and I was there till 3:00 or 4 um pretty much Monday through Friday. I worked every single weekend and it was it was it was really rough. And so when I had the opportunity, I actually left about six months early to go take that investor job in San Francisco at at the private equity firm. I was I was very eager to do that and and and then it was a much smaller team in in private equity.
Still learned a lot and that really gave me the foundation to kind of go anywhere in in finance which I thought was was really awesome. Learned a lot. It was a very interesting sort of like I don't know atmosphere just being like so mal dominated and you know it's like the you know like the investment banking you know dudes and and everything and so um but you know it it gave me I think the tough skin that um you kind of need to be or at least that I I think I needed um to be successful in in in finance from there.
Yeah, each of each of the startups was so different. Um beauty Hollywood was not cut out for me. Uh it is you know it is it is for some people. I think it was a really awesome experience. It was a really small team. We got to do really neat things like launch internationally and I I I got really cool placement in in Sephora and Ulta and you know getting to work with you know these really big companies um that you know I was a buyer and a consumer at for so long was really interesting but it's very much like a copycat sort of sort of industry.
And so um after about a year I was like ah I feel like there isn't much else we can do except for copy other products and and and so for me I I wanted to move over to tech. I wanted to move back to the Bay Area and um and and joining the space company. I I essentially was the first the first business person that worked with all rocket scientists was a which was like a really interesting experience. Um and I'm and I'm still very close with with a lot of those folks today. Actually, one of the co-founders is working for NASA now and he's doing a Mars project and so he's actually on Mars right now but actually in Texas.
Um, so kind of building these relationships with with colleagues throughout through throughout the journey has has been one of my favorite things. Uh, and what do you like the most about your work at Cloudflare? Um, yeah, what don't I love about my work at Cloudflare? Um, again, I kind of think of my role internally and externally. I I love that I get to work with so many different people internally. I I mean from engineering to sales to marketing and events and legal and everybody in the CFO or it's phenomenal. And so I I feel like we kind of sit like right in the middle and and a big part of my job is answering questions from you know we have a thousand institutional investors.
Literally we have over a thousand. And so um you know and a big part of my job is is just open Q&A. And so they could ask anything from, you know, dilution to, you know, I want to double click really deep into the workers architecture. And so it's my job to be really wellversed on all of that. And so getting to, you know, especially being in Lisbon, I I've I've I've built some really amazing relationships with the developers here. I feel like my developer and like technical knowledge has grown exponentially just by I I I actually prefer to sit by the developers.
I just I'm a sponge. I just get to hear it all. Um and and it's made me so much more sophisticated and I can speak to these topics so much um so much more intelligently which I think has been really really awesome. And so I feel like I'm also growing externally. I really enjoy just getting to craft the narrative for Cloudflare and you know it's like you take these really technical concepts and and and technical innovations and you break them down for example to like explain them to like your mother, your grandmother, right? because I mean these are people who are just they're not technical people and so you need to help them understand the story and kind of create this narrative in a way where you you you take really complex things and you break them down and help them understand the value and the strategy behind them to really move the markets.
My job is to like spread the Cloudflare gospel and it's a very awesome gospel to spread and so yeah I've been doing it for gosh it'll be seven years in September and just having a ball. Uh one achievement at Cloudflare you're most proud of. So when I first joined, I I remember Jason Noland at the time, he was our head of investor relations and strategic finance. He was like, I I I know you're like in like your first hour of onboarding, but we need a share forecast like now. And then also like 2 days later, like we need you to start building all of the financial statements and everything for earnings.
And so I'm like opening up Word and Excel and and and if you go back to like you can actually go to the IR site and open up our very first earnings, you know, back from like November 2019, all of those documents I created and in Word and Excel and now everything's systematized. We have an entire team that runs all of that. Um and I was like, I'm not an accountant. Like you give me the numbers, I'll make them pretty. I'll put them in the stuff. But um but but to to really like build a function from the ground up was is just a really cool thing to do and and even today there's so many things that that we're still building and systematizing and and and and and making world class like within our function that it's it's it's been a really fun experience regarding the women's empowerment month.
Anything you want to say about this month in particular? I feel like I'm I'm somebody who has gotten to where I am by leaning on others and asking questions and and having, you know, just really incredible mentors. And so, it's something that, you know, I I always look to also do and and and and share. And so, you know, for for folks who, you know, have any sort of questions, like please reach out like I I I will always carve time. I I still meet with mentors like when I initially was a mentor what was it like three and a half years ago like we still have our quarterly syncs because it's it it's it it's just I enjoy them they enjoy them and so especially in finance you know folks tend to think in like a zero sum game but but leadership is just not like that and so you know you you you grow by giving your time and sharing your platform and mentoring and that just that that builds these little communities that are just so important and so it's really important to me.
One thing about finance that most people don't realize, but they should. Oh, good question. For me at least, and and I'm not sure if this is really the question you're you're asking, but I but I think it's an important thread, which is at the beginning of my career, I kind of like looked back and I was like more of a processor. And so I was like, okay, this is the what and and the what is really important. So like the what is in the email and the what is in the deadlines. And it took more time than I'd like to admit to realize that the why was is is really the most important thing.
And so you need to be a sponge for the why and not the what. And I think that's really important in finance like I in in particular. And so I'm kind of bringing to your question, but but understanding the why allows you to think of like more creative solutions, but also like make sure that the the the why of why a customer has a certain pain point is is is is really important. not just the what of what they're asking, but the, you know, the why. And so, you can kind of like apply it to whatever you're doing.
It's it's it's not really just finance, but for me in finance, I think once I started looking at the why, like why does this matter? Why is this really important? Like, why could this be really powerful, I I started to just operate in a totally different manner. And so, I would almost say like I think that is really important in finance. And also maybe some of the advice that I would give others. Uh, what's the best the way you've used AI so far? I use AI to script all of these answers. No, I'm just kidding.
Um uh so a a big part of my job is um is having my finger on like the pulse of the markets and understanding um macro concerns in in in the markets, competitive analyses, things like that. Uh let's see, just the other day we had uh another one of our competitors report earnings. And so I dropped 30 analyst reports into into the AI model and and was like pull together a very comprehensive, you know, write up on this for our executive team. And I was like, you know, and pull together a summary of all of their financials for the last eight quarters, all of these key metrics.
I mean, it's amazing. And then you kind of copy and paste that and then kind of add your own things. You're like, well, you missed this, you know, do this better next time. Uh, but it's it is really fantastic. and then and then going into earnings making sure that you know I'll almost like treat it like a colleague. These are some areas that um you know folks could be concerned about help me understand like where there are holes in this narrative um you know kind of working like a colleague. But I mean I I use it for everything.
I I've I've probably spent three hours in there today uh with with Gemini. We're we're bffs now. Your go-to productivity hack? go to moving to Lisbon because I get half a day where the rest of the world sleeps. No. Um, so, uh, yeah. Yeah, I think being really vigilant with my calendar and and and and making sure I I have focus blocks on there is is really important. But but I am I I am serious. Moving to Lisbon was was pretty incredible because you get you kind of get this like 9:00 am to like noon or two 2:00 p.m.
window where where the United States is sleeping or investors are sleeping and analysts are sleeping. And so while my day has kind of shifted, it has given me this this morning window of productivity that's been pretty incredible.
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