How to achieve hypergrowth in your business and career | Carilu Dietrich (Atlassian)

Key Elements of Hypergrowth

Carilu Dietrich: In order to get hypergrowth, you have to have organic, inbound, and viral word of mouth. You can’t pay enough to grow at those rates and have a viable company. The biggest thing is an amazing product that people love to use, right? I mean ChatGPT is the most hypergrowth product that we’ve seen in history potentially, because people are so excited to use it and it’s working in interesting ways.

And then I think the third thing is really riding the lightning, I would call it. Hypergrowth companies go through the stages of growth that would take other companies five years or 10 years, right? They’re going from 10 to 50, they’re going from 50 to 100, they’re going from 100 to 200. They’re jumping. And so they really need to keep hiring 2X and 3X leaders who have seen the next stage of growth, because it’s going to be here before you know it.

Building a Long-Term Career

Lenny: Welcome to Lenny’s Podcast, where I interview world-class product leaders and growth experts to learn from their hard work, experiences building and growing today’s most successful products.

Today my guest is Carilu Dietrich. Carilu is a former CMO and has advised the CEOs and CMOs of hypergrowth B2B companies like Segment, Miro, 1Password, Bill.com, Productboard, Sprout Social, Weights & Biases, and most notably was head of marketing at Atlassian through their IPO.

In today’s episode, we cover what hypergrowth companies have in common, how to make big changes to your growth strategy to unlock new channels of growth, why COs don’t trust CMOs, and why most CMOs get fired. Also, why most CPOs get fired. Plus, the benefits of waiting a long time to hire your first salesperson, bundling strategy, and a ton of incredibly insightful career advice. A huge thank you to Elena Verna for suggesting Carilu for the podcast. And with that, I bring you Carilu Dietrich after a short word from our sponsors.

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Carilu, welcome to the podcast.

Life’s Ups, Downs, and Shortcuts

Carilu Dietrich: Thanks, Lenny. Happy to be here.

Lenny: You’ve had this incredible career. You worked at all these incredible companies. I’d love to just dissect what you have found to be most important and effective in building a career long term, just broadly. And then specifically if you’re trying to get to an executive role someday, what have you found to be some more important habits, behaviors, tactics, lessons?

5 Mindsets for the C-Suite

Carilu Dietrich: I’ll start by saying that everyone has their own calculus about the trade-offs they want to make on pursuing their career and the sacrifices they might need to make versus the other things in their life, their family, their hobbies, their passions. And so I think the executive track isn’t for everyone because there are a lot of trade-offs.

Because I think that some of the most important aspects of getting to the executive suite are working harder, learning more, pushing yourself, taking on more responsibilities and opportunities, maybe even in the white space, that aren’t your job or aren’t in your regular time.

When I was young in my career, I decided I wanted to be a CMO. And at the job where I had decided I wanted to be the CMO, I worked two hours later than everyone else on the team. And I had this thought in my brain that two hours every day for five years would get me how many more years of experience than someone else? And I could do that when I was young, and I didn’t have kids, and I was willing to make those sacrifices.

But you look at a lot of the top CMOs and they have sacrificed a lot of things to read all of the books. And again, if I go back to that first job, I was a PR manager, and we went through a tough phase and we lost a ahead of product right before the major launch of a major product. So I volunteered to moonlight in the product department and run the beta, and do release engineering. And taking on other responsibilities gave me insights into other departments that made me more successful, early in my career and later on.

And the same thing happens as you’re growing, right? If a department head leaves and you can spend extra time doing your own job and being the interim for this other function, you can really show the top executives that you have the appetite and the skill to take on more responsibility.

So I think learning as much as you can about your expertise, working really hard, and taking on more responsibilities, and having a great attitude and a strategic mind are probably what I think helps people get to the C-suite on the personal level. And then I have another set of five things that are what specific ways do you need to train your mind?

Lenny: I know there’s this backlash against working really hard that happened for a while, but I’m on the same boat as you have of success will come from working really hard. And sometimes that sucks, but that’s usually how it goes.

Relationships and Choosing a Company

Carilu Dietrich: I think there’s ebbs and flows in your life. You’re going to have a baby here soon, congratulations. Thank you. And so maybe you take your foot off the gas for a little bit. But really, there’s no shortcuts. There’s no shortcuts to knowing a lot.

One of the people I admire most is Tomasz Tunguz, who was with Redpoint and now started his own VC firm. And I was talking to him about his blog and he was like, “I’d just wake up 5:00 or 6:00 AM every morning and write three to four blogs a week for 10 years.” Damn. That is self-discipline and insight and drive. So yeah, no shortcuts. I think. You look at Denise Persson at Snowflake, and she’s worked really hard to get there.

So the five things I think you need to do to get to the C-suite that are not personal side are you need to think about how your responsibilities tie to revenue. You need to think and talk in the terms of the CEO and the board. And that can be tricky when you’re junior because you don’t have exposure to it. But getting a strong handle on finance, and how the finances of the business work, and how the revenue of the business works.

I went on a tour of the Tesla factory with my daughter’s field trip a couple weeks ago. And the guy who was giving us the tour was like, “So I delivered and stocked all these different parts at the plant and then I would take a list. And after work every night, I’d go to each part of the plant and try to figure out what they were working on and what the challenges and opportunities were. And that’s how I moved up.”

So it’s just understanding how the whole thing works together. Because if you want to be in the C-suite, it’s a job about how the system works. So I really encourage tours of duty between different departments. I told you about my tour of duty and product. I thought CMOs had to do every function, so I took a tour of duty in every function in marketing, but really getting a sense for other departments.

The next thing is the relationships. So building really strong relationships with people by doing good work and helping them. And then the last thing I think is the quality of the companies you work for. So your career and your ability to transcend, which is really moving faster than other people to get bigger jobs, is fairly dependent on the momentum of your company.

So I was a leader at Oracle for five years, and my team grew from five to seven over five years. And I was a leader at Atlassian for four years, and my team grew from 15 to 100. And so if you pick the right company with the right momentum, you have a better chance of getting higher level experiences and accelerated career growth.

And then I guess one little footnote. If you pick great companies, great people work for those companies, and go out and work at other companies and also give you opportunities. So I ended up at Atlassian kind of in a stroke of good luck because I had worked for Jay Simons, the president, at two companies before. So the quality of the first company, Plumtree, really helped propel my whole career.

10 Metrics to Evaluate Great Companies

Lenny: There’s so many things I want to double click on there. The last piece, it’s the advice I always give people when they’re early in their career is to go find a company that’s going to do super well. That one experience is going to transform your entire career. Having the logo on your resume, the people you meet, the experience you get financially. But that begs the question, how do you find that? How do you pick a company? I think in your advising today, you join later where it’s a little more obvious. “Okay, they’re doing great.” Do you have any advice or lessons about how to identify earlier where to go work and how to be lucky in that pick?

Carilu Dietrich: Isn’t that the billion-dollar question? So I worked for-

Career Growth in a Down Economy

Lenny: For investing too.

Carilu Dietrich: Yeah. I worked at Atlassian, which was phenomenal. Then I worked for Classy, which was a company that helped nonprofits raise money.

Lessons From Big Ad Campaigns

Lenny: I’ve used that product.

Carilu Dietrich: Thank you. And we were acquired by GoFundMe. And it was fine, but it was no Atlassian. And then I spent the next five years trying to figure out, how do you pick your next Atlassian? So my advice would be for people earlier in their careers, it’s easy to pick the winners if you go work for a big company that’s a winner. I would love to work for Tesla, or AWS. Or right this second, I would die kill for a job at OpenAI. You know some of the big companies that are successful… Salesforce has totally been a career maker to so many top executives.

So early in your career, working for big name high momentum companies. I think you can’t wimp out. You’ve got to want it and go for it. And maybe you apply year after year, and you meet people, and you try for it early in your company.

Later in your career, I think what you just said, picking later stage versus earlier stage gives you a better view of their momentum. I actually have a Post-it note, got it here, about what I look for. 10 parts of what would evaluate to see-

What Hypergrowth Companies Have in Common

Lenny: You just have that Post-it note around?

Harnessing the Lightning

Carilu Dietrich: I do. It’s one of five Post-it notes on my board.

Paths to Non-Viral Growth

Lenny: I want to hear what the rest are too. But keep going.

Carilu Dietrich: I have to look at it for advisory. I only take eight to 10 clients. I’m always full. And so it has to be a phenomenal company. So how do I know if it’s a phenomenal company? Here’s my list. Rule of 40, which is your profitability and your costs together. The quality of the investors. Are they really top tier investors? Are they mid tier or some you’ve never heard of? Investors do a lot of due diligence, but you also want to look at their most recent rounds, because they could have phenomenal early stage and have slowed down. I think the later the size, the more reliable, because they’ve just made it farther.

Their Net Promoter Score or their customer satisfaction. Do people really rapidly love this product or is it like meh? Their net dollar retention, which is, how fast is their revenue growing? And I should have it on my Post-it note, but Snowflake was the benchmark. I think they were growing at 142%.

Word of Mouth vs. Virality

Lenny: I think at one point it was 180, whatever.

Carilu Dietrich: Yeah. That sounds right. 180, 165. Net dollar retention, if you have a customer and they just renew at the same dollar rate, it would be 100. So 180 is almost doubling just their customers. So they didn’t even need new customers, almost doubled their business. A phenomenal net dollar retention means it’s a really strong healthy business.

I looked at their growth rate last year, their burn rate, are they going to run out of money? And then ideally, are they number one in their market? Do they have a Forrester or a Gartner Magic Quadrant? People tell you if they’re number one.

And then the last thing is I look at their Glassdoor. Is it just a bad place to work and where people unhappy? Because they don’t actually survive as long as companies where people are happier.

Doing Things That Don’t Scale

Lenny: I love this list. You should turn it into a blog post, and there’s another idea for you. Can you share what the other Post-its are around you? Even broadly.

Carilu Dietrich: I can. One says, “More Yoda, less Wonder Woman,” which basically is ask better questions. The second one was-

Atlassian and Product-Led Growth

Lenny: Ask them backwards too.

Coexistence of PLG and Sales

Carilu Dietrich: Yeah, right? Ask them backwards. Which is funny, because the other Yoda thing I have up Is… Here wait. “Do or do not. There is no try.” Backwards. I have another one that says, “Hell yes or no.” When opportunities come to you and you’re like, “Should I do this or should I not do this?” You only have so much time in your life. And so if it’s not something that really excites you and gives you energy, it’s tough to be the best at it. And so hell yes or no.

And then the last one is, “Worrying is wasted energy,” because I think we live in this economic pressure cooker, and there’s a lot of fear and uncertainty. But we just need to take that fear and uncertainty and thank it for giving us urgency. And then make the list of what can we control now and what should we do next.

Founder Advice: Hiring Your First Salesperson

Lenny: That’s actually a perfect segue to my next question. And by the way, that was amazing. I’m glad that I asked about your Post-its. That’s a whole life philosophy right there in Post-its.

Carilu Dietrich: Yeah, I should do a BeReal. This is what is looks like at this side. These are all the Post-its.

Retool Case Study and Hybrid Models

Lenny: Okay. So the question is around, I don’t know if we’re technically in a recession, but maybe we’re on the verge of recession. The market’s not great. And a lot of people are being laid off, or have been laid off, or are worried about being laid off, or just graduating college and looking for jobs. And I’m curious if you have advice for people trying to find a job in this market or just generally trying to accelerate their career. What is your advice for just how to deal with this environment while also trying to advance your career?

Carilu Dietrich: I’d like to take in two parts. One is if you’re unemployed and one is you’re in a job. So if you’re unemployed, it’s tough. It’s a tough time. There’s a lot of supply. And so I think you just really need endurance and grit. And the sticker worrying is wasted energy, because you will get another job. It’s just going to be a little bit more of a bumpy ride than some other years.

And the best executives I know have had down periods in their careers, where they were out of work for a while, where they were fired by a CEO, who this or that. And what they have in common is endurance. They’re just back in the ring. So I think it’s important to not lose endurance.

It’s also important not to settle on a crappy job or a crappy company. Each job you have prepares you for the next job, and each logo you have prepares you for the next job.

So I’d spent a lot of my career trying to also chase waves. My first job in college, I was in nonprofit, and then I wrote a book on the giving programs of the top 50 tech companies. And I realized that tech companies had a bunch of money in 1999, and were giving it away to charities. And I wanted to go into tech, because that’s where the growth and money was. And I thought I could give it back to the world and good, but I could be inside the bubble.

And then within tech, I moved my way to B2B. And within B2B, I moved my way to SaaS. And within SaaS, I’ve moved my way into dev tools, and collaboration, and now AI.

There’s this book called The Millionaire Next Door, which talks about how the very best antique store makes one or 2% profit. And the very worst oil and gas company makes 35% profit. And we know that some of the worst software companies make 65% profit.

So picking your industry will propel your career, and picking the right company will propel your career, and then doing a good job will propel your career. So I think that there’s no magic bullet to getting a job. But working your network, sticking with it, and continuing to grow your skills are the three most important things.

Key Drivers of Growth Transformation

Lenny: Big part of this conclusion is don’t feel like your career needs to slow down in this period.

Carilu Dietrich: And I think if you’re in a job, some of my greatest career growth came in the economic downturns. In the 2000s, in the 2008. Because other people take their foot off the gas, and you can put your foot down. If you’re willing to learn more, hit yourself into new roles or new responsibilities that no one’s covering at your company. When they don’t hire tons of people for everything, there’s lots of open projects where you can raise your hand and grow. You just can’t be as focused on title and salary right now. You’re kind of building up value that you’ll be able to monetize on the other end of this recession or downturn.

How the C-Suite Drives Strategic Shifts

Lenny: Let’s segue to chatting about growth. And I thought it’d be fun to start with your story of running some very expensive ad campaigns. I know the founders are always kind of flirting with this idea of buying a bunch of billboards, running TV ads, maybe subway ads and bus ads. And you’ve done a lot of that and you’ve spent a lot of money doing that, and particularly non-digital advertising. And so I’m curious what you’ve learned from your experience and approach to this sort of marketing spend.

Carilu Dietrich: Yes. I’ve spent hundreds of millions of dollars on it actually. I ran global awareness advertising for Oracle, and did all of the airports, and the front page of the Wall Street Journal, on the back page of The Economist, and take over in the middle of Salesforce in downtown San Francisco. And we did the Ironman movie sponsorships, and the sports teams and arena sponsorships.

Trust Between the CEO and CMO

Lenny: That sounds very expensive.

Carilu Dietrich: Super expensive. And then Atlassian to a lesser degree, we spent several million dollars on different awareness campaigns to get chat noticed, or to associate Jira with the Atlassian brand. Advertising is sexy and super expensive for the benefits. It’s a multi-year benefit of awareness. People have to see things many times, and it has to really resonate with them.

So my advice to founders is that the most important thing is the quality of your product. Oracle spent a ton of money, and people still didn’t like us in a lot of ways because they had poor experiences with the salespeople, or they didn’t like Larry, or the product had kind of languished since it had been acquired by the company. So your product has to really be fantastic. And then also to do good brand advertising, it has to be sustained over a long period of time.

So Oracle had the front page of the Wall Street Journal, back page of The Economist, this boring advertising template with the red bar, but it made it memorable. We would do market tests, and two or three or 10 times more people would recognize the Oracle brand without the logo, because of the consistency versus SAP or or IBM.

So you really need to be thoughtful about spending consistently over a longer period of time, and a smaller amount on a fewer number of things can be really effective. So Snowflake, for instance, has always gotten credit for doing a billboard on 101, and people think they do lots of advertising. But for many years, it was only the billboard on 101. It was just sustained and strategic.

Why CMOs and CPOs Are Replaced Most

Lenny: So I guess two things that I take away from that is one, you can spend a lot of money, and if your product’s not actually incredible, it’s not really going to do much. And correct me if I’m wrong. And then two is sometimes, just one very targeted spend is worth a lot more than just blanketing a bunch of ads.

Carilu Dietrich: Absolutely. I was telling you a story that at Atlassian, we did a big advertising campaign on our HipChat product, which was head-to-head with Slack, and it was an Office Space spoof with Bill Lumbergh. But the product had some uptime issues, and some feature issues, and Slack pulled ahead, and the advertising wasn’t what would’ve made it or broken the product. It’s really the product experience, and the advertising just amplifies.

The Growth Stage: $30M to$500M

Lenny: I think you also shared with me this HipChat ad, that’s maybe my favorite billboard ever. And I don’t even know why looking back, but it made me laugh so hard. Back in the day, it was this meme of some early meme stick figure guy saying, “Why you no use HipChat?” Looking back I’m like, “Okay. I don’t know how funny.” But I think in the moment that was a really popular meme, and it really stuck with me.

Carilu Dietrich: Well if you think about the best advertising, it’s something that has a little twist of humor, or personality, or truth that sticks in your brain. So yes, that was a successful advertising. And kudos to my team, because of course I don’t write it myself as the head of marketing. But yeah.

And some of my other favorite ads are also others that highlight the customer. So New Relic did an advertising campaign around data nerds. When data nerds were not really popular, they were still nerds. And they had these tattoos that said nerd life, and they featured customers on billboards talking about cool data nerds. And some of those campaigns that really stand out have something that’s funny, unexpected, and then true to the product.

Strategies for Product Bundling

Lenny: I remember those, one of the ads featured, our CTO at Airbnb, Mike Curtis, and everyone was very excited to see his face on the Billboards.

Carilu Dietrich: Yeah, Salesforce has done a great job with those over the years too, really highlighting the customers.

Lightning Round Q&A

Lenny: So zooming out a little bit, you specialize working with companies that are going through hypergrowth. And you’ve worked with companies like Miro, Segment, Bill.com, which I don’t know if people know is just a massive, massive business. And also 1Password.

And on the topic of 1Password, interestingly I didn’t realize how big and how fast 1Password has been growing. And just last week I saw this report from Okta where they have all this interesting data about which products people are using, and they put out this report showing which products you’re getting the most new customers. And then on a different axis, which companies are getting the most users per new customer.

And there’s this six companies in this quadrant. Figma, Miro, Snowflake, Sentry, HubSpot, and 1Password, which blew my mind. And interestingly, you work with two of them. And so all that to say, what have you noticed about what is most in common with companies that are going through hypergrowth? What is most in common in terms of what has contributed to them being that successful?

The Philosophy of Hypergrowth

Carilu Dietrich: The biggest thing is an amazing product that people love to use. I mean ChatGPT is the most hypergrowth product that we’ve seen in history potentially, because people are so excited to use it and it’s working in interesting ways. So Miro, whiteboards were the number one most uploaded asset in Jira forever. Because people all get together and they write their ideas on a whiteboard, and then they need to remember it and iterate on it. And that bringing that concept to life just hit a cord that people wanted to use. And when one person uses it, another person uses it.

1Password similarly, I’ve been a 1Password user for more than 10 years. We used it at Atlassian, as a corporate. And then they have the family plan. So I used it at home and then my dad got elderly, so I had a family that I was the administrator for, and then I go into different companies and you bring it with you.

And one of the other companies I advise is Productboard. And I became an advisor of Productboard because 1Password’s CPO had it in another company, brought it into 1Password, rolled it out company-wide to get alignment and visibility on the product roadmap.

So in order to get hypergrowth, you have to have organic, inbound, and viral word of mouth. You can’t pay enough to grow at those rates and have a viable company, especially in this economic efficiency market. So has to be an amazing product, has to have some viral activity. So we just talked about Miro or Atlassian. You could have an individual person use it and then they say, “Hey, I’m going to present at this meeting with Miro, come join me on my board. I’ve got these confluence pages we’d set up as a wiki about these engineering topics, and I want your team to collaborate on them.” So those natural points where your users are selling to other people is way more efficient than having sales people that have to sell to other people.

And then I think the third thing is really riding the lightning, I would call it. So hypergrowth companies go through the stages of growth that would take other companies five years or 10 years. They’re going from 10 to 50, they’re going from 50 to 100, they’re going from 100 to 200, they’re jumping. And so they really need to keep hiring 2X and 3X leaders who have seen the next stage of growth. And then the people inside can be homegrown talent, but it’s tricky to keep up.

So my whole business is based on people who are trying to be homegrown leaders, but don’t know what the next stage of growth looked like. And so a lot of hypergrowth companies hire ahead, hire advisors. Leaders need to really think about mentors and friendships of people who know what great looks like at the next scale, because it’s going to be here before you know it. And so I would say those things. Amazing product, viral movement, and company that can ride the lightning.

Favorite Interview Questions

Lenny: I imagine founders listening to this that don’t have insane virality or huge word of mouth are like, “Is there no path to being a really successful company?” And then I think about companies that did succeed with other channels, like say paid or SEO. And so I guess the question for you is, do you need to grow in this environment, I guess, primarily through word of mouth, organic reality, growth engines? Or do you still see opportunity for companies to grow other ways, say paid, or SEO, or sales eventually?

Carilu’s Favorite Products

Carilu Dietrich: For sure. All of the things are important. I think what I wanted to say first as you were talking was that it’s easy to look at a company after they’ve been viral and be like, “That’s amazing.” I would like to start a newsletter. I have. It’s carilu.com. Lenny has a newsletter. How can I ever grow like Lenny’s virality? But Lenny started with one blog, and then another, and the consistency.

And when I look back at Atlassian, people would be like, “It must have been so easy to go from 100 to 500 million.” And it never felt easy. It was a slog to do exactly what you’re talking about. New features, listen to customers, strong SEO. Actually SEO was the number one marketing motion that we used, and SEM. We spent probably between 15 and 25% of our leads from paid search marketing at the time. Now I have a ton of customers that are pretty deep into account-based marketing.

Getting to virality and getting the hypergrowth is not a magic bullet. It’s consistency, customer obsession, incremental improvements across all parts of the business. So I think founders just need to double down on having a product that’s differentiated and does something that their customers really love. And each incremental step is a step forward.

Small Changes, Massive Impact

Lenny:

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Say that you as a company are seeing word of mouth in some virality, and you want to think about accelerating that, leaning into word of mouth. Obviously you want everyone to be talking about how awesome you are sharing with their friends. Is there anything that you’ve seen as a good way to lean into word of mouth and accelerate it?

Carilu Dietrich: I think there’s two or three things. One is really empowering the people in your company to be thought leaders. So early days, Atlassian’s founders were on all the developer boards. And in fact, I remember, we were maybe 150 million or 200 million, and Scott Farquhar the CEO was still participating and going back and forth in different dev forums when I was like, “I don’t know, should we elevate your status? Should we have evangelists and engineers that do this?”

And we did, right? And look, one of my clients now is Weights & Biases, the ML ops company helping lots of different AI companies with their ML models. And they have really thoughtful technical people who know more and write more on the blog and engage with their community. And that creates a word of mouth, because they’re providing both a product and concepts and learning. That’s one of the HubSpot secrets was all of their really thoughtful, helpful content, certifications for marketers.

So I think going back to summarize, word of mouth can be driven by thought leadership, which is hiring the right people to really be deeply engaged as super experts. Having a really strong content strategy that’s either in communities that already exist, online communities, open source communities.

And then third I would say building your own community. So no one sells your product better than your own happy customers. And if I go way back to the very beginning of my career, I worked on a marketing team where I owned demand gen just for net new prospects, and a peer owned demand gen just for existing customer upsell. And we would have different field events.

And the existing customer ones were smaller than if we’d invited the prospects and had more buzz. And the prospect ones were very salesy. Whereas if we brought them together and you had customers talking to each other and prospects listening, everyone had a better time.

So Atlassian, one of our secrets was this amazing user group community where we just paid for beer and a pizza, and we’d facilitate local in-city leaders, and people would meet up and talk about our products, and talk about development generally, and grow their careers and grow their network. So I think those are the three. The right people, the right content, and the right communities.

The Secret to Meditation

Lenny: As you were talking, I was reminded, I was just chatting with the founder of Gusto about their journey early on. And he said that for the first 200 customers, he sat there with them running payroll, watching how they react every step of the payroll process and how they feel at every moment. And that was a big part of what helped them build the product that people actually continue using, and love, and stick with. And if it wasn’t in person, it was on a phone call. And it’s like the epitome of doing things don’t scale, just like for hundreds of new customers watching them use your product. Pretty wild.

Carilu Dietrich: I mean that’s the secret. That’s the secret sauce. And I’ve heard some early stage startup advisors say that you should build processes that don’t scale first. Because when you’re in the super early stage seed A under 10 million, you’ve really got to go deep at that stage.

And in fact, I see that that’s one of the problems that companies experience as they get much bigger, when product managers can’t meet with customers, or they get limited customers, or maybe they can only meet with a junior user, only the administrator, and not lots of the users. So that insight into the daily struggles and experience of your customers, it’s harder to get as you get bigger I think.

Lenny: I want to drill into Atlassian. You’ve brought them up a couple times. You were at Atlassian for a long time. You were there from early days of growth to IPO. And one of the most interesting elements of Atlassian and something that comes up a lot on this podcast is product led growth.

And Atlassian I think is one of the most classic examples of a product led growth company. And from what I understand, y’all waited a long time to hire your first salesperson. So my question is what did you learn from that experience about when is the right time to start leaning into sales and hiring sales, and what are the trade-offs of waiting longer or doing it earlier?

Carilu Dietrich: Atlassian was a super unique company at a super unique point in time, because the founders never took outside money except for one late stage financing to buy out some early employees, to give some liquidity. So we never had VCs or private equity that had a voting share that was significant, that could overrule the founders.

So the founders were going through this experiment that turned out to be really successful, where they took all the money they would’ve spent on a sales org and plowed it into engineering and product. I’m going to pull up a slide here that tells the Atlassian story about the ratio of the sales and marketing to the product and engineering.

Lenny: Amazing. And by the way, check this out on YouTube if you’re listening to this and check out this slide.

Carilu Dietrich: So this is a representative sample of what we did in Atlassian’s history, and what ratios still exist today, even several years later. Where we spend way less on sales and marketing. Marketing spent less than other marketers. And also we had almost no sales org, or a sales org that was really focused on renewals, or now an assisting sales org that’s focused more on enterprise. But relative to other companies, a much smaller, much more efficient sales org. And we took all that money and put it into product. So here we’re spending two times, three times as many dollars in R&D as many other companies that we’d benchmark against to make a product that really sold itself.

Lenny: It’s interesting. So I’m looking at the slide. And again if you’re listening, check this on YouTube because it’s pretty crazy. This slide of bar chart of spend in sales and marketing and R&D, and Atlassian is the very lowest amount of spend in sales and marketing, and the highest spend in product. And it’s interesting that it’s from 2020, so it’s not even in the early days. It’s like still today basically.

Carilu Dietrich: Right. I’m going to close this down and keep telling you a little bit more about it. There’s some unique things that people can take now and incorporate. So the real strategy in sales, sales is the most expensive vehicle, right? Expensive people that spend a lot of time. So the Atlassian model was to sell only to people who were already customers really. If several people or a couple groups had purchased, we’d help them with their renewals. And now in the later incarnations of our sales orgs at Atlassian, it helps a lot more with larger enterprise companies who need enterprise deals, or does more cross-sell and upsell, but doesn’t really do prospecting. Net new prospecting is a really expensive way to get new customers.

So we see different trends coming now with companies, because almost no one can do pure product led growth. Because your investors want to see accelerated growth, and most people believe that adding an SDR or adding an AE will add a predictable amount of revenue. And so it’s difficult because product led growth and sales have to coexist.

But the whole transition in marketing that’s happening to account-based marketing and intent-based signals is trying to do some of what we were doing at Atlassian, only to engage salespeople with customers that are actually likely to buy. And if you look at other hyper-growth companies, Airtable, Miro, both of those I know from the inside have had strategies where the salespeople really only engage after some threshold has been hit of number of users that have already been paying for the product on their credit card. But sometimes it’s a high number of 20, 40 people at an account have to be engaged before a salesperson engages.

Lenny: Based on that, what is it you recommend to founders these days that maybe are product led and just self-service [inaudible 00:40:00] oriented. Do you kind of take this experience and wait as long as you can to hire your first salesperson? I know it’s very specific to the situation, but what kind of advice do you generally give?

Carilu Dietrich: You and I are both like [inaudible 00:40:14] who was just on your podcast earlier this month. Product led growth depends so much on your product and your buying market. There’s some buying markets that are less likely to use salespeople, and you need to go in from the beginning. HR might be one, right? Whereas a lot of the hyper-growth companies in the dev tool space can use product led growth because developers both hate failed people, and really love to research themselves. So you see [inaudible 00:40:47] taking off because people engage and kind of self sell.

So I would recommend, get closer to their customers and read the signals. If your product is good enough, the people can get time to value in a couple of days instead of weeks or months. You can have a product led growth motion. If your product needs to be put in context, and customized, and assisted, sales teams sometimes are expensive services arms to cover over product issues and help customers buy it until it’s fixed. Or if you’re in a market where your buyer just really doesn’t buy online with research and a demo, then you need to have salespeople. But I would say try not to hire too fast and too far ahead in sales and inside sales, because it seems like it’s going to add revenue, but it actually is a huge cost and a huge drain on the business if the product isn’t getting that kind of resonance.

Lenny: I just had a conversation with the founder of Retool for this series that I’m working on, and he basically found the same thing you found where they thought it could be a product led experience where you’re building internal tools using their product, but it turned out nobody really understood how to do it themselves and it took a lot of handholding to make it work. So they became sales led from the beginning, even though it feels like a tool that has a lot of potential to be product led and self-service.

Carilu Dietrich: I think the other hybrid I’m starting to see is people who turn their SDR, sales development reps, into sales engineers, researchers. So instead of having a salesperson who’s like, “Would you like to have a meeting with another salesperson?” The first touch for customers that are maybe kicking the tires or trying a product led growth is a person who can help guide them on the path. And I like this hybrid nature because basically it extends product led growth, but helps people in this case where you’re talking, where the product itself isn’t so intuitive that you can get all the way to the buy itself.

Lenny: It also sounds more fun to talk to a sales engineer than a salesperson.

Carilu Dietrich: I know. I always wanted to be a sales engineer. I was a salesperson, and I crushed on the sales. Engineering team who knew everything and could draw all the architectures.

Lenny: Oh wow, I didn’t know that. A couple more questions around this stuff. So you’ve worked with a lot of different companies. And you kind of come in and help them figure out ways to grow faster, unlock growth opportunities. What do you find often gets most in the way of making big changes to the way they approach growth and approach different growth channels? And maybe on the flip side, what do you find is most essential to making big changes at a company around how they think about growth?

Carilu Dietrich: The big growth levers are pretty consistent across companies. You start with one product, and you have a couple choices on how the go-to-market works. Product leg growth or sales assisted. You get a little bit bigger and you add an incremental product, or you start to add new segments. You’re going to focus on a vertical like finance, or you’re going to go global, or you’re going to add new sales channels like a partner channel.

And what I’ve seen with the big growth levers is that it can’t ever be an individual department’s goal without being a cross company strategy goal, if it’s really going to make a difference.

So you’ve talked about it in your newsletter and on your podcast, but growth isn’t just like a person in the engineering team that hacks by themselves. It really has to be funded and thoughtfully constructed so that there’s the right content and experience, and product features, and virality features a customer to continue to drive growth.

And similarly, lots of companies right now are trying to move upmarket because the economy has created so much pressure in S&B that they’re going to try to move to enterprise, or they’ve trying not to sell as much just to tech companies because tech companies are under pressure and so they want to move to different parts.

Sometimes the marketers get blamed or sales gets blamed, we don’t have enough leads. But really it’s a company strategy problem where the company hasn’t decided, “Hey, we’re going to all move in this direction and if we’re going to sell the enterprise, marketing’s going to bring in leads, products going to have a roadmap, and some meaningful features to enterprise. The customer research is going to start thinking about them. We’re going to hire some customer support people who know how enterprises work. We’re going to hire some salespeople who sell differently to enterprises than S&B.” The big growth levers are strategy problems, not individual departmental problems.

Lenny: And what do you find needs to happen for that to change? Is that like CEO needs to be like, “Here’s what we’re doing, everyone get on board,” or something else?

Carilu Dietrich: I think it can come either way in the C-suite, right? So my job, I advise hypergrowth CEOs and CMOs of companies, 30 million to 500 million. Often if I’m advising a 30 to 100 million company, the more junior marketer with a CEO who’s often a first time founder, who doesn’t necessarily know if the marketer’s good or not. Hasn’t done run marketing before, doesn’t know if they should trust what the marketers saying.

So often the marketer is saying,” Hey, we’re having problems because the company’s not delivering on this promise you want us to sell.” And sometimes the CEO doesn’t know if they can trust it, a judgment. And so in that case, someone like me who’s an advisor comes in and is like, “That’s right, it’s not a marketing problem, it’s company strategy problem. Let’s have an offsite and build some OKRs where we all go after enterprise and we win it together.”

You’ll see at bigger companies or when a new CMO comes in with more senior or seasoned, they’ll have the social capital to push back into the executive suite. Or a new head of engineering who will say, “Look, I know you want to move ahead faster, but we actually have to catch up on this technical debt.” And they’ll push back and get that strategic space that they need. So it can either come from the CEO or it can come from the C-suite really coming together to solve those problems, instead of pushing them under the rug.

Lenny: You touched on this nuance that a lot of times, there’s not a lot of trust between the marketing head and the CEO. And I’m curious what you find helps build that trust.

Carilu Dietrich: There’s a couple things that are really critical for senior marketers, and I actually have a blog coming up based on a podcast I’ve recorded about why CMOs mostly get fired. And the issues are generally one, that the CMO isn’t focused enough on the revenue. So some CMOs get focused more on the pipeline or the awareness, and the CEO doesn’t feel like they really have a partner in driving the revenue. Or they don’t feel like the CMO really has a handle on what will drive the revenue.

So marketing’s tough because it’s a big spend category, and lots of the spend doesn’t convert in quarter. Some of it doesn’t convert in year. Advertising campaigns, some take multiple quarters.

So it’s really important for CMOs to have a handle on the metrics, a solid prediction of what growth levers they can use, and to be able to talk in the terms of the CEO and the board.

And I think that that’s the biggest gap that I generally see. And then of course, there’s a whole bunch of table stake stuff. They have to be running their business well. They have to be a good leader that people want to work for. They have to hire a great team that elevates them and the company, they have to be thoughtful and strategic about the market space that the company’s in. They’re not just working the levers in the factory. They’re thinking, “What new markets should we enter? What new growth areas should we employ?” Like we just talked about. “What new companies should we acquire?” They also need to be thinking ahead. And I think being good on metrics, good on strategy, and good on market helps CMOs spar with CEOs in a way that builds trust.

Lenny: It’s interesting that you say, that blog post you titled Why Most CMOs Get Fired, and it connects with something. Casey Winters noted, that most CPOs also get fired chief product officers. I forget the quote, but it’s something like, “The most you can help for is a couple swings at the bat before you get fired as a CPO.” Why do you think this is so common for these chief C-suite roles to startups to not work out?

Carilu Dietrich: They’re incredibly hard jobs. The chief product officer and the chief marketing officer are both strategy jobs with difficult to measure results because some of them are direct and some of them are indirect. And I think both of them get swept up when a company’s not performing well too. If company’s not performing well, you can kind of swap out the head of product, and the next one will be more strategic and deliver faster.

And in fact, I’ve worked in one of the roles, the CFO was really after my chief product officer, and ultimately got him fired because he wanted to move everything offshore, and develop faster, and he didn’t want to re-platform, and he didn’t want to deal with the technical debt. And the CFO was sure that it was the CPO’s fault, and then they got rid of the CPO, and the CFO tried his plan and it didn’t work. And then you bring someone in who’s like, “No, that guy had the right plane.”

So both of them are tough jobs. And they require a high bar of excellence, a high connection of trust, and then I think just endurance to keep going and find the next role where you’re really a fit and the company really has momentum.

Lenny: It also reminds me, I was just talking to, I think it was Canva. Where their first engineering hire is now their CTO still, and their first marketing hire is their CMO still. So it does work out on occasion.

Carilu Dietrich: It works out on occasion. And in fact, I’ve been playing around with a 10 part series about those CMOs in the CMO world, because there’s about 10 to 15 CMOs who have started when it’s really small and grown all the way. And they’re the ones we really want to learn from. And I know a lot of them and really admire their work, and have learned so much.

Lenny: You should absolutely do that. That sounds very cool. You talked about how you work with companies from 30 million to 500 million. What is it about that stage that’s unique, and what happens after 500 million, and what’s the difference before say 30 million? I know it’s not an exact number, but how do you think about that range?

Carilu Dietrich: No, it’s not an exact number. My bottom number is because there’s this early stage of product market fit where the founder and the company are trying to figure out who their real ideal customer profile is, and can they sell to them consistently?

So I’ve worked for some early stage startups where we’ve tried lots of different things, but they’re not repeatable. You can’t scale it. “This product works for this. This product works for this too and it works for this,” but those are all kind of unique cases studies. And so my skill is in helping people scale.

And so if they’ve already found product market fit and they’ve gotten some funding or they’re bootstrapped, but have enough funding to really be trying to build out marketing in a marketing team, that’s when I know what each stage looks like. So I know what $30 million great teams look like, and 50 million, and 100, and 150 million, 200 million. My ride at Atlassian was from about 100 to 500.

And then over 500, the act of going public, being an early stage public company, I know what that all looks like. And then beyond that, there’s public company consultants I think more, that do more specific things. I more help the CMO and CEO structure for the next stage of growth, because they’re going through it so fast, they haven’t hired someone yet who’s already seen.

Lenny: Got it. One very nuanced question I want to ask you is about bundling. So there’s HipChat and Slack kind of ate their lunch, not necessarily through bundling, but there’s Slack. And then Slack, I don’t know if it’s true, but it feels like Microsoft Teams is eating their lunch with bundling. And I’m curious, what do you think of bundling as a strategy to win long-term? And also, how do you compete against say, a Microsoft that may one day bundle your product for free, and you might be in big trouble?

Carilu Dietrich: I think it’s two separate questions, so let me take them separately. The first is, what do I think about bundling? So small and medium-sized companies will go from being a single product company to a multi-product company in order to progress. Because you need a diversified financial model, because you need to be able to sell new products into your customer base who should already be friendly to you if they like your products. And because you need to really expand your total addressable market to get to be $1 billion or$2 billion company. But I believe in bundling is a growth strategy.

Specifically for product led growth companies, bundling is not a great land strategy. So at Atlassian, we had a number of products and experimented with different bundled lands. And it really slowed down the product led growth motion. So we ended up going back to land with a single product, high velocity, single person uses it quickly starts to get value, and then come in with other things.

So from that perspective, product led growth bundling is not very effective. Bundling for a sales led motion is pretty effective when you’re at the right stage of growth.

And then as far as the question of competing against Microsoft, there’s these two parts of the philosophies. A best of breed and an all in one. An Oracle was an all in one, and Microsoft is an all in one. You can buy all the things and your CFO can get a discount by spending a whole bunch of money on a bunch of things. But in the all-in one, some of the pieces aren’t as good as the best of breed.

And so Slack for a long time was the best of breed. People were willing to pay more because they thought it was markedly better than the other instant messaging options.

But there’s shifts between best of breed and all in one in economic wins. So right now, CFOs are putting the squeeze. Is Slack really that much better than Microsoft if the Microsoft one is free with all of our other purchases? It’s tough. It’s tough to go head-to-head with a powerful, big investing, all-in-one competitor. The only way to win is to be the best and have a product that’s so much better, that it’s worth the extra money.

Lenny: Interesting. So essentially in a tough environment, bundling is most effective almost. And then this other interesting point about [inaudible 00:55:47], you want to stay focused on one specific pain point. What is it that Atlassian tried to do that they tried to pitch all your planning products in one suite? Is that kind of what we-

Carilu Dietrich: Well, Jira was the issue tracking. And then we also had Confluence, which was the Wiki page. So let’s say there was a business bundle that could have been HipChat, Confluence and Jira. Or there were developer combinations that could have been Jira, Bitbucket, and maybe Confluence too for an engineering team.

Basically, if you have to evaluate multiple products to purchase something, it’s not a fast and easy online self-service buy. Because you’re like, “Do I need all three products? Can I break them apart? Do they all work? Are each of them best of breed?” Whereas if you’re like, “I need issue tracking, I’m going to buy Jira, this looks good. I’ve tried it out, I’m ready to go.” That can happen in seven days. Whereas if you add in multiple products, it takes more days and just leads to fewer conversions.

Lenny: That makes absolute sense. I can see someone thinking the complete opposite and then now realizing how we see. I see why this isn’t working.

Carilu Dietrich: You should always test it. Right? I mean, the secret to product led growth is can you test it? And so we tested everything. We tried bundles. We didn’t try bundles. We tried different things in the bundles. We tried different days. Data led insights are better than anything any pundits would say on a podcast.

Lenny: Amazing. Well with that, we’ve reached our very exciting lightning round. Are you ready?

Carilu Dietrich: I’m ready.

Lenny: Okay. What are two or three books that you recommended most to other people?

Carilu Dietrich: The number one book is a life book called Tao Te Ching, the Stephen Mitchell translation. And the Tao Te Ching is a philosophy about the flow of life. And I love it. I’ve carried the Pocket Guide with me for 25 years.

The second one is business focused. Never Split the Difference, which is a great book about negotiating written by a former CIA hostage negotiator, which also helps me with negotiations at work and with my children. So that’s a great book.

Lenny: Actually, I’ve been trying to read that book on audio. What’s something you’ve taken away from me? Because the stories are so interesting and I’m always like, “What should I actually do in my day-to-day life?” What stuck with you?

Carilu Dietrich: It’s kind of the obvious thing that I wasn’t good at. It’s that you just really want to put yourself so deeply in the shoes of the other person, that you can figure out what make the win for both of you, right? Basically he says, “You can’t win the negotiation by strong arming what you want. You really get to get to a win-win,” which is probably every negotiation book ever. But he texturizes it so much. So I just felt like I was really able to… In my last office, we moved last year. I actually had the CliffNotes of his book printed out and posted on my wall because he had a series of questions to help you get deeper and deeper into the mindset behind people.

And connected, but not connected the book How To Win Friends and Influence People, that’s the 1932 bestseller, is basically that. People don’t want to hear about you. They want you to be thinking about them. And then you can make friends with them, or you can negotiate with them, or you can get your hostage back.

Lenny: I read How to Win Friends and Influence People when I was very young. And specifically, the chapters about there’s no better sound in the world to someone than their name. Carilu.

Carilu Dietrich: It’s true. Thank you. You said it correctly.

Lenny: Okay, moving on. Favorite recent movie or TV show?

Carilu Dietrich: My favorite movie is Everything Everywhere All at Once. It’s basically a sci-fi about all the different ways your life could turn out if you made different choices. And it was really a mind bender that made me think about all the different ways tiny decisions have changed my life, but then also an appreciation for the life that you have. At the end, it doesn’t ruin the story, but she has this love of what she has, even though it’s not as good or as different as some of the other options.

Lenny: I love it.

Carilu Dietrich: So I bought this poster. I don’t think you can see it on the bath, but it says, “Gratitude turns what we have into enough.”

Lenny: Very Buddhist.

Carilu Dietrich: I like it. Read the Tao Te Ching.

Lenny: Not a Post-it, but art. Another teaching from Carilu. I think this needs to be a second newsletter of yours. Life advice.

Carilu Dietrich: Which is funny. I’ve been thinking about that one. It would be called The Tao of Hypergrowth.

Lenny: Oh my God. I love that.

Carilu Dietrich: And actually, I was thinking about doing it and taking actual clips from the Tao Te Ching, and doing textural analysis about how it applies to our. I’ve been thinking about this actual podcast for a while because I used to want to do the… I mean blog, the Tao of Parenthood. Because basically parenting, you try to control and fix all the things you didn’t do right in your life. But actually, it’s the act of providing freedom that lets them go out and explore and then come back to your way of being. So, I don’t know. The Tao Te Ching, I love it.

Lenny: I see so many opportunities. You got to stop what you’re doing. Just write all these things.

Carilu Dietrich: I know. But I love the hypergrowth customers, clients.

Lenny: All right. Next question. What is a favorite interview question that you like to ask?

Carilu Dietrich: So this is a little heavy, but it actually is my favorite. It’s, “How many people have you fired? And tell me about each of the experiences.” So the reason I ask this question is because generally, I’m managing teams of managers. And generally, I need people who have managed many people for a longer period of time. Or even if they’re junior managers, how long and how many people they’ve managed is indicated by how many people they’ve fired. Because if you’ve never fired anyone, then you haven’t managed very many people for very long, unfortunately.

And firing people is the hardest part of a leader’s career. So how they talk about it, their compassion, and their need to drive the business, and the circumstances, “Was it layoffs? How did that work? Did you have to performance manage someone out? How did it work? Did you just have to restructure the team because of business goals? How did it work?” Gives you a lot of insight into their experience and their humanity in a way that they’re not prepared for. So you really get the real story, and get a sense for what they would be like as a leader under a lot of pressure and difficult situations.

Lenny: I’ve never heard that one before and I love it. Reminds me of a episode with Matt Mochary where we talk about how to lay people off really successfully and elegantly.

Carilu Dietrich: It’s a hard.

Lenny: Yeah. Next question. What’s a favorite product that you’ve recently discovered that you love?

Carilu Dietrich: So I follow my favorite products to the companies that I advise. I love 1Password. I’ve got my 85-year-old grandfather and all of my family and friends set up on it. I love the cross-platform nature.

I love Miro and whiteboards. I joined Productboard because of this cross-company alignment and views into what’s coming up on the roadmap, which is really the most important thing for the company. Momentum, as we talked about, having a great product and a great product strategy.

And then I’m dabbling in all the AI things. I want to be excellent in AI visualization and art. I’m experimenting with Midjourney, but still kind of flailing. I’ve hired my 13-year old as my strategic advisor. And yeah, I’d love to work for OpenAI and ChatGPT. It’s really interesting.

Lenny: What’s something relatively minor that you’ve changed in the way a product is built or just the company operates, that has led to tremendous impact on their ability to execute?

Carilu Dietrich: On the product side, one of the concepts that I really like is the Amazon concept around writing the press release at the beginning of a product ideation. So one of the issues between marketing and product is the product will work so hard on something, and there’ll be lots of different features, that it won’t really be a theme that the marketing team can talk about. And then someone hands it to marketing and says, “Make this marketable.” One of my mentors had this comment, “It’s a bag of doorknobs.” What do I do with this bag of doorknobs? Who wants to buy a bag of doorknobs? They want to buy the door and the concept.

So I like this idea of writing a press release. Start with the end in mind, and then negotiate. Is this good enough? Will this really resonate? Or is this really what we’re trying to build? Or is this really the outcome we’re trying to get with the product? So I’ve heard about Amazon do it. We experimented with it at Classy. I haven’t done it at mass scale, but I love the concept.

Lenny: Final question. I know you’re a meditator. We’ve talked a little bit about your Buddhist nature. What’s one tip for people that have been trying to meditate and just can’t make it happen? What’s your one tip for helping people meditate more often?

Carilu Dietrich: So I’m a cheater because I was groomed to meditate. I don’t remember how early, but I remember that the first meditations my mom had me listen to was a rainbow butterfly as I fell asleep when I was in kindergarten.

So I’ve been meditating my whole life, with mixed success. And the real secret is just that there’s no right way, that there’s no wrong way. That it’s just making the time to be present, and breathe, and sense, and be here now.

And so I use guided meditations mostly, because I’m not the best at quieting my own mind. I’m thrifty. So I use some free meditations. I use Tara Brach, who’s a great meditator, who has short and long concept meditations.

And I like this old one called Meditation Oasis, which actually isn’t in publishing anymore, but it’s still a podcast. And I re-listen to all theirs over and over. So stick with it is the secret to meditation, and any benefits you get from being present in meditation, hopefully carry over to be being present in life.

Lenny: My whole body just relaxed as you were talking through all that. So you have a skill. Carilu, this was amazing. We learned how to grow products, how to live better lives, how to become more mindful. Two final questions. Where can folks find you online if they want to learn more, reach out? And/or how can listeners be useful to you?

Carilu Dietrich: Follow me on LinkedIn, or I have a new blog carilu.com on Substack. Thanks to Lenny for the inspiration. And I still have one more advisory slot open, and I’d love to work with more AI companies. I just joined Weights & Biases in the ML op space. But if you know of other great scale up AI companies, I’d love to help junior marketing executives or first time founders see what the next stage of growth looks like and get there.

Lenny: Amazing. And again, if they are interested in that, how do they reach out to you?

Carilu Dietrich: On LinkedIn or through carilu.com.

Lenny: Amazing. Carilu, thank you again so much for making time and for being here.

Carilu Dietrich: Thanks for having me, Lenny.

Lenny: Bye everyone.

Carilu Dietrich: Bye.

Lenny: Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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