Growth lessons from Darren Chait (beehiiv CMO /ex-Calendly)

Darren Chait is not trying to make beehiiv the brand readers remember. As CMO at beehiiv and former Head of Growth at Calendly, he wants creators, publishers and B2B teams to own the relationship with their audience while beehiiv stays as the infrastructure behind newsletters, podcasts, websites and digital products.

That stance comes from a marketer who learned growth under unusual conditions. Darren began as an Australian corporate lawyer, co-founded Hugo in San Francisco, then led growth at Calendly with millions of meetings booked each week and close to a million signups a month.

His view of marketing is blunt: the best CMOs think like CFOs. That lens shapes how he starts a role, why he treats growth bets like a portfolio, and why he believes a newsletter only works when someone actively wants you in their inbox.

This interview has been edited for clarity and concision.

Tom: beehiiv deliberately sits behind the creator’s brand, and readers are not naturally your next customer. How does that philosophy shape the product and the growth model?

Darren: One thing we would hate is for our customers or brands to be building a beehiiv newsletter. They are building a Demand Genius newsletter, or their own brand, and we are the infrastructure that enables them to publish newsletter content, host a podcast or sell an ebook. Their brand is front and centre.

I find it interesting when people say they are building a Substack or they are tweeting, because that supports someone else’s platform. It is your knowledge, your expertise and your perspective. Philosophically, it is really important to us that you own your audience and are not supporting another business’s brand.

I think about it as Shopify versus Amazon. If I sell a product through Amazon, Amazon controls who sees it, how it ranks and takes a cut. Shopify is infrastructure for Tom’s store, not a Shopify store. That is how we view beehiiv. We do not take a cut of what anyone earns on our platform, and it is about custom domains, white labelling, your own site and your own brand. You can turn beehiiv branding on or off. It is your business.

Calendly has this remarkable product-led growth loop. When I book time with you, I see that you sent me a link powered by Calendly, I have a good experience, then I can sign up and do it myself. At beehiiv, especially on free plans, we do see traffic and signups from footers, but our growth model is not about turning the reader into the publisher. Only a small percentage of subscribers are going to become great creators tomorrow. It is not naturally a viral loop.

We would rather be indispensable to you and help you make money and scale your audience than try to get a few signups from your audience because they know where you are hosted. We have a free tier up to 2,500 subscribers, and our ad network is another significant revenue stream. It is just shy of a third of our revenue. We source ads that are relevant to a publisher’s audience, they can drop them in, and we pay for each click.

Tom: You started as a corporate lawyer in Australia and ended up leading growth at Calendly. Which part of that path formed the way you think about growth?

Darren: I had a very non-conventional start. I started as a corporate lawyer in Australia and did not like it much at all. I learned a lot, but professional services and billing by the minute, or in six-minute increments, felt crazy to me.

I was interested in the inefficiencies there, then got into tech because I was excited about making money while I slept. Product-led growth does that. The idea of building funnels, going to sleep and waking up with customers was mind-blowing.

After a couple of years I moved to San Francisco and co-founded Hugo, a meeting workflow platform for notes, agendas, actions and summarisation before the AI explosion. I naturally ended up focused on growth, which sat at this intersection of marketing, product, numbers and the technical side. In summer 2022, Hugo was acquired by Calendly and I came in to lead growth there.

Calendly was the most formative because you learn growth with real volume. In a startup, you do not have the numbers to experiment properly. Calendly was booking millions and millions of meetings a week and had close to a million signups a month at one point. We could try anything. I could run an experiment in 24 hours on some funnels, which was an amazing hands-on crash course in any channel or product-led growth lever.

Tom: You have said the best CMOs are actually CFOs. What did that advice change for you?

Darren: The advice came from Shane Murphy-Reuter, who was the CMO at Webflow and then became president at Calendly. He told me on day one that to be a great CMO, you have to be an awesome CFO.

As I dug into that, I realised the only way to be an effective CMO is to deeply understand your business. You need to understand the waterfall, the mechanics, what drives traffic, signups, conversion, expansion and churn, and the different levers that affect each stage.

If you understand your business better than anyone else, as if you were the CFO, you will be an incredible marketer. Marketing is knowing which channels and tactics to use when. There is no shortage of ideas. You can sit down with Claude and ask for ten campaigns. The easy bit is generating ideas; the hard bit is knowing which levers to pull and where to apply them.

Everyone wants to make more money, assuming that is the goal. You can drive more traffic that converts the same way, improve the quality of traffic so it converts better, improve average revenue per user or average order value, drive expansion or improve retention. Understanding all of that is what lets me apply the hands-on work, the copy, the creative and the optimisation. At beehiiv, week one was building the waterfall, building dashboards and deeply understanding the business, not sitting with a whiteboard coming up with the next out-of-home campaign.

Tom: When you join a marketing leadership role, how do you learn the business quickly enough to make good bets?

Darren: I start with three things. Step one is building the dashboards or spreadsheets, or whatever helps me understand the business. I interview a lot of people internally, get access to data and rebuild the basics: how many people hit the website each month, what percentage signs up, what percentage activates and what activation means.

That has never been easier. You can use Claude, connect MCPs to analytics platforms, and if you do not know SQL, Claude can generate it. I still need analysts, but not for basic reporting. I need them for insights and deeper work.

Step two is the customer side. It sounds clichéd, but you need to hear from customers directly. Listen to call recordings, email customers, use platforms like Wynter or Respondent if that helps. Ask what beehiiv does for them, what they would do without it, what they did before, what would lead them to churn and how they describe the value. After five, ten or fifteen customers, the penny drops quickly.

Step three is learning from the team. There is a lot of institutional knowledge, but you have to thread the needle because “we have always done it this way” and “that never works for us” are not helpful by themselves. I do not need to reinvent the wheel. Once I have the data, the customer voice and the team’s learning, I can think like a portfolio manager: which bets are big, which are small, which are safe and which are high risk.

Tom: Calendly had huge volume and a discrete scheduling problem. beehiiv asks customers to choose a platform for their audience. How does that change the growth work?

Darren: At Calendly, with that volume and hundreds of millions of ARR, we looked at things incrementally. What happens if we make this change to the booking flow? What if we expose free users to this next time they come into the app? What can we do from a lifecycle standpoint? You measure carefully and make go or no-go decisions. It is much more scientific.

beehiiv is more about big swings. The business is doubling year on year, and it is very hard to double a business by making a small change to a checkout flow. We should still make those changes because I do not want to waste percentage points of conversion, but that will not be enough. We need big campaigns, big stories and big launches.

The product is also more complicated by design, even if it does not feel complicated. When someone signs up for beehiiv, they are making a platform decision. They might be moving an audience, starting a newsletter, hosting a podcast or building around digital products. The funnel is longer and more complex than Calendly, where the tool solves a very discrete problem.

My dream campaign would be out-of-home. I would take over a couple of cities with an insane out-of-home spend, because brand is the biggest moat you have in 2026. If I take over the subway station you get on and the station you get off, you might tell someone beehiiv is everywhere. I may only have hit two stations for $50,000 a pop for a week, but if I know our ICP lives in one area and commutes to another, that can surround the right people.

Tom: AI is removing a lot of production work. What still has to stay with the marketer?

Darren: I do not think marketers lose anything by using LLMs and AI tools to do their jobs. The speed at which they can get things out means they can learn more. The mistake is outsourcing the job, just as a leader would make a mistake by living in slide decks and telling teams to “go have fun” without caring how the work gets done.

AI tools are giving everyone an army of slightly more junior employees, even if you are an individual contributor. Poor performers are easy to deal with because you can cancel that agent.

Judgment still matters. When I studied accounting, we learned ledger journal entries even though tools like Xero, QuickBooks and MYOB automated a lot of that work. Marketing is similar. A good designer can use AI to create variations, but they still know how to push pixels and edit design. A good content marketer still needs to know how to write, tell a story and recognise what great looks like.

The biggest shift for me is connecting LLMs to the tools I use. MCPs have changed how I work because I can query Ahrefs or Semrush, connect to analytics platforms, schedule jobs and get Monday morning context without spending hours pulling CSVs. That busy work used to take hours and did not add much value. Now analysts can spend more time on real modelling, regression analysis and business decisions, not just reporting and dashboards.

Tom: What separates a newsletter someone wants in their inbox from another email campaign?

Darren: A newsletter is real knowledge from someone I trust, that I have subscribed to, teaching me or sharing something I care about. That is a big transaction. Someone has given you their email address and permission to enter their inbox every week, month or day. It is not a feed they scroll past or a Chrome tab they close in three minutes.

Successful publishers on beehiiv are not usually producing complete newsletter content with LLMs. They might use AI for outlines, subject lines or to understand what resonates with their audience, but the core is their brain and their perspective.

Consistency matters more than people realise. If Kyle Poyar publishes regularly, I may not be able to tell you the exact day, but if it has been a while I lose the habit, trust and expectation. That cadence is critical.

The other trend is multi-channel publishing. Build the newsletter audience, then send people to a podcast, a guide, an ebook, a webinar, coaching, a digital product or a website that brings it together. At that point you are more than a newsletter author. You are a publisher or creator with a direct relationship, rather than someone relying on an algorithm to decide who sees your work.

That does not mean every newsletter has to be built on one person’s name. Carta has a unique perspective because it sees cap tables, compensation and outcomes through M&A or IPOs. Time has a strong newsletter product because people trust the brand and the reporting. HubSpot has acquired three newsletters in the last year, and B2B brands like Ramp and Brex are realising that high quality thought leadership can become pipeline.

The difference from email marketing is the relationship. A newsletter is someone saying, “Here is my email address. Please give me more of this every week.” Email marketing is usually you pushing something onto someone who has not engaged in the same way. In a newsletter, I think of my audience as my crew. They want to be there, learn something, share something, visit my site, listen to my podcast or buy my products.

For another example, I like Growth Daily by Marketing Max. It is valuable curation for marketers: what happened, what algorithm changes matter, which campaigns worked or flopped. It is also impressive how naturally he promotes his product and drives a funnel from high quality content to leads for his business.