CEO -> CTO -> IC 🪃
Scratching a passionate itch, catching the PMF lightning twice, and an unlikely B2B brand bet.
Welcome to the 95th edition of The SaaS Baton.
A fortnightly newsletter that brings you hand-curated pieces of advice drawn from the thoughtful founder-to-founder exchanges and interviews taking place on Relay (curated with 💛 at Chargebee for Startups) and the interwebz. So, stay tuned!
In this edition, you’ll find the following instructive and inspiring pickings:
#1: HashiCorp’s co-founder, Mitchell Hashimoto, relates how his role evolved from a founder-does-everything start to a spirited reclaiming of what he had always wanted to do.
#2: Amplitude’s co-founder and CEO, Spenser Skates, explains how new innovations and mature product processes often pull in opposite directions; and how that realization led to their second largest success.
#3: tl;dv’s co-founder and CEO, Raphael Allstadt, goes beyond the surface sheen of their bold, original foray into comic B2B skits and talks about the thinking behind running with this unconventional channel.
🗞 Recently on Relay:
➡️ Heuristics and Hunches (April 19th) — “I Don’t Think You Can Have a Great Product Unless It’s Freemium” and Other Notes on Growing in an Established SaaS Category with Loops’ Co-Founder, Chris Frantz
— Not just another email tool
— Selling into an established category
— Moving towards a self-thinking app
— Aiming for an unclaimed vertical
— Introducing freemium confidently
#1: CEO -> CTO -> IC 🪃
(From: HashiCorp’s Mitchell Hashimoto) (Source: The Stack Overflow Podcast)
I was naive, I guess, or so young, mentally. As I had never done a startup before…I didn’t really know what to expect. My original thought was that I was so passionate about building these tools, I would start this company and I would be able to spend all my time building these tools.
That couldn’t have been farther from the truth and reality.
One thing I quickly realized was (and I tell new founders all the time) when you start a company around your passion, it’s not to enable you to work on that passion, it’s enabling you to enable others to work on that passion and just realize that dream or that vision.
So you don’t get to really be hands-on. I would say, I was hands-on. As much as I could…for the first year to three years, depending on how activity ebbed and flowed. But I was splitting my time so much with the managerial duties and executive duties.
As much as you could call someone an executive at that stage, but it was like financial management, fundraising plans, ensuring growth, thinking big picture, how are we going to commercialise, thinking about the next X hires that we have to hire. Things like that.
It settled in really quickly. I think within the first eighteen months I was programming as much as I could but probably working very long hours to do other stuff too.
…
One thing I don’t want people to think is like I hated not programming… I didn’t dislike those [other] jobs. I found being a manager really rewarding in a lot of ways. I loved helping people grow and being a good manager (I tried to be, most times hopefully).
But what I realized was that I drive a lot of my passion really was programming. The thing that drove me was really programming. So while I found the management stuff interesting and fulfilling in certain ways, it was taking away from this thing that gave me the most happiness.
I wasn’t worried about losing skills or anything. Because one thing I always think about is that a good way to identify your passion or something you really care about is that I always made time for programming, even when it probably wasn’t healthiest to do so.
I could have worked a 10-hr day without programming once, then I would program for two hours. I didn’t have to. I probably shouldn’t have. But I wanted to. I think seeing that over a long time, just made me realize, that was the direction I wanted to head back towards, eventually.
….
The CTO thing happened, three-four years into the company…That was really a realization of me actually, actively disliking the CEO role. The executive team building, the financial planning. Fundraising. All that sort of stuff.
…
My point of view is 1) I didn’t like that, 2) I had an investor, someone on our bored who told me something, they never pressured us…But one thing he told us was start-ups have a 90% failure rate and so for an investor to invest in a startup, it’s because they think they’ve identified some sort of trait that can help beat those odds.
For us, that trait was always our engineering vision and our engineering ability. So, me spending time being a CEO was putting us into the odds of the 90%. It wasn’t giving us the advantage we needed to beat that 90%….
He just made me think if this isn’t something that you want to be passionate about, do what makes you happy and do what would give company the best chance for success.. And me and Armon both thought that was being engineering leaders. Not necessarily having a keyboard. But being engineering leaders rather than CEO….
Another way to look at it is that we’re capable of being a CEO but we would make mistakes. We wanted to hire someone who had already made the mistakes and knew what to do. While we wouldn’t make mistakes and knew what to do on the engineering side.
…
As the company kept growing, the job description changes a bit. As we started to hire more VPs, introduced some senior directors, my depth away from actual engineering was growing. It became much more of a headcount planning/financial planning, long-term visioning type of role and I wanted to get closer back to solving a specific problem.
At the sane time, we had grown to so many more people and so many more products. So the stuff I was doing as a CTO had to be done but it would take all my time. I couldn’t program anymore, I had to get rid of that part.
…
So I had this fork on the read: Do I keep doing this thing, which I don’t dislike? Or do I get back to programming, is there a way to get back to programming that I know I absolutely love?
#2: New products as pre-PMF startups 💥
(From: Amplitude’s Spenser Skates) (Source: SaaStr)
It was hard enough to catch lightning in a bottle and find product-market fit for your first product. How the hell are you going to find it for your second product? I want to share a few tips that we learned after a bunch of failed attempts.
A lot of companies will create a new product innovation team, but the problem is they have that innovation team sit right next to the central product team…The problem is the things that work for a mature product at scale are completely the opposite of what you want to do when driving innovation for the first time.
As an example, your product team may set quarterly goals and have quarterly plans. It turns out while you’re trying to innovate, quarterly goals don’t really help you that much.
They may set long-term product roadmaps to be able to communicate to customers. Again, when you are innovating on a new product you don’t have a long term product roadmap because what you may do may change next week or even tomorrow.
Another thing that’s done is coordinating with other teams whether it’s go-to-market or compliance teams like security. Or teams like support teams…makes a ton of sense for a mature product with tons of users and is exactly the opposite for how you want to run a new innovative experiment.
All those things that help a central product team be successful are huge distractions for your early team. So, as a leader, your job is actually to quester them off from the rest of the organization and protect the team from those distractions so they’re able to innovate and drive really, really quickly.
…
The very first product we did successfully was experimentation. Outside of analytics. First time we tried to do It, we had this as part of the quarterly planning process. We ended up failing and having to redo it.
What we did the subsequent year is we sequester them up, we didn’t include them as part of quarterly planning. The only meeting we had was a meeting every two weeks, where I would ask the same question: how many paying customers do you guys have this week?
And get them to maniacally focus on that.
And not worry about everything else.
Don’t worry about how it integrates with our existing product, don’t worry about what the long term roadmap is, don’t worry about what metric what metric we’re trying to optimise yet, don’t worry about compliance…just get something out there that has paying customers. Do that.
We ended up doing this to great success. Experiment is now our second-largest product after the core analytics.
#3: The best marketing is unattributable 👟
(From: tl;dv’s Raphael Allstadt) (Source: Relay)
I wish I knew how best to measure this work.
When you scroll LinkedIn these days, you can easily come across posts that are fixated on either killing/championing marketing channels. “Don’t do SEO,” says one expert, “do it like this,” says another. “Do paid.” “Don’t do paid.”
This particular moment is quite interesting as well, where a lot of go-to-market work stands to get (and is already) getting disrupted because of AI. We’re yet to see how that plays out.
There’s this “hard to swallow pills” meme which essentially says that the best marketing is unattributable. I think that’s completely true. It just makes logical sense.
If you reach people that you know can buy your product and you make them laugh/learn often, if your product is actually valuable, everything comes together.
Because humans aren’t dumb.
When we do customer interviews, almost 50% say they discovered tl;dv through socials.
As we scale, we’d definitely: track/benchmark more, diversify our funnel better, and run a lot more experiments. But, right now (a sort of 0-1 stage), I feel our decisions can be very qualitative and gut-driven.
This certainly varies from channel to channel and how attributable it is. With paid social, you can definitely put a number to every ad unit. In terms of what it takes to acquire a customer and such.
The funny influencer campaigns we’ve been running are much harder to attribute. So our goal is to grow profitably across our marketing mix. With a healthy knowledge of what we can/cannot measure.
Put another way, I don’t lose sleep at night because we don’t have a number attached to all our marketing channels. Primarily because attribution, to me, is in general a false flag. As it’s the final click.
People who discover us on TikTok, google us because that’s more convenient for them. We’d count that as a brand search on Google with no mention of TikTok.
Even self-reported attribution is broken. As everyone forgets things. That’s why we don’t obsess too much over attribution. We constantly review the overall marketing mix and see what makes sense for our goals.
Then, the last thing here is that if it’s obvious, it’s obvious. We ran an influencer spot and there was an immediate, obvious spike right after. So we made sure to optimize our spend there and got the most out of it.
I know this is not super scientific. But that’s it. That’s how we’ve been making it work.
🤝 Founder social:
Thanks for reading! 🌻
Team Relay (Chargebee for Startups)