"Bloat is Beautiful" 🎨

The problem with saying no, a product’s (fast approaching) next acts, and an economist-turned-founder’s take on sales improvements.

Jul 19, 2023

Welcome to the 77th 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! And thanks for reading!

In this edition, you’ll find the following instructive and inspiring pickings:

#1: Summit’s founder and CEO, Matt Wensing, narrates the experience of coming across a fundamental fissure in the opinionated, Excel-and-Photoshop-hating, always-be-pruning product mindset and realizing how “freedom matters far more to the user than our opinions.”

#2: WorkRamp’s co-founder and CEO, Ted Blosser, notes an already-underway shift in how often SaaS scale translates into establishing product-market fit over and over again.

#3: Leapsome’s co-founder and co-CEO, Jenny von Podewils, describes a simple yet splendidly rigorous practice of recording points of friction across the sales process.

Finding these discerning founder takes valuable? Please consider sharing this edition with an ever-curious teammate or a much-cherished SaaS friend. 🙂 New readers can sign up here.

🗞 Recently on Relay:

Heuristics and Hunches (July 14th) — Scaling an Open Source Tool While Running an Agency, Giving Back Control with On-Prem Deployments, and Bootstrapping Decisions with Flagsmith’s Founder, Ben Rometsch

— Why build an open source, feature flagging tool
— Running an agency alongside an at-scale product
— Bootstrapping and the genius of upfront, multi-year deals
— Having the time for an ICP to emerge on its own
— Serving on-prem and Flagsmith’s open source philosophy
— How to choose a fitting open source license

#1: “Bloat is Beautiful” 🎨

(From: Summit’s Matt Wensing) (Source: Matt Wensing)

Letting Go
When customers demanded new features out of my rebuilt (for the second time) release of Summit, I blanched. Where had I gone wrong? Had I not made it clear that what I had given them was the better way? Why can't they appreciate the beauty of its power and simplicity?!
Deep breath. Ooda, Matt. OODA.
Observe: People are asking for lots of things. Lots of different things. This thing. That thing. Another thing. Then over here another thing.
Orient: No matter how much I give them, they want more, because these things have nothing in common. In fact, what they have in common ... is that they have nothing in common.
Oh my.
What they have in common is ... they have nothing in common ...
They're asking for flexibility.
Okay. Okay. I like this. That's a word I can put on it. Flexibility. They need it to be flexible. So what's the problem with that?
My goodness — I'm the problem. I'm the bottleneck. They're trying to do something, to express something, and every time they need a new, a new ... piece, a new building block, a new color ... I'm forcing them to ask me before they can have it.
Well ... isn't that ironic.
It's as if I've created some kind of writing medium, invited them to use it, but then forced them to submit a feature request any time they want to write a word that's not on the approved list.
What have I done?
Decide: Summit isn't a product at all. What is it? Some sort of medium for expression? People are trying to express themselves. I need to give them that ability. That's what people want!
Act: What choice do I have? I've got to tear this down again and give them something more like — a language? Something where they can become the developer, where I'm out of the way.
Four months later, Summit relaunched as "a whiteboard that does math", a visual canvas for users to create and define their own mathematical building blocks, powered at its core by a language user's could write themselves.
I was out of their way.
And the requests? They stopped.
(Summit before, Summit after.)
Bloat is Beautiful
There was a vision, once upon a time in the 1960's and 70's, that the future of software would be creative. That users, like us developers, would be engaged in products that allow them to express their thoughts in new ways and mediums.
To some degree, we've realized that.
But I also observe a persistent hatred for ‘bloated’ tools like Microsoft Word, PowerPoint, Excel, Adobe Photoshop (and inevitably, Figma) that exposes a lingering, gross misunderstanding.
These products are insanely successful. Yacht-to-canoe more successful than the more opinionated products that piously resist the urge to add buttons when users ask for them.
Is this because the mass market has inferior taste? Because no Steve Jobs has yet descended to teach the market they only need 4 buttons, not 400?
Far from! These buttons and inputs, clumsily implemented as they may be, give the user the widest, most powerful and flexible set of options through which to build their own things, in their own image.
Hate the thought of more buttons? Maybe you can offer them their own scripting language. Maybe you can ship a text area for a configuration file. Maybe you can provide a tiny escape hatch or sandbox where they're allowed to run amok.
However you meet the need, this freedom matters far more to the user than our opinions.
Are all of their creations beautiful? No. Do they make the right choices given that flexibility? Definitely not. Will they jam too much into that tiny space you gave them and wonder why it's crashing? Certainly.
But are they happier? Very much so.
And as a founder searching for greater fit, nothing else matters.

Related Relay reads:

Matt on when to switch on the customer-led mode and pivoting (4 times) towards PMF

Trello’s co-founder, Michael Pryor, on two things that are relevant to any product creator

#2: The need for multiple PMFs ⏩

(From: WorkRamp’s Ted Blosser) (Source: Product Market Fit)

There’s this perception that you only need to find product-market fit, maybe twice/three times in a company’s history. And I think that was true for these earlier generation of companies.
I remember SaaStr having a podcast hosted with the Amplitude founder, so they did their second product around $100m or so. I could be wrong on that. But they waited a while…
A lot of people talk about the 2nd acts of companies like Uber going to Uber Eats and that kind of saving them through the pandemic vs Lyft.
And so historically, I thought of that as ‘hey, when you’re at big scale, you need a second act and you need another product-market fit.’’
But what I think has happened lately in SaaS is that scale has been reduced to a much smaller time frame. And you need to do it more frequently because the disruption is happening so quickly.
So… the example for us, specifically, is essentially for every fundraise round we’ve had, we’ve gone through seed, [series] A, B, and C, so 4 major fundraising rounds.
Every one of those rounds was based on an inflection point that was kind of based off of another product or product-market fit phase in our business.
I really got this advice from our board member Jack Altman (from Lattice). Where he sat me down (this was before he was a board member), he said, ‘every time we grew at Lattice significantly, it was with a new product introduction that was successful.’
Right now, I can’t remember the exact count, they have close to 8 products or something. You’re seeing this with Rippling with their Compound Startup concept. Similar thing with WorkRamp.
In the seed phase, I talked about product-market fit with the sales enablement buyer. Then that got us to our series A. Heading into series B, we got product-market fit on our customer education platform, the customer learning cloud, which was essentially our 2nd product.
Then, heading into series C, we were getting product-market fit on what we call our content product, which is off-the-shelf content offered within our platform.
And also based off of our vision of what we call the learning cloud now, which is this all-in-one LMS platform. So these were the 3 major inflection points of the business.
Again, we’ve been around 8 years but that’s roughly 3-ish product market fit moments and we’re not even at public scale yet…
We’re not like Uber-size, we’re not Amplitude-size, we’re still in the 10s of millions of ARR and have already hit PMF over and over again with a multi-product strategy.

Related Relay read:

Productboard’s co-founder, Hubert Palan, on building an all-in-one product

#3: Capturing day-to-day sales frictions ⛸️

(From: Leapsome’s Jenny von Podewils) (Source: Project A Ventures)

We are a really process-driven company. Both founders are economists. So we live and breathe processes to some extent. Doesn’t mean it’s bureaucratic. But that we try to do repeatable things and then learn from [them] and tweak [them].
Something that’s been really effective for us in terms of tweaking processes with the insights of the team and just making them work in the best possible way for the sales team is that we collect frictions in an ongoing way.
[Just] like you might have a feature request report or feedback report, we have a sales process frictions report in Notion. Where basically, any sales rep can report any kind of friction.
It might be something small. It might be something bigger. Like “this bit of the process just doesn’t work for me.” So we collect these frictions on an ongoing basis. We remind people, when they complain about something, to write a really quick friction down.
Then we constantly, on a regular basis, we look at both the impact and the effort to fix them. And we basically always at least look at them on a quarterly basis when we review OKRs.
We’re also doing OKR surveys where we ask the entire sales team: “What works? What do you need from CS? What do you need from marketing? What do you need in terms of sales process iterations?”
So we have this quarterly survey plus we have the ongoing [reported] frictions, so we can really focus on fixing, iterating, levelling up the parts of the sales process and the organization that’ll ultimately lead us to the highest impact and that really brings a lot of focus on improving everything.
That’ll be the second lever for me to really optimise the sales organization.