Userlist’s Jane Portman (@uibreakfast) remains — through the form, substance, and open grace of her inquiries — an exemplar for the building-in-public movement.
A correction: Actually, a model for what it could be.
Hers is the opposite of a dominant mode of founder expression that equates everything — alphabetized startup decks, regurgitations from Daniel Kahneman’s work, and newly minted sleep routines — with tweetable ‘competitive advantages.’
Neither does she attempt to find certainty and polish where none exist. You made a pivot. Great. It had its reasons in a sudden realisation/inventive research/both. Perfect. Tell us all about the decisions you made. But it’s more than a little strange to then proceed to write about all the types of pivots there are and then prescribe a six-point checklist to pick one.
It seems, in rushing to ‘outteach’ the competition, we’ve forgotten what must precede teaching of any kind. Learning. And learning is, especially for those starting up, customarily messy. Error-prone. Uncertain. Anxious. Queasy, even. And undeniably intuitive.
It should be okay to say, ‘well, fellow founder, this is what we had intended, hypothesized, and hoped for, and this is how it really went. We don’t quite know why yet. There’s no framework to share. Just something we attempted; something we felt, something we learned.’
Sadly, only a few can keep it real.
Jane Portman does.
Despite consulting with founders for close to a decade, authoring acclaimed UI design books, running a podcast (still as refreshingly titled and curated, UI Breakfast) with millions of downloads, and having built a SaaS product (Tiny Reminder), Jane admits how she wasn’t entirely prepared for what Userlist’s early days had in store for her.
“My illusion was that if we fix all these product mistakes that I did with my first SaaS, we’re not going to do this silly stuff again, then things will go much faster.”
A major lesson she had learned was to deliberately choose the spiky, albeit much more rewarding terrain of creating a ‘pain-killer.’ Something that could solve for the unaddressed reaches of an established software category.
What follows are some highlights drawn from Jane’s consistently earnest accounting of making that very messy startup path navigable.
I. Knowing —
Few turns of the scratch-your-own-itch dial and you might just have traction.
Or not.
ProdPad’s co-founder Janna Bastow once made the following eloquent, autobiographical observation:
“I think it’s remiss to assume that the best thing I could have done was to solve the problem closest to me. Had I taken a bigger step back, I could have explored a wider range of potential problems to solve, and likely found other opportunities that were just as, or even more lucrative than the path I went down.”
This came to mind as Userlist’s own first (‘why we’re building this’) blog post, documenting the particular email automation itch that the founders had experienced, was published on Feb 20th, 2018. A whole 18 months prior to their public launch.
Given Jane’s first-hand window into the problem, one would be surprised to learn that part of what still came about in this pre-launch period was some painstaking research.
Beginning pre-product, with ~20 interviews that Jane’s co-founder, Claire Suellentrop, ran to probe and define the struggles of their ideal customers (and their deep-rooted habits and needs given the everywhereness of email).
"Defining your ideal customer means getting much more specific than saying you serve ‘SMBs’ or 'founders.’ If you’re B2B, what company model does your ideal customer own or work in? What industry or niche? How mature is their business? Is it profitable? Well-funded? Lean? Rapidly expanding? What challenges do they face in doing their work well (or better)?”
Conversations where they sought to learn of specific situations (“What happened that eventually made you say, ‘Okay, Intercom is going to work for us’?”) and of specific behaviours and necessities (“What’s still really painful at this point?”) that drove these users towards their choices.
This had the effect of tuning their ears further towards the unimagined nuances of the problem. Informing not just the MVP, but also their go-to-market approach. For instance, they learned that Userlist must feature very early in a founder’s product-building journey.
Beta began. So did their next phase of learning. Coupling sales demos with discovery. Qualifying users’ needs to fit a focussed profile was important, what mattered most, though, was to continue the work of active listening.
Jane had sat through one of those storied, Superhuman onboarding calls and had felt too acutely the pang of being a user fitting into some grand piece of software versus the other way around. Jane, being her kind self, asserts that perhaps that’s the approach that works for Superhuman. Userlist’s demos had to be structurally different:
- They made sure at least two of the three co-founders were available for each call during this initial phase
- Their chief goal was to “learn enormously” about the worlds their beta users inhabited
That selling and research could coexist had more than a tinge of early-stage scrappiness. They figured they had to draw a line between the two, however thin, by considering each call a problem-solving session. Noting motivations and reasons as thoroughly as they had done before and suggesting relevant solutions, theirs and others.
By this stage, their understanding of the core user issues was incredibly concrete. They could confidently map the when, where, and how of any automation journey. Yet, they were realizing that it took a while for people to grasp Userlist’s promise. Their elevator pitch failed to capture the depth of their hard-won know-how.
They had a positioning problem.
And in April Dunford’s well-lauded work on the subject, a likely solution. Thus their third concentrated research effort was kicked off.
Central to April’s message is her insistence on moving from positioning theory to practice. And the practice demands, first and foremost, the leaving of existing assumptions at the door. Which, Jane shares, “is never easy as you get buried in your own product.”
A way out, often recommended, is to bring in someone from the outside world. A distant pair of eyes that can see through some of the “positioning baggage” founders may have acquired.
The other approach — the only one the early stages usually permit — is to do it yourself.
What helped Userlist, here, too, was their cataloguing regimen. They didn’t have the advocated positioning blank slate, in fact, they had something even better.
Research, when done well, is fertile ground for — surprise, surprise! — doubt. Not answers. Not patterns. Those are rare by definition. You identify and articulate uncertainties first. Scramble through a ton of them. And maybe then, some connections appear. Maybe.
When a connection does happen, especially one coloured in a founding team’s conviction, it is too tempting to discard all the missing pieces in its wake.
Turns out the Userlist team didn’t do that.
So the many explanations and comparisons that seemed to require too much human-product triangulation were all captured and available for them to diligently sort. In this case, to be poured into April’s framework.
The outcome? An immediate sense of direction on most, if not all, related concerns.
(Userlist’s Positioning Canvas)
For example, in her book, April lays out three ‘styles’ of positioning a business:
1. Head to Head: Positioning to win an existing market.
2. Big Fish, Small Pond: Positioning to win a subsegment of an existing market.
3. Create a New Game: Positioning to win a market you create.
For Userlist, the second approach appeared the most viable.
“Our answer is clearly the ‘big fish, small pond’ strategy for Userlist, with the general existing market dominated by Intercom. This general market category is ‘customer messaging tools’ — that’s what Intercom calls themselves, and it’s easy for people to understand.
Previously, our market category was ‘email automation tools’ which clearly didn’t work. People started comparing us with Drip, ConvertKit, ActiveCampaign, etc. — and we struggled to explain why we’re better. Email automation tools have way more advanced features that we’re not planning to implement soon (rich visual templates, A/B testing, visual workflow builders, analytics).
While ‘customer messaging tools’ don’t require these features, and align fantastically with our plan to introduce in-app notifications. Our ‘small pond’ would be a subcategory of SaaS companies who need a focused, less complex messaging tool … We decided to stay ‘open’ about this subcategory and fine-tune it later, as we grow and learn more from our paying customers.”
The knowing continues. The positioning vector — always calling for further revisions and tact — has Jane and team improvising, again. As of this writing, they’re in the process repositioning themselves as a much broader email automation tool for SaaS companies.
Jane adds that they’ve “finally crystallised their competitive advantage: precise focus on SaaS needs, SaaS-specific integrations and features. For example, Userlist can handle company accounts which is crucial for any software company that serves teams.”
Now, all that astounding, continuous learning had to be turned — not to mention, in parallel — into something that people valued.
II. Building —
MVPs, by design, are far from perfect. Even plainly stating this seems like a harsh reading of the concept. Isn’t that very lack of firm footings, a fundamental virtue? Well, it is.
But when you’re attempting to make a dent in a SaaS category that has been around for more than a decade, one that has seeped into numerous job titles and descriptions, one that has spawned a baffling array of tools, that inherent incompleteness can quickly turn into a fundamental flaw.
Given the pervasive relevance of Userlist’s own category, then, this coveted distance from perfection was always up for renegotiation.
As we’ve learned, though, Jane and team were methodically iterative, constantly redrew their assumptions, and continued to gather startling volumes of feedback, carefully observing most core MVP principles and practices.
In fact, when asked about her guiding product belief, Jane cites Gall’s Law: ‘A complex system that works is invariably found to have evolved from a simple system that worked.’ An axiom that has, arguably, been at the heart of lean thinking.
Even their podcast is called, ‘Better Done than Perfect.’
At the same time, Jane explains how they “never had an ‘MVP’ — we were gradually building a solid product, feature by feature. Email automation is not the industry to launch a half-functioning MVP into the wild.”
What they were trying, you realize, was to locate their stride amid these two confounding truths that tend to dictate most B2B paths today. The necessity of being nimble and gleaning voraciously from adjustments, while serving the exceedingly weighty expectations of users who cannot risk much.
“So we developed ‘our way’ of doing things — for new features, we always build the smallest, simplest thing first. It should look great, it should work great, but it will be limited in scope. No custom settings, or anything like that.
For example, we launched Userlist with a single email template, only allowing users to customize their link color (even that was available upon request first, without the UI). Clean and beautiful, but not customizable. This lasted for a couple years, even though — you would think! — a template builder is an essential part of an email tool. Turns out, it matters more when you send an email, and what you say there, as opposed to how it looks.”
In John Gall’s 1978 work, Systemantics: How Systems Work and Especially How They Fail, there is another intriguingly obvious axiom that precedes (and qualifies) the one Jane refers to and abides by: “A simple system may or may not work.”
In Userlist’s case, their simple systems had to work flawlessly.
This already conflicted impulse toward speed is further freighted by all the infrastructure that must surround a must-have product.
- Dizzyingly complex compliance (GDPR and others) requirements,
- Exceedingly high documentation standards,
- And attentively drafted terms of service and privacy policies.
To name but a prominent few.
“Sure, we could’ve launched without the knowledge base, or neglected the legal docs, but it’s not ‘our way.’ Our customers trust us with their own customer data, so we wanted to set a high standard.”
Another no less thorny challenge, Jane was beginning to notice, was product adoption.
What’s often sold as the marquee reward of creating a ‘pain-killer’ over a ‘vitamin’ is also perhaps its most striking deterrent. High retention comes with a high switching cost.
“Userlist is extremely sticky, but so is our customer’s previous tool,” Jane notes.
Which leads to longer sales cycles once consideration has begun. And necessitates an unmanageably frustrating slip on the part of the incumbent tool, for the consideration of alternatives to start in the first place.
As these initial, tiring deliberations wear off, the practical jumble of launch timelines, developer availability, and other implementation routines must be dealt with.
This has informed how Userlist onboards its users among other things. The operative thought, they’ve held, is to inspire, not instruct. To consider the larger context a user brings in and only then seeing where Userlist figures within that.
(“Our goal with this video is very simple: build a personal connection without interrupting the flow too much. The video is under one minute long, and is easy to skip, so the user doesn’t feel obliged to watch it at all.”)
This email flow partially illustrates that understanding:
- A short welcome email, greeting & offering help.
- A follow-up email offering a personal onboarding call.
- An email offering multiple resources for inspiration (blueprints, templates, knowledge base, etc).
- A check-in email offering technical help (only if the user hasn’t started tracking data).
- A check-in email offering strategy help (if the user started tracking data, but hasn’t created any campaigns yet).
Jane, again, humbly notes that their onboarding system may not boast crazy trial-to-paid ratios, but “we’re certain that this onboarding system represents our values, and helps us onboard new users with maximum care and respect.”
They’re well aware that there’s more to these adoption difficulties. So they’ve also been working towards a more fundamental change. Calling into question some of their core assumptions, again.
As mentioned above, Userlist is opening up for marketing emails. Again, a customer-driven (“I want all my SaaS email in one place”) bet on the idea that one could start with a low-friction mailing list and then add behavioural data later.
Another sign of their nimbly-perfect (and perfectly-nimble) approach to building.
While concluding an exceptionally detailed post on their pre-launch efforts, Jane makes the following reflective admission:
“Launches are tricky.
On one hand, you get an enormous emotional uplift and community support. On the other hand, actual numbers can get disappointing. It’s true with any product, but it can be especially painful with a B2B SaaS. Such products have generally lower engagement rates than, for example, books or other impulse-purchase products.
We say, don’t let the numbers ruin your spirits! After all, it’s only the first day of your journey, and there’s many more to come. There’s rarely a SaaS success overnight.”
They had launch goals, of course. They even charted most of them successfully. Topping the day’s Product Hunt tally, for instance.
Jane’s premise, as we interpret it, isn’t about forgoing founding ambition. Far from that. Instead perhaps to nurse a more thoughtful and considered version of it. A welcome antidote to the all-or-nothing narratives that are compulsively retold in the startup world.
Also perhaps to think and write in public (whenever one can make time for it, that is) not with an aim of glorifying wins or even abject failures, and certainly not to share metrics because everyone does so — “we didn’t want our customers to link a small MRR number to the quality of our tool (because there was no correlation),” Jane writes in a piercing truth.
But to record the small surprises, the honest attempts at grasping evolving unknowns, the bet-by-bet experience of building something, in all its plain, undetermined, inherent boldness.
“I value that little phrase ‘I don’t know’ so highly. It’s small, but it flies on mighty wings.” — Wisława Szymborska
Further reading/listening:
Why We’re Building Yet Another Tool for SaaS Founders | Userlist blog
Benedikt Deicke of Userlist on Competing with Intercom in an Established Market | Getting to Ramen
Combining Sales Demos and Customer Research with Jane Portman | Awkward Silences
Onboarding with Jane Portman | Metamuse
Thanks for reading! 
At Relay, we believe there’s no one way to build a SaaS business and thus the existence of playbooks and other settled notions, must be constantly questioned using diverse founding philosophies.
If you’d like to pick Jane’s brain on her incredible journey, just hit ‘participate’ to post your questions. If you aren’t on Relay yet, request an invite here!
