How (not) to find your marketing groove
Shouting about features doesn't help your message resonate with users.
I have never had the word "Marketing" in a job title.
But I've been a startup founder, and a founder (or founding team) quickly learns the marketing ropes, or they are banished to startup purgatory, a not-dead but not-crushing-it middle ground that honestly is quite a bit worse than a quick and definitive failure in many cases.
My crude attempts at marketing in the early days kept us in that startup purgatory for longer than I’d care to admit. To understand what actually resonates with potential customers of a B2B software product, I want to give a glimpse into just how bad I was at marketing a decade ago. Here are a few actual screenshots from my first deck for "Bloomfield", the working name of a startup project that ended up evolving into my first venture (later renamed “StackSource”).
My crude attempts at marketing
Don’t you see? Using our product instead of a telephone would give you Efficiency, Intelligence, and Value! How could anyone miss out buying those? And how could an investor miss out on jumping on this rocket ship?
Sarcasm over and unfortunately yes, these slides were present in a deck that I used for both potential customers and investors. Yikes.
If my visuals leave you wondering what the heck I thought I was actually going to build and why it mattered, you wouldn't be alone. I had a vision for my startup in my head, and boy did it feel clear to me, but man did it get muddled between my brain and our marketing. In those days I probably would have told you that I was good at "strategy" and planned to hire someone who was good at "marketing" later.
Of course, it didn’t work out that way. As the founder, I had to find a message that resonated with our target audience, and the product had to deliver that same value. A lack of understanding in this area becomes a roadblock to successfully hire a productive marketer (or sales leader) anyway.
While I’m sad to say my design skills really haven’t improved, I’ve picked up some important lessons related to messaging since then.
How to find messaging that resonates with users
There are famous examples of founders who (seem to) have an uncanny ability to predict what the world needs next, and then sprint forward with an early version, nailing it on the first try. Intuition absolutely plays a role in shaping startup offerings in a complex, shifting world of human beings.
But even founders with better than average intuition need a structure for engaging people with their fledgling product, gathering feedback, and then iterating. Marketing is present even if that feedback is coming from one person in a “sales” pitch, because marketing is any message you share about your product and its value for that audience.
Feedback on a marketing message can be collected and measured in many ways. Here are some common methods:
Direct conversation related to a sales pitch or demo
Analyze the traffic patterns of your website or landing page
Formal marketing feedback (live)
Formal marketing feedback (async)
Blind product test or comparison
UX interviews
Free trials/samples
Analyze performance of email sequences
There’s a time and place to collect and analyze feedback from all of the channels above and other creative ways, depending on the stage of the company. Every method shares the underlying principle of exposing a product’s value to an outside party and then recording how the message is received. It can be tricky to get the “truth” about what a user will do in “real life” rather than relying on their feedback itself and requires enough understanding of psychology to run a reliable feedback process. Getting “objective” feedback is the North Star that we never quite fully reach, as these are humans we’re talking about, and no message or recipient can be stripped of all emotional factors and extraneous thoughts.
Once our best available feedback is received on a marketing message, it can be used to iterate on the message, and then try again.
How my messaging evolved to better fit user needs
A key theme in the evolution of my startup’s messaging was shifting from feature-centric to benefit-centric. While multiple advisors helped me in that evolution in my marketing thought over time, one of the clearest communicators on building a clear, benefit-focused value proposition was executive coach Kristen Connor, an advisor who helped our team through a formal brand refresh. Kristen had been a key executive at one of the fastest growing online mortgage platforms in history, and would constantly remind us to keep user benefits at the center of our messaging.
How it started (feature focus) —> How it grew (benefit focus)
Connect to top technology-enabled capital sources —> Connect with top capital sources
Manage Capital inflow (wft was I talking about?) —> Close with the right financing
Create competition through bidding & negotiation —> Achieve your optimal combination of rate, leverage and recourse.
I could show you more dumb slides from my early marketing decks, or the 2017 version of the StackSource website, but I’ll summarize by saying that you’d just see more feature-shouting.
The shift that unlocked growth was dialing it down to “hey, you’re going to get better financing here” instead of “this is a really advanced capital platform”.
Do I change my messaging or my product?
As you find the messaging that resonates with your users, you need to back it up or back off. The options include:
Upgrade your product offering to fit with the promise you’ve made to your users (requires time and resources)
Back off that messaging and user promise (blow to vision and ego 😨)
Find a way to bridge the gap right now while working toward #1
The startup world is full of founders trying to bridge the gap between the vision of their product, especially if they’ve found strong demand, and today’s product offering. This is an inherently stressful situation, moreso if you’re under resourced and/or have competitors sprinting ahead to the same goal. Some amount of this stress is wonderful when the founders are mentally healthy and prepared to work through it. Too much of this stress, too often, can prove fatal to the business by burning out the team.
One of the big ways we bridged our gap between vision and reality was through service, rather than tech features. There was a lot that our tech couldn’t do yet, or couldn’t do on its own to achieve the desired outcome for the user. So we went big on emphasizing expert support through the process, where our humans (“Capital Advisors”) could bridge the gap for our customers.
There were both benefits and flaws to this approach that emerged over time, but more on that in a future post.
Good at strategy, huh?
Maybe I had something going for my high-level startup strategy since a lot more competitors jumped in later, a couple of them as blatant copies, and a couple others with many times more funding than we were able to wrangle.
But I can’t get as much strategy credit as I’d like. Marketing really is a reflection of strategy, and my early marketing held us back. A great strategy for what I wanted to accomplish would have doubled and tripled down on just one key message that resonated with our users and then beat that drum for as long as possible. In hindsight, I see multiple ways that could have been accomplished, saved resources on engineering, increased speed of traction, and propelled us out into the market with more force.
I can’t roll back the clock, but I can aim to learn from my earlier mistakes and from every expert I meet along the way. Hopefully on the next run, my vision won’t be held back quite as much by my product marketing strategy.