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Posts tagged “marketing”

LLMs and Buttondown

I say this sincerely because I am a big fan of Buttondown and how Justin runs the business—this couldn’t have happened to a nicer guy:

Our month-over-month growth rate in Q1 2026 was double our growth rate in Q4 2025. Buttondown has, roughly, grown a little less than 2x every year of its existence; this — its eighth year — is poised to shatter that, if trends hold.

Almost all of that incremental growth, meaning the growth in addition to our historical trend, I attribute to LLMs. We ask people when they sign up what brought them here, and an answer that went from surprising to banal to overwhelming over the course of Q1 was: an LLM. Users of all stripes cite an LLM as the reason that they ended up at Buttondown’s front door.

You should click through for the whole post because he explains why he thinks this happened:

People have asked why I think we have been the beneficiary of this genre of growth. There is one fairly interesting reason: we have accidentally built a very LLM-friendly business in this space.

I’ve always been a big believer in API-first design, and this feels like an almost accidental enormous additional benefit to that approach. Anyway, all that to say… my newsletter is on Buttondown, and yours should be too.

The invention of "classic rock"

Daniel Parris wrote a statistical analysis of when rock became “classic rock”, and it’s not the story I expected.

He assumed the genre emerged organically from music nerds debating on message boards and in the pages of Rolling Stone. Instead:

What I found was a deliberate realignment engineered by music executives chasing an ephemeral advertising demographic. Like many entertainment industry decisions, it was a small (mostly male) group of executives quietly deciding the future of popular culture behind closed doors.

The data shows two concentrated periods when stations rapidly switched to classic rock: the mid–1980s (to capture aging Boomers entering their peak earning years) and the mid–1990s (after the Telecommunications Act enabled Clear Channel to buy up local stations and prioritize low-risk, high-profit formats).

The kicker is that this rebrand was designed around economic incentives that have since eroded. Radio isn’t the default distribution channel anymore. On streaming, music can just exist without being packaged for a hyper-valuable consumer cohort.

Another reminder that so much of what feels like culture is really just business decisions made in conference rooms.

The US Population Could Shrink in 2025, For the First Time Ever

Well, today I learned about the consequences of population decline:

The U.S. cannot grow through native-born fertility alone. As immigration collapses, the US population will stagnate and even shrink. Urban economics will buckle. Fields will go unharvested. Homes will go unbuilt. Sick Americans will go untreated. Life-saving medicines will go undiscovered. Many voters hated the era of record immigration. They might hate the era of record deportations even more.

Yes I know this sounds dire. But read the whole essay, Derek brings receipts.

Source: The US Population Could Shrink in 2025, For the First Time Ever

A Deadly Gravitational Pull in PLG B2B: Individual-Centric Experiences

Elena Verna on the importance of focusing on team experiences in B2B products:

The key to any successful B2B Product-Led Growth (PLG) strategy lies in connecting end-user adoption to enterprise-level deals. But because B2B PLG often looks like, smells like, and acts like consumer product, it pulls product and marketing teams into a deadly gravitation pull of crafting consumer-like experiences focused solely on the individual value. While acquiring individual users is a natural first step, failing to consider the dire need to connect that individual to a team and a company level value WILL sabotage your future growth.

Dolly, Beyoncé, and Differentiated Value

Thanks to April Dunford for this fantastic reminder about positioning (and life!):

My favorite positioning quote is from Dolly Parton, who said, “Find out what you are and do it on purpose.” A great positioning exercise is a structured process that allows a team to get real clarity on exactly “what you are” so marketing and sales can “do it on purpose.”

Come to her article for the Dolly Parton quote, stay for the Beyoncé positioning lesson…

What is strategy—explained with a useful puzzle metaphor

This is about content marketing but Fio’s post What is strategy—explained with a useful puzzle metaphor is very relevant to product people as well:

At its core, that’s what strategy is: taking a problem, discovering what makes it hard, and finding the right way(s) to solve it. The concept is super obvious when applied to a puzzle: you intuitively know that picking random pieces from the pile and expecting them to slot right into place is not a sensible approach…

…and yet, that’s often how content folks expect marketing programmes to work: we bypass the diagnosis and guiding policy phases, jump straight into picking tactics, and expect that all the pieces will automagically fit together in the end.

Another reminder (which I think we need to hear almost every day) not to jump into implementation too quickly. Take time to understand the problem and the opportunity first.

Sales-First Storytelling

Great post by April Dunford on how marketing teams and sales teams need to tell different stories about a product:

Our goals in marketing are very different from our goals in a sales situation. Often in marketing, we are simply trying to capture an audience’s attention and get their permission to continue marketing to them. […] Sales, on the other hand, is generally dealing with the folks who have already raised their hand in some form and are in a purchase process. Our primary job in sales is to help guide prospects through the purchase process.

However, both approaches to storytelling need to come from the same positioning source:

Sales and marketing should use the same inputs for whatever storytelling structure they choose, and those inputs should come from our positioning. Both marketing and sales communicate the value that the product delivers that no other solutions can. Both have a common definition of what a good-fit prospect looks like. Both teams need to understand the alternative approaches, including the status quo and more direct short-list competitors. Our positioning defines the inputs for marketing and sales content—we ultimately need commonality across marketing and sales because our positioning defines where we win and why.

The Product-Led Growth Trap

Oliver Jay wrote a 3-part essay about what he calls “The PLG Trap”, where product-led growth companies grow to a certain point and then suddenly sees that growth slow with no obvious ways through the slowdown. From the introduction to the essays, Oliver says this usually happens after an initial (and initially successful!) expansion into the enterprise market:

Quite simply, despite the complex security and administrative features you’ve launched, your product has not evolved to becoming broadly “enterprise-ready” for the majority of your enterprise prospects.

At this point, you may feel trapped–the PLG Trap. You’ve set growth expectations externally and internally based on how revenue (in particular, from the upmarket segments) has grown in the past few years.

However, what drove revenue in the past, in terms of your product offering as well as your sales and marketing motions, is unsustainable. There is no more bottoms-up, low-hanging fruit to feed the larger sales and marketing engine you’ve built. To pursue sustained revenue growth, you must tolerate a lower efficiency…only to now be punished by the public markets in what appears to be the beginning of a recession.

The essays go through several reasons why companies fall into this trap, and also how to avoid it by making smarter decision about sales, marketing, and product roadmaps early on.

B2B Product-Led Sales Guide

Elena Verna presents a great guide to product-led sales for B2B products here here:

In a traditional top-down sales approach, the sales team is motivated to close the largest and newest deals to account for the high acquisition cost and ensure profitability.

In contrast, in a product-led sales approach, the sales team gets involved with the account much earlier in the problem lifecycle, and the initial contract value is smaller. It’s important to note that in top-down sales, the buyer is typically captured during the high maturity stage of the problem. In contrast, in product-led sales, the account is acquired earlier in the lifecycle. Therefore, the landed annual recurring revenue (land ARR) is not comparable between the two channels. Product-led sales’ primary goal is to expand by continuously growing with the account, which is where most of the revenue is generated. Overselling the account during the initial contract can be detrimental as it may disrupt the expansion journey.

There are a couple of other recent posts on product-led sales that I found useful:

Why Do Developers (Actually) Hate Marketing?

Why Do Developers (Actually) Hate Marketing? The Heavybit team has some good advice in this post:

  • Don’t: Create product-led content that shoves the product into your reader’s face.
  • Do: create a transparent guide to what your product can and can’t do. But make sure you don’t over-promise (or even sound like you’re overpromising).
  • Don’t: Write thought leadership content that relies on cheesy trend predictions.
  • Do: Create thoughtful, technical essays based on experiences from engineers and founders. But make sure your claims are authentic as well as relevant and well-supported as well as novel.
  • Don’t: Produce hollow, manicured case studies.
  • Do: Create technical case studies that describe, in detail, what a customer’s experience was really like – including the gains, the stresses, and the adoption and integration processes. But make sure the focus remains on the customer’s problem and not on your solution.