Now: how do you report this to a board?

The board wants a number that increases to the right. Traffic used to be that number. Clean, measurable, universally understood. Every marketing leader in the world knew how to report traffic. Entire careers were built around growing that number.

It’s becoming meaningless. Not because traffic doesn’t matter, but because the link between traffic and business outcomes is breaking. When an AI system reads your content, synthesizes it, and delivers it to a user who never visits your site, you’ve influenced a decision without generating a pageview. Your content worked. Your dashboard doesn’t know it.1

———

This is a specific version of a bigger problem. The most important work now produces outcomes we can’t measure with existing tools.

We don’t need better metrics. We need metrics that haven’t been invented yet. We’re in the gap between one measurement paradigm and the next.

My team spent over 80 hours producing 11 pieces about AI solutions. By traditional metrics, they were a failure. 101 visits total. By any standard ROI calculation, you’d kill the program. But those pieces are now cited in AI responses across multiple platforms, shaping purchase decisions that will never show up in our analytics.

Try putting that in a slide deck.

———

The temptation is to pick a side. Defend the old metrics because they’re familiar, or abandon them because they’re incomplete. Both are wrong. The old metrics still matter, and they’re increasingly insufficient. You have to hold both.

What you actually need is a measurement system that’s explicitly provisional. Here’s what we know. Here’s what we think we know. Here’s what we’re investing in measuring even though we can’t prove it matters yet.

That last category is what separates leaders building for the next era from leaders optimizing for the last one. It requires asking your organization to trust you. The metrics won’t justify themselves. You have to justify the metrics. That takes conviction that no spreadsheet can provide.

We’re all building for metrics that don’t exist yet. The only question is whether you admit it.2

The real structure of work is: things were one kind of messy, then they became a different kind of messy, and they will continue being messy forever. There is no “after.” There is no point at which you’ve figured it out. There’s just the next mess, which you’re slightly better equipped to handle because of the last one.

I call this the permanent messy middle. Accepting it is one of the most important things you can do as a leader.

———

The messy middle is the space between strategy and success. Between knowing what to do and having done it. Between the promise you made and the delivery of that promise. Most of us permanently operate here. Not at the visionary planning stage or the victorious completion stage. Somewhere in between, covered in the dust of execution.

We don’t talk about this because it’s not a good story. Nobody wants to read a case study that says “we tried a bunch of things, most of them partially worked, we’re still figuring it out, and we probably always will be.” But that’s the honest version of almost every operation I’ve ever seen.

Right now, we’re producing 160 pieces of content a month. From the outside, that looks like a well-oiled machine. From the inside, it’s held together by duct tape and determination.

There’s always a workflow breaking, an editor overloaded, a tool not working as expected, a stakeholder whose requirements just changed, a quality issue that slipped through. Always. The question isn’t whether the machine will have problems. The question is how fast you can fix them.

———

AI will make the messy middle messier, not cleaner. The tools themselves are changing faster than you can build processes around them. You implement a workflow based on one AI capability, and three months later, the capability has changed so much that the workflow needs to be redesigned.

This is permanent. The rate of change in AI tools is not going to slow down to let your operations catch up. You’re going to be redesigning workflows continuously, indefinitely. The organizations that succeed will be the ones that build change fitness. The capacity to absorb continuous disruption without falling apart.

Change fitness isn’t something you learn once. It’s a muscle you build through repeated exercise. Every time you scrap a workflow and build a new one, you get slightly faster at scrapping and building.

Every time you navigate conflicting stakeholder demands, you get slightly better at holding contradictions. Every time a metric becomes meaningless, and you have to invent a new one, you get slightly more comfortable with ambiguity.

———

The messy middle isn’t a phase to endure. It’s where real work lives. The sooner you stop waiting for things to stabilize, for the tools to mature, for the strategy to clarify, for the metrics to settle, the sooner you start operating effectively in the only environment you’re ever actually going to get.

Build boring systems. Adapt every six months. Lead through ambiguity. Find force multipliers. Build for metrics that don’t exist yet.

And accept that you’ll be doing all of this forever. That’s the job.

Welcome to the messy middle.

Not in those words exactly. But the message is clear. Once you’re in the room, your job isn’t to complain about constraints. It’s about manufacturing success with whatever you have. Conventional wisdom gets conventional results. If you want something better, you have to make unconventional bets and execute them.

I think about this constantly.

———

Satya’s framework boils leadership down to two levers. First, the environment you create for your team: clarity, culture, energy. Second, where you put resources: time, money, people. That’s it. Those are your only moves.

But here’s the part that matters most. He supports bold bets. He even supports failure. What he doesn’t support is intellectual dishonesty. His protocol is four steps: have a plausible theory of how you’ll win. Align every resource to that theory. Monitor whether the theory is holding. And when it stops being plausible, pivot immediately.

The keyword is plausible. Not certain. Not proven. Plausible. You’re allowed to be wrong. You’re not allowed to be vague.

———

A mentor once told me something I didn’t understand until years later. Spend every dollar of your budget. Every single one. I pushed back. Isn’t that wasteful? Isn’t that the opposite of being responsible?

No, he said. Think about it. After you’re fired, what’s the point of that 100k left in your budget?

He wasn’t talking about blowing money. He was talking about conviction. If you believe in your theory of success, fund it completely. Don’t hold back a safety net that only protects your reputation while starving your strategy.

The leader who underspends their budget isn’t being prudent. They’re hedging. They’re keeping one foot out the door. They’re telling their team, through resource allocation, that they don’t fully believe in the plan they just presented.

———

There’s a concept in some African philosophical traditions called Ubuntu. “I am because we are.” The part that connects here is the idea that your word is your currency. You’ll never hurt the 99 people you say no to. But the one person you said yes to and didn’t follow through? That hurts.

This is the same principle Satya is describing, from a different angle. Your word is your resource allocation. When you say “this is our strategy,” you’re making a promise. Not that you’ll be right. That you’ll commit. That every dollar and every hour will point in the direction you said they would.

The worst leaders I’ve worked with weren’t the ones who made bad bets. They were the ones who made no bets at all. Who said yes to everything. Who spread resources so thin across so many “priorities” that nothing got enough investment to succeed. They confused activity with progress. They managed decline and called it a strategy.

———

Jeffrey Snover, translating Nadella’s framework into operational questions, asks something that should keep every leader up at night: Does your actual resource allocation match your stated strategy? If not, you have a dream, not a plan.

That’s the test. Not whether your strategy is brilliant. Whether your calendar, your budget, and your team’s time reflect what you say matters. Most don’t. Most leaders have a strategy deck that says one thing and a resource allocation that says something completely different. And they wonder why nothing changes.

The second question is just as sharp: Do you have the data to detect failure before you run out of time to pivot? If your feedback loop is longer than your runway, failure is inevitable. You won’t see the wall until you’ve already hit it.

Ambiguity doesn’t resolve. Not in this era, probably not ever. The room will always be foggy. You’re always going to be making bets with incomplete information, satisfying stakeholders with conflicting scorecards, and committing to directions you can’t fully validate.

The skill this demands isn’t decisiveness. It’s the ability to hold multiple frames at once and act anyway. To say: I believe in this direction. I could be wrong. We’re committing because waiting for certainty costs more than being wrong.

And then to be intellectually honest about what happens next. Monitor. Measure. Pivot when the theory breaks. But never hedge so completely that nobody knows what you’re doing or why.

Trust isn’t built on being right. It’s built on being consistent. Make the bet. Align the resources. Honor your word. That’s not a temporary condition of uncertain times. That’s the job. Welcome to the room.

None of it lasted. And for a long time, I thought the problem was discipline.

It wasn’t. The problem was the frame. I was trying to engineer productivity by adding. The answer was to engineer it by removing.

———

There’s a line from complexity science that changed how I think about this: “Emergent phenomena are not more than the sum of their parts. They are fewer. Emergence is defined by what is not there. By constraints.”

Emergence is about removing options until the remaining ones have no choice but to combine in interesting ways.

Shakespeare’s best work came out of the tightest boxes. Fourteen lines, strict rhyme, iambic pentameter. The limitations forced creative solutions that unlimited freedom never produces.

The same principle applies to work.

———

When our team went from producing 15 pieces of content a month to 150, the breakthrough was constraining the process. We reduced the number of content formats from twelve to three. We cut the review cycle from five stages to two. We limited each piece to a single core idea with a single call to action.

Output went up. Quality went up. Stress went down. We eliminated the decisions that were eating our energy without producing results, and everything else took care of itself.

Every decision you don’t have to make is fuel for the decisions that matter. Most people exhaust themselves choosing between twelve formats before they’ve written a word. We removed eleven of those choices. The writing got easier because there was less to think about before thinking could begin.

———

Goals work the opposite way. A goal says: here’s something to add to your life. Run a marathon. Launch a product. Hit a revenue number. Goals are aspirational. They point you toward more.

Constraints say: here’s something to remove. No meetings before noon. No more than three active projects. No content piece longer than 1,000 words. Constraints are architectural. They shape the space you operate in.

The difference matters because goals require motivation and constraints require only compliance. You have to want to run a marathon every single morning. You just have to not schedule a meeting before noon. One depends on how you feel. The other doesn’t.

This is why constraints compound, and goals fade. By March, most goals are dead. A well-designed constraint is still working in December because it doesn’t ask anything of you. It just removes an option that was hurting you.

———

The practical application is uncomfortable because it means your job as a leader is to figure out what to eliminate. Which meetings. Which approval steps. Which tools. Which options.

Most organizations are drowning in optionality. They have fourteen communication channels, nine project management tools, and an infinite number of ways to format a slide deck. Every one of those options costs cognitive energy. Every one is a micro-decision that adds up to decision fatigue by 2 pm.

The most productive teams I’ve seen all have one thing in common: a leader who’s willing to kill things. Who looks at a workflow and asks, “What can I remove?” before asking what to add.

Subtraction is harder than addition because it requires judgment. Anyone can add a tool. Knowing which tool to remove requires understanding what actually matters. But that’s the work. Emergence is defined by what is not there. Build your systems the same way.

The entire cast of Friends has the same story. Jennifer Aniston built a real film career after. The other five had varying degrees of success. But all six of them, decades later, are still the Friends cast first and everything else second.

Most people hear this and think it’s limiting. I think it’s liberating.

———

You only need one hit. One project, one role, one company, one idea that lands so well it becomes your identity. The rest of your career can build on it, extend from it, or even contradict it. But that one hit is what opens every door.

Career advice tells you the opposite. Diversify your skills. Build a broad portfolio. Be well-rounded. Don’t put all your eggs in one basket. This sounds reasonable, and it’s mostly wrong.

Well-rounded people are forgettable. The person who’s known for one specific thing gets the call.

———

I’ve been called “the 0 to 1 guy.” I’ve also been called “the scale guy.” Both labels came from the same instinct: find the thing that works, then double and triple down on it until there’s nothing left to squeeze.

That’s how spikes form. You don’t discover your spike by exploring widely. You discover it when someone else names it for you. When you hear “you’re the X guy” enough times, pay attention. That’s the market telling you where your hit lives.

Wes Kao calls this your spiky point of view. A perspective so distinct, so identifiably yours, that it can’t be copied. Most professionals spend their careers building plateaus.

Competent at many things, exceptional at nothing specific enough to be memorable. The spike is the opposite. It’s the one area where you’re so deep, so opinionated that people either love your take or push back hard. Both reactions mean you’ve found it.

Go deep on one thing. Make it yours. Let it become your identity. The breadth comes later, after the hit, when people already know who you are and what you stand for.

———

Finding the hit takes time. Mastery in any field takes 7 to 10 years of real work. You can’t shortcut it, and you can’t fake it. But you can be intentional about where you invest those years.

Pick the area where your curiosity runs deepest, and the competition is thinnest. Go deeper than anyone around you is willing to go. And when you hear someone call you “the X guy,” stop diversifying and start squeezing.

Month 7 through 12, the early chaos settles into patterns. The metrics look promising. People notice.

Month 14, the ground shifts.

———

In management, they call this second-year syndrome. A team has a breakout first season, and the second year, everything falls apart. The environment adapted. Opponents studied the playbook. The element of surprise is gone.

The same thing happens in projects and companies. Year one, you’re the underdog. Year two, you’re the incumbent. Your own success sets the expectations. And scrappy execution, founder energy, and sheer novelty were never supposed to scale into year two.

———

The systems you built for month 6 are breaking at the month 14 volume. The team that ran on excitement is grinding through repetition. Stakeholders want results they can put in a board deck.

You look at the metrics and can’t tell if you’re consolidating before the next jump or slowly dying. From where you’re sitting, both look identical.

Here’s the part nobody says out loud: quitting at month 14 feels rational. You have real data now, and it’s underwhelming. The original excitement wore off months ago. Every alternative looks better because you haven’t lived through its month 14 yet.

The people who kill good projects at this stage are making reasonable decisions with incomplete data. They’re reading the dashboard correctly. The dashboard is just lying to them.

———

I’ve watched good projects die here, and bad projects survive. The difference between persistence and denial only becomes visible in hindsight. You can’t tell which one you’re in while you’re in it.

What carries you through month 14 is the systems you built during the good months. They keep producing while you figure out whether the strategy still makes sense. Motivation died around month 10. Systems don’t need motivation. They just run.

Having been through it before helps too. The first time, you think something is broken. The second time, you recognize the feeling. Third time, you build for it from day one.

Most case studies skip from “we launched” to “we scaled.” Fourteen months of confusion compressed into “after some initial challenges.” I’d trust the ones that describe the trough more than the ones that pretend it didn’t happen.

We’d been struggling with positioning for months. Then a customer nailed it in one sentence without trying. That sentence became our lead positioning for six months. Every pitch deck, every first call, every conference talk.

Your customers are your best marketers. You just have to listen.

———

The best customer language shows up when they’re not performing. Not in formal interviews. In offhand comments on calls. In DMs and messages where they’re celebrating a win.

Your job is to listen when it happens and to write it down exactly as they said it. The moment you polish customer language into marketing language, you’ve killed the thing that made it work.

We built a shared doc where every customer-facing team member drops exact quotes. Once a month, we pull out the lines that make us stop scrolling. Those become the actual messaging.

Not paraphrased. Not “inspired by.” The actual words.

This wasn’t always true. My father did the same thing for 40 years, and the core skills barely changed. But the rate at which professional skills expire has been accelerating for decades, and AI just hit the fast-forward button.

I think the actual half-life of a professional skill in 2026 is about six months. Not the foundational stuff — critical thinking, communication, judgment. Those compound. I mean the specific tactical skills: the tools you use, the workflows you follow, the techniques that make you efficient. Every six months, a meaningful chunk of that becomes obsolete.¹

———

The natural response to this is anxiety. A lot of people are anxious. But there’s a more useful response: stop identifying with your skills and start identifying with your ability to acquire new ones.

There are two types of professionals emerging right now. The first type defines themselves by what they know: “I’m a React developer,” “I’m a content strategist,” “I’m a data analyst.” The second type defines themselves by how fast they can learn: “I figure things out.” The first type is increasingly fragile. The second is antifragile.1

I watched this happen in real time with content creators. The ones who survived weren’t the ones who rebranded on LinkedIn or reshared hot takes about the future of content. They were the ones who quietly changed what they did all day. They learned the full pipeline — ideation to distribution.

They picked up a new tool in a week while everyone else was still debating whether to adopt it. They broke their workflows and rebuilt them, over and over, without waiting for permission or a playbook.

The shift is subtle but profound. Writers ask, “Is this good?” Content engineers ask, “Does this work?” Both questions matter. Only one scales.

———

The companies that understand this are investing differently. Instead of training people on specific AI tools, which will themselves be obsolete in six months, they’re building what some call “change fitness.” Not the capacity to adapt to any specific change, but to change itself.

This sounds abstract. It’s actually concrete. Change fitness means: can you spend 7 hours a week learning a new tool while maintaining your current output? Can you abandon a workflow you spent months perfecting because a better one emerged? Can you be a beginner again at something, repeatedly, without it destroying your confidence?

Most people can’t. Not because they lack intelligence, but because being a beginner is uncomfortable, and humans are wired to avoid discomfort. The six-month shelf life means you have to be comfortable being uncomfortable, permanently.

That’s the real skill. And unlike everything else, it doesn’t expire.

This is completely wrong.

The hard part is building systems that execute at scale without you. And by “scale” I mean something specific: can you go from producing 5 things to producing 50 things without the quality falling off a cliff and without you personally touching every single one?

Last year, our team went from 5 videos a month to 50. Same team, same budget, roughly the same number of hours. The strategy didn’t change. What changed was the system underneath it — the workflows, templates, review cycles, and escalation paths. The operational plumbing that never makes it into a strategy deck but determines whether the strategy actually works.1

———

Nobody gets promoted for building a great checklist. Nobody gives a conference talk about their editorial calendar. But the difference between 45 pieces and 50 pieces in a month isn’t a strategy problem. It’s a system problem. And the difference between those two numbers is the difference between “we got close” and “the system is predictable.”

Predictability is what lets you take risks. When you know your baseline is solid — that 50 pieces will ship on time, that quality is maintained, that the pipeline doesn’t collapse if one person gets sick — then you can experiment. You can try a new format, test a new channel, or invest in a weird idea. The machine keeps running while you explore.

Without predictability, every day is firefighting. And firefighting feels productive. You’re busy, you’re solving problems, you’re clearly needed. But you’re not building anything. You’re just preventing collapse.

———

The irony of AI entering the workplace is that it makes systems thinking more important, not less. Everyone’s excited about AI automating individual tasks. But automation without systems just produces faster chaos.

You can use AI to write ten blog posts in the time it used to take to write one. But if you don’t have a system for editing, fact-checking, optimizing, publishing, and measuring those ten posts, you’ve just created ten problems where you used to have one.

Strategy is a story you tell about the future. Systems are what make it happen.

The leaders who will thrive in the AI era aren’t the ones with the best strategies. They’re the ones who can tell you exactly what happens to a piece of content between the moment it’s ideated and the moment it’s published. Step by step. Every time. Fifty times in a row without it breaking.

They don’t spend their time on the things AI can automate — scheduling, reporting, performance tracking. Those are the tasks they do at 9 pm after a day spent doing the thing no one wants to talk about: absorbing ambiguity.

A CEO sets a direction. An individual contributor needs a task. Somebody has to convert one into the other. That somebody is a middle manager, and the conversion process is almost entirely illegible.

It involves understanding that when the CEO says “we need to move faster,” she means something different than the VP of Engineering does when he says the same thing. It means knowing which of your team members needs explicit direction and which needs room. It means having five definitions of success and knowing all of them are right.

———

I’ve watched this play out in content operations. You have a CEO who wants AI visibility proof. A CMO who wants messaging proof. A board that wants traffic growth. A team that wants to know if their work matters. Same company, same quarter, completely different scorecards.

No AI agent is going to sit in a room with those four stakeholders and navigate those competing truths. Not because the technology isn’t good enough. Because the job isn’t information processing. It’s meaning-making.

What will actually happen is something more interesting than mass elimination. The middle management layer will split into two types. The first type — those who primarily route information and enforce process — will indeed be compressed. AI is already better at this. It tracks tasks, surfaces blockers, and generates status updates. If your primary value is being a human router, you should be worried.

The second type — the ones who translate, interpret, and absorb contradiction — will become more important, not less2. Because as organizations adopt AI tools, the gap between “what the tool can do” and “what the organization needs done” will actually widen.

Somebody has to bridge that gap. Somebody has to figure out that the AI-generated analysis is technically correct but organizationally wrong, because it doesn’t account for the political dynamics of the last board meeting.

———

The real risk isn’t that companies will eliminate too many middle managers. It’s that they’ll eliminate the wrong ones. They’ll keep the process enforcers because their work is visible and measurable, and cut the ambiguity absorbers because their work is invisible and unmeasurable.

And then they’ll spend two years wondering why their AI transformation isn’t working, why strategy isn’t translating to execution, and why teams feel lost despite having better tools than ever.

The messy middle of an organization is called that for a reason. It’s where all the mess lives. You can automate a lot of things, but you can’t automate the willingness to sit in confusion until it turns into clarity. That’s a human function. It might be the most human function there is.

You optimize for it. You tell yourself you’ll do everything to achieve it. The number becomes the north star, the ultimate validation of your worth.

After a few years, you realize chasing money for money’s sake doesn’t really work.

You discover Ikigai, personal growth, memento mori. You realign your work and life around deeper meaning. You realize the problems you solve, the niches you operate in, the rabbit holes you explore, and the large surface area for luck—these are what actually matter.

Then you start figuring it out. It all clicks together.

Fifteen years in, you’re a leader in your space. You have great self-awareness. You’ve developed a healthier relationship with money. You understand the game you’re playing.

Then begins your mid-life reinvention.

You work really hard to detach your work identity from your personal identity. This leads to an identity crisis: Who am I without my niche? Without FAANG on my resume? Without those fancy ARR outcomes?

Two things can happen here.

Path One: You successfully mold your work and personal identity into one cohesive whole. Your second coming becomes clear—founder, creator, consultant. You have a network that allows you to reinvent yourself into who you think you should be.

Path Two (the more common reality): The conflict becomes extreme.

You hold onto your work and keep getting hired for what you’ve done in the past. But it’s not appealing to you anymore. Your second coming isn’t clear. Maybe you’re not cut out to go out on your own.

At this point, you have a rich personal life—passions outside of work, kids, relationships, depth beyond your professional achievements.

And this is where you circle back to where you started.

All work can give you now is money. So you start optimizing for it again.

You fear ageism coming for you. You feel time running out before age and AI push you out of relevance. You start dreaming about “fuck you money”—every dollar becomes runway for the day you finally quit.

You fantasize: Maybe I’ll run a laundry franchise. Generate passive income. Become a farmer and grow my own food.

You’re comfortable with leisure now. You realize retirement isn’t about sipping mai tais (they’re too sweet anyway).

But you feel disconnected from your craft. You’re desperately trying to figure out your second act, your encore performance in this professional theater.

Here’s the uncomfortable truth: You’re not even halfway through life.

If you’re unlucky, you’ll live to 80. If you’re lucky, you’ll die sooner.

But if you end up with those extra decades, what’s your plan for the next 40-50 years?

Invitations and DMs are a whole other matter.

A few hours later...

****************

All characters and events depicted in this are entirely fictitious. Any similarity to actual events or persons, living or dead, is purely coincidental.

Funnel, flywheel…whatever floats your boat.

******************

All characters and events depicted in this film are entirely fictitious. Any similarity to actual events or persons, living or dead, is purely coincidental.

When I’m starting at $0 in MRR, how should I think about Content Marketing?

This post is an attempt to build a simple, step-by-step playbook to answer that question.

The five-step approach to startup content marketing.

• STEP 1: Questions as a growth strategy

• STEP 2: Bottom of the funnel SEO content

• STEP 3: Outsource content to customers

• STEP 4: Curation

• STEP 5: Thought Leadership

STEP 1: Questions as a growth strategy

As an unknown startup, optimize your first content strategy for conversations. Your objective is to get responses from customers. This means you need to be open to listening and have a response strategy.

I’ve outlined the Power of Questions as a growth strategy; I’m bullish on this approach; especially for young startups.

To headline it,

"Can you lead with a question in every piece of communication you put out?"

This overarching communication strategy should be the first thing you should nail down.

Once you have this down, the next step is figuring out a short-term strategy. This should give you some traction to get you going; your first win, while you figure out your long-term strategy.

STEP 2: Brand-focused, bottom-of-the-funnel SEO content

If you want to get to the top; start at the bottom.

Optimize for the bottom of the funnel.

Grow & Convert has two fantastic guides:

1. Pain-Point SEO: How to Produce SEO Content That Drives Conversions

2. SaaS Content Marketing: Why You Should Focus on Bottom of the Funnel First to Drive Signups

This is a small excerpt from the two posts on what you should be focusing on.

1. Comparison posts – this framework objectively compares your product or service to your top competitors. 

Example: Hubspot vs. Marketo: A Side-by-Side Comparison

My take: Go one step further; objectively compare two competitors on your website; without promoting your product. Don’t think you can do it objectively? Get a neutral writer and publish their piece without any editorial intervention. Put out a clear disclaimer on how the piece was commissioned.

1. Best product or service lists – this framework helps searchers discover the best products or services in the category they’re searching for.

Example: The 7 Best Marketing Automation Tools & Platforms in 2020

My take: Don’t be an idiot and publish your tool as #1. People will read this on your website. Chill.

1. Alternatives to X – this framework helps searchers discover alternatives to your competitor’s products. Here’s an example

Example: 8 HubSpot Alternatives for Marketing Automation

My take: Double down on this approach. If Marketo is on this list of alternatives; publish a separate post on Marketo alternatives. Include tools that are not on the Hubspot list. This way, you’ll cover a wide range of brand keywords in a specific niche.

1. Articles that talk about pricing – This framework talks about the pricing of your own product or service (if you have this hidden) – you could also do this for your competitors if they’re not forward about pricing. 

Example: How Much Does Marketo Cost (And is it Worth it)?

My take: Clearly articulate the total cost of ownership of a competitor versus you. Use this to tell people why you are cheaper or more expensive with a clear set of reasons. Think of this as the call to close the deal; what would you say? Say it here.

1. Product or Service Use Cases – this framework helps searchers figure out how to solve a problem they have and presents your product or service as a potential solution  – ie. how to increase leads from content marketing (note the subtle tie-ins to SEMrush throughout the post).

Example: 7 Secrets to Increasing Your Lead Conversion with Content Marketing

My take: This is a great investment for retention and churn reduction as well. These posts will be a great way to pre-board and onboard customers. Convert these into a use-case library and drive your existing customers to it.

Use these tactics to create your first 100 posts with a high-velocity publishing pace. You’ll notice some posts perform better than others. Some brand keywords convert best for you. Double down on this again. Set up separate landing pages for specific keywords; run paid campaigns to drive traffic to these pages.

You also know which competitors’ customers or prospects are converting best. Use this information to bid on competitor keywords on Google and drive them towards the best performing landing pages.

Next: How can you get your small startup marketing team to punch above its weight?

STEP 3: Customer-generated content

Marketers can consistently punch above their weight and create the illusion of plenty.

1. Gong is a widely-talked about brand; but, has fewer than 15 marketers on the team.

2. OpenView's high-quality blog and newsletter are run by three people.

3. I was the only marketer on the team at my first job in SaaS until we were doing seven figures in ARR. This is true for many other SaaS companies.

It's common to still have single or double-digit employees, while you have hundreds, sometimes several hundred customers.

You don't always make the most of them.

In my startup marketing days as a lone wolf, my CEO and I would open our Trello board for our marketing activities and see how we could outsource as much as 50% of those to our customers.

Creating content was by far the most challenging and time-consuming. We decided to invest time to build a program to outsource it.

Our customer-generated content included; (at three levels)

1. Why do you exist? What problems are you solving? What's your story? (company level)

2. Webinar/podcast series with persona. (persona level)

   1. Have 100 CMOs (whoever your persona or champion is) weigh in one topic or question (easily automatable outreach)

   2. Use that as a "foot in the door" to set up an individual CMO interview series. Double down; have them curate book lists, podcasts, newsletters, etc)

3. How are you using our product? (product level)

   1. Repackage to 1-sliders, case studies, testimonials

   2. Templates, use-case library

These people further feed into your advocate program.

You can have these customers speak with other prospects; over email or calls. Heck, we've had customers send out proactive reference emails and join prospect demo calls.

You should have each logo refer to at least one other new logo.

My biggest takeaway in running advocacy programs for years is; JUST ASK.

People want to say yes; all you need to do is ask. You will not believe how many people will say yes.

Make it personal

Not everyone can end up writing for Forbes or Fast Company. A lot of people don’t have the time or incentive to publish on social media or their own blog.

But, they want to be heard. They have burning topics on top of their mind that they want to express.

Some of them just want to appropriate their space on the internet. So that they get that byline and their article is found when people search for them on Google.

Make it compelling

1. Your blog is visited more than 100,000 people or that you have x number of email subscribers.

2. Showcase domain authority or previously published authors.

3. Show overlap in prospects and customers. Show that you cater to a similar demographic. And, this is their opportunity to get their personal and company brand in front of them.

Get it over the line.

Most people will say yes, start a project, and abandon it.

It’s funny that people have so much trouble going from 0-10, and again from 90 to 100.

Help them with both.

Write out the headline. Figure out the angle for them. If need be, write out subheadings as well.

Again, finally when they’re ready to abandon. Do a final edit. Get the images. Make them sound good.

The only investment we made was to hire a professional editor to ensure the quality of the content was consistent.

The idea is to pitch 10 stories a week. Some will get stuck. But, your volume will ensure you’re consistently publishing to get value for your efforts.

At this stage, you’re leveraging:

1. The power of questions and conversations

2. The link juice and visibility of other brands and competitors

3. Your first 100 customers, your promoters; the people who are keeping you afloat

Next: A tactic that’s criminally underrated in marketing: Curation.

STEP 4: Curation

What happens when you curate?

You become a thoughtful and helpful brand. 

Curation involves doing the dirty work of going through tons of resources. You combine the intelligence of all those resources in a consumable format. This saves your readers time and effort and more importantly, from information overload.

You rise above petty competitive politics. 

You simply promote a viewpoint that enriches the debate in your industry, even if it comes from a competitor.

You stand on the shoulders of great content.

“Honor by association” is a strong psychological tactic. People automatically elevate your brand, because you associate with a brand or person who’s already known for great content.

• Maria Popova of Brain Pickings curates from 500 years of books, letters, anything she can get her hands on.

• The Daily Skimm and Morning Brew have curated the news to become million-dollar businesses.

• The Scroll’s weekend reads are why I look forward to Sundays. Pocket Picks is my direct go-to reading list. (I never have to go directly to say the NY Times, The New Yorker, or The Wire)

Value of Curation for you = Your brand value * sum of all brands you curate from.

The power of this formula drives rapid readership and conversion. But, curation isn’t just a tactic; it’s a reflection of how you think of delivering value.

Here are 5 simple ways to start creating by curating.

1. When you start a blog post, e-book, or almost any form of content, bring in historical context for your reader.

You’ll see a lot of journalists start their articles with,

“In 1996” or “On one sunny day in Maine”

They give the reader some sense of how we got here, through a story or a key historical incident.

Or, they start with the genesis of their idea,

“I was reading a book or article.” or “I was walking through the streets of a city.”

Your curation starts from here. After they’re done reading your piece, they’ll want to perform the same action you did; visit the city or learn more about the historical incident you quoted.

When they like it, they’ll remember it was recommended by you. And, they’ll come back for more.

2. Link both internally and externally.

Whenever you’re writing, heavily quote and reference other works.

The story becomes meatier. Your narrative will flow. Your reader will feel confident because they know you’ve done your homework. By extension, they’ll want to hear your opinion on the matter. Sometimes, they’ll even want to pass it off as their own.

One caveat: Distraction.

Linking too much can lead to distraction— so much so they may abandon you to read something you linked to.

1. Tell the reader at the beginning, that there’s a reading list at the end of the post

2. Don’t hyperlink all your sources; add them to the reading list

3. Make sure all links open in a new tab; simple, yet important

3. Industry News, Best Of, Listicles, News Jacking, Skyscraper

Pick your niche. Go to the top authorities in the niche and pick out what they’re saying. But, if you stop there, you’ll only be known as the mouthpiece of established opinions.  As a curator, go to individual experts, smaller companies who have alternate views. 

Combine these resources with your own storytelling. This balance you maintain is why your readers will come back to you.

Create “best of” posts or listicles; heavily feature independent voices. Your content has the opportunity to be shared widely and you’ll build partnerships for the future.

Newsjacking has been widely abused in the past. But, it’s a powerful tool.

“Today, as a brand, you need to pick sides. You need to show up. You need to tell the world who you are, and what you stand for. If you don’t, then you don’t exist.”

Pick a cause you care about or an issue that is impacting the world deeply, right now. Tell your readers where you stand. Be lavish in praise or sharp in criticism. Be emotional, yet thoughtful.

Thanks to Backlinko’s Brian Dean; the Skyscraper Technique is a great way to turn content into high-quality backlinks. Plus, AuthorityHacker’s Shotgun Skyscraper technique is a super-actionable method to automating backlink outreach.

Pick a popular topic or trend in your niche that’s fairly well covered.

Improve upon existing content; new format, updated numbers, added research.

Reach out to people who’ve linked to similar content and ask for a backlink.

Underutilized Tactic: Personally, I’ve also seen great results from updating and optimizing old blog posts. It’s a tactic that’s captured very well by Hubspot here: The Blogging Tactic No One Is Talking About: Optimizing the Past.

4. Publish Your Swipe File, Review Your Software Stack, Write About People Who Inspire You

A swipe file is a collection of things that inspire you, that you want to replicate or steal. Every brand should have this. If you’re a B2B brand and you notice a great B2C brand, talk about the perspective of what it means to your industry.

Great examples,

• Swipe Files run by Corey Haines

• Marketing Examples run by Harry Dry

Another great way to curate is through reviews. Even small companies today use tens of software tools. Pick out a few of them and write how a specific team in your company is using them.

This also means, the software/company you’re reviewing will also promote this content and would be open to co-marketing in the future.

Interview amazing people and ask those people to recommend great books or other people to follow. This network effect is powerful.

5. Hidden Channel: Bonus, Bonus, Bonus.

We waste hundreds of interactions with prospects and customers.

Did you send out a cold outreach to a prospect? The response said not interested, right now? Close the conversation with something useful to read.

If you’re sending a round-up of webinars or upcoming events; add a bonus section to include something interesting to read, listen to or watch.

Don’t let any open conversation; think website live chat, support interaction, social media, even invoices—end without recommending something to read or consume.

All your teams; from support to customer success, should have a ready list of blurbs and links to promote.

At this stage, your content engine should be fairly solid. You would have also found your tone, voice, and publishing cadence that’s bringing consistent results.

Next step? Level up to deliver thought leadership.

STEP 5: Thought leadership

In one of the companies I worked at, (<5 million ARR at that time), we wanted to create a benchmark report for an industry that had zero access to such data, in the past.

We had to put in resources to crunch data, write the actual report, get high-quality graphics; the outcome was a thin paperback book. It was a lot to pull off for a small marketing team.

We promoted the book as a free giveaway for our flagship user conference. We promoted the report extensively and gave people small bits of data that got them really interested. This meant, people paid for the event, just to get their hands on the report.

After the event, the word-of-mouth was so powerful that we started receiving inbound queries from companies who were not even our customers. They wanted to buy the report.

At this point, we decided to monetize the report. We were converting content into revenue, while also starting conversations with potential customers. How sweet is that?

“That was a big step for me towards discovering what thought leadership looked like—when people want to pay money to listen to what you have to say.”

1. In Rework, Jason Fried talks about how Basecamp generates over a million bucks in just book sales.

2. Drift and Gainsight; category creators in Conversational Marketing and Customer Success, respectively—use books effectively to evangelize their categories.

When you get thought leadership right—it can have a multiplier effect on your business.

What happens if you can’t get it right?

"27% of decision-makers said reading a company's thought leadership directly led them to not awarding business to an organization."

Source: Edelman- LinkedIn Thought Leadership Study 2020

Here are 5 key elements to deliver real thought leadership.

1. Create aha moments with your content.

Explore potential challenges or new opportunities that your reader had not considered before.

2. Become quotable.

Showcase deep thinking and intellectual rigor. Offer actionable competitive intelligence and thorough high-quality research.

3. Establish authority. 

Offer a new, substantial, and potentially game-changing perspective on a specific topic.

4. B2B doesn’t need to be boring.

Entertain. Use bold, imaginative, and visual storytelling.

5. Question everything. 

Play the contrarian or unexpected angle. Couple it with the challenger sales model and you have a winning formula.

If you’re a small brand on a non-existent budget, how do you get started with thought leadership?

Start small. Aim to create,

1. 10% thought leadership content

2. 50% or more on curation or co-marketing content

3. The rest should be your branded content that includes product marketing, tactical tips, and tricks

Remember, if you get it right—the 10% can create 60 to 80% in outcomes. If you fail, you still minimize your impact on outcomes, because you fall back on the 90%.

As you start to get it right, increase the % of little by little until half of your content mix is only thought leadership. This requires journalistic rigor, a clear voice, and a curious passion.

How to get started?

Tap into early customers.

Go to your early backers; first 10 customers. Get the leadership to throw their weight behind you. If you pick 5 large verticals; get each leader to verticalize their content, so that you get a foot in that domain.

Outsource a small piece of thought leadership.

Could be a long-form post that has the potential to rank high on google, an ebook, or a short video that can be a lead magnet.

Write your own story

You started your own business, and made it to 100 or 1000 customers—there’s a fascinating story in there. Get a professional journalist or editor to write an essay out of it. Or maybe even a small book—who knows, what it will lead to.

Which step of the stair are you on? What’s stopping you from moving to the next level?

When I started at my current role, I was staring at a blank screen, lost.

I just spent the first month running a variety of pilots on the customer base.

The idea was to test various hypotheses on what would unlock expansion (up-sell + cross-sell) growth in the high-velocity segment.

I tested free trials, extended trials, discounting, (turns out; they all were terrible ideas) (that warrants a separate post) referrals, among other approaches.

I ended up finding an answer to a question I did not ask. What’s an effective communication strategy? Turns out, this was the “why” that needed figuring out first.

I knew, regardless of the tactic, channel, or offer; I'd figured out a scalable over-arching communication strategy to unlock growth.

I summarized it as,

1. Start a conversation.

2. Talk to customers like we know them and they know us.

   1. For example, instead of asking do you know about <Product X>, I took the liberty to ask, why are you not using <Product X>?

3. Do not start the conversation with discounts, prices, or an offer.

I distilled all this learning into one piece of actionable, tactical advice for me and the team I would build.

"Can we lead with a question in every piece of communication we put out?"

Can questions be an answer to unlocking growth? Especially with an aggressive eight-figure target?

I'm not even talking about the conversational marketing babble; this wasn't about the channel or technology.

This was about going back and ripping apart the SEO-driven, product-obsessed, inside-out drivel and replacing them with genuine questions with curiosity.

As is common in marketing, you just keep discovering the most basic things over and over again. Just with different levels of vigor and clarity.

Digging into questions

The Surprising Power of Questions published by HBR under Managing People may well have been published under marketing.

"Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards."

What’s the power of questions in sales?  Gong studied 500,000 business-to-business sales conversations—over the phone and via online platforms.

It found a strong connection between the number of questions a salesperson asks and his or her sales conversion rate.

The data also shows that top-performing salespeople tend to scatter questions throughout the sales call, which makes it feel more like a conversation than an interrogation.

Chris Voss, the ex-FBI negotiator, knows a thing or two about asking the right questions. In his book Never Split The Difference, he digs deep into the power of questions in a negotiation.

1. Asking people "why" can put them on the defensive and force them to defend their position. It's a good way to be assertive without being aggressive.

2. Replace "why" questions with "what" and "how" questions. They are the best words to start a question. "Does this look like something that would work for you" becomes "how does this look to you?"

3. "How am I supposed to do that?" is one of the most powerful questions, it's asking for help while moving them in the direction you want.

Closer to home, Dave Gerhardt's 1-line cold outreach email is a great example of a question done right.

Back to my experiment.

While my pilots validated the power of the strategy; I still had to put it into action, get results, and achieve scale.

I was mainly concerned about three things

1. I was worried that customers would face question fatigue

2. I had to orchestrate questions into campaigns (the funnel nonsense that comes with it plus to pick the right channels)

3. I also needed a response strategy.

As marketers, we're wired to drive the customer to take action. Sending them off to blogs, landing pages, sign up pages, calendars, etc. But, we, typically, don't have a response strategy (that more sales' territory). But, having a conversation means both sides are listening and engaging. I set aside marketing bandwidth to listen and respond to customers.

Converting questions into dollars

In early 2020, I wanted to put this into action in a big way.

My first big-bet campaign, now prophetic, asked our customers, Share Your Pain with us in 2020; what's the biggest challenge you're looking to solve in 2020?

The answer did not have an option for a pandemic or a recession.

By early March, it was clear that it would be insensitive to continue asking this question.

So much for a grand plan. What a dud.

But it did give us an opportunity. We genuinely wanted to know how our customers were doing.

So, we went back to the same strategy, and asked our customers, two simple questions,

“How are you doing?” & How can we help?

That resulted in an outpouring of responses.

Businesses that were shutting down told us their horror stories. Some were doing fine. Some wanted monetary relief. Some grew their business 4x overnight.

We found out who was doing well, who wasn't, and who needed help. This helped us save a significant dollar number in churn. 

Buoyed by the responses, I was celebrating my first win. And a measurable dollar number to boot.

With that momentum, I went back to the entire customer lifecycle and mapped out questions for each part of the life cycle.

Top 10 customer life-cycle marketing questions:

1. What is the one thing you're looking to accomplish with our product?

2. Why did you not upgrade? What did we miss?

3. Did you consider any other product besides us? If so, which ones?

4. Why did you choose to buy from us as opposed to from our competitors?

5. What's the one thing we can improve in the upcoming year?

6. What's the one thing that impressed you the most in the last year?

7. Which product aligns with your business need, and you would be interested in trying it out next?

8. Can you write us a review?

9. Would you like to be a sales reference for other prospects?

10. Can you refer a friend or business to us?

Insight: The power of questions compound; we got 4 times the number of responses than we would normally, whenever the question followed an action by the customer. Signup, a download, a page visit, etc. Follow up immediately for the best results.

Action: I see your trial expired and you did not upgrade.

Response: What did we miss?

Action: I see your NPS promoter response

Response: What other products are you interested in?

Action: Web activity or competitor web page visits

Response: Are you evaluating X?

For demand generation, we aligned question packs to each product.

For example, if you’re selling an email marketing software, your question could be,

What are your key email marketing priorities in 2020?

1. I want to send trigger-based or personalized emails based on web activity

2. I want to improve my deliverability and email engagement

3. I want to improve lead nurturing through email automation

4. Other <type in your response>

You’ll have a set of similar questions aligned to email marketing that’s ready to use across channels.

The other side of this strategy is; what questions are our customers asking?

This is a key focus area for 2021. Can we go back to all your customer interactions and pull out 25 of the most asked questions by our customers?

Then, spend the entire year answering these questions with honesty and depth. (save us the SEO-driven, product-obsessed, inside-out drivel)

I'm headlining this for the upcoming year; ask the right questions; answer the right questions.

I was zooming with the founders of a pre-PMF company.

The call started with, “who should we sell to.”

They were selling their B2B SaaS product to three different personas—still trying to find the best fit.

When they were building the product; it was clear to them that the product was for the CEO persona; a typical product or tech founder.

However, once they launched the product; it was best adopted by Customer Success teams. The CS persona was sticky with the product and was consistently achieving the "activation" metric the founders set for the product.

But, typically, after a couple of months of using the product, they started churning.

Curious, the founders started to dig deep.

They found that while the CS group was the primary users of the product, they were using the tool to consolidate data. Then, they would take the information to the Product Management group for them to act on it.

At this point, there was friction with the PMs because they wanted to use their own tool.

Vetoed by the PM group, the CS persona would cancel the subscription.

So, why not then sell to the PM group, right?

Selling to the PM group meant modifying the product roadmap, and jumping into an overlapping space with a ton of competition.

Stick to your guns or change course?

When you build a product for a specific persona; it’s fair to trust your gut to see if you can build traction with that persona.

The point of the founders, both veterans in tech, was—they were eating their own dog food and they couldn’t function without it.

The counterpoint?

While their ICP was companies with more than $1 million in ARR; it was clear that as revenue grew, the founder would abandon the product and eventually pass it off to another persona. It was in no way a lifeline software.

In Merchant of Doubt, Erik M. Conway & Naomi Oreskes, write;

“If we read an article in the newspaper presenting two opposing viewpoints, we assume both have validity, and we think it would be wrong to shut one side down. But often one side is represented only by a single ‘expert’.”

Take away: Always trust your judgement. But, listen closely to the market and be ready to change course.

Power vs function

When it came down to Product Management v Customer Success; it was a trade-off.

The product was popular and well adopted by the CS persona. But, the shortcomings were clear.

The CS group did not have the purchasing power for the product (despite low-ticket size), and in the internal power struggle—always lost out to the PM group.

That's two strikes;

1. The persona does not have the means to buy

2. When pitted against another buying group, they did not have the power or influence to sway the decision

With that new evidence, both traction and activation go out of the window. They're worthless without the ability to monetize.

In fact, they'd be better off looking at a better activation metric; one that’s tied to monetization or retention.

Takeaway: Always pick a persona with the means to buy over one that uses the product more; if it ever comes to that. Always side with the power structure. Don't bet against it.

Selling to the PM group means a significant detour in their product roadmap and entering an adjoining space; one that’s super-competitive.

While this is a competitive space, it has its upsides too; it’s a validated market. The time-to-PMF would be way faster.

Two other smaller players have both made it to six and seven figures in ARR. And, then, there's the behemoth that exists in the space.

Selling to the PM group would almost be a new launch and a huge challenge. They'll be selling a new, under-developed product to an over-marketed-to persona.

Takeaway: Only time will tell.

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An aha moment is quite literally when a user says “aha” to themselves on the discovery of a moment of value while using a product or service.

So how do aha moments translate into actual actions?

For example,

1. When you've sent 2,000 messages on Slack, you're 93% more likely to stay

2. When a Pinterest user saves pins for 4 weeks after signing up, they’ve been activated

3. When a Facebook user adds more than 7 to 10 friends, their usage will only go up

Now, when you’re using Slack, you don’t care about how many messages you’ve sent or how many friends you’ve added on Facebook.

For the customer, the ‘aha’ moment is more emotional or a moment of true value—it’s an experience.

The earlier customers experience an aha moment, it leads to a chain reaction;

• Driving these actions in your onboarding journey leads to early activation

• Early activation leads to faster time-to-value

• The faster people see the value, the sooner they enter your growth flywheel

So, what is pre-boarding?

Pre-boarding is when your customer has already experienced aha moment(s) even before they go through your onboarding journey. Almost as if, they already knew how to get value from your product.

But, why is pre-boarding important?

Short answer: Churn.

Pre-90 churn (customers canceling or abandoning your product before the first 90 days) is a massive problem for SaaS products (more so for low-ticket products sold to SMBs). With pre-boarding, you’re able to prevent or reduce pre-90 churn.

Typically, companies focus on activation milestones only after a user signups for a trial or a free version of the product.

For example, Canva might want you to create your first image and download it as soon as you sign up. The sooner you do that, the stickier you’re going to be.

But, let’s flip that. Wouldn’t you love to create your first image on Canva even before you sign up? However, as you can see, Canva is purely intent on getting you to sign up.

If you deliver your aha moment before sign up, it can:

1. Help increase the quality of your conversions; trial --> activation --> monetization

2. Increase the likelihood of feature discovery; “Oh, I didn’t know, you could do that.”

3. Convert people who’re wary of giving up their email just to trial software

Suddenly, your customers can now experience outcomes through your product, even before day zero— outcomes they would otherwise experience only on the 7th day or 10th day.

Trello does this well. But, not completely intentionally.

Case 1: Trello

The primary call to action is still for you to sign up, but not experience the product first.

However, when you scroll down the page and click on “templates”, you land on a beautifully sorted library of crowd-sourced Trello boards, most of them publicly available.

The idea is to give you a starting point, rather than have you start from scratch.

There are your first ‘aha’ moment/s. You look around. Get the feel for the software. Discover tiny quirks and capabilities. And, when you’re ready, you’ll start somewhere.

Trello is also lucky in how people use it. Most publicly available roadmaps are built on Trello.

For example, this is Buffer’s product roadmap.

Let’s say I’m a Buffer customer and I have an enhancement suggestion. Even if I’ve not heard of Trello,

1. I end up Discovering Trello

2. I have to use Trello’s features to post my enhancement (I’m going through my ‘aha’ moment, without realizing it)

3. I have to sign-up to Trello to post my suggestion

This is the very definition of a "Viral Loop."

Another company that’s doing pre-boarding admirably is CloudSponge.

Case 2: CloudSponge

CloudSponge enables users to import their contact book when they want to share something.

For example, you might have just read a great version of The Morning Brew, and want to forward it to a few of your contacts (This is how I discovered Cloud Sponge). Instead of manually adding these contacts, you can use Cloud Sponge’s contact picker to multi-select contacts and do this in a cinch.

Cloud Sponge understands that it operates in a space where users are touchy about sharing contacts and have privacy concerns.

So, instead of pushing people to sign up, it has two distinct CTAs that help deliver the aha moment before they sign up.

On clicking CTA 1; "Try it With My Address Book" you land on a ‘live demo’ as the page suggests. Here, you go through the same experience your customer would have if you ended up buying CloudSponge. And, you experiencing it, without even signing up.

Second, it understands that its success also lies in the hands of engineers. So, it provides a sandbox option to safely try the product, and win over its adopters. Callout to how clearly the step-wise process is outlined; gives a clear indication of the effort required from an engineering perspective.

1. If I’m a marketer who’s evaluating Cloud Sponge, I care about the customer experience. Now, I understand; how it works.

2. Since technical integration is necessary, the sandbox option wins over the engineers.

True pre-boarding win.

How can you strengthen your pre-boarding experience?

Believe your product is good enough. Tell your story through your product.

1. Start small. Start with making sure to have product screens on your website and you explain value and outcomes through them.

Example: Be meta. Freshworks uses its own bot to promote its bot offering. (Disclosure: I was involved in designing this.)

2. Even if you cannot open up your product, see if you can have publicly available demo instances for customers to poke around and experience aha moments.

Example: Host a treasure hunt within your product. Bury information deep into your product and giveaway gifts for people who find that information.

3. Rethink your CTAs

Example: CloudSponge, above is a great example. A sign up can continue to be your primary call to action—have a secondary call to action that drives people towards experiencing your product's aha moment.

Switching to product-led is a big step because, in the short-term, you'll possibly see;

1. Fewer signups

2. Inability to track all user actions and tie them back to a specific user or account

3. Slew of bugs and product suggestions reported by users

But, in the long-term, your payoff will come in the form of results that actually matter,

1. Reduced churn (especially pre-90 churn)

2. You'll see significantly higher conversions, whether it's trial —> paid or free —> paid.

3. The more open the product becomes, the more invested your users are. It's way easier to do drive adoption and advocacy in a community-led model.

4. You won't need to invest heavily to hire sales or sales support resources.

Rabbit Hole:

1. Watch Tim Soulo talk about SaaS Onboarding at Ahrefs. He calls the concept of delivering the aha moment before sign-up as "pre-boarding."

2. Why Email Registration is Dead. How Removing it Improved Retention by a Surprising 4.5%