Peep Laja

CEO @ Wynter. 3x Founder. Insights over assumptions. Host of How to Win podcast.

Most of your future revenues are gonna come from future customers. 

If you knew *exactly* what your target customers

think about your category (and your company in particular),
what their top priorities and very big problems are,
what unsaturated channels they use to learn about solutions, 

this is what'd happen to your business:

- you'd nail your messaging, speaking exactly to their pain points
- your conversion rates would go up because your pitch resonates better,
- your CAC would go down as you'd use the right channels with the right message,
- you'd create more meaningful content that moves the dial,
- you'd be more deliberate and accurate in providing more value at every touch point,
- you'd know how to price your products to maximize willingness to pay,
- you'd know how to differentiate,
- you'd know where your go-to-market strategy is off, and could fix it. 
 
The beautiful thing?

You can know all of this with Wynter in under 48 hours.

We asked 101 B2B SaaS CMOs: "Where do you start when searching for new software?"

The results prove that most marketing teams are optimizing for a world that no longer exists.

Here's what they turn to:

∙ Google Search: 72% 
∙ AI/LLMs (ChatGPT, Claude, Gemini, Perplexity) 68% 
∙ Peer communities: 65% 
∙ G2/Review sites: 52% 
∙ Vendor websites directly: 38% 
∙ Analyst reports: 28% 
∙ LinkedIn: 24% 
∙ Reddit: 12%

The headline looks normal. Google still on top. Nothing to see here.

But dig into the data and the story changes completely.

Only 9% *start* by googling a software category.

The other 63%? They use Google after they already have a shortlist. Google has become the verification layer, not the discovery engine.

Meanwhile, 68% now start with AI tools before traditional search.

One CMO told us: "I use Perplexity so I can do a natural language search to find software types. I use Google only if I have certainty about which specific products I want."

Another: "ChatGPT gives me a shortlist in 30 seconds that would have taken me hours of Googling."

Here's what this means for you:

If you're not showing up in ChatGPT's recommendations, you're not showing up.

84% of CMOs use AI for vendor discovery now. 68% start there. Before Google. Before your website. Before your content.

The battle for initial consideration has moved. Most vendors haven't noticed yet. They're still optimizing for a Google-first world that ended sometime in 2025.

The CMOs who buy your software? They're asking Claude "what are the best tools for X" while you're publishing another SEO blog post nobody will read.

Also buried in the data: Reddit at 12%.

Why? One CMO explained it perfectly: "Real users complaining about real problems, that tells me more than any marketing site."

Your unhappy customers on Reddit are now part of the buying process. Fun.

The new discovery stack:

∙ Ask AI for landscape view
∙ Cross-reference with peer community
∙ Check G2 for social proof
∙ Google for red flags
∙ Then visit your website

If you're invisible in steps one and two, they don't get to step 5.

(This is a finding from Wynter's 2026 CMO Software Buying Survey. Link to full report in comments and Wynter website).

AI can't buy your software.

AI can't feel the pain of a broken workflow. It can't sit in a budget meeting and fight for your deal. It can't get burned by a competitor and carry that grudge into the next vendor search.

A human does all of that. And humans are weird.

An example: We surveyed 101 CMOs and VPs of Marketing on how they buy software, here are some things we learned:

Most CMOs still prefer buying through a sales rep. Not self-serve. Not a chatbot. They want a human to walk them through it. 

When a vendor leads with AI in their messaging, many buyers are less interested. They see it as hype. One marketing director told us flat out: "slightly less likely to consider them, sounds like hype, makes them doubt it all." 

A CMO at a PE-backed company told us their investment firm says "No one should be adding more people because AI is gonna deliver that extra capacity we need. I'm watching my budget get slashed while pipeline targets go up." 

That's not a sentiment you get from a synthetic persona. That's frustration with a very specific power dynamic.

A field marketing director shared that small roundtables are outperforming their big signature events and webinars. People want intimate, shorter, smaller. That's a nuance shaped by what happened in their org last quarter, not a general market truth an AI could infer.

This is the thing about B2B buyers.

Their decisions are shaped by internal politics, past vendor trauma, budget timing, org structure changes, what their CEO read on LinkedIn last week. 

An LLM doesn't have access to any of that. It can give you a plausible average. It can't give you the actual answer.

Use AI to analyze responses faster. Use it to write better survey questions. Use it to find patterns in data.

But when you want to know what your buyers actually think? Ask them.

A real buyer can tell you what you didn't expect. And the stuff you didn't expect is where the actual insight lives.

Map & Fire

Map & Fire is a Los Angeles based research and brand consultancy. We help you own a unique space in your market with a mix of research, positioning, and messaging – so you can connect with more customers and grow with confidence.

View happy client testimonials at: https://mapandfire.com

Founder, Brand Strategist

HelloAdvisr LLC

Strategy Advisor

TVGla

• Led a team of 14 producers and was responsible for defining the department's vision and planning, managing overall budget, conducting individual reviews, setting goals and providing guidance on all project work.

• Provided strategic insights and oversaw production efforts for the agency's two largest Digital Agency of Record accounts, Wheel of Fortune and Jeopardy!, along with a wide array of campaigns for companies including Sony, Universal Pictures, Paramount Pictures, Hard Rock Cafe, Cinemax, A&E, History Channel, Dreamworks and Gruppo Campari.

• Unified and facilitated cross-training of a production department that had been historically split between a team of digital banner producers and web/app-focused producers. In addition, established dedicated production support for the company's quickly expanding social department.

• Worked to build strong relationships with all team members by providing personal support, empowering them to take on deeper responsibilities and challenging them to work on projects outside their immediate areas of expertise.

• Improved overall efficiency and expertise of the department through process refinement, mentorship and the introduction of improved project management and communication tools.

Executive Producer

• Played a key role in building the strategy and relationship that led to the agency's first major Digital Agency of Record account with Wheel of Fortune.

• Beyond production responsibilities, provided additional insight and value by helping to guide UX decisions, as well as input on creative and technical implementations.

• Led over 75 projects for clients such as Google, Sony, Universal Pictures, Mattel, and FOX. 

• Managed and oversaw between $1.5 - 2MM of project revenue annually, consistently delivering work under projected budgets.

Senior Producer

Better You

• Founding partner in startup, responsible for full UX, product management, and technical life cycle of project.

• Wrote business requirements, defined user experience, user flows, and created interactive wireframes for the entire site.

• Designed graphical UI elements for site and prototyped frontend experience.

• Managed developers to build out front and back end coding on a LAMP platform.

Co-Founder, Head of Product Development

Bird Branch

• Worked in a variety of roles including brand strategist, UX designer, creative lead, and developer on over 150 projects.

• Collaborated with a wide assortment of clients on projects ranging from the entertainment industry to consumer products to health care both in project lead and contractor roles.

• Extensive experience with both UI and graphic design.

• Developed front and backend code solutions utilizing existing frameworks as well as fully custom implementations. 

• Responsible for managing project budgets, tracking progress, and coordinating work both with clients and additional resources.

Founder, Strategy, UX, and Design Consultant

G4 Media

Senior Web Developer

Avacus Corporation

Web Developer

O'Neil Data

Unigraphics Solutions

Software Developer

Win with a brand built on research, not guesses | Founder Map & Fire 🔥, SmokeLadder | Contributor at Foundr Magazine

I use a mix of research, positioning, and messaging to help founders and marketing leaders connect with more customers and grow with confidence. 

My writing on strategy and research has been featured in Foundr Magazine and AdWeek. 

More about my background:

I've spent the last 20 years dreaming up and then bringing to life multiple startups as well as a wide range of digital projects. With every twist and turn of that journey there’s been a consistent thread of weaving together strategic problem solving, creative expression, and a curiosity to better understand how people think and make decisions. 

In the businesses I created or co-founded, my primary focus has always been on strategy and user experience. For others, I've worn lots of hats from Executive Producer, to Designer, to Copywriter, to Developer. I've also enjoyed an unofficial Account Services role where I carefully honed the craft of client therapy.

Over the years, I've collaborated with countless passionate small businesses along with several Fortune 500 brands including Google, Sony, Universal Pictures, Mattel, FOX, Dreamworks, CBS, A&E, Home Depot, Roland Keyboards, G4 TV, and the LA Times. 

When not doing mental gymnastics, I like spending time with my amazing wife and son, hiking, surfing, and watching things that make me laugh.

Clay Ostrom

Looks like we’re running it back this fall! 


As part of my year of doubling down on relationship building, heading back to Exit Five's Drive in September was a no-brainer. 

To take it up a notch they’re having it at a giant ski lodge up in the mountains (but luckily it’s early fall so no concern of getting snowed in, The Shining, etc.)

Also, I finally joined the Exit Five community so this time I’ll get the *true* insider experience. 

Fresh air, mountains, and a bunch of awesome people hanging out for a few days. Definitely worth another cross-country flight. 

I'm already getting hydrated...let me know if you're going! 🙌

Founder Map & Fire 🔥 // SmokeLadder.com | Research + Positioning + Messaging | Contributor at Foundr Magazine

Going back to Exit Five's Drive this fall!

This has been many years in the making, but 37 5-star reviews later and Map & Fire has hit #1 on Clutch. 


I know there’s a matrix for everyone these days, but this really is a product of a lot of hard work. 

What I’m especially proud of is that we did this with a *tiny* team. Most of the other companies on that list are waaaay bigger. 

So, here’s to all the little Davids out there going toe-to-toe with (and sometimes taking down) those Goliaths.

There’s always a place out there if you treat people extremely well and do great work. 

Over time it adds up. 🙌

Map & Fire - #1 on Clutch for Market Research

One of the most important rules about positioning: Your brand doesn’t exist in a vacuum. 


When you live inside a brand 24/7 it’s easy for your view of the world to get warped by your own value (and features, capabilities, etc). 

But for everyone else (i.e. your customers) they have a *much* noisier perspective. 

When they’re consuming your content they’ve got all kinds of information dancing around in their head.

Essentially they’re scrambling to make sense of:
1) What you even do
2) How you fit into their understanding of the category and their needs
3) Whether it makes sense to choose you

And they do this by mentally (and manually) comparing you to the other options they know that do something similar.

Or to put it in simple terms:

Your value is relative to the competition. 

On its own your product or service may be really strong in a bunch of ways: saves time, reduces effort, lowers risk, improves marketability, etc, etc. 

But what does that same value look like when you stack it against competitors who are also fighting to provide the same kind of value? 

How about when you compare it against 3, 4…10 other competitors? 

The noise in your customer’s brain is at 11. 

The solution?

You have to find that small combination of points where:
1) You provide value at a very high level
2) And it has some separation from the competition

In this video I do a quick demo of this with a brand I really love, Tella – a video recording tool (this is not a sponsored post, I’m just a fan…and used them to create this video)

It shows what their unique value curve looks like on its own – and what it looks like when you stack it up against: Loom, Descript, and Riverside.

Seeing the overlaying value curves of 4 brands competing in the same space really drives home what that noise feels like. 

But it also shows how you can start to spot areas of strength to lean into by looking at the relative value. 

If you’re trying to figure out where to double down in your positioning and haven’t done an exercise like this with your category, now’s the time. 

The landscape is only getting noisier. 🎧

You can’t fix a leaky bucket with a firehose. 


When your positioning and messaging aren’t dialed in, the leaks are everywhere:
- People immediately bounce (don’t understand your value)
- They don’t engage (can’t see how your offering is different)
- Try it once or run through a demo and never return (weren’t the right fit to begin with)

But rather than address these issues it’s tempting to try and mask them with morrrre traffic.

There will definitely be a burst of more bodies in the short term…followed by way more people leaving for the same reasons they already were.

If you’re seeing those symptoms take a hard look at the bucket for leaks. 

- Is our offering crystal clear? (the core value you provide and the category you’re in is understood in a few seconds)
- Is it obvious what we do different from other known solutions? (the 1-2 points where you have real separation)
- Does our target customer see themselves represented here so they can self-select? (the identity and characteristics of your ICP are front and center)

Once you’ve got those locked in, by all means turn on the firehose. 

Then you can worry less about patching holes and put all your sweat into building a bigger bucket. 


Shoutout to Alon Even for his post last week about trying to spend your way out of a broken system that sparked this idea. 👏

And a big shout to Finn McKenty who has a ton of great posts on using tools like Weavy (starting with hand drawn sketches!) to create custom content – I finally did it! 😅

It was cool to be a part of Brand24's new prompt book…but the best part is seeing the contributions from so many big brains in marketing...


Truly some of my favorite people on LI (who you should obvs follow) sharing their prompts for many of my favorite topics:

Lashay Lewis on competitive intel: “Use this prompt to get a sharp, decision-ready view of your competitive landscape. It’s built to move past surface-level comparisons and uncover how competitors actually win.”

Mina Mesbahi on VoC analysis: “While this doesn’t and shouldn’t replace listening to calls or doing proper customer research, it’s a low-lift, high-impact way to keep a pulse on the conversations that matter most.”

Sara Stella Lattanzio on business-driven content audits: “Use this analysis to move past isolated KPIs and understand the relationships between traffic, engagement, and revenue. Ideal for B2B teams who want data-backed decisions about which content creates value, not just visibility.”

That's the just the start.

There are 20+ in the book…including my approach for helping to analyze positioning and differentiation. 

It’s already been a great resource for me, not just for the prompts but to spark ideas on how these other smart, creative people are using these tools. 

Well worth the free download. Link below 👇

Thanks Alicja Mękarska for including me! 🙌

AI Prompt Book

There’s a word I’ve been getting increasingly obsessed with when I think about my product (and really anything with AI)...


Context. 👈

I’ve had a lot of interesting conversations lately with folks using AI to build products. Vibe coding speeds are already insanely fast….and only getting faster.

Which leads to the question of “what’s your moat?”

Previously I’ve always pointed to 3 things:

1) Data – I’ve been building up a fairly big database of positioning and messaging analysis over the past 1-2 years. We’ve now got a million+ qualitative and quantitative data points specific to these areas.

2) Frameworks – The product is built on 10+ years of developing expertise in the space of positioning and messaging, and the product leverages those learnings / POV / experience.

3) Presentation – Not just making it easy to run analysis on a brand and research competitors, but making it clear how to use the results to differentiate a brand you’re working on.

Number 3 is the weakest. Though it’s not as simple as just spinning up a clean UI , this is a specific type of problem that requires real thought and UX to make it consumable.

Still, it’s the most surface level.

Where I think the real value is – and the deepest moat – is a mix of (2) + (1).

That’s where Context comes into play.

If you’re using a vanilla LLM to run analysis…or if you’re really ambitious and building your own tool…you’re doing your work in a bubble. 

You have whatever data and learnings have been sucked into the LLM to help guide its output. And it’s the same content that everyone else has.

The advantage I have with SmokeLadder is that we’re able to use all of our data + the learnings / POV / experience to guide and inform the output. 

We (the royal product “we”) have insider knowledge about:
- The overall problem space of positioning and messaging
- Category benchmarks based on analysis across thousands of brands
- Insights about the messaging and positioning of specific brands

All of that creates context to make the outputs we provide unique. 

Every time you run analysis on a brand you get to dip into layers and layers of context.

And by running that analysis…it makes our context stronger.

Will all this context be a deep enough moat to protect the product for the long haul? We’ll see! 😅

But for now I at least feel like it’s heading on the right path to create something as defensible as possible.

I’ve been thinking about a new idea / theory / framework lately: “Strong ICP, Loosely Held”.


This has been on my mind for a while but crystallized a couple weeks ago after I officially signed our first big, Fortune 100 client to my product.

The cool parts:
- This client found the product cold via good old fashioned Google search
- They were looking for a product that could help with their internal positioning and messaging work
- They explored a bunch of options, got some demos, and SmokeLadder was the only product they found that fit their needs

Awesome! ...Right?...

The thing is, Fortune 100 companies were *not* on my radar. 

The ICP I’ve been focused on are small to mid-sized agencies (and some individual consultants). 

That’s who all of our paying customers are.

Agencies are constantly working with new clients / brands that either:
- Need them to actively fix or refine their positioning and messaging to help them differentiate
- Or at a bare minimum need a better understanding of the client’s positioning and messaging to execute their work
- (along with the positioning and messaging of their competition)

As it turns out this Fortune 100 company (I promise I’ll talk about who they are as soon as I can) is kinda like an agency. Their team of brand strategists manage hundreds of internal products. So like an agency they’re doing this work all the time.

But unlike a small agency, a product-led growth approach wasn't quite enough. 

They’re not just used to a longer, more hands-on sales process, they *require* it.

The procurement process for this was 2+ months…and involved many rounds of hoop jumping.

So…the key question:

When does a new customer type deserve real attention? 

What’s worthy of shaking that strongly held ICP loose…at least a little?

Is it:
(1) Revenue? Yeah, but one enterprise customer can easily give a deceptive signal of revenue opportunity…
(2) Consistency? Do you really understand how this new customer found you…and is it repeatable?
(3) Customer Fit? Is this customer representative of this segment or more of an outlier? 
(4) Sales Fit? Is your team equipped to handle this new segment?

For me, (1) is of course interesting…(2) is encouraging but TBD…(3) deserves more investigation…(4) curently a solid no (i.e. I am not built for an enterprise sales process, at least right now). 

I think these are at least the right questions…but there's some real work to do to find the answers.

What else should I be thinking about? 🤔

Ps- I *never* write text-only posts so very curious how this will land. Good sub-meta experiment. 🤓

Thinking about a slightly different angle on positioning: What parts of your product/service make your competitors the most nervous?


We’ve all seen the classic competition comparison charts. Usually it’s:
✅ We’re all green-checkmarks
❌ They’re all red-x’s. 

But when competitors do an honest evaluation it can be pretty revealing.

I came across this analysis from a competitor for SmokeLadder that I wasn’t aware of previously. 

(I only discovered their content because Alertmouse gave me a head’s up - shoutout to Rand Fishkin!)

This company Theo, offers positioning analysis reports for brands using a mix of service and AI. Basically you send them a site and they assemble a report for you.

As an example of their service they naturally analyzed their own competitive space…and identified SmokeLadder as their top competitor. 

What’s interesting is that it revealed some key strengths about SmokeLadder from their pov:

1) First mover advantage – SmokeLadder has been in the market for 2 years now (1 year beta, 1 year taking on paid users) and is one of the only products truly focused on positioning and messaging

2) Data accumulation – We’ve collected 1MM+ data points on positioning and messaging across 10K+ brands over that time

3) Freemium PLG model – You can jump into the product and run analysis instantly, no waiting for reports

4) Methodology expertise – The product uses frameworks and proprietary processes built on 10 years of experience in the space


Of those factors only (4) is a place they can compete with – 1-3 aren’t things they can quickly change and/or just aren’t part of their model.

Together it creates a strong case for why they might be anxious.

So that’s the question to think about – Not just where your product or service is strong….but what might make your competition sweat because they either: 
(a) Can’t replicate it
(b) It’s fundamentally different from their model

If you take a deep look at your competitors they may even be spelling it out for you. 👀

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