Behind the Brief | Honest Stories from the World of Marketing

I went into my conversation with Apurva expecting to talk about global product marketing.

I came away thinking about context.

Because we talk about PMM playbooks constantly.

Positioning frameworks.Messaging frameworks.Launch processes.ICP research.Competitive analysis.

All useful.

But the more I listened to Apurva talk about working across different markets, the more I kept coming back to one thought:

A playbook is only as good as the context it was built for.

My biggest takeaway

I don’t think the lesson is that playbooks are useless.

It’s that PMMs need to understand the thinking underneath the playbook.

Because when the market changes, the buyer changes or the context changes, the execution may need to change too.

That’s what made this conversation so interesting to me.

🎙️ Episode 34 of Behind the Brief is live now.

Watch / listen →

There is a particular kind of career anxiety that comes from wanting a job you can’t seem to qualify for.

You look at the job description.

“3+ years of product marketing experience.”

You look at your resume.

No PMM title.

You close the tab.

I’ve heard versions of this story so many times, which is why I wanted to talk to Jenn Holcomb.

Today, Jenn is a Senior Product Marketing Manager at Interplay Learning.

But she didn’t start there.

She was a teacher.

A financial aid counselor.

A tech support rep.

A BDR.

A field marketer.

And at one point, she discovered she had actually been doing product marketing without knowing there was a name for it.

That conversation left me thinking about five things.

1. Your detours might be your differentiation.

Jenn’s BDR experience taught her how sales works. Her technical support experience gave her deep product knowledge. Her teaching background became evidence that she could influence people, communicate complex ideas, and keep people moving toward a goal.

Then she found a company where her higher-ed experience + B2B SaaS experience made her unusually relevant.

She didn’t need to be the best candidate in every category.

She needed to be the candidate who made sense for that particular problem.

A quick word from this episode’s sponsor: Eddie fixes the gap between shipping a positioning update and it actually sticking. It turns your enablement docs into short, trackable Slack coaching sessions — so you can show what landed, not just hope it did.

Check out : https://www.geteddie.co/

2. Don’t just list your skills. Build the evidence.

Jenn gave one of the most practical pieces of advice in the conversation.

Take a job description.

Copy every requirement into a document.

Then, underneath each requirement, write a specific story that proves you’ve done something similar.

Do this enough times and you start seeing patterns.

You realize you’ve been doing more relevant work than you thought.

And if there’s a genuine gap?

Now you know exactly what you need to go learn or practice.

3. Getting the title doesn’t mean you’ve earned the trust.

This might be my favorite PMM lesson from the conversation.

When Jenn first moved into product marketing, she quickly realized that having the title wasn’t enough.

So when someone challenged her recommendation, she started doing something very simple:

She’d go talk to five customers.

Then she’d come back with their actual words.

That changed the conversation.

Not because “customers always know best.”

But because she was building a reputation for validating assumptions instead of defending opinions.

That is product marketing.

4. AI is fantastic at the middle of the job. But it can also make all of us sound the same.

Jenn has built an automated competitive intelligence newsletter that lands in her inbox every Monday.

It scans the things she actually cares about: competitors, industry news, research, market sentiment.

That’s a great use of AI.

But there’s a line she won’t cross.

Customer proof.

Statistics.

Quotes.

Anything where getting the details wrong can damage trust.

And then we got into a bigger question:

If AI can generate competent marketing content so easily, where does the human advantage live?

Her answer was essentially:

Judgment.

Differentiation.

Customer conversations.

Influence.

Taste.

The things that make you say, “Everyone else is saying this. We shouldn’t.”

5. Find somewhere to practice.

One of Jenn’s most interesting suggestions wasn’t another certification.

It was finding a hobby, volunteer project, or local business where you can actually practice marketing.

Because you can watch another 20 webinars.

Or you can try something.

Make a positioning mistake.

Rewrite the messaging.

Talk to a customer.

Get feedback.

Try again.

That’s where the learning happens.

And maybe that’s the bigger lesson from Jenn’s career.

You don’t always know what your career is building toward while you’re living it.

The BDR job doesn’t announce that it’s teaching you sales.

Teaching doesn’t announce that it’s teaching you influence.

Tech support doesn’t announce that it’s teaching you product fluency.

The pieces only start making sense when you look backwards.

So if you’re staring at a PMM job description thinking, “I’m not ready yet,” maybe don’t ask yourself whether you’ve had the perfect career.

Ask: What have I already done that proves I can do this?

That’s a much more interesting question.

And it might lead you somewhere.

Keep learning, keep experimenting, stay curious.

Shruti

Watch it here:

Happy Friday Folks!

Two days before I recorded this episode, I put the laptop down and went back to pen and paper.

Not as a productivity experiment. More as a rescue mission. I’ve built so many workflows for myself over the last year — scheduled tasks firing at 9am EST, a note-taker in every meeting, an AI assist on every draft — that I looked up one morning and thought: where am I in any of this? So there’s a notebook next to me right now, and it’s the least optimised thing I own, and it’s working.

I mention it because it turned out to be the whole theme of the conversation I had that week.

Maylee Jacob is a fractional marketer with fifteen years across CPG, e-commerce, and B2B tech. She gets brought in when the foundation is unclear and the work is half-built — the messaging that’s been “almost final” since Q1, the case study stuck in a doc waiting on somebody’s legal team, the webinar everyone agreed mattered and nobody had time to produce.

That unglamorous middle is where most of our real work lives. Almost nobody talks about it. She’s built a practice inside it.

Here’s what I took away.

1. Fractional means owning the work, not renting hands.

Her definition is the cleanest I’ve heard: “fractional marketing means stepping into work that already matters” — it just hasn’t been owned by anyone.

The tell is in the first week. A contractor arrives with a list of questions. A fractional operator arrives with “here’s the problem I see, here’s what I’d do next.” Maylee’s framing of the failure mode stuck with me: you don’t hire somebody for judgment and then stand there being an instruction giver.

But she put the responsibility on both sides, which I appreciated. Task-level access gets you task-level output. In her words, you can only do so much with the information you have — half-baked context, half-baked result. If you want someone to walk in and diagnose, you have to let them into the room where the actual problem lives.

And the best line on why anyone hires fractional at all came from her being a mom: the point isn’t more hands, it’s taking things off your plate that you hadn’t even registered were sitting on your shoulders. Mental load. That’s the product.

2. “We need more content” is almost never about content.

This one reframed a decade of briefs for me.

Maylee’s take: a lot of teams don’t have a content problem, they have “a clarity problem that keeps showing up as content.” Someone comes to her with “we need blogs,” and two questions in — what are you hoping to achieve, what’s making you say you need content — it turns out they haven’t decided who they’re speaking to, what they believe, or what the work is supposed to do.

You can absolutely go produce the blogs. It just won’t fix the unclear thinking underneath, and now you’ve got more surface area to maintain.

Her closing line on it is the one I keep repeating to people: “sometimes more content is just more stuff for people to ignore.”

3. The direction problem hiding behind a vendor problem.

I asked about the teams running three agencies, two freelancers, and no shared picture of what any of it is doing. Vendor problem or direction problem?

Direction, every time. Vendors can all be doing good work in isolation — that’s exactly what makes it hard to see. Her example: the paid media agency that sends a spreadsheet of numbers every month, is quick to claim the wins, and goes quiet on context when something isn’t working.

The fix isn’t hiring an expert in every channel. It’s having one person with enough visibility to ask the right questions and tie the work back to a business goal.

She refuses to call her approach a playbook, by the way — “if I had one, I feel like I should sell it on Gumroad” — which sent us on a very fun tangent about the passive-income playbook economy. (My honest position: most of it is a clickbait loop, and I’d love to be proven wrong by someone with real numbers instead of screenshots.)

What she does instead is walk in with an outsider’s eye — she hasn’t drunk the internal juice yet — and run something closer to an audit. What have you been doing, what’s performing best, how are you measuring success, who is your best customer and why did they actually choose you?

That last question is where it usually falls apart. Ask a team why customers pick them and you’ll hear “because we do great work.” Cool. So does the company across the street.

4. “We save time and money” is the least interesting version of the truth.

Maylee walked past a booth in a mall with that exact headline on it and nearly lost it in public.

Is it true? Sure. Is it useful? Cover the logo and you could paste seven million companies behind it. She’d name it as “the least interesting version of the truth,” and “AI-powered” is now sitting right next to it.

I ran this exact test last year on cybersecurity homepages — five to ten vendors, all AI-powered, AI-native, AI-something — and you genuinely could not tell them apart with the logos hidden. Different industry, identical disease.

What I liked is that she didn’t stop at diagnosis. The fix is better questions, and she rattled them off: what does the customer get to do better, what risk goes away, what time gets unlocked, what were they doing before, what were they comparing you against, what changed after working with you.

And the part most B2B copy forgets entirely — it’s not about making the company look good. It’s about making the buyer look good to their boss.

Where does that language come from? Not just the Gong recordings. Support tickets, reviews, transcripts, and actual conversations with actual humans. Her point, which I think is the most important idea in the episode: AI has made generic marketing effortless to produce, so real customer understanding should be worth more now, not less.

5. Positioning is not a sacred text. Neither is your ICP.

You don't need perfect clarity, you need useful clarity — enough shared understanding for the team to make better decisions than they made last month. Waiting for perfect just means you never get anything in front of a customer to learn from.

Bonus — the one that stung: customer stories die in the handoff.

When I asked what half-built thing she sees stranded most often, her answer was customer proof. Everyone wants case studies, testimonials, voice of customer. Almost nobody owns the path.

Why you should care

Teams are smaller. The work didn't shrink. AI has made producing more the easiest thing in the world, which means output has stopped being a differentiator — quietly, while everyone was busy celebrating the velocity.

Listen to the full thing

Prefer watching? The full episode is on YouTube:

I want to start with the part I’m least proud of.

For roughly half my product marketing career, I was a task-taker. I was the only marketing-slash-product-marketing hire, the CEO wasn’t sure what the role was either, and I was thrilled to be busy. Every request that landed on my desk felt like proof I was needed. I said yes to all of it.

I was well liked. I was completely burnt out. And I was doing almost none of the work that made me want the job.

A quick word from this episode’s sponsor

Eddie fixes the gap between shipping a positioning update and it actually sticking. It turns your enablement docs into short, trackable Slack coaching sessions..so you can show what landed, not just hope it did.

Check it out here: Geteddie.co

I told Mina Rath this on the podcast last week and she didn’t even blink. She’s inherited entire teams in that condition. Her words: they’re well liked because they’re doing all the tasks, but it doesn’t do them a service. And they know this.

That’s the part that stings. We know.

THE ARGUMENT

Mina has 20+ years in this role. Telecom, then two decades in B2B SaaS, mostly Fortune 2000 accounts. She’s reported to CMOs, CPOs, and CEOs. Different boss every time. Different definition of the job every time.

Her position - and she blogs it daily, so she’s not hiding from the pushbac, is that product marketing should be an independent department. Not under marketing. Not under product. Its own function, with a seat at the table.

Here’s where it gets uncomfortable, so I’ll just say the thing.

If you report into the CMO, you have been structurally demoted and nobody told you.

That’s not a knock on marketers. It’s a knock on the org chart. The CMO is measured on pipeline. On lead gen. On what they present to the board about Q3 and Q4 numbers. Those are real goals and they are not your goals. So when you sit under that function, your strategic work becomes overhead against someone else’s target, and the requests you get will reflect that. Write the blog. Build the deck. Fill the webinar calendar.

Mina put it plainly: the CMO turns to the product marketer and says, hey, tell me what to do. And that, she said, is an awkward position to be in.

It’s worse than awkward. It’s the mechanism by which the role gets hollowed out. Not through malice — through reporting lines.

THE PART THAT ACTUALLY WORKED

At one company, Mina reported directly to the CEO. Five months in, he told her nobody understood what she did — they thought she wrote brochures. So he asked what she thought about renaming the department to product strategy.

She said yes. And it changed everything.

Marketers started coming to her meetings. Developers started coming to her meetings. Same person, same work, same output. Different word on the org chart.

I’ve thought about that more than anything else in the conversation. We spend enormous energy trying to earn credibility through output — better decks, tighter messaging, cleaner launches — when a significant chunk of the problem is that the word “marketing” in our title tells everyone where to file us.

FIVE THINGS I TOOK AWAY

1. The title is doing damage in both directions. “Product” makes you a catch-all — every miscellaneous request arrives with “you’re the product person” attached. “Marketing” makes you a lead gen resource. You’re neither, and the name gives everyone permission to misfile you.

2. Three non-negotiables, in order: understand the market, own the strategy, tie yourself to revenue. That third one is survival. Not “I generated the revenue” — “we changed this messaging and Salesforce shows we closed this many more deals.” Executives start seeing you as senior the moment you speak in that currency.

3. Don’t become a task-taker. Mina’s line: once you’re the task-taker, you’ll always be the right-hand person for whatever nobody else wants. And the precedent is close to irreversible — they get used to it fast.

4. T-shirt sizing is how you say no without saying no. Small, medium, large. A small release doesn’t move revenue, so it gets a customer note. A large one gets the full go-to-market. Agree the sizing with product and marketing up front, and pushback stops being personal — it becomes a shared framework.

5. Buyer enablement is the 2026 shift, and most teams are asleep on it. Your buyers are using AI to compare you against two or three competitors right now, optimising for one thing: which choice won’t get me fired. Gartner found 67% of buyers move forward when they know what happens after purchase. So build the business case template. The ROI calculator. The “what to know before you buy” guide. Not sales enablement. Buyer enablement.

WHY YOU SHOULD CARE

Because the hiring market is brutal right now and the instinct under pressure is to become more agreeable. Take the tasks. Be the team player. Prove you’re useful.

That instinct will bury you. Mina’s been watching this exact pattern for 20 years and it has never once corrected itself from the bottom. It corrects when someone in the room can point at the market and say: if I’m doing this, who’s watching what our buyers are doing?

Nobody else in the building is going to ask that question.

So the practical version. Pick one of the five above. Not all of them — one. If you’re mid-career and stuck in the task cycle, start with tying your work to revenue, because it’s the only one that changes how executives see you rather than how you feel. If you’ve just started somewhere, use the first 30 days properly: understand the market, meet every stakeholder weekly, and do not wait to be assigned work. Mina’s rookie mistake warning is that your boss will fill that vacuum with tasks nine times out of ten, and the precedent sets in weeks.

And if you’re the one asking whether the confusion is you — it isn’t. It’s been 40 years. The textbooks agree with you. The job descriptions agree with you. The room just hasn’t caught up.

Prefer watching? Watch the full conversation on YouTube.

Prefer listening? Spotify or Apple Podcasts.

I’ve done win-loss work. So I went into this conversation half-expecting to nod along politely and half-expecting to disagree. Instead I came out with a cleaner way of thinking about a problem I’ve been circling for years.

Shayaan Jagtap started Opptrack about eight months ago, with an old coworker and a hunch about competitive intelligence. It began as a LinkedIn scraper. It’s now a win-loss engine built off more than 120 product marketing interviews. What I loved about this one is that he didn’t sell me the polished version. He walked me through the tumbling, evolving, occasionally embarrassing middle. Which is exactly what Founder Stories is for.

Five things I took away:

1. Win-loss is a prioritization problem before it’s a data problem.You lost 100 deals. You can’t interview 100 people. The one-call no isn’t the same as the six-figure loss at the finish line. Knowing which losses to dig into is half the battle, and it’s the half nobody talks about.

2. More than half your losses are already in your calls.This reframed things for me. You don’t have to start with surveys and gift-card bribery. A big chunk of your losses is explainable from sales calls and CRM data you already own. Interviews are for the decisions that happened off-call, behind closed doors.

3. A loss is easier to explain than a win.His line: a win can be complex, but a loss usually comes down to one or two critical things. Pricing. Timing. A missing SOC 2. Find those and you’ve explained the deal. (His dating analogy for this was rough, and he knew it. It still landed.)

4. Saying no is the founder skill.Ten good ideas, and you have to kill nine. Every user conversation spawns more features you could build. The discipline isn’t having ideas. It’s throwing away the month of work that isn’t earning its place, and not getting emotionally married to it.

5. The AI-slop panic is punishing the wrong people.He got banned from four subreddits for posts he wrote by hand. The genuine slop gets through. We both felt this one. The old distribution playbooks are creaking, and the detection is catching real voices while missing the machines. What survives, we agreed, is a genuine voice. You can feel when a person actually wrote the thing.

Why you should care:If you’re a PMM doing win-loss manually, this is a map of where the real leverage is: stop trying to interview everyone, mine what you already have, and reserve human conversations for the deals that went dark. If you’re a founder, it’s a clean look at what the unglamorous middle actually feels like.

Prefer watching? Watch on YouTube. Here:

Prefer listening? Listen on Spotify or Apple Podcasts.

Until next time: keep learning, keep experimenting, stay curious.Shruti

The PMM Skill AI Still Can’t Automate

A few weeks ago I sat down with Swati, an AI-systems-focused product marketer who’s scaled B2B SaaS portfolios from $50M to $90M in ARR. I went into the conversation half-convinced I already knew what she’d say about AI. I didn’t.

The gathering work is gone. The judgment work isn’t.

She described what her job used to look like before agents: one human being, going through Power BI and Salesforce and email, downloading a thousand spreadsheets and trying to force them into something that made sense. “There’s only one Swati and there’s only one brain,” she said. “Every Excel requires one brain.” Now that same gathering work, pulling from Jira, from old positioning docs, from prior sales calls, gets assembled into a first draft of a battlecard in the time it used to take her just to find the right file. That part of the job, she said plainly, is automated now.

But she drew a hard line right after. Positioning itself, the actual decision about what a product means to a specific buyer, is still human centric. An agent can summarize a customer call. It can’t sit across from that customer and notice the thing they didn’t quite say out loud. That’s still on her.

Sales enablement is where PMM’s fingerprints stay visible

The part I keep coming back to is her answer to a question most PMMs quietly struggle with: how do you prove any of this is worth the money? Her answer wasn’t the website. It was sales.

In enterprise B2B SaaS, almost nobody buys off the homepage. There’s a full sales cycle, and everything inside it, down to the one-line cadence email a rep sends to a prospect, runs through product marketing. “They can’t even send an email if I don’t write it correctly,” she said, half-joking, mostly not. Content marketing and demand gen teams often end up rewriting that same positioning into blog posts that collect their own impressions and their own credit, which makes it genuinely hard to trace PMM’s fingerprints on revenue through a website. Sales enablement doesn’t have that problem. If the sales team is closing faster and closing with confidence, that’s a straight line back to the work.

What this means if you’re building a personal brand while doing all of this

The second half of our conversation had less to do with product marketing and more to do with the mindset it takes to post consistently while doing this job. Swati’s framing was simple: building in public is a mindset problem before it’s a tools problem. Everyone goes through a period where the content is genuinely bad, and the people who keep going are the ones who’ve made peace with that period, not the ones who found a better app.

One reframe she uses when she catches herself over-scrutinizing her own content: imagine a loved one posted the exact same thing. Would you be that harsh with them? Almost never. It’s a small shift. But it’s the kind of small shift that actually changes behavior, which is rarer than it should be in advice like this.

My Take

Here’s what this means for product marketers: if you’re feeling replaceable right now because an agent can draft a battlecard in ten seconds, you’re measuring yourself against the wrong part of the job. The drafting was never the moat. The judgment about what goes into that battlecard, and the relationships that make sales actually trust it, are.

Here’s how founders can actually apply this: stop asking your PMM to prove ROI through the website. Ask your sales team how fast they’re closing and how confident they sound doing it. That number was always the real scoreboard. We just kept looking at the wrong dashboard.

Curiosity Corner

If we had another hour...

* I’d ask her to walk through one specific battlecard, start to finish, and show exactly where the agent’s draft ended and her judgment took over

* I’d explore how she measures “sales confidence” in something other than a gut feeling, is there an actual signal she tracks

* I’d challenge her on whether the loved-one reframe holds up under real public criticism, not just her own self-doubt

Full conversation with Swati is up now on YouTube, Spotify, and Apple Podcasts. If you got something out of this, forward it to a PMM who needs to hear it.

Most people think great SaaS products start with a brilliant idea.

Joseph Lee’s started with a customer saying:

“Your website wasn’t very clear... but now I get it.”

That moment changed everything.

On the latest episode of Behind the Brief, I sat down with Joseph, CEO & Co-Founder of Supademo, to unpack how one customer interaction turned into one of G2’s fastest-growing products.

A few takeaways that stayed with me:

→ Customers don’t buy features. They buy understanding.

→ Product demos shouldn’t just tell. They should show.

→ Growth rarely comes from one channel. It’s the result of hundreds of small decisions executed consistently.

→ Storytelling is becoming one of the biggest competitive advantages in SaaS.

One insight I especially loved:

Instead of pitching prospects, Joseph’s team would build a demo for them first.

No hard sell.

No aggressive outreach.

Just value.

That simple shift helped create trust before asking for anything in return.

And maybe the most important reminder for anyone building in public:

Perfection is overrated.Consistency wins.

Listen to the full conversation below 👇

What’s one marketing lesson you’ve learned that only became obvious after doing the work?

#BehindTheBrief #FounderSeries #ProductMarketing #SaaS #Startups #BuildInPublic #MarketingLeadership

And the thing is, I don’t even think the products are bad.

I think product marketing just hasn’t fully caught up with what AI products are becoming.

Over the last few months, I’ve noticed the same terms showing up everywhere:AI agents.MCP.Agentic workflows.AI-native systems.

Everyone is using the language.Very few people are explaining what actually changes because of it.

So I recorded a Behind the Brief episode as a bit of an experiment, partly to simplify these ideas for other PMMs, but honestly also to process what I’ve been noticing myself.

Because I think we’re entering a pretty major positioning shift:AI-assisted → AI-native.

And that changes the messaging game entirely.

For a long time, AI products were positioned like helpers:“AI makes your workflow faster.”“AI helps your team move quicker.”“AI assists with execution.”

But AI-native systems are different.

The AI isn’t helping the workflow anymore.The AI is becoming the workflow.

And buyers can feel that shift, even if they don’t always have the language for it yet.

That’s why vague messaging is starting to break down.

Buyers are asking sharper questions now:

* What does the AI actually do?

* What data does it touch?

* What happens when it fails?

* How autonomous is it really?

And honestly, I think a lot of AI jargon right now is just positioning confusion wearing technical clothing.

One thing that’s become very obvious to me from working in cybersecurity and AI product marketing is this:

Invisible systems only work when buyers trust them.

Nobody can “see” how your AI model works.They can’t see the decision logic.They can’t see the training data.

So messaging becomes the trust layer.

And that’s why “AI-powered” by itself is no longer enough.

One simple exercise I’d recommend:

Open your homepage and look at every place you use the word “AI.”

Then ask:

Does the next sentence clearly explain:

* what the AI is doing,

* for whom,

* and what changes because of it?

If not, your buyers are probably already feeling that gap.

I unpacked all of this more deeply in the latest Behind the Brief episode, including:

* AI agents

* MCP (Model Context Protocol)

* Agentic AI vs generative AI

* AI washing

* And why positioning is becoming the competitive advantage in AI

Curious what’s showing up in your world right now.

What’s one AI term everyone keeps using in meetings that nobody actually explains properly?

Reply and let me know, I might decode the next one.

Watch the full video explanation here:

We spent an hour talking about Instagram.

But not the kind you usually hear about.

No “post 5 times a day.”No “use this hashtag.”No “hack the algorithm.”

Instead, we spoke about:

* loneliness while building something new

* the fear of putting yourself out there

* and why most creators never make money

One thing stood out to me:

Consistency is not glamorous.It’s repetitive. It’s boring.And most of the time, it feels like nothing is working.

Until suddenly; it does.

If you’re someone sitting on drafts right now…this might be your sign to just hit publish.

🎧 Full episode:

When I first started working in cybersecurity, I assumed the confusion was my fault.

I thought I wasn’t technical enough.I thought I didn’t know enough terminology.I thought I was behind.

But the more I worked in this space, the more I realized something important:cybersecurity is genuinely hard to understand — not because PMMs aren’t capable, but because the market itself is fragmented, reactive, and driven by very different buying dynamics.

This episode of Behind the Brief is a continuation of a conversation I had earlier with Sachin. After that episode, both of us felt like we had only scratched the surface.

So we decided to slow down and spend a few episodes talking specifically about the cybersecurity market — how it works, how buyers think, and where PMMs usually struggle when they come in from traditional B2B SaaS.

In this episode, we talk about:

* Why cybersecurity doesn’t behave like one “big market”

* How fear and timing influence buying decisions

* Why the user is often not the buyer

* What PMMs should unlearn when they enter cybersecurity

This conversation isn’t about mastering security concepts.It’s about understanding the space well enough to position, message, and tell the right story.

If you’re a PMM working in cybersecurity — or trying to find your footing in it — I hope this helps.

🎧 You can listen to the episode below.