Dark Social & Evangelism @ Chili Piper | Co-Founder @ Revenue Era | Sales Rep Turned Marketer

I'm a unique breed of B2B marketer, one who's actually carried quota and closed deals.

8 years in SaaS sales + 4 years in marketing = a unique lens on what really drives revenue. While most marketers optimize for vanity metrics, I optimize for buyer behavior. Because I've been on both sides of the table.

My superpower? Combining sales instincts with marketing scale to create GTM strategies that break through the noise.

I help B2B SaaS founders and marketing leaders build Modern GTM strategies that turn prospects into customers and customers into advocates. 
My focus: buyer enablement, ecosystem marketing, and creating revenue engines that scale.

The future of B2B isn't about traditional company focused marketing. It's about collaborating together through partnerships, community, and customer-led growth.

The old playbook is broken. Time to build something better.

DM me to discuss your GTM challenges and jam about the future of GTM!

🌶️Arthur Castillo

Product Marketing @ Beekeeper

I help early-stage founders and teams deliver great products to people who need them.So far, that's looked like matching rare disease patients with clinical trials, helping seniors navigate health insurance, and keeping teams connected through workplace technology. Outside of work, you’ll find me DJing, hosting events for Startup Grind Chicago, chasing my dog, tinkering with AI, or playing basketball.Interested in meeting interesting people, DM me if we should chat!

Sid Khaitan

This weekend I hosted “The Grateful Gather”: a rooftop dinner with a room full of people who were down to get real.

This is the part of product work people forget.

Before roadmaps, Figma mockups, or AI… great products start with great human insights and experiences.

Watching people open up, laugh, and reflect is market research in its purest form. 

Not in a survey. Not in an analyst report. But in real life.

It reminded me why I started building Milan in the first place.

Not because I wanted to build another app.

But because I noticed 3 things:

1. Social isolation is at an all-time high, even though we supposedly have all the tools to prevent it

2. Most conversations are well intentioned but go nowhere and don’t leave us feeling much better

3. People are asking for ways to make deeper connection feel easier. Even within their immediate circle!

Every time I host one of these, it becomes clearer that products aren’t about features. They’re about feelings.

For users:

The feeling of being seen. Of belonging. Of not having to pretend.

For buyers:

The feeling of being heard. Of confidence. Of not having to doubt. Of forward progression.

And tbh, creating these events and product experiences feels like my calling. The biggest impact I can have on this strange world, while doing what I love and am halfway decent at.

Am I crazy? Also..best caption wins

Product Marketing @ Beekeeper by LumApps | Founder @ Milan Meetups | Community @ Startup Grind Chicago | Host of Product Marketing Life

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Who wants to go to the Chicago PMA Summit next week?

I have an extra ticket. 

If you're a Chicago PMM that's in-between jobs, please comment or DM. First person to comment or DM gets the free ticket!

If you haven't bought your ticket yet, get 20% off using the discount code "SPEAKER20"

Last week I got to lead a roundtable on one of my favorite, most underrated topics:

Early Access programs (closed/open betas)

They’re one of the best ways PMMs and PMs can work together.

But most EA programs fall apart because they’re missing one (or all) of these:

1️⃣ Clear exit criteria

How do you know when it’s time to move a beta to GA?

There’s product utilization, # of happy customers, outcomes. 

Example: Did 5 customers save 10% of their time on a core workflow using the beta?

Any mix of these is better than nothing.

If you don’t define this upfront, features can get stuck in beta limbo.

I’ve seen companies leave features in beta purgatory for over a year. Credibility drops, momentum gets killed. Exit criteria prevents that from happening.

2️⃣ Clear scoping and PRD

What’s available today vs. what’s coming tomorrow?

This is the only way to set expectations with Sales, CS, and customers.

Otherwise you end up selling a future that doesn’t exist yet.

3️⃣ Real discovery

How are customers using the thing?

What do they love? What’s confusing? What’s breaking?

Who are our early champions that will advocate for this and be the case study?

Skipping this means flying blind.

We end up taking something to GA without the story, the proof points, or the confidence to sell it.

---

I’ll be talking about this more. As someone who’s helped multiple companies figure out this process, and is now also building my own product, I see both sides:

PMs + engineers carrying the pressure to deliver under a cloud of ambiguity

PMMs trying to make sure whatever ships actually lands in the market

If you’ve run (or survived) an Early Access program…

What are your tips?

(Featured: a really bad quality pic of me on screen)

Are we overcomplicating interactive demos?

The tools I've used make me feel like I’m doing IT support for them. Debugging, waiting on tickets, hacking together workarounds

So when Geoff and Gab asked me to try Guideflow, I said yes…mostly because I like them. And because I’m always down to pressure-test new tools.

But instead of giving you another boring B2B feature walkthrough…

I figured I’d show you an interactive demo of something actually useful:

How to save $5/month on your HBO subscription.

Guideflow made it super easy. Like…fun easy. (see attached GIF)

I loved being able to pick the time between steps when exporting video. Simple folder structure, custom share options, solid analytics.

I don’t really endorse products. Mostly because no one ever asks or pays me to.

But I like the people behind this one. And the product honestly surprised me.

Take it for a spin!

👉 https://lnkd.in/gd3Sdkg8

#antiinfluencer
#sponsoredpost
#guideflow

I was gonna post something clever today like:

“Imagine if product prices were like salary ranges…$95K-$180K…”

Then I realized in SaaS…it can be worse 🥲

How do you get out of “launch mode” as a PMM?

Had a great conversation with Sedall Asante  about how to build a sustained lifecycle program.

We covered what it takes to get everyone bought in and set expectations with leadership.

How he went from being a banker to a PMM.

And how product marketing looks different in the FinTech world.

Give it a listen by searching for Product Marketing Life in all the usual places!

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The Battle

🌶️Arthur Castillo

Sid Khaitan

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The Battle

🌶️Arthur Castillo

Sid Khaitan

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Sid Khaitan's LinkedIn Performance

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Performance ScoreSid Khaitan's LinkedIn Performance