Jared Robin ⏭

Helping Founders & GTM Leaders Go-to-Market Collaboratively | Founder of RevGenius community of 40k+ GTM leaders | Startup Advisor | “The most important thing you can do in sales and life is be a homie” - Bloomberg

The loudest don’t win. The most resonant do.
I help founders turn audiences into movements.

I’ve seen how resonance scales:
•Built RevGenius from 0 → 55,000 members & 7-figure revenue in 3 years
•Scaled multiple startups from 0 → 7 figures, including 2 exits
•Advisor to 12+ SaaS startups

,I work with founders & GTM leaders to:
•Clarify their POV so it resonates
•Build audiences & communities that compound
•Spark movements that define categories

If you’re ready to grow by resonance, not noise, let’s connect.

Writer

Launched a newsletter helping Founders, Fractionals and GTM Leaders go-to-market collaboratively.

I'm deleting 10,000+ LinkedIn connections.

Here's why:

I hit the 30k connection limit and realized most of them don't see my content and I don't see theirs. The algorithm buries us to each other.

I'm shouting into a void of people I haven't talked to since high school or past jobs. They're doing the same to me.

So I'm trimming down to the community I'm actually building with - people in the trenches of revenue, growth, and go-to-market. Founders building the future of their spaces.

It's not personal. It's about making this platform work.

Resonance > noise.

(Using LeadDelta to bulk remove because doing it one by one was brutal. No affiliation.)

Community is the ultimate leverage.

Jared Robin

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li_at

I help founders create markets, not fight for them 🏴‍☠️

I had no job, no money, and a 380 sq ft apartment in the East Village.

So I sent 300+ LinkedIn DMs a day with one simple ask: "Want to join an inclusive sales, marketing, and RevOps Slack community?"

10%+ said yes. That's 900 people a month.

It worked because I struck a nerve. Covid hit, people were isolated, and every other community was either exclusive to leaders or wasn't really a community at all.

I saw the gap and built something different- a place where everyone belonged.

RevGenius took off. 1,000-3,000 new members joined a month once word of mouth spread. The vibes were immaculate.

It started with a 27-person LinkedIn group chat that was so active the app crashed multiple times a day. I moved everyone to Slack and went all in.

That chair between the windows? That was my office for a year. I was surviving on unemployment, drinking too much coffee, staying up too late.

But the mission mattered more than my job search.

5 years later: 60,000 members.

Grateful I never stopped building.

It only took me 10+ years on LinkedIn, but I did it! Hit 50k followers.

Been on LinkedIn prospecting since I first got into tech. 

Since, I've seen a MASSIVE evolution in gtm & the platform:
- from not being allowed to 'social sell' to a key motion
- from tons of cold dms to building content.
- from prospecting to building community
- from climbing sales ranks to solopreneurship
- from manual work to automation to ai
- so much more

Through this platform I built a community of 55k revenue professionals. 
Through this platform I built a new career path for myself.
Through this platform I built a professional friend group unlike any I could have imagined.

Thank you all for contributing to over 50k followers here, 80k on our company page and more importantly, being a part of the change.

Here's to the next 50k 🚀

I've known Leslie for a few years now. And she just continues to level up.

Watched her launch her own business.
Watched her drive amazing results for her clients.
Watched her build her brand and speak everywhere.

And now, if that wasn't enough...

Watched her write a book that soared to the top of the charts.

She invited a bunch of incredible GTM leaders (and friends) to a luncheon last week which she hosted.

Hung with the homies Joshua Bailey, Jacob Fleisher, Katrine Reddin 🦕, Julia Carter, Ben Bartolone and so many more as vibes flowed. 

As wonderful as the book "Profit Generating Pipeline' is (a USA Today top 50 bestseller), Leslie is way better. 

I mean look at her energy in the background supporting Josh and I homie-ing it up :)

Appreciate you to the moon.

I help founders stand out from the noise 🏴‍☠️

When the homies Michael Petery & Benjamin Douablin invite you to dinner, you show up.

Had a blast talking about wild investment stories, the data space, and thinking differently.

Loved getting a chance to also hang with Jacqueline-Amadea Pely, Charles Crnoevich, Santtu Koivumäki, and David Walker, a group of tremendous revenue leaders building the future of GTM.

Big props to FullEnrich for going into a commoditized space and forging a new category (data optimization?)! 

Shout out to Wegmans Food Markets too - who knew they could launch a Michelin Star restaurant in a prime location?!

GTM is hard. Building a community of leaders gives us all the support we need.

Thinking about creating new markets to make going to market less noisy is the added sauce.

I want to start hosting some dinners in NYC. Who's in?

I had zero fashion experience. Zero magazine experience. I was 30 years old. 1 year later I was being invited to 40+ fashion shows a season and was in line to become an ambassador to Korea.

Here's what happened in between:

I launched Deux Hommes Magazine with my co-founder Carlos. We were newly obsessed with menswear. We wanted to make money eventually, but first we wanted to build something that mattered.

At the start, we wrote about the same mainstream brands all the big publications covered. We weren't being seen, and honestly, our content wasn't as good as theirs. How could we compete? Did we even want to?

Everything changed when I walked into Shop Untitled, a boutique in the West Village. The entire store was filled with brands I'd never heard of. Avant-garde designers I'd never seen in any major magazine.

And the fashion was better.

I took photos of every label. Hit Google. Found more boutiques, more designers, more incredible work that nobody was covering.

These brands wanted exposure but couldn't get it- too young, no PR budgets, no connections. The big mags ignored them.

I found our niche.

For the next four years, we built a team of writers and editors from schools like Parsons. We featured exclusively emerging designers. I was making $0 and working 40 hours a week on this- on top of my day job.

After a slow start, things clicked.

We hit 10k monthly readers. We threw the biggest men's NYFW party. Top trend forecasters followed us. Design schools discussed our work. We won international fashion film awards.

We stopped competing where we couldn't win, and solved a problem nobody else would.

I showed up for dinner. I left with proof that everyone complaining about outbound just sucks at it.

John Basar is a killer (to the right of me) - 30-40 meetings booked a month at HockeyStack.

The dude crouching in the middle of the front row?

Meet Gautam: 200 meetings booked in his first 6 months. 

Over 50% of meetings booked via cold call. Savages.

I went to this dinner last week expecting a nice meal and to hang with the spectacular company I advise. I ended up with a lesson in outbound.

And its not just these 2. It's the whole team. 

Discussed hiring, outbound, and so much more. Learning a ton.

Alex Choi and Emir Atli (Hiring AEs) have this team humming. 

Had an amazing time hanging with the homies Lily Roosevelt, Amulya Vadrevu, Daniel Garcia and so many more.

What I love the most about Hockeystack is they are absolutely crushing the inbound game. And, yet, they have taken the time to make sure their GTM doesn't end there. 

Oh ya, and they are building something different than those in the 'attribution' space (where they started). 

Don't let the gurus tell you outbound is dead. It's alive and well for those that know what's up.

Join the movement.

LFG 🏴‍☠️

Clay gets a 30-40x multiple. Most data companies get 3-5x.

Same revenue. Wildly different valuations. Here's why:

GTM has 3 metrics that matter - not just revenue.

1. Drive actual revenue

This goes without saying. If it's not consistently filling the pipeline and closing deals, it's theater. Brand plays and awareness matter, but only after you've proven you can make money.

But doing this alone? You're playing in somebody else's category and subscribing to the average valuations thereof.

In the data space, hit $10M ARR and you'll get a 3-5x multiple. That's solid - but it's not 10x.

And it certainly isn't 30-40x like Clay.

The reason? You're capped by the category leader's potential.

Clay didn't just build better data tooling. They built orchestration, a system for action. They sculpted a new space. Time will tell how big it gets, but they're not competing on data multiples anymore.

2. Expand category potential

Whether you're creating a new category or redefining an existing one, marketing needs to create hunger for the problem you solve. When you frame, name, and claim a category - demand converts to revenue automatically.
Airbnb didn't compete with hotels. 

Uber didn't compete with taxis. Salesforce didn't compete with on-prem software.

They found problems with the old way and built solutions that created a bigger pie.

The markets for each FAR surpass the original "competing" space. And they've owned it ever since.

3. Increase company valuation

Investors don't buy what you've done. They buy what you could become.

Marketing shapes the story of massive category potential and positions your company as the inevitable winner.

Category kings get higher valuations (Clay, Airbnb, Cursor) because the categories they create are expected to build exponentially bigger pies.

The metrics - revenue growth, customer growth, margins - just validate the bigger vision.

Props to Christopher Lochhead 🇺🇸🇮🇱🏴‍☠️ for first exposing me to this framework.

When you align your entire GTM team on these three metrics - not just sales on revenue - you stop competing in someone else's category and start building something that actually matters.

Down with silos. 🏴‍☠️

8 pm yesterday - we won Thanksgiving.

Grateful for:
- a family that doesn't take themselves too seriously
- a partner who supports me endlessly
- a network and community that are friends first
- the privilege to be able to put it all on the line
- all the texts yesterday with folks I lost touch with
- my beautiful nieces who are so funny and fun
- my health, food on the table, and roof over my head
- whoever took this photo (still unknown)
- being able to build on a tremendous foundation
- the leftovers we have for weeks because we cooked too much

Drop a 🦃 if you also ended up horizontal by 8pm. 🤣

This week a company made me schedule a 45-minute discovery call with an SDR to buy payroll processing. For one employee.

I was looking for a new payroll provider this week. Just for a single employee company.

Expected the process to be quick and easy. Nothing to negotiate, no unique integrations needed - just needed to understand who could do the job.

Payroll processing.

And maybe to see if I was eligible for PEO. No site would confirm or deny if I was. (Note: it’s not rocket science, it’s based on employee opt in count)

Here’s what buying payroll looks like in 2025:

All 3 websites: No clear pricing. No details on PEO eligibility. All required I speak to someone.

Company 1- called me right after I submitted the form - startled me in a way I welcomed. The challenge? She needed to coordinate with 2 other reps depending on the program(s) I required. That would lead to another call just to get the answers I needed. That call - you guessed it - would have to happen on another day.

Company 2- (who I already work with for our international contractors) required I coordinate schedules with 2 reps which took a couple days of back and forth on email. They had the best solution for me but required an annual contract which was a non starter. No flexibility or desire to escalate. We’ve worked with them for a few years.

Company 3- the 45 min inbound SDR meeting. Filled out the form on their site. Got a calendar link. Realized I couldn’t get a same day call. Scheduled this 45 min call for the next day.

45 min calls may be the worst.

WTF would a company want anyone, let alone inbound SDRs, chatting for 45 mins call 1?

I just had 2 basic questions.

Waited the day. Hopped on the call.

They asked me “where I was calling from” on Zoom. Fuming.  I can’t be the only one that hates “canned” small talk?

Here are MY questions - I qualified myself out in 3 mins.

The process I had to go through for a simple purchase showcases a massive problem with the legacy buyer journey.

This doesn’t just happen with payroll. I’m seeing it across the board.

It works the way a company has structured it to work.

Not the way a buyer actually buys.

This is the perfect example of a movement that’s needed.

Who’s going to lead it?

Just got off a call with 2 founders saving their clients between 50-90%+ on tech stack costs alone. And that's not even including savings from employees they don't have to hire and time they don't have to spend.

This is the future - autonomous gtm.

Today you 'can' build whatever you want in tools like n8n but it requires a technical person who needs to spend hours building workflows who ends up babysitting them daily because of breaking points.

Most companies don't have that resource nor time (or costs) needed to stitch together dozens of point solutions. 

Just because you have a collection of point solutions with AI in it, doesn't mean your whole system you are building is autonomous.

Often the ai just optimizes the point solution (if that) and not the whole system. 

They've built tools like rb2b, birddog, usergems, and so many more in a matter of minutes in the same system. Easily unifying the data and workflows.

Cost savings? 

On just building rb2b, 60% or more. 
On unifying all the systems? multiples in time and revops manpower.

For a Series A (soon to be B) company they work with 50% savings month 1.
For another company, who's stitching many tools together? 90%

Allowing revops to not need to be systems babysitters? 
Priceless. Now they can become growth strategists.

Companies are using a system of record, a system of action, and theirs. Maybe one day they'll replace one or both of them too.

This is what an autonomous future looks like in gtm.

🏴‍☠️

6sense just changed from intent data to signals.

Note: their product is seemingly the same. They just changed the wording.

I'm just trying to make sense of how 'revenue marketing' differs from regular 'marketing'. It's a thinker...

Do you even vibe bro? Over 400 GTM leaders have signed up for Vibe Week:

1.  Masterclass: Learn how to build custom agents in n8n - Today
2. Vibe GTM Hackathon - Thursday

Explorium came to us wanting to help more GTM leaders learn how to build in AI.

So we put together this incredible week to make it happen.

Omer Har CEO of Explorium x Jane Farris Head of Data Science at Explorium are helping us with the fundamentals in building custom agents in n8n today.

And on Thursday we have a competition with about $5k in prizes ($1k Amazon Gift Card + Explorium credits). 

If you're going to flex your workflows, may as well make some guap doing it - https://lnkd.in/eaf9grCR

the 'modern gtm stack' puts too much onus on the operator - lots of tools, workflows, moving parts, and expenses to manage. 

the 'future gtm stack' will be less tools with at least the same (probably more) power.

clay is the closest thing today to it for sure. but some other point solutions are often still required.  tomorrow you'll be able to do way more in a single system.

plus there will be ai at core so truly autonomous gtm will be possible.

Josh Schachter

UpdateAI

Chief Executive Officer

BCG Digital Ventures

Served as General Manager and Advisor to multiple ventures, overseeing multi-disciplinary workstreams across Product, Design, Engineering, Marketing, and Operations and helping to bring startups to life. 

Brought to market four new digital businesses on behalf of Fortune 500 companies, and advised many more during their initial incubation and build phases. Led the construction of DV startup methodologies such as Hypothesis Mapping and the Startup Ops Pyramid. 

Managed the Product Management summer internship program, created the DV Mentorship Program, and served as the Global Director of the Energy Practice at BCGDV.

BCG Digital Ventures is a corporate investment and incubation firm that invents, builds and invests in startups with the world’s most influential companies.

GM, Product Director, Global Director of Energy Practice

Boston Consulting Group (BCG)

Director

Setel

Managed international, cross-functional team that launched Malaysia's first seamless digital payments platform for retail fuel. Handed off my role to the current CEO based locally in Kuala Lumpur.

Liveguide, LLC

Josh co-founded Liveguide with his friend and MBA classmate. The two have led all ideation, build phases, operations, and business development with local institutions. 

Liveguide is a SaaS based B2B technology platform that enables university and graduate program Admissions office to meet their recruitment goals through virtual and live story sessions from existing students. The platform has successfully piloted at multiple institutions in Southern California and has generated a Net Promoter Score of 80+ as surveyed by prospective student participants.

Co Founder

Intuit

Team Leader of a subscription and SEO-based business within the Quickbooks Small Business group. Led cross-functional team of ~12 and reported all metrics to group leadership.

Senior Product Manager 

National Football League

Helped build engagement platforms for fans across desktop and mobile web. 

Won 2013 Emmy Award for "Outstanding New Approaches in Sports" for launch of fitness site NFL UP.

Launched NFL Madden fan voting platform in strategic partnership with EA Sports. 

Designed and ran the "NFL Case Competition" for MBA students - participating schools included UCLA Anderson, Berkeley Haas, USC Marshall, and SDSU (http://bit.ly/1tlEBDy)

Product Management

eHarmony.com

PM responsible for the design and development of the company's core product features, including the company's major site redesign (onboarding, profile, & photo management experiences).

Founding member of the Product team at Jazzed.com, eHarmony's incubated web and mobile start-up.

Oversaw the design and planning of the company's International businesses. This included constructing the international roadmaps for eHarmony Brazil, Australia, and the United Kingdom.

Product Manager

Interactive Sports Network, LLC

Interactive Sports Network (ISN) is an affinity-based sports social network. The company's inaugural property, HockeyBarn.com, is a platform dedicated to ice hockey players, teams, and fans. 

Launched company and secured seed funding from early stage angel investors. Responsible for all budgeting and P&L. 

Executed 2009 pivot of product's core services and positioning, resulted in 850% YoY traffic growth. 

Designed hyper-local media model and managed editorial staff across New England -- partnered with local news outlets to syndicate original site content on a revenue share basis. 

Designed and negotiated marketing partnerships with Easton-Bell sports, Upper Deck, and Zamboni & Co.

Founder and CEO

Steve & Barry's

Served as eCommerce project manager Steve & Barry's, a private-label clothing retailer with international operations, 300+ retail outlets, and celebrity brands including BITTEN by Sarah Jessica Parker, ELEVEN by Venus Williams, STARBURY by Stephon Marbury, and others... 

Promoted to lead inter-departmental team assigned to launch $25 million eCommerce channel for all S&B clothing brands.

Project Manager (eCommerce)

Built reporting team and constructed KPIs to evaluate labor efficiencies of 2 million sq. ft. distribution center in Columbus, OH. Responsible for designing picking/packing, and loading/ unloading processes to increase warehouse throughput and reduce cost. Efforts resulted in a 50% reduction in cost per case distributed from the facility.

Operations Analyst

Founder, Investor, and Fan of Customer Success

Entrepreneur and Product leader with experience building consumer-facing user experiences across multiple platforms, including Desktop, native Mobile, Facebook, and Mobile Web. 

Strong analytic background with a focus on optimizing around funnel conversion, user engagement, LTV, and SEO acquisition. 

Specialties: (i) launching subscription-based and transactional products and features, (ii) devising effective business plans and implementation strategies, (iii) running multivariate testing, (iv) and building relationships with strategic partners.

www.update.ai

I spent this week with people way smarter than me – at Stage 2 Capital’s Annual Summit inside Google’s offices.

Five conversations that won’t leave my head:

1️⃣ The Uncomfortable Pattern

Mark Roberge pulled up the 12-month forward P/E ratios of today’s top public companies. 
He showed us the 2000's dot-com collapse. Then 2020’s ZIRP bubble.

They looked the same.

Nobody knows for sure if we’re in an AI bubble. But Mark has a track record of calling these things (and when he raises his hand, I listen).

2️⃣ 94% Churn Prediction Accuracy

Kevin Knieriem (President at Clari) shared something wild: 

→ Their team can now predict churn 12 months out with 94% accuracy.

They backtested a full year of customer activity data, identified behavioral patterns, and built risk signals that trigger a year before a customer leaves.

They did it with QuadSci.ai – and it’s exactly the kind of CRO–CMO–CCO collaboration that actually changes outcomes.

(He’s coming on the #Unchurned podcast soon. I need the full playbook.)

3️⃣ Pricing Is About to Get Wild

Kyle Poyar called it: Outcome-based pricing is about to explode.

When AI agents take on the actual work, seat-based pricing stops making sense. He expects outcome-based pricing to represent 25% of overall SaaS pricing within 3 years.

This isn’t theory anymore btw. It’s already happening.

4️⃣ OpenAI’s “AI Adoption Managers”

Ashley Kramer from OpenAI made me smile: they don’t have Customer Success Managers – they have “AI Adoption Managers”.

She said the “AI” prefix will start replacing a lot more job titles.

At OpenAI, naming matters – because it defines the mission.

5️⃣ Sell Before You Want To
 
On a panel, I talked about selling UpdateAI to Gainsight.
The biggest takeaway everyone agreed on: 

If you *might* sell someday, start those conversations now.

At UpdateAI, we started building relationships years before we ever thought about selling. The process took longer than expected…

But those early relationships sealed the deal.

Sharing the best examples of AI transformation in Post-Sales

A friend reached out last week to share some good news - he finally landed a new role after a long search!

Four months.
Twenty-five companies.
Eighty interviews.

When he told me that number, we both just laughed. (There’s only so much rejection one person can take before it stops stinging and starts feeling absurd.)

He said something I keep thinking about: “Honestly, I got off easy.”

He’s right.

Yes, Customer Success roles are coming back — you can feel it across the market — but there are still plenty of talented people waiting for their turn.

Some between jobs.
Some hanging on in roles that don’t fit but feel safer than risking change.

I’ve been there. And I know how heavy that season can feel.

So here’s what I’m offering:

✅ If you’re looking for your next opportunity and find a hiring manager you’d like to reach — check if I’m connected to them.

✅ If I am, even if it’s just one of those random “phantom” LinkedIn connections, I’ll make the intro.

Gainsight has given me a platform that lets me do more than post about the industry — it lets me help people move forward in it.

If you ever need that nudge, comment “intro” or send me a quick DM.
I’ll do what I can.

We all get where we’re going faster when someone’s willing to open a door.

When I started building the GTM strategy for Atlas – Gainsight’s agentic renewal product – I noticed something that didn’t sit right with me:

Why were we only focused on the very top companies in our Rolodex?

It felt narrow. Why not go broader, faster?

But over time, I realized the team was right. And after listening to Jen Abel on Lenny’s podcast this morning, I can finally articulate why.

Tier 1 companies are under relentless pressure to stay on top as the market leader.
Especially now – in the era of AI transformation – it’s adapt or get left behind.

They don’t have time to test every new tool.
But when something aligns with their vision of where they need to be, they make the time.

That’s exactly what we’re seeing with our Atlas renewal agent – and with partners like DocuSign.

They understand that managing the long tail of renewals isn’t just a workflow problem anymore.
It’s a survival problem.

They see what many others don’t yet: retention is existential, and AI is finally making it scalable.

We share a vision for what comes next – humans and agents working together to deliver coverage, consistency, and customer experience at a scale the old model could never reach.

If you lead CS, watch what the Tier 1s are doing now.

They’re not just early adopters.
They’re defining what modern Customer Success will look like in the AI era.

That’s a wrap on my first Pulse Europe 🎬

Unfortunately, this was the view I saw most of the week because of a 24-hour bout of food poisoning 🤢

But I rallied just in time for my session with Jenny Calvert,, where we shared the incredible AI transformation story of Cloudbeds under the leadership of Colin Slade.

From what I could see (and hear), Dublin was another standout event from Kat Leong and the entire Gainsight events team:

- Buzzing conversations about Chuck Ganapathi’s view of SaaS → RaaS
- Big energy around the future of Digital CS
- Continued excitement for Staircase and Atlas

And of course, plenty of folks “splitting the G” at Temple Bar (IYKYK).

Safe travels home to everyone who joined us. Looking forward to next year.

Every leader needs someone who brings out the best in them.

For me, that person is Jenny Calvert, – and we’re coming up on our one-year anniversary of working together. 🥂

Funny enough, Jenny was the first paying customer at my startup, UpdateAI.

Even back then, she stood out – sharp product feedback, deep operational instincts, and a real passion for customers.

So when I suddenly needed help running our CS program a year ago and learned she was available, I didn’t hesitate. She already knew our product. More importantly, I already knew I could trust her.

And that trust has only deepened since.

Over the past year, Jenny has absolutely crushed it – leading our customer program through the acquisition to Gainsight, managing the post-M&A transition, and now serving as the glue behind nearly every major initiative in my current role leading Strategy and Market Development.

But what makes this partnership special isn’t just her talent…

It’s the psychological safety we’ve built.

I can be completely myself with her (quirks, neuroses, all of it).

No posturing. No over-managing. Just two people creating together, challenging each other, finishing each other’s sentences.

That kind of safety unlocks real creativity.

It’s where the best decisions come from – not fear or hierarchy, but trust and openness.

Case in point: during our weekly workplanning, I asked her to take on a pretty tedious operational task.

I said, “This isn’t going to be fun…Are you okay to do it? Regardless, I need you to do it.”

Then I laughed and asked, “What management style would you call that?”
Without missing a beat, she said, “Josh style!”
We both cracked up.

Find someone you can be your full self with.

Someone who makes you sharper because you feel safe around them.

Find your Jenny.

I just landed in Glasgow 🏴󠁧󠁢󠁳󠁣󠁴󠁿 for the weekend before heading to Pulse Europe in Dublin 🇮🇪!

But this stopover isn’t business.

John Anderson  and I met over 20 years ago — the summer before our senior year of college.

I was at Columbia. He was at the University of Glasgow.

We were part of a small entrepreneurship program helping local Scottish businesses write business plans.

Somehow, through careers, countries, and time zones… we’ve kept it going.
Every couple of years, we find a way to meet somewhere in the world. He’s one of my closest friends to this day. 

The best part? Every reunion starts the same way:
No words. Just laughter. Immediate, uncontrollable laughter.

This trip is extra special because I finally get to meet John’s new daughter, Maeve.
(He missed my wedding this summer for a good reason: his wife Shirley was about to give birth.)

Careers evolve, life gets busy — but the people who still make you laugh two decades later are worth the effort.

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When Cloudbeds CS leader Colin Slade had critical roles to fill, his CEO gave him a challenge that changed everything:

“Don’t hire anyone unless you can prove AI can’t do the job first.”

Colin had zero hiring budget. Zero tools budget. And a team at 120% capacity after a RIF. 

Most CS leaders would see this as impossible.
Colin saw it as a forcing function.

Nine months later, his team at Cloudbeds serves 40-50% more customers – with the same headcount.

→ 150+ AI workflows in production
→ 95% accuracy on knowledge queries
→ $4.5M saved in avoided headcount costs
→ What took 3 months now takes 1 week

Here's how he did it:

✅ Instead of waiting for the “perfect” AI platform, Colin took his CS Ops team (who'd never built AI before) and said: "Stop everything else. You're now the AI team."

They started small: Sentiment analysis on support tickets. Three buckets – happy, pissed, neutral. That's it.

Then they added another agent. And another. 147 agents later, they had a system that scaled.

✅ But the real breakthrough? Colin optimized Cloudbeds’ help articles for LLMs.             

Traffic to their knowledge base from ChatGPT and Google jumped from 2% to 80%. Customers now get answers where they actually are (not just where CloudBeds wants them to be).

But here's what matters most:

Colin didn't have special resources. 
He had one director-level champion, a few company knowledge experts, and a small team of  operators willing to learn. 

He dropped other projects and went all-in for 90 days.

And the team that was burning out nine months ago? 
They're now building AI solutions that other departments are begging to replicate.

🎙️ Want the full story?

Colin joined me on Unchurned to break down the failures, breakthroughs, and what he’d do differently. (Link in the comments.)

We're also publishing a Substack article that dives deep into his story.

Capitalism isn’t compatible with the post-AI era.
That’s not me talking.
That’s Mark Roberge, former CRO of HubSpot, co-founder of Stage 2 Capital, and Harvard Business School lecturer.

He said it while we were recording the #Unchurned podcast last week.
And I wasn’t expecting it.

We were talking about go-to-market AI.
Sales productivity.
The usual stuff.

But then, courageously, he went there. 👇

| “We need a new philosopher - someone who can see where we’re going and blow up the whole system.”

Five days a week.
Eight hours a day.
Two weeks’ vacation.
Work from 22 to 65.
Not being as good a parent as you could be.
Not being as good a neighbor.
Not taking care of your health or hobbies.

“We have to reframe all of it.”

Because here’s what Mark sees:
We measure success by GDP growth: but the US ranks 22nd in the global happiness index.
Twenty-second.

The most powerful country in the world.
Strong military.
SOTA healthcare.
Real freedom.
Dropping happiness.

That’s the problem.

Adam Smith’s Wealth of Nations worked.
It lifted people out of poverty, gave us healthcare, shelter, and food.
But it has diminishing returns: have we swung too far?

People are chasing billions at the expense of being good parents, good neighbors, good to themselves.
We’ve been wired by 100 years of capitalism to believe our identity is our job.

Everyone says “I can’t wait for Friday.”
Nobody says “I can’t wait for Monday.”

So here’s his vision for what comes next:
Shorter work weeks.
Shorter work days.
Balanced supply and demand of labor.

AI can now deliver healthcare, shelter, and food for a fraction of today’s cost.
That means smaller government.
Lower taxes.
A better baseline life.

If you want more?
You create. You innovate. You build.

Because AI can’t do true innovation -not yet.
It can’t write a better novel. Paint a better painting. Create better music.

We become a creative society.
AI handles execution.
Humans focus on originality.

The world Mark described isn’t dystopian -it’s overdue.

We’ve spent a century equating “hard work” with “worth.”
AI finally gives us the chance to separate the two.

For the first time, we can design a world where living well doesn’t require burning out.

I tend to agree with Mark on this one:
The next revolution isn’t about automation.
It’s about redefining what success, and work, actually mean.

Are we ready for that shift??

(This doesn't mean capitalism is dead; it just needs to be re-thought)

Your AI pilots are stuck at 20-30% adoption. Here's how to triple that in 30 days.

I sat down with Cat Valverde, founder of Enterprise AI Group, on #Unchurned and she shared a deceptively simple framework that's transforming how enterprises roll out AI tools.

The problem isn't what most leaders think.

It's not just fear of job loss. Cat's research across 250 enterprise employees found the real adoption killer: cognitive overload mixed with fear of looking incompetent during training.

Her solution? The 15-Minute Rule.
Four weeks. 15 minutes per week. That's it.

Here's the framework:

➡️ Week 1: Micro-commitment. 

Just click around for 15 minutes. No pressure, no follow-up.

➡️ Week 2: Choice architecture. 

Pick one feature that interests you and explore it for 15 minutes. This builds autonomy while reducing overwhelm.

➡️ Week 3: Social proof. 

Volunteers share 30–60 second takeaways in team meetings. This creates peer-driven momentum instead of top-down mandates.

➡️ Week 4: Real-world application. 

Use your chosen feature for one actual task — summarizing a client call, triaging emails, whatever aligns with your workflow.

The results across their post-mortem study:
 → Adoption jumped from 20-30% to 60-80% 
→ Training costs cut in half (from $1,000 to $500 per user annually) 
→ Performance improved 2–3X across enterprises and mid-market orgs

Cat's background in organizational psychology informed this approach. She's applying principles from habit formation — micro-commitments, proximate objectives, collaborative learning — to AI adoption.

The genius is that it works with human psychology, not against it. 💡

For CS leaders rolling out AI agents, this framework addresses the real barrier: making adoption feel manageable rather than mandatory.

Listen to the full conversation on [Un]Churned to hear Cat break down each week in detail. (Links in comments.)

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The Battle

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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);}Jared Robin ⏭'s LinkedIn Performance

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