☁️ Cliff Simon

Polaris Ops

CEO & Founder

Pavilion

- Lead invitation-only community of sales, marketing, and operations executives
- Guide strategic development for growth-focused companies in Philadelphia region

Executive Chapter Head - Philadelphia

GTMfund

GTMFund Member

noble

Strategic Advisor

HubSpot

Revenue Council Member

Wizards of Ops

Community Partner

Sales Hacker, Inc.

Member

RevOps Co-op

RevGenius

RevGenius is a community of revenue generating sales and marketing professionals brought together to learn, share, support, and grow with each other. The extended work family.

Ambassador & RevOps Community Founding Member

RevOps Rise

RevOps Rise celebrates the brightest in RevOps while creating a safe, collaborative environment for community-led innovation.

Founding Member

RevOps-as-a-Service ® | We Make RevOps Easy!℠ | GTM & RevOps Leader | Advisor

With nearly two decades building revenue engines across Fortune 20 companies and high-growth startups, I specialize in RevOps strategy and fractional leadership for SaaS companies navigating rapid scale. HubSpot recognized me as a 2024 Modern Sales Leader, and Pavilion named me a Top 50 CRO to Watch.

Outside of work, Cliff is married and lives with his wife and three small children. He keeps active playing soccer & hockey, woodworking, and volunteering with their local church.

Coming in fresh this week from our first AI Roadshow in SF.

This set a high bar. 

Dozens of GTM leaders in one room, testing ideas, challenging assumptions, and putting AI into practice.

Highlights that stuck with me:
A CRO showing how they cut sales cycles with AI without adding headcount.
How a Top 3 PE Firm saved months on tiering and framing account lists based on perceived pain points.
A late-night debate: is AI a “teammate” or just a tool?

Thanks to our sponsors: Avarra, QFlow.ai, & Rev Intelligence.

This is why we built the AI Roadshow. Small, curated rooms. Honest conversations. Plays you can take back to your team the next day.

Really interesting to see what Box is doing with their forays into AI. Thanks to Amanda Nielsen & Dan O'Leary.

Next stop: Washington, DC - Sept 23 with Ebsta (now part of Fullcast) & Spara and we're hosting it at SalesIntel.io's offices.

Special shoutout and congrats to Spara, fresh off a $15M raise, who will be joining us as a sponsor in DC. Another signal that GTM + AI isn’t theory anymore. It’s funding rounds, faster sales cycles, and real competitive edge.


If you’re leading GTM in the age of AI, this is the room you want to be in.
👉 Register here: https://luma.com/jpl716jp

AI isn’t the future of GTM.
It’s the present.
And most revenue teams are still fumbling it.

That’s why on Sept 10 in San Francisco, we’re hosting the AI Roadshow. It’s a workshop-style event built for operators, CROs, and GTM leaders who are done with theory and ready to execute.

What to expect:
A room full of forward thinking execs.
Hands-on roundtable discussions. No panels, no fluff.
Real plays on how AI is changing sales, marketing, and customer success today.
Three sponsor-led talks from leaders pushing AI-first GTM forward.

Networking + happy hour after to keep the conversations moving.

👉 If you’re in SF and leading revenue, ops, or growth - grab your seat here: https://luma.com/0ymqtvm7

Every go-to-market system falls into one of three buckets:

System of Record: where the truth lives (CRM, CVP, CRW).
System of Information: where you enrich that truth (ZoomInfo, SalesIntel, Clay).
System of Action: where you actually do something with it (sales engagement, marketing automation, workflow automation).

Individually, these systems have been around forever. But the real shift is happening in the middle.

Jordan Crawford and I we're having a great conversation about this a few months back: the Model Context Protocol (MCP) layer. Like a server brain firing data and actions between corners of a triangle. It’s the connective tissue that makes automation actually work across silos.

Every vendor in this space is moving toward the same center. CRMs are building automation. Data platforms are moving into activation. Workflow engines are trying to own the whole stack. Everyone wants to be the hub.

The result is an unintentional collision course. The lines between “record,” “info,” and “action” are blurring. The winners will be the ones that don’t just bolt on features, but actually reimagine how these systems play together when the MCP layer runs the show.

Do you feel prepared to orchestrate the entire loop?

What tools are you using and seeing traction with today?

INBOUND isn’t just a conference, it’s a snapshot of where the industry’s focus is shifting.Here’s what stood out to me this year, and why it matters for GTM leaders:

AI → Hype vs. Execution
AI was everywhere. But there is a divide between hype chasers vs. operators actually building durable systems. That gap is only going to widen, and if you’re not in the second camp, you’re falling behind.

Alignment → Silos Will Kill You
Sales + Marketing. RevOps + GTM. Product + CS. The message was loud and clear. The leaders who figure out cross-functional execution are the ones who’ll set the pace in this market.

Authenticity → Humans → Playbooks
In a year where automation is everywhere, what resonated most were the conversations that cut through the noise. Katie Lambert shared their vision for making sure that this is the elevation of the human experience. Buyers want to be treated like humans instead of like lines on a spreadsheet. The GTM leaders who remember that will win.

Some of the best moments weren’t even on stage. They happened in all the nooks and crannies around SF. Honest debates, lessons shared over coffee, and operators comparing what’s actually working in the wild. That’s where the real state of the industry shows itself.

My takeaway: AI will keep evolving, but the fundamentals don’t change. Alignment, clarity, and human connection are what make GTM work. The leaders who hold onto that while adapting fast will be the ones left standing.

Shout out to the great activations from Chili Piper, A fun dinner with QuotaPath, and a great pickleball session with Morgan J Ingram, Daniel Cmejla, Rahul Jain, Aaron Leeder 🏒, and a few others.

If you've been following along with me on here for the last 4-5yrs, you've definitely seen how often I'm on the road. It's a drag being away from my wife and kids. It's hard on the body. Sometimes its hard to get up for it, even as an extrovert.

 Not this week. I'm stoked cause this week is one of my favorite events of the year, Pavilion's #GTM2025.

So many of the smartest people i know in tech will be there. There's always something to learn. 

A lot of conferences are full of fluff, vendor pitching, and dodging the real questions. 

That’s exactly why GTM2025 is so exciting.

👉 It’s built for VPs, CXOs, and Founders. The people actually making the calls.
👉 Every session is vetted to cut the fluff. Tactical instead of theoretical.
👉 Workshops, breakouts, and real talk that actually sharpen your GTM.

If you want sugarcoating, skip it. If you want to tear apart your GTM assumptions and leave sharper, get in the room.


Bring your hardest questions. That’s why we’re there.

attendgtm.com

Open article: GTM2025 Home by attendgtm.com

Some people just talk about doing cool things. Others actually make it happen.

Jordan Crawford is in that second category, and today he's hosting a session built for people who want to cut through the noise in go-to-market. 

While everyone else is chasing prompts and piling up tools, this session shows how to actually connect with customers. You’ll see the full Cannonball GTM methodology in action, battle-tested with 1,700+ GTM pros and proven to deliver 3x higher meeting rates and 2.5x better SQL conversion.

Only 100 seats. Only a few spots left.

Grab your spot:

Open article: AI barfed on my carpet (and my customer stepped in it) · Luma by luma.com

AI barfed on my carpet (and my customer stepped in it) · Luma

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