Kyle Norton

📈 CRO 📈 @ Owner.com (Hiring), SaaS GTM Advisor & Investor

As CRO for Owner.com, Kyle leads a team of world class go to market professionals who help independent restaurants grow their direct, online takeout and delivery channels. He currently owns the sales, partnerships, onboarding, demand gen, revenue operations and enablement portfolios.

Kyle is also a Limited Partner (GTM Fund, Stage 2 Capital), Advisor, and Angel Investor for several SaaS-focused funds and startups, where he shares his insights and expertise on scaling, selling and servicing SaaS products.

Additionally, Kyle is a founding member and Co-Chapter Head of the Toronto chapter of Pavilion, a global community of revenue leaders and operators and host of the Revenue Leadership Podcast.

💥 Owner.com Sales Open House 💥 

I'm in town next week and hosting a Sales Open House on Thursday, January 15th, 2026 at 6:00-8:30 PM ET! 

Come check out our brand new Toronto Sales Hub located at 185 Spadina Avenue, 3rd Floor, Toronto for an evening designed specifically for early career sales professionals in the community, with a special focus on Sales Development Reps (SDRs) and Business Development Reps (BDRs).

🗣️ Hear directly from those who’ve done it and what it really takes to go from XDR → AE → Leadership
🤝 Networking with local sales professionals
🍕 Food, drinks and opportunity to meet like minded folks in your sales community!

🚀 Drop in & meet our team, mingle with other sales professionals in Toronto, and be part of this amazing sales community!

If you’re planning to attend, please fill out the registration form below to secure your spot.

📈 CRO 📈 @ Owner.com, Host of the Revenue Leadership Podcast & SaaS GTM Advisor & Investor

🏢🏢🏢 I'm hiring an Office Coordinator! 🏢🏢🏢

With our beautiful new Toronto HQ now humming and a massive sales hiring push underway (20+ reps in the next 75 days), we need someone exceptional to help make this office run like a well-oiled machine.

Owner.com is on a roll right now and we're gearing up for a transformational 2026. A big part of that transformation is building a world-class in-person experience for our Toronto team.

I'm looking for a proactive, detail-obsessed Office Coordinator who takes genuine pride in creating a space where people love to work.

What you need to know about this role at Owner:
🌍 You'll be the heartbeat of our Toronto office. From ordering supplies to coordinating catering to greeting guests — you're the person who makes the magic happen behind the scenes.
🎉 You'll help plan and execute incredible events. Team lunches, offsites, team-building activities — you'll be instrumental in bringing our culture to life.
🛠️ You're tech-savvy and solutions-oriented. Wi-Fi acting up? Conference room AV issues? You're calm, resourceful, and get things sorted.
💙 When we say we're customer obsessed, that extends to our internal team too. You genuinely enjoy creating a welcoming, seamless experience for employees and visitors alike.
🏆 We hold a high bar. This is a performance culture and we expect effort and outcomes. There's pressure in that but you also get to be part of a winning team.
💵 We pay competitively. $96,000 – $127,000 CAD base plus a generous pre-IPO equity package.
🚀 Low ego, high ownership. You're willing to jump in wherever needed — nothing is beneath you and nothing falls through the cracks.

As always, I'm really grateful for the incredible candidate volumes we receive on applications but it's really tough for us to get back to the right candidates in a timely manner. With that in mind, please only apply if:
1️⃣ You have prior experience in office coordination, office management, hospitality, or similar operational roles.
2️⃣ You're genuinely warm, service-oriented, and take pride in creating an exceptional office environment.
3️⃣ You're organized, detail-obsessed, and can juggle multiple priorities without dropping balls.
4️⃣ You are located in Toronto or can relocate. This is 100% in-office.
5️⃣ You're comfortable working beyond standard 9-5 hours when events require it and can handle light physical tasks (we've got an office move coming up!).
6️⃣ You friggin LOVE operations and are energized by solving problems, building systems, and making people's work lives better.

If this sounds like the type of environment that you want to be a part of, shoot me a message and apply below.

I noticed something at 10:30pm last Tuesday that I can't stop thinking about.

One of our Biz Ops team members requested a Slack app install for a side project. It was 1:30am his time. No deadline. No one breathing down his neck. 

He was just excited to build.

When I looked at Slack, there were a bunch of other people online for the same reason. Including me.

I've been accused of being a workaholic but this is something fundamentally different. Psychologist Robert Vallerand's research actually names it: harmonious passion vs obsessive passion. 

Both drive long hours. Only one is sustainable and improves performance.

I recently asked one of our senior product leaders what separates 10X engineers from the rest. I assumed he'd say decision-making or grit.

His answer: "Love of the game."

Some people just can't stop thinking about their work. They ruminate on problems in the shower, on walks, at 2am—until they crack it in some elegant way. You can't train that. You can't incentivize it with comp plans.

Elena Verna once said her job is her hobby. I think we've accidentally built a company of people like that at Owner. And I'm realizing it might be one of our biggest competitive advantages.

In this week's newsletter, I break down: 
→ How to screen for this in interviews 
→ How to attract these people 
→ How to keep them (hint: let them cook)

Link in comments 👇

Everyone's chasing AI tools.

The top-performing CROs are chasing something else: disciplined execution.

📈 Jeremey Donovan just surveyed 150 CROs for Insight Partners. He advises 500 B2B SaaS companies on GTM strategy. 

The data is clear:

There's no silver bullet AI use case separating winners from losers.

Top performers and average performers are adopting the same tools in the same order. The difference? Top performers were already disciplined before AI showed up.

Tight deal reviews. Rigorous pipeline inspection. Clear ICP focus.

AI amplifies what's already there. It doesn't create discipline from nothing.

Two things that stuck with me:

1. One CRO ripped out an AI tool that auto-filled MEDDIC fields because "the AEs were getting stupid." The tool worked perfectly. But it removed the thinking that made reps sharp.

2. 70% of outbound opportunities are still booked via phone. Not email. Not AI sequences. Human effort still wins.

The real unlock? Stop optimizing existing processes with AI. Rethink the processes entirely.

Full conversation on this week's Revenue Leadership Podcast.

Link in comments.

🏆 Sam Darnold is going to the Super Bowl. 🏆 

Four years ago, he was the poster child for "NFL bust." The guy who was "seeing ghosts" against the Patriots. The #3 overall pick who looked like he might never start again. 

Now he's the first quarterback from the stacked 2018 draft class to reach a Super Bowl. Before Josh Allen. Before Lamar Jackson. Before Baker Mayfield. 😲 

Two lessons here that apply way beyond football:

💡 Environment is everything 💡

Darnold spent three years in the Jets' dysfunction (sorry Christopher Moreira). Then two years in Carolina's mismatched scheme. 

He looked cooked.

Then he took a backup job in San Francisco. Sat behind Brock Purdy. Learned how to actually prepare and study under offensive mastermind Kyle Shanahan. "It was huge," he said. "Just being able to learn how they do things over there."

He parlayed that into 14 wins with the Vikings. They still let him walk. Handed the keys to their rookie.

So he landed in Seattle with Klint Kubiak running an offense that fits how he plays, surrounded by a roster built to win now. 

Same player. Radically different results.

Your environment isn't a nice-to-have. It's the game. This is why I say that you should optimize for company quality over anything when you're planning your next career steps. 

💡 Belief compounds 💡

Darnold spent 5 years failing. 

Most people would've accepted their fate as a career backup. Darnold just kept working. He kept improving each season and never lost belief in himself. 

Then he had a career year in Minnesota but Darnold choked in two massive games last season. Week 18 against the Lions. Wild Card against the Rams. Nine sacks. 

The "bust" narrative came roaring back.

And here's the part that gets overlooked: his new team believed in him too. After he threw four picks against the Rams in November, linebacker Ernest Jones said, "He's our quarterback. We got his back. And if you got anything to say, quite frankly, f*** you."

His coach Mike Macdonald called him "unflappable." His receiver Jaxon Smith-Njigba said, "The building believes in him. The city believes in him."

That belief came from watching his preparation. From seeing how he showed up every single day despite the noise.

Darnold's own words after winning the NFC Championship: "As long as I have belief in myself, and I believe in my teammates, there's nothing that you can't do."

💡 The takeaway: 💡 

Put yourself in the right environment. Keep working when everyone writes you off. Find people who believe in you because of how you prepare, not just how you perform when everything's going right.

And it's never too late to turn things around!

Sam Darnold was supposed to be a cautionary tale. Now he's one win away from being a champion.

And, of course, Go Hawks.

Here's an uncomfortable truth that actually led to the most unsubscribes I've gotten on a newsletter 😅 

If your RevOps function hasn't fundamentally transformed in the last 24 months, you're already losing. 

Not "at risk of losing." Already losing.

I'm watching a massive divergence happening right now between companies that get this and companies that don't.

The companies pulling ahead share three things:
1. They fixed their data foundations first.
Most companies are trying to bolt AI onto a messy CRM. That's like putting a Ferrari engine in a car with square wheels.

At Owner, we made Snowflake our system of record (not CRM) and put tons of resourcing against data quality. AI is only as good as the data underneath it.

2. Their RevOps leaders think like engineers.
The RevOps leader who isn't in Claude Code, doesn't understand data architecture, and isn't shipping experiments weekly? They're going to be replaced by someone who can.

This isn't me being harsh. It's just the new baseline.

3. They understand the flywheel.
A 4% efficiency improvement doesn't sound sexy. But it compounds into faster growth → more product investment → stronger brand → better talent → more efficiency.

Our reps are 3-4x more efficient than competitors. That gap isn't closing. It's widening.

The conventional wisdom of "let's wait and see how AI plays out" is going to get companies killed.

The reckoning is already here.

I unpacked all of this in my newsletter this week, including what I think needs to change with sales engagement platforms (hint: they need to be rebuilt from the ground up).

Harry Stebbings asked me a question after we wrapped my 20VC episode:
“Who are the best Seed stage founders you’re working with?”

I gave him one name. 

David Patterson-Cole, Founder of DataLane, and made the intro right there.

Last week, DataLane announced their $22.5M Series A led by 20VC.

Here’s why I put my reputation on the line with Harry:

At Owner, we sell to mom-and-pop restaurants. If you’ve ever sold to local businesses, you know the pain.

Your reps spend 30-40% of their time manually researching accounts. Google listings. Yelp pages. Facebook. 

Stitching together data that’s outdated a month later.

It’s slow. It doesn’t scale. And it crushes your unit economics.

David lived this exact problem. He started a food delivery app in college selling to the same restaurants we serve today. He couldn’t find the data he needed then—so he built the solution now.

That’s founder-market fit.

We were Datalane’s first customer and the results for us have been tremendous. 

DataLane is a key factor in the efficiency of our GTM machine.

Better data. Better targeting. Faster reps. More revenue per headcount.

Simple math.

Congrats to David, Ganesh, Harry and the entire DataLane and 20VC teams. 

This is only the beginning.

If you sell to local businesses, talk to them.

I've started to chat with Claude Code via iMessage, asking it to clear my inbox and do deep research on my upcoming calls. I'm now convinced that if Steve Jobs were around, he'd spend all of Apple's $3.4 trillion market cap to buy Anthropic.

Apple + Anthropic would win because
1. Apple controls the perfect interface to Claude
2. Claude is local-first and needs great hardware
3. Anthropic's core risks are cash and supply chain

First, Claude Code is obviously the future of computing promised by Siri. Even though it's a decade late, you can now talk to your computer and it'll just do what you say - whether it's editing videos or making phone calls or searching the web with tools like Parallel Web Systems just using MCP tools and skills. This is how Apple displaces the importance of the Google search box.

Second, it's local-first and hardware-first. Apple has spent the past 20 years trying to figure out how it fits into a cloud world. They've launched and failed iCloud and MobileMe and other services with no success. Yet now it turns out, being local and owning the on-device compute is the future. Claude is churning through files and folders (remember those?) and doing on-device video generation and analysis and searching through people's Messages database locally. Models will eventually run locally and it'll all be private and avoid the endless nightmare of API permissions.

Third, Apple has cash and chips expertise. Two things that are existential risks to Anthropic. Forget cars and the other moonshots. This is it. Turn those iCloud data centers into compute powerhouses. Bring all that offshore cash back onshore and buy GPU's and build out data centers. Tim Cook was built for this supply chain moment.

If Apple were to offer Claude Code via Macs and iPhones, soon there would be a Mac on every single desk - including corporate desks that have stayed tied to Windows for decades.

This is it. This is what Apple has been building toward for decades.

How much would you be willing to pay for them?

A bunch of us at Owner have gravitated to Claude Code over the last few months so this was very confidence building to see!

We’re entering a new era of GTM from ChatGPT > Clay > Claude Code. Here’s how I see the change…

Owner.com

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Results oriented sales professional experienced in creating personalized outreach strategies for consistent sales pipeline growth.

2+ years of sales experience using outbound sales strategies to produce 5 figures in sales and build relationships with C-Level Executives and director-level roles, adding value to their B2B Company.

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