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…

Jeff Riseley

Helping Sellers Win The Mental Game - Stress Less, Sell More

Sales is a mental game and too many sellers are losing. 🧠

I help sellers win it.

After training 10,000+ sales professionals and writing the Amazon best selling book Stress Less, Sell More, I’ve learned this: 

High performance doesn’t come from grinding harder, it comes from mastering your mental performance.

But that’s not what most sales cultures teach.

The data speaks volumes:

- 89% of sellers are burned out (Gartner, 2024)
- 70% are struggling with mental health
- 79% of sellers are stressed or highly stressed

And fatigue, stress, and sleep issues are now the norm.

So I built Project Mamba which is a mental performance program and community designed for quota-carrying professionals who want to win without burning out.

It’s where sellers learn how to:
✅ Defeat burnout using a 4-step resilience system
✅ Improve quota attainment with daily mental health habits
✅ Use breathwork, play, and mindset to optimize performance
✅ Build sustainable sales routines that don’t destroy your life

If you’re a sales leader or rep who:
- feels off your game
- struggles to focus or sleep
- senses the edge of burnout approaching...

Then you don’t need another script or tactic.

You need to rebuild your inner game.

Let’s fix the real performance bottleneck: your mindset and mental performance.

💡 Follow me for research-backed insights on sales, burnout, and high performance.
💬 DM me to learn more about Project Mamba.

TESTIMONIALS: 🔥🔥🔥🔥🔥

"If you want to build elite teams and operate at the highest levels individually, there’s nothing more important than understanding how your mind and body work and optimizing your mental performance. Jeff's training is purpose built for the jobs we're in and can take your team from surviving to thriving in a matter of weeks."

Kyle Norton, CRO - Owner.com

"Thanks to Jeff's guidance, I can handle stress better, communicate more effectively with my loved ones, and maintain a positive mindset. I'm grateful for the life-changing experience that has made me a better salesperson and an even better person." 

Miguel Castillo, Client Support Specialist at Ergeon

"Sales Health Alliance provided insights to me and my sales team that helped reps and their leaders better understand how to live with the stress our chosen career is guaranteed to create and how to build resilience to use it as fuel for our success."

Mark Kosoglow, VP Sales at Outreach

Founder

Mental Health = Mental Performance.

It's that simple.

The biggest mistake leaders make today is thinking Mental Health only applies to people who are unwell.

This couldn't be more false.

Mental Health applies to everyone and it is the single most important driver of how salespeople and knowledge workers perform every single day.

When you approach Mental Health from the perspective of high performance, you understand that proper stress-management, mindset, resilience and Mental Health training helps move employees towards a place where they're thriving.

The High Performance Zone.

It also means giving them a toolkit to help navigate the unique stressors they face in their role and outside the workplace in a way that keeps them there.

So remember...

Mental Health = Mental Performance.

This is non-negotiable and if you're not consistently investing into this area as a leader, your team is very likely underperforming.

Period.

Author, Stress Less 🧠 Sell More💸 | Sales Leader @ Jobber | Mental Performance Speaker, Founder, 2X Cancer Survivor

One of the best ways to improve your Mental Health is to change your relationship with anxiety. 

Anxiety is your "Spidey-Sense" (yes - I'm a huge superhero nerd). 

You need to work with it rather than against it. Our body and mind loves "control". When you feel in control of your environment, relationships and abilities your brain thinks: 

"I'm safe and I cannot get hurt." 

This is your comfort zone. Your brain can relax because it has achieved its primary purpose of protecting you from danger. 

The problem is this primary objective conflicts with another extremely important goal we all have which is to live a meaningful life without regrets. 

This requires us to venture out of our comfort zone and seek discomfort. We have to put ourselves in vulnerable positions that make us feel out of control and unsafe. 

Doing this triggers your Spidey-Sense and anxiety goes off like an alarm. 

Most of us respond by avoiding these situations and jumping away from them, but the key to working with your anxiety is jumping towards them. 

We need to treat these as special moments in life as Alarms for Growth instead of Alarms for Danger. 

When they go off, it means your anxiety has found a meaningful experience that will help you learn, grow and expand your comfort zone. 

The more you do this, the more you'll learn to embrace your anxiety as a friend instead of a foe.

Have you ever had trouble sleeping the night before a big meeting?😥 

You’ve spent all week preparing for it, but just as you shut your eyes to go to sleep you think:
​
“I need to get a good sleep tonight or else I won’t perform tomorrow.” 🤔 

And then “it” happens.

Even though you’re well prepared for your meeting and were dead tired a few moments earlier, your mind finds some superhuman reserve of energy and starts to wake up.

This alertness is created by your stress response releasing stress hormones, because it perceives a big threat as your mind starts to spiral:

If I have trouble sleeping…
I’ll forget what to say...
I’ll lose the client...
I’ll be embarrassed...
I’ll let my manager down...
I’ll lose that promotion...
Maybe I’ll lose my job? 😨 

“If I have trouble sleeping tonight, bad things will happen tomorrow.” ⚠ ​

As your mind cycles through these thoughts, they get louder and louder, making it impossible to fall asleep.

This is performance anxiety in its purest form. 😰 

However, this anxiety is less about how you’ll perform in your meeting tomorrow and more about your sleep performance. 

Performance anxiety happens when we put too much pressure on an outcome and in this case, that outcome is falling asleep. 😴 

To prevent this from happening in the future, here is a 6-step step process you can follow when you have trouble sleeping:

1 - Follow a strong bedtime routine.
2 - Label "it" as performance anxiety.
3 - Burn it off with a journaling brain dump.
4 - Acknowledge you can still perform on bad sleep.
5 - Put a plan in place for the next day.
6 - Inhale 4 seconds, exhale 6 seconds (10 rounds)

Obviously there is a lot more nuance that goes into this and I'm sure you have other ways to maximize your sleep.

What are your best practices for falling asleep the night before a busy day you need to be sharp for?

Burnout 😣 is like that sneaky subscription service you forgot you had and is silently chipping away at your bank account every month 📉 

When we're struggling with high stress and burnout...

- Emails that should take 5 minutes, take much longer.
- Motivation you should have, is non-existent.
- People you enjoy working with, grind your gears.
- Goals that should feel achievable, feel impossible.
- Healthy choices are swapped with bad choices.
- We stay up later and wake-up earlier.
- Set backs that should feel manageable, crush us.
- Buyers and deals we should close, we lose.

As our mental performance declines, so do our commission checks 💸 

It's quite literally taking money out of your pocket.

But how much is it taxing your mental performance in sales?

Is this a $2 subscription that is meaningless or a $1,000 subscription that is preventing you from ever achieving Presidents Club 🤔 

Well now you can find out.

Below you'll find a Burnout Calculator that will help you estimate just how big an impact burnout and stress is having on your daily productivity.

No email required - get results instantly.

So - how is your 🧠 doing?

Ready to cancel your burnout subscription?

Open article: Burnout Calculator by saleshealthalliance.com

Are you a Sales Leader who wants to check in on your reps Mental Health more but don't know how?

Using a Mental Health Traffic Light can be an amazing tool. 🚦 

I've outlined what they are and why they work in this article.

https://lnkd.in/exxUSmZE

Open article: The Mental Health Traffic Light In Sales by saleshealthalliance.com

Making smart health choices in sales feels like trying to diet at an all-you-can-eat buffet.

Stress, rejection, and long hours push us toward quick dopamine hits like late-night scrolling, junk food and another drink...

While the habits that actually fuel performance get ignored.

That's why I love this quote:

"Life is all about the C between the B and the D." - Jean-Paul Sartre

Life is all about the Choices we make between Birth and Death, which means we can make choices to support and strengthen our Mental Performance each day.

Sounds easy enough right?

Unfortunately when we're experiencing burnout and feeling overwhelmed, it can start to feel a lot like the choices we make at an All You Can Eat buffet.

Making the right choice becomes HARD.

It's hidden behind all of the temptations of fatty foods, high carbs and dessert bar.

Seriously - who ever goes to the salad bar?

Making the right choices in life can feel the same way.

They are hidden behind distractions like social media, technology, drugs, alcohol and sex which make it EASY to escape the uncomfortable emotions we're feeling.

Distractions that feed our most immediate desires but end up hurting our mental performance.

We choose what we WANT - like watching Netflix...

Instead of what we NEED to get in the right state of mind for high performance the next day - like journaling, exercising, calling our Mum or meditating before bed.

So today if you're experiencing burnout...

Ask yourself:

What do you NEED right now, but don't WANT to do?

Do that thing.

It's normally the right choice. 🧠

A lot of posts lately are telling people to "Stop comparing yourself to others online..." which isn't really possible. 👇 

Just like our brains are naturally programmed to focus more on negative experiences than positive ones (i.e. it's better to avoid the charging bear, than pick the fruit)...

Our brain is programmed to compare ourselves to others in order to survive.

This is because, as hunter gatherers, knowing where you fit in the hierarchy of a tribe was important to survival for thousands of years. 👨‍👩‍👧‍👦 

Feeling like you were stronger and healthier than others in your tribe usually meant safety, while feeling weaker or sicker than others meant danger.

We can't just shut this programming off. 🙅‍♂️ 

In fact, research has shown that 10% of our daily thoughts involve comparison, regardless of whether or not we're on social media, which is why we need to learn how to work with the systems in our body rather than against them.

Here are three best practices that have helped me do this:

1 - Acknowledge "today" is not normal. ⚠ 

Your biology is programmed to use comparison effectively in small groups, communities and tribes.

It can be helpful and even motivating, to compare yourself occasionally to a group of 50-100 people you know.

You're not designed to compare yourself effectively against 1000s of strangers online for several hours a day - which means nothing is wrong with you if you feel crappy and it's okay to take a break.

2 - Put language around the emotions you're feeling. 💞 

Prior to labelling the emotions I was feeling, I'd just feel "stressed" and feel unable to take a break from social media.

Journaling helped me unpack the uncomfortable emotions that were hijacking my mood and proper language helped me make sense of the internal story I was telling myself.

It usually followed this pattern of emotion:

I see something online that makes me feel "inferior"...
As a result I'd feel "threatened"...
And because I felt threatened, I'd start to feel "guilty" for taking time off.

Dismantling "stress" into "inferiority", "threatened" and "guilt", allowed me to explore why I was feeling each emotion individually, rather than let these emotions drive me towards burnout.

3 - Compared myself more. 📈 

Some people enjoy posting content 2-3 times a day, 7 days a week and it's easy to feel like you're never doing enough.

This is the same for those salespeople on your team who might be working 10-12 hours a day.

Comparing yourself to others, allows you to be more consciously aware of the tradeoffs others are making and decide if you want to make them too:

What would you be willing to give up?
Do you want to spend more time at work/online?
Maybe they're getting external help?
Do they have more experience than you?
What is enough for YOU?

The best part of life is you get to set your own goals and set your own pace.

It's not a competition and the more we realize this, the happier we'll be with our own progress and success 🧠

taplio

The Battle

Kyle Norton

Jeff Riseley

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The Battle

Kyle Norton

Jeff Riseley

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Engagements

Likes

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