📈 CRO @LassieAI 🎤 Host of the Revenue Leadership Podcast. 🕰️ Formerly Shopify, Owner.
San Francisco, CA
Joined August 2012
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Kyle Norton retweeted
Kyle Norton met with 30 to 40 vertical AI founders before deciding where to go next, and he chose to become CRO of @LassieAI.
He first met Lassie's founders as an advisor, telling them their traction was strong enough to hire a real CRO, before coming back a few weeks later wanting the job himself.
What sold him:
- Retention that looked like a Series D company's, from SMBs on month-to-month contracts
- Founders who did back-office admin work alongside small business owners before writing a single line of code
- Almost entirely organic growth, from a 15-person team with no marketing function and just three people selling
"My thesis with Lassie was, they solved the hardest, most high-trust, high-credibility, most difficult problem in the healthcare practice, which is managing their money. Getting them paid."
Kyle is looking for obsessive learners with a history of excellence, long-term players, and builders who root for the little guy, the independent practices and small businesses Lassie serves.
Lassie is hiring across GTM, engineering, ops, finance, and design: a16zjobs.substack.com/p/kyle…
@kylecnorton @steijnpelle @fredericrenken
In June, I promised my wife I wouldn’t do another startup and that promise lasted a total of 41 days 😅...
I recently joined @LassieAI as CRO because small business is in my blood and I couldn't resist the opportunity to bring AI to main street.
Kyle Norton retweeted
thrilled to share that @kylecnorton is the new CRO at @LassieAI
kyle teaming up with @steijnpelle and @fredericrenken is an absolute force to be reckoned with
and, he's hiring!
we brought him on the @a16z pod to get the full story: a16zjobs.substack.com/p/kyle…
In June, I promised my wife I wouldn’t do another startup and that promise lasted a total of 41 days 😅...
I recently joined @LassieAI as CRO because small business is in my blood and I couldn't resist the opportunity to bring AI to main street.
Thank you @steijnpelle and @fredericrenken for the trust, and @arampell, @katiekschwartz and @tdoggyholhol at @a16z for backing us and helping tell the story.
Time to build. 🫡
Kyle Norton retweeted
"Never hire a CRO / VP Sales that doesn't have a few truly great sales execs lined up to follow them. Wherever they go.
If they can't intro you to 2-3 top execs ready to jump with them, do not make the hire.
The best sales leaders always have at least a few ringers ready to start with them at their next role.
Always. Because they're always recruiting."
I talk about this with my team a lot even though we sell to SMB. The prospect shouldn't feel like "sales is being done on them". That's when prospects get psychological reactance (aka the ick) and pull away even though there is a good solution fit.
I experienced this as a buyer recently and we basically just left the rep out of next steps and worked directly with the solutions team. "Doing sales" to me ended up having the opposite effect.
there’s nuance here; yes, great AEs ask for the next meeting while they’re still on the call - agree
but if you ask to book time live, the prospect says “let me get back to you once I align calendars with a few others,”
and you push again with “let’s just grab a hold, we can always move it”...
you’re the reason AEs get a reputation for being “salesy”
when a prospect responds like that, it’s usually one of two things:
1) it’s not a priority or urgent (right now)
2) they genuinely need to coordinate with others they want on the next call
you aren't sure yet which one it was, so being too pushy could have them be turned off if #2
if I asked to get back to a seller and they bulldozed past that because persistence is “what good AEs do,” I’d be annoyed AF
(re: Isaiah's take, I don't have the full detail + not assuming the full context behind this take, just adding my POV since I hear this a lot)
Kyle Norton retweeted
Today we're launching the new standard for how to sell with AI, built with 10 of the most-followed voices in enterprise sales.
For 30 years, we've perfected how sellers run a deal.
We have MEDDPICC, Challenger, Command of the Message. Sales leaders spend months turning them into sales process docs with exit criteria, qualification rules, and forecasting guidance, then ship them to the field.
But nobody shows reps what to put in front of the buyer to win. Aside from a generic pitch deck, everything else is left to interpretation. No templates. No examples. No standard.
So the top 1% of reps build their own: tailored first-call deck, champion enablement doc, mutual action plan. Everyone else guesses.
AI has turned this gap into a crisis by giving every seller the power to create content for buyers without knowing what good looks like.
The end result: buyers are drowning in polished but ineffective content, and they're tuning out.
So we built the missing half. We teamed up with 10 of the sharpest minds in enterprise sales to map what the top 1% do at the ten moments that matter most, and how AI is changing each one.
Introducing the 𝗕𝘂𝘆𝗲𝗿 𝗘𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 𝗚𝘂𝗶𝗱𝗲:
@KnuthJen23597 on building the account POV behind $50M+ closed with C-level buyers
@kylecnorton on building the best outbound and cold call strategy we've ever seen
@aprildunford on the first-call pitch she's built for 200+ companies
@Chris_Orlob on the demo lessons from thousands of recorded calls
@NNasrall on the business case that lets your champion close the deal without you
@samfjacobs on how to connect with execs and pitch the Economic Buyer
Rippling's Ricky Peca on the deal room that helped him hit 300% of quota
@JamesKaikis on scoping pilots that align teams and convert
@NickCeg on the seven-figure pricing proposal a CFO will actually read
@RomeenSheth and @travisjgood on the AI security playbook that answers 90% of buyer questions
Every moment comes with their playbook, where reps go wrong, how to avoid AI slop, and ready-to-use templates.
Who it's for: reps selling AI products, sales leaders chasing a higher win rate, and the enablement and product marketing teams who equip them.
Grab all ten templates, with the expert breakdown behind each:
mutinyhq.com/selling-with-ai
P.S. Mutiny's sales assistant is trained on these templates and sales frameworks. Join the early preview for free on our homepage.
Then hire to the ceiling. "Headcount is easier to add once the machine is working better."
Why this matters more for 2027: AI is handing reps hours back. Those hours only become revenue when a qualified conversation fills them.
Where it breaks: my teams were transactional, so we could test fast. Long enterprise cycles don't give you that luxury.
Before you raise anyone's 2027 number, figure out where the extra opportunities come from.
BCG report: bcg.com/press/19october2026-…
