Ryan is joined by the Co-Founder and COO of Obie insurance, Aaron Letzeiser, who shares how identifying one costly mistake led him to pivot and embrace AI for growth. Listen as Aaron talks about the critical decisions that make-or-break start-ups; from avoiding common founder missteps to leveraging partners for customer acquisition. Aaron also brings a tactical playbook for scaling with limited resources and shares actionable growth tactics.

Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  

Explore becoming Superhuman here: https://superhumanrevenue.beehiiv.com/

KEY TAKEAWAYS
Aaron pivoted from a free platform to a paid insurance offering based on 200+ customer discovery interviews
Partner with non-competing software platforms to embed services and decrease churn
Stay laser-focused on a single niche before expanding into adjacent markets
Use AI to drive core insurance underwriting and operations via visual recognition models
Market conditions like rising interest rates can significantly impact lending partners
Revisit sales processes and tighten SOPs during rapid scaling to ensure quality

BEST MOMENTS

"We really should have continued to listen to our customers and utilize that as the guiding principle of what we ended up building."

"Do one thing and do it well. That was advice we should have taken sooner."

"AI is endless. We use visual models to identify fire hydrants and drive insurance underwriting."

"As the team grows, how do we ensure the quality does not also drop off?"

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

Ryan is joined by the Co-Founder and COO of Obie insurance, Aaron Letzeiser, who shares how identifying one costly mistake led him to pivot and embrace AI for growth. Listen as Aaron talks about the critical decisions that make-or-break start-ups; from avoiding common founder missteps to leveraging partners for customer acquisition. Aaron also brings a tactical playbook for scaling with limited resources and shares actionable growth tactics.
Join 2,500+ readers getting weekly practical guidance to scale themselves and their companies using Artificial Intelligence and Revenue Cheat Codes.  
Explore becoming Superhuman here: <a href="https://superhumanrevenue.beehiiv.com/">https://superhumanrevenue.beehiiv.com/</a>
KEY TAKEAWAYS
<ul>
<li>Aaron pivoted from a free platform to a paid insurance offering based on 200+ customer discovery interviews</li>
<li>Partner with non-competing software platforms to embed services and decrease churn</li>
<li>Stay laser-focused on a single niche before expanding into adjacent markets</li>
<li>Use AI to drive core insurance underwriting and operations via visual recognition models</li>
<li>Market conditions like rising interest rates can significantly impact lending partners</li>
<li>Revisit sales processes and tighten SOPs during rapid scaling to ensure quality</li>
</ul>
BEST MOMENTS
"We really should have continued to listen to our customers and utilize that as the guiding principle of what we ended up building."
"Do one thing and do it well. That was advice we should have taken sooner."
"AI is endless. We use visual models to identify fire hydrants and drive insurance underwriting."
"As the team grows, how do we ensure the quality does not also drop off?"
Ryan Staley
Founder and CEO
Whale Boss
ryan@whalesellingsystem.com
<a href="https://www.ryanstaley.io/">www.ryanstaley.io</a>

How do you grow like a VC-backed SAAS company without taking on investors? What are the secrets that SAAS CEOs have that the rest of us don't? Do you want to create a lifestyle business, a performance business, or an empire?  How do you scale to an exit without losing your freedom?


Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best SAAS Founders, CEOs, and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.

This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Gina Bianchini (Founder of Mighty Networks and prior Co-Founder with Marc Andreessen) and Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin). This is where Scaling and Sales are made simple in 25 minutes or less.

Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Sales, Business growth strategy, Founder, VP of Sales, CRO, Chief Revenue Officer, Technology, Leadership, CEO, Management, Hyper-Growth.

How do you grow like a VC-backed SAAS company without taking on investors? What are the secrets that SAAS CEOs have that the rest of us don't? Do you want to create a lifestyle business, a performance business, or an empire?  How do you scale to an exit without losing your freedom?
 Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best SAAS Founders, CEOs, and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak), Gina Bianchini (Founder of Mighty Networks and prior Co-Founder with Marc Andreessen) and Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin). This is where Scaling and Sales are made simple in 25 minutes or less.
Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Sales, Business growth strategy, Founder, VP of Sales, CRO, Chief Revenue Officer, Technology, Leadership, CEO, Management, Hyper-Growth.

The Scale Up Show

How do you grow like a VC backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire?  How do you scale to an exit without losing your freedom?
Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO’s and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset.
This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),  Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more
This is where Scaling and Sales are made simple in 25 minutes or less.

How do you grow like a VC backed company without taking on investors? Do you want to create a lifestyle business, a performance business or an empire? &nbsp;How do you scale to an exit without losing your freedom? Join the host Ryan Staley every Monday and Wednesday for conversations with the brightest and best Founders, CEO&rsquo;s and Entrepreneurs to crack the code on repeatable revenue growth, leadership, lifestyle freedom and mindset. This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World&rsquo;s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),&nbsp; Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more This is where Scaling and Sales are made simple in 25 minutes or less.

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