Ryan Staley interviews Randy Wootton who shares his incredible journey from the U.S. Navy to working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing. Randy reveals the seven secrets of success for SaaS CEOs, offering invaluable insights on navigating the challenges of scaling a business.

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
Randy Wooten transitioned from a successful career in the U.S. Navy and working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing.
As a CEO, Randy emphasizes the importance of delivering shareholder value, establishing a winning strategy, shaping company values and standards, building an effective executive team, managing the board and investors, allocating capital strategically, and investing in your personal growth.
Randy discusses the challenges of selling to CFOs compared to CMOs, highlighting the need for a different go-to-market motion that involves bringing in influencers and references, as CFOs tend to be more introverted and rely heavily on relationships when making purchase decisions.
Maxio uses the McKinsey Horizon Model to allocate funds for current and future growth, dedicating resources to core business (Horizon 1), near-term opportunities like payments (Horizon 2), and long-term game-changing initiatives (Horizon 3).
Randy believes that AI will significantly impact go-to-market strategies, with boards expecting companies to incorporate AI efficiency assumptions into their fiscal year 2025 planning, and he advises businesses to start experimenting with AI tools now to stay ahead of the curve.
To navigate the challenges of being a CEO, Randy recommends finding a mentor who has been in a similar position, working with a coach to improve interpersonal effectiveness, joining peer groups like EO or YPO, and cultivating a personal advisory board for support and guidance.
Randy highlights the importance of being a system of record and having differentiated data that can be leveraged with AI to create intelligent engines that offer benchmarks and insights to help customers run their businesses more effectively.
By sharing his experience co-founding the VetForce platform at Salesforce, which empowers military veterans, Randy demonstrates his commitment to making a positive social impact alongside his professional achievements.

BEST MOMENTS

"I am there to deliver shareholder value. That's primarily driven by delivering the results." 

"One of the things when I became CEO, the first time was I wanted a mentor, someone who had been in the same context." 

"I think for my own career growth, I had reached this inflection point where I thought, gosh, the patterns that I've seen in this scenarios, would it apply to a different vertical in this case, selling to the CFO?"

"Unless you're absolutely crushing it and everyone's gonna make a whole bunch of money, like there is [something] everyone starts to revert to it's like Maslow’s hierarchy of need. They're all nice until it becomes, okay, how are we going to carve up the pie?" 

"I think anyone who's truly appreciative of what's happened in their life will also recognize how much luck has played and connections, and we'll be willing to give back to other folks." 

Ryan Staley

Founder and CEO

Whale Boss

ryan@whalesellingsystem.com

www.ryanstaley.io

Ryan Staley interviews Randy Wootton who shares his incredible journey from the U.S. Navy to working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing. Randy reveals the seven secrets of success for SaaS CEOs, offering invaluable insights on navigating the challenges of scaling a business.
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>Randy Wooten transitioned from a successful career in the U.S. Navy and working for tech giants like Microsoft and Salesforce to becoming the CEO of Maxio, a company that has integrated a platform with over 2,400 customers and $13 billion in annual invoicing.</li>
<li>As a CEO, Randy emphasizes the importance of delivering shareholder value, establishing a winning strategy, shaping company values and standards, building an effective executive team, managing the board and investors, allocating capital strategically, and investing in your personal growth.</li>
<li>Randy discusses the challenges of selling to CFOs compared to CMOs, highlighting the need for a different go-to-market motion that involves bringing in influencers and references, as CFOs tend to be more introverted and rely heavily on relationships when making purchase decisions.</li>
<li>Maxio uses the McKinsey Horizon Model to allocate funds for current and future growth, dedicating resources to core business (Horizon 1), near-term opportunities like payments (Horizon 2), and long-term game-changing initiatives (Horizon 3).</li>
<li>Randy believes that AI will significantly impact go-to-market strategies, with boards expecting companies to incorporate AI efficiency assumptions into their fiscal year 2025 planning, and he advises businesses to start experimenting with AI tools now to stay ahead of the curve.</li>
<li>To navigate the challenges of being a CEO, Randy recommends finding a mentor who has been in a similar position, working with a coach to improve interpersonal effectiveness, joining peer groups like EO or YPO, and cultivating a personal advisory board for support and guidance.</li>
<li>Randy highlights the importance of being a system of record and having differentiated data that can be leveraged with AI to create intelligent engines that offer benchmarks and insights to help customers run their businesses more effectively.</li>
<li>By sharing his experience co-founding the VetForce platform at Salesforce, which empowers military veterans, Randy demonstrates his commitment to making a positive social impact alongside his professional achievements.</li>
</ul>
BEST MOMENTS
"I am there to deliver shareholder value. That's primarily driven by delivering the results." 
"One of the things when I became CEO, the first time was I wanted a mentor, someone who had been in the same context." 
"I think for my own career growth, I had reached this inflection point where I thought, gosh, the patterns that I've seen in this scenarios, would it apply to a different vertical in this case, selling to the CFO?"
"Unless you're absolutely crushing it and everyone's gonna make a whole bunch of money, like there is [something] everyone starts to revert to it's like Maslow’s hierarchy of need. They're all nice until it becomes, okay, how are we going to carve up the pie?" 
"I think anyone who's truly appreciative of what's happened in their life will also recognize how much luck has played and connections, and we'll be willing to give back to other folks." 
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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