391 episodes

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 Ryan Staley

    • Business
    • 4.9 • 56 Ratings

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.

    Mark Roberge: Co Founder of Stage 2 Capital Part 1

    Mark Roberge: Co Founder of Stage 2 Capital Part 1

    Join Ryan for part one with the legendary Mark Roberge, former CRO of HubSpot and current venture capitalist. They dive deep into the world of AI companies, discussing the immense opportunities and potential pitfalls. Mark shares his unique perspective on identifying promising AI start-ups and provides invaluable insights for entrepreneurs and investors alike.

    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


    AI is a generational technology, potentially bigger than the internet, but currently in a massive hype cycle similar to the dot-com era.
    Most current AI ideas are basic integrations into existing workflows, not reimagining the workflow, and are likely to be disrupted.
    Joining an AI company now provides valuable experience, even if 90% fail, as the winners will scoop up experienced talent.
    The AI technology creating operational efficiency in the short term may not be the same as the disruptors redefining industries over the next decade.
    Understanding prompting, the foundation of AI language is crucial for developing micro-workflows, agents, and eventually autonomous swarms.
    The innovator's dilemma and appropriate beachhead selection are key concepts for AI startups to consider when building for the long-term vision.
    RevOps, once seen as supporting humans, may flip to AI doing the job with humans tweaking and refining.
    Technical issues like hallucinations and latency will likely be ironed out as the technology matures, revealing AI's true potential.

    BEST MOMENTS

    "I've never had more conviction for my students that come up to me. Like, 'Hey, what's up? Professor, like what, what should I do? Like, I want to be, I want to go into startups. Like, what should I do?' And I, I've always had like different opinions. I was like, do you have to go to AI? Like every tech company is going to, in like six years is going to be native AI. You have to get that experience now."

    "I think all the tea leaves are similar to like 1997. Let's not forget that in that time, we dialled up to the internet using AOL, launched a Netscape browser and did searches through AltaVista, right? Where are those companies? Lycos, right? Is, is, is, yeah, is OpenAI Netscape or is it Google? Like we got to figure that out, right?"

    "The AI technology that's going to create significant operational efficiency and growth this year and next for companies, especially these bigger companies that my CROs are from is not going to be the trillion dollar new company that disrupts the space."

    "I've kind of come to the conclusion that the AI companies, vendors, technology that is going to create the most operational efficiency, even for our start-ups in the next year is not going to be the same AI technology company, et cetera, that becomes the disruptor over the next decade and redefines the sales and martech sector."

    "RevOps has become huge, didn't even exist 15 years ago. And for the most part, RevOps is seen as an organization that supports the humans to do their job. And that flips with what you're saying. Is, at some point, it flips where RevOps does the job and humans there to tweak it."

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 27 min
    How to Turn Chaos Into Scale with 4x Executive Stephanie Valenti Part 2

    How to Turn Chaos Into Scale with 4x Executive Stephanie Valenti Part 2

    🎙 Exciting news! I recently had the pleasure of having Stephanie Valenti on the Scale Up Show for part 2 of our conversation. We dove deep into the topic of retaining perceived value in a fast-moving market, especially with the rapid advancement of AI and technology. If you're looking for insights on how to navigate this challenge, this episode is a must-listen.

    🔍 In the episode, we discussed strategies for retaining perceived value in a fast-moving market, drawing from my experience in various leadership positions across B2C, B2B, and enterprise environments. We also explored the impact of AI on client relationships and continuous value creation. 

    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


    Embrace constant creativity and think outside the box to bring value based on your organization's strengths
    Understand the initial impact that made clients choose your business and continue to focus on that throughout the relationship
    Leverage AI to supplement human experiences and provide consistent value to clients
    Stay informed about competitors, AI advancements, and work closely with product teams to deliver value rapidly
    Prioritize human elements like co-selling, sponsorships, and events that AI cannot replicate
    Be proactive in client communication at the executive level to gather feedback and address any lack of value
    Segment business and assign executive ownership for constant communication and proactive feedback gathering
    Consolidate client feedback, identify trends, and take action to maintain and enhance value

    BEST MOMENTS

    "It's constant creativity on a leader's part, how are you thinking outside the box to make sure that you're bringing value based on what your organization can provide."

    "You've got to think about what is the human element that can supplement an AI experience."

    "It's the human element. It's the co-selling. It's the sponsorships. It's the events. And it's no surprise why those are at the top. It's because it's human and that can't be replaced, at least yet." -

    "You generally don't know if you've lost perceived value until it's gone if you're not proactive

    "Proactivity is key. After that, if you start to lose, then you're just playing catch up and that can be a really dangerous game."

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 18 min
    How to Turn Chaos Into Scale with 4x Executive Stephanie Valenti Part 1

    How to Turn Chaos Into Scale with 4x Executive Stephanie Valenti Part 1

    Stephanie Valenti, a four-time executive operator, shares her insights on turning chaos into scalability in organizations. She emphasizes the importance of creating structure, processes, and a strong team to achieve long-term growth. Valenti also highlights the need for pre-work, such as defining mission, vision, and values, and setting clear goals. She advises founders to slow down and celebrate successes, analyze what worked, and prioritize and prune initiatives to avoid shiny object syndrome. The conversation will continue in part two, where Valenti will discuss retaining perceived value in a fast-paced environment.

    Don't miss Part 2 of our conversation for more insights on retaining perceived value in a fast-moving market. Stay tuned!

    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


    During COVID-19, Stephanie recognised she had a gap in knowledge where ‘wider’ business was concerned as she had always worked in fortune 500 companies. She then became a COO for a manufacturing company where she learnt an incredible amount.
    Start-ups operate differently to large businesses, in the early stages it’s more about trial and error than planning.
    Understanding structure allows start-ups to move into the next phase of their business and to scale effectively.
    Sometimes you need to slow everything down to be able to then scale and grow. This is especially true when trying to figure out product market fit.
    Tracking things early on with help you choose the strategies and tactics that work further down the line. It helps you avoid ‘shiny penny syndrome’ as a founder and aids you in making effective decisions.

    BEST MOMENTS

    “I could do four whole podcast shows talking about my experience and the mistakes and successes that I had”

    “In a start-up, it’s in the moment, it’s let’s throw spaghetti at the wall and see what sticks”

    “What would a structure look like at $100 million? What roles would we need? What types of people would we need?”

    “Slow down to speed up”

    “When money is involved it’s super emotional so of course then want to keep moving it forward”

    “Just because something worked once, doesn’t mean it will again”

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 16 min
    99% are falling behind with AI because of these 3 Mistakes

    99% are falling behind with AI because of these 3 Mistakes

    Get ready to supercharge your AI game with Ryan as he shares three mind-blowing mistakes 99% of people are making with AI implementation. Discover how to overcome these pitfalls and join the 1% who are revolutionizing the way they integrate AI into their 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


    Treat AI like a person, not software, to maximize its strengths and adjust for its weaknesses
    Provide context to AI about its role and experience to improve output quality
    Understand that AI excels at complex tasks but may struggle with simple ones like math
    Document what AI does well and poorly for your specific use case
    Leveraging AI effectively can free up time and allow you to focus on things you love
    AI is advancing rapidly, and staying ahead of the curve is crucial for success
    Psychological patterns can hinder AI adoption, leading to missed opportunities
    Integrating AI into your business can have positive downstream effects on personal life and relationships

    BEST MOMENTS

    "The expectations that people have are that it does everything amazing. Now, what I'm going to get into are the three mistakes that people are making, but I wanted to kick it off and show you that because that's that key understanding of how to use it, it's not going to be a straight line going across, there's going to be tasks that it's amazing at, and then tests that it's not so good at is going to be some of the keys to the castle."

    "You need to expect it to act like a person, right? And as weird as that sounds, it's not a person. It's not sentient.”

    "If you could free up like 10 hours a week how amazing would that be? Or if you could just offload. To an AI intern, like the things that you hate about your job and do the things that you love doing, like how cool would that be?"

    "This is a psychological pattern that I see people falling into that's stopping them from literally using one of the most powerful things that we've ever had in terms of mankind, and it just kills me inside."

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 12 min
    Unveiling Personal Significance in SaaS AI Revenue Boosts with Jeff Mains of Saas Fuel Podcast

    Unveiling Personal Significance in SaaS AI Revenue Boosts with Jeff Mains of Saas Fuel Podcast

    In this episode, Ryan dives into the world of AI, sales strategies, and customer success together with Saas Fuel Podcast host, Jeff Mains. From leveraging AI in sales and Go-To-Market strategies to maximizing customer success stories, this insightful discussion is a must-watch for SaaS founders, leaders, and entrepreneurs. Join us as we explore the intersection of technology, sales, and human touch in today's business landscape.

    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


    Maximize customer success stories by capturing before and after states to create compelling case studies that showcase your solution's value and build trust with potential customers.
    Foster strategic partnerships with industry influencers and associations to expand your reach, tap into their audience, and gain credibility.
    Invest in targeted content marketing that addresses specific pain points and positions your product as a solution to your target audience's challenges.
    Leverage AI to automate repetitive tasks, accelerate skill acquisition, and enable your team to focus on high-value activities.
    Implement an acceptable use policy for AI tools within your organization and provide foundational training to empower your team to innovate.
    Encourage curiosity and experimentation with AI tools to unlock new possibilities and drive innovation across your organization.
    Integrate AI into your go-to-market strategy by understanding the KPIs, challenges, and emotions that drive your target audience's decision-making process.
    Cultivate technical literacy and AI skills in the next generation to prepare them for the rapidly evolving business landscape.

    BEST MOMENTS

    "Nothing speaks louder than success, but not your success, their success. The solution is about them. It's not about you."

    "You could basically go in there and tell it to act like the chief HR officer at a hundred million dollar SAS company that's publicly traded."

    "I think 2023 was a year where everyone was focused on integrating AI in their product, specifically tech companies. And I think 2024 is the year where you want to integrate AI in your people."

    "Curiosity is what I would say. Yeah, that's kind of where I was headed."

    "I would say like acceptable use policy, step one, step two is like, you know, what's the model that is sanctioned by the company that you're going to use temporarily. And then step three is basically embrace it."

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 53 min
    AI Secrets for Explosive Growth with Michael Fauscette of Disambiguation Podcast

    AI Secrets for Explosive Growth with Michael Fauscette of Disambiguation Podcast

    Join Ryan as he interviews fellow podcaster and tech analyst Michael Fawcett. They explore how AI can revolutionize sales strategies and supercharge business growth and outline the incredible potential of AI to streamline processes, enhance skills, and boost productivity.

    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


    AI can dramatically reduce time spent on tasks, automate execution, and provide custom training to rapidly upskill sales teams.
    Leveraging AI for deep work tasks like deal strategy and revenue leader tasks can lead to significant time savings and improved outcomes.
    AI enables salespeople to acquire new skills such as graphic design, music, and video creation within seconds, enhancing their capabilities.
    Onboarding time for new sales reps can be reduced from months to weeks by using AI to create custom learning plans and role-playing scenarios.
    Retention can be improved by using AI to automate tasks that salespeople don't enjoy or excel at, increasing job satisfaction.
    Small and medium businesses can use AI to focus on their top 20% of customers and multiply outcomes without adding headcount.
    The sales professional of the future should focus on gaining attention through depth over quantity and consistently look for ways to leverage AI in their daily tasks.
    Tracking progress and iterating on AI usage can lead to becoming a leader in the organization and future-proofing one's career.

    BEST MOMENTS

    "You have the capability to become superhuman and offload a lot of the things that you don't like about your job, acquire new skills at an insane rate and do things that you've never been able to do just by using words."

    "I tested it on basically the KPIs of the executives that we were selling to... It got like 95 per cent of the way there with one question. I was like, okay, this is scary, but exciting at the same time."

    "If you enable your team, specifically with prompts and a prompt library, and a whole innovation environment around AI, what will start to happen is they will naturally start to want to find ways where they could automate the things that either they're not good at, or they don't like."

    "Customized learning is huge. You could take the data set from what the company does, who they sell to, their ICP, and then you could probably even download the new employee's job experience from LinkedIn and factor that in and have a whole learning plan customized based on that."

    "I would just make it a priority for my team and my org to use and innovate with these tools. Make it a priority, do a weekly meeting with your team, give them a running start by you learning as a leader, and then having them come back and identify the best practices after the first week and then innovate on top of that every week thereafter."

    Ryan Staley

    Founder and CEO

    Whale Boss

    ryan@whalesellingsystem.com

    www.ryanstaley.io 
    Saas, Saas growth, Scale, Business Growth, B2b Saas, Saas Sales, Enterprise Saas, Business growth strategy, founder, ceo: https://www.whalesellingsystem.com/closingsecrets

    • 38 min

Customer Reviews

4.9 out of 5
56 Ratings

56 Ratings

PeteSteg ,

CRO gold

Another stellar episode from Ryan Staley. I especially valued the ideas about treating Rev Ops as an investment and not a cost center.

I can count on consistently fresh ideas on growing my business without losing my autonomy to investors.

HillGamingCompany ,

Loved the episode with Shay from ActiveCampaign

This show continues to be a leading resource for growing SaaS. I loved the deep dive into where we are headed as an industry and the future of AI. Look forward to more A-tier guests!

Dave1060 ,

Solid practical advice

This guy has good energy, appreciate his perspective and advice 10/10 would listen again

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