Ryan Staley – Whale Boss -Sell Effectively to Your PCP Through Emotional Connection and Quantifiable Outcomes

Quote of the Show

Look at the last 12 months of data that you have with your 5 biggest wins, your 5 fastest wins, and your 5 biggest losses, and then put it through that lens of what's the vertical, what's the revenue size, what's the ownership structure on top of it. Two, what's the outcome you've created. And last but not least... the actual tangible people you're working with.

Key Takeaways

  • You can double your deal size by knowing your customers and figuring out who your best buyers are, also called the PCP.
  • Double down on knowing the problem you solve to avoid spending too much on marketing to customers who are not a good fit for your product.


Episode 61 – Ryan Staley

Jared Robin: The guest of Episode 61 is somebody that I’ve known for quite some time since the early days of RevGenius. He has 20 plus years in sales and sales leadership. He’s scaled a business group from zero to 30 million ARR with four salespeople in five years without any marketing or demand gen.

He also hosts a podcast called the Scale Up Show, where he has interviewed over a hundred SaaS CEOs this year alone. Furthermore, he has taught his proprietary system, which he used to scale from zero to 30 million, to over 800 CROs and VPs of sales. Please welcome the current founder and CEO of Whale Boss.

Ryan Staley: Happy to be on the show. It’s a bit strange being on the other side of the mic, but I’m excited. It’s been a while since I’ve been in this position, so I’m happy to be here.

Jared Robin: It’s really cool to interview you after knowing you for a couple of years and seeing how you’ve turned your successes into actionable systems for others. I think it will be interesting to hear your insights. It’s been great reconnecting with you.

Ryan Staley: Yeah, it’s great to have you too. Going back in time, Jared was actually interview number eight on my podcast when I first started. Now I’m at around 228 or 230 episodes by the time this one is launched. It’s been around 220 episodes later for us to reconnect in this format. I’ll have you on my show as well, so it’s going to be a lot of fun.

Jared Robin: Absolutely. Both of us have been discovering our niches. I’ve been focusing on community, and you’ve launched your own product. It’ll be great to dive into it. But before we do that, let’s get started. Ryan, could you debunk a myth about generating revenue today?

Ryan Staley: Sure thing. I would say the myth is that SaaS companies truly know their customers. It sounds insane at its core, but after speaking with over 120 SaaS CEOs on my show alone, and engaging with another 50 through masterminds and consultations, I’ve noticed a recurring pattern. That’s why I wanted to address it. To break it down further, there are three key aspects to this:

  1. SaaS companies don’t intimately know who their best buyers are within their perfect customer profile (PCP). Implementing this one thing, which I’ll explain in the next 30 seconds, can completely change everything for them. They need to identify their best customers in terms of deal size, fast closing, and profitability. Some companies find that 20% of their clients create 80% of their revenue, or it could be a different ratio like 30/70. Within that, there’s often a subset of customers that deliver amazing insights, which we can discuss later.
  2. SaaS companies focus heavily on the product experience, as they should because they are tech companies. However, they often overlook the emotional experience, which is where the real value lies. Research shows that 50% of purchase decisions are based on emotion, 38% on logic, and 20% on scarcity and urgency.
  3. Many SaaS companies struggle to quantify the outcomes they deliver to their customers. I once worked with a company with 30 million in ARR, and the only person who could identify the quantifiable outcomes was the CEO. It was a massive gap that needed to be addressed. If companies can understand and quantify their outcomes at a financial, speed, and efficiency level, they can differentiate themselves from 98% of the market.

Jared Robin: You covered a lot of ground there, from understanding the perfect ICP to quantifying outcomes. It’s fascinating. How can companies implement these strategies and align their reps with what they close best?

Ryan Staley: Absolutely. I’ve personally experienced the benefits of implementing these strategies as a revenue leader and business owner, and I’ve seen them work for other companies as well. The process has evolved based on real-world experience rather than being pulled out of thin air. Primarily focusing on B2B SaaS, I’ve noticed that many solutions work across multiple verticals, sometimes even 12. However, there’s often a sweet spot within a few key verticals that generate most of the revenue and lifetime value (LTV). For example, one client with 30 million in revenue found that four verticals accounted for 83% of their revenue and 87% of their LTV over a three-year period. By redirecting the team’s focus to these top-performing verticals, companies can experience explosive growth.

Aligning reps with what they close best is crucial. As a rep, implementing this approach saved me 20 hours per week and increased my quota attainment from 100% to 130%. By targeting and focusing on the right customers, reps can eliminate wasted time and work with high-quality opportunities. This approach also provides amazing insights, as companies are often drowning in data but starving for insights. Going beyond verticals, factors like ownership structure, whether they’re PE or VC-backed, or bootstrapped can further enhance this approach.

Jared Robin: That’s truly remarkable. By aligning your team’s focus and considering the nuances within your target verticals, you can achieve outstanding results. It’s fascinating how understanding these dynamics can significantly impact revenue generation.

Ryan Staley: Yes, and it’s not only about knowing your product and how quickly deals can be closed. It’s also about aligning your sales representatives with the verticals they excel in. When I implemented this approach as a rep, I reduced wasted time by 20 hours per week and achieved 130% of quota instead of just 100%. It empowered my team to double their deal size each year because they were focused on the right prospects. The insights gained from this process are invaluable, especially when companies are drowning in data but hungry for actionable insights. There are even deeper levels to explore, such as ownership structure and other factors beyond verticals. By addressing these aspects, you can differentiate yourself from the majority of the market.

Jared Robin: It’s evident that your strategies have tangible results, both at the individual and organizational levels. The focus on the right customers and aligning reps with their strengths can drive exceptional outcomes.

Ryan Staley: Exactly. These strategies have evolved based on real-world experiences and successes. They’re not mere methodologies created in a vacuum. With the right focus on your target verticals, you can unlock explosive growth in your business.

One example of the CEO being the only person knowing… Yeah, being able to identify. And I don’t just work with $30 million companies. I have clients ranging from $2 million ARR to over $100 million. It all depends on the specific problem, but it falls under the umbrella of B2B SaaS. That’s my sub-niche, if you will.

Jared Robin: So, how can organizations enable themselves to understand this better? Is it just about enabling them, or what solutions are you seeing?

Ryan Staley: I think this needs to happen at a strategic level. One highly valuable recommendation I have, especially as we approach the end of the year (although you might be listening to this at a different time), is to look at the data from the past 12 months. Identify your five biggest wins, five fastest wins, and five biggest losses. Then analyze them based on the vertical, revenue size, ownership structure, and the outcomes you created. And of course, don’t forget to consider the specific individuals you worked with. It’s crucial to ask those third, fourth, and fifth-level questions to truly understand the tangible value delivered to customers.

It’s interesting because, theoretically, as salespeople, we should know why someone bought, but many deals are closed without a clear understanding of the value they will receive. Comparing the initial buying reasons to the actual realized value can be an eye-opener. And in terms of reassessing the value of the product to customers, the cadence depends on the stage and the volume of deals. Even at my stage, with revenue below a million, I still evaluate it a couple of times a year and analyze it through that lens. It’s like having an adaptive market engine that allows us to be hyper-responsive to the market and identify the heat maps.

And so, I would say biannually, at least if you’re getting a lot, a lot of deals flowing through, um, I should say revenue wise, it depends on how many deals. But if, if you’re above. Maybe 10 million. You could do it quarterly. That is valuable because if you look at it, you’ll truly understand like now’s the perfect time too.

Especially when the market is completely changing. Your ICP at the beginning of, or at the beginning of this year, of 2022 can be completely different now your perfect customer profile. Because of the market that’s responsive in a down market versus an up market.
So it could be completely flipped on it.

Jared Robin: What are some of the aha moments, like after helping a client? Like there’s some of the obvious ones, but I’m sure that there’s some aha, like after doing this with some of your clients. I’m curious.

Ryan Staley: What I would say is like, like people just, it’s easier to look at the generalities of everything. By identifying unique aspects and diving deeper, companies can unlock new streams of revenue. For instance, understanding the stages of VC backing can have a significant impact. I’ve seen cases where companies work well with tech companies backed by VC or private equity, but when we dig deeper into the specific stage of VC funding, different priorities and operations emerge. This level of insight is eye-opening.

Another fascinating observation is the contrasting operations between VC-backed and bootstrapped companies in the SaaS space. It’s mind-blowing to witness how bootstrapped companies, similar to PE-backed firms, focus on profitability and make adjustments when faced with market challenges. On the other hand, VC-backed companies may experience more pressure to grow rapidly, resulting in staff reductions. These insights have been enlightening, especially in recent weeks, as I’ve had numerous conversations on the topic.

Jared Robin: You’re absolutely right about understanding the problem you’re solving. It greatly influences product direction. By gaining a deep understanding of your customers’ needs, you can make strategic adjustments that lead to better demos, smoother sales conversions, and overall revenue growth. Product and growth are intertwined, and aligning with your customers’ needs is crucial for success.

Ryan Staley: Moreover, it’s not just about helping customers. Emotional connection and a positive human-to-human experience are essential elements that many SaaS companies overlook. Even as a CEO, I’ve experienced the onboarding and support processes of various SaaS products, and in most cases, they have fallen short. Regardless of the price point, whether it’s a lower-tier product or a high-end solution, there are simple steps companies can take to enhance the onboarding experience. Automation can play a significant role in streamlining processes and providing a better customer experience, regardless of the price point.

Overall, the key is to focus on understanding your customers deeply, delivering exceptional experiences, and constantly reassessing and adapting to the evolving market landscape.

Let me tell you an example: One thing I do when I have a podcast guest is automate sending them a thank-you gift. It doesn’t have to be expensive, just a gesture of appreciation. I usually send them a book that has had a significant impact on me and share it with them. People love it, and it’s a small investment. The same concept can be applied to onboarding new customers. Sending an automated letter or email from the CEO with a video expressing gratitude and welcoming them to the company can make a difference. It’s about creating a positive experience from the start and showing that you value them as a customer.


Jared Robin: I agree with your original point about knowing the problems you solve and how it relates to success. It’s not just about selling a product; it’s about helping customers overcome challenges and achieve their goals. When customers invest in your product, they expect it to solve a problem or remove a bottleneck that has been hindering their progress. If the onboarding experience doesn’t help them get on the right track quickly, they may churn. Understanding the problems you solve and confirming if those problems are common among your target audience is essential. By focusing on the core problems and delivering value, you can improve the overall customer experience.

Ryan Staley: When it comes to quantifiable outcomes, financial metrics are often straightforward. However, the challenge lies in identifying the relevant KPIs for your specific solution. For example, in the case of an HR tech platform, the quantifiable outcomes could include cost savings from replacing manual recruiting processes, faster time to fill positions, improved candidate quality, and reduced turnover. It’s important to engage the customer in co-authoring these metrics to ensure they resonate and align with their goals. By quantifying the outcomes, you can demonstrate the value your product provides.

As for turning time into money, it can be a bit trickier, especially when it comes to administrative tasks. However, you can approach it from a different angle. For example, instead of focusing solely on time saved, emphasize the transformation of data and information in a CRM from being disorganized or incomplete to becoming valuable and actionable insights. Highlighting the benefits of having usable data and driving better demand generation efforts can demonstrate the value of your solution. It’s about reframing the narrative and showing how your product contributes to overall efficiency and results.

Currently, my biggest challenge is juggling multiple responsibilities as a solepreneur. I’m handling marketing, sales, revenue operations, finance, being a dad, and trying to maintain a personal life. It’s about learning to say no to the right things and staying exclusively focused on the most important tasks at hand. Rather than worrying about scaling right now, I need to prioritize and tackle what’s essential in the present.


I made a mistake early on by trying to do too many things and not focusing enough on what was in front of me. I was trying to scale too quickly without taking care of the present. It’s important to break things down into simple steps and focus on the essentials. Prioritizing is key, and it depends on whether you need immediate money or can play a longer game. Sometimes short-term sacrifices can lead to long-term gains.

I empathize with the challenges of running a business and the uncertainties that come with it. It’s important to enjoy the journey and appreciate the progress along the way. I want to make a positive impact on the world and create something that benefits others. Family is also a priority for me, and I strive to be a great husband and father.

Jared Robin: I think that’s pretty much it. Wow, that’s powerful. Holding onto that check was a significant reminder for me. I went through a period of mental health struggles, and I had a prescription for anti-anxiety medication that I filled for the first time in my life. I placed it in my medicine cabinet, and it served as a wake-up call for me to focus on introspection.

Ryan Staley: It’s incredible how the journey unfolded. I found myself crying every night during that time. It’s important to have symbols like that check or receiving money from my dad, even though I didn’t end up using it. Each person’s situation is unique, and sometimes accepting help or medication is necessary. Having those reminders can be motivating.

To get in touch with me and connect, there are two simple ways. First, check out my podcast, the Scale Up show, where I interview SaaS founders. They share their challenges, growth opportunities, and lessons learned on their journeys. Second, reach out to me on LinkedIn and mention that you heard me on Jared’s show. I’m currently revamping my website, so LinkedIn is the best way to reach me.

Jared Robin: And yes, you’ll hear me on Ryan’s podcast soon as well. It has been an awesome experience. Thank you, Ryan, for joining us today. It’s been a lot of fun reconnecting, and I’m looking forward to flipping the script and being a guest on your show. This has been another fantastic episode of Revenue Today with Ryan Staley. Stay tuned for more episodes. See you next week!

Wow, another great episode of Revenue Today. For show notes, links, and mentions, visit revenuetoday.live. A special thanks to the Rev Genius community. It has been a pleasure spending this time with you. Feel free to DM me with any feedback or ideas in our Slack channel or on LinkedIn. If you’re not part of Rev Genius, join us at revgenius.com. It’s free, takes only a few seconds, and you’ll be joining a community of 37,000 revenue professionals. We have it all. Looking forward to seeing you there. Catch you on the flip side.


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