Episode OneHundredFortyEight

Why Personal Development Helps You Land Bigger Deals

Guest: Ryan Staley, VP of Strategic Accounts at FlexPrintMPS

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About This Episode

You only see your kids for like 15 minutes tops.

You’re constantly doing work on your phone over the weekend.

Everyone else is landing huge deals, but not you.

I grabbed half an hour to chat with Ryan Staley, VP of Strategic Accounts at FlexPrintMPS, about why you should invest in personal development for yourself. 

Ryan shared his gut-wrenching wake-up call, the moment when he knew he needed to change his life: “I got home early and wanted to see my daughter who was about two. She wouldn’t even give me a hug. She wouldn’t even come by me.”

Ryan went from being a stranger to his family to having exponentially better relationships after investing in personal development. 

This led from developing himself to developing his team — and helping them execute on really large deals. “Over the last six years, we’ve grown annual recurring revenue by about $30 million with a team of three or four people,” Ryan said.

A successful career without sacrificing what matters

Ryan learned the hard way how to balance sales with life. He shared two tips for learning from his example.

1. Take a look at who has the ideal lifestyle in your profession. Get to know them and deconstruct how they do things.

Do they have the relationships that I want? 

Do they have the business results that I want? 

Do they have the work/life balance that I want? 

“I have different people who I work with that are mentors,” Ryan said. “I’ll pick which characteristics or which advice I want to follow.”

2. Ask questions.

“If you ask a few questions, you could chop off years of learning,” Ryan said.

There’s so much information out there — books, articles, people. Find someone who actually has the results and ask them how they did it.

If you tell someone you want to be them and ask them how they earned their success… that vulnerability could kick off a great relationship. 

Instead of specializing in an industry and then learning sales or specializing in sales and then learning an industry, you should invest in what advances you toward the outcomes you want.

For a while, people were hiring based on emotional intelligence. Now it’s adaptability — knowing how to flex and how to learn. 

“I don’t think you need to specialize in the industry,” Ryan said. “There are core skills that you could learn within sales, and the great thing about sales is you get access to some of the smartest people in the world.”

How to transition to bigger sales

“If you’re looking to make that jump, you need to have a lot of mental stamina,” Ryan said.

In other words, it takes grit. “You need to have persistence over a long period of time and to be willing to delay instant gratification,” Ryan said.

You also need to understand how bigger sales differ from small and medium businesses.

In SMBs, the decision making happens linearly.

But as you go up market, the decision making structure is spread out over three or four different departments. “If I want to get this opportunity, not only do I need to connect at a deep level with potentially nine people in the account, I also need to directly align my solution benefits with each individual department,” Ryan said.

Take the perspective of a wider platform with different people and align to each one of those individuals.

P.S.: Value means something different to big companies. Ryan landed a $20M+ contract because the company wanted to grow without adding any headcount, and his solution would offload 15 full time executives.

Finally, look at bigger deals like an investment portfolio. 

You need a balanced portfolio, a holistic strategy. Some small, some medium, some big. Manage your risk in terms of your whole strategy.

Work/life balance tips

Understand that your career has seasons. Sometimes you work a ton, and sometimes you can level up. “It’s faith over fear,” Ryan said. “If you have faith that you’re going to execute, but also modeling the top performers, you’ll cut so much time off your learning curve.”

Take a never ending improvement mindset. Ask your manager about your top three strengths and top three weaknesses — and not just once.

Batch your activities. Instead of checking email as it comes in, set aside one dedicated hour on the weekend. “Everybody talks about health like eating good and working out, but they don’t always combine it with a mental health recharge,” Ryan pointed out.

Ryan’s top 3 takeaways

  1. Align yourself with the right people to compress decades of learning into just days.
  2. Any skill is learnable if you have the right resourcefulness.
  3. Set your goals not just for work, but for your relationships and other parts of your life — and then your work opportunities will naturally expand as a byproduct.

Connect with Ryan on LinkedIn to keep this great conversation about work/life balance going.

For more engaging sales conversations, you can subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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