When we think of strong leadership in an employee benefits agency, an obvious answer comes to mind: Billy Bridwell. Sales people  are not often wired to move from selling and running their own book of business to leading and coaching others to grow and thrive with their own books. But Billy has made this transition and he's made it look easy (from the outside anyway!). 

How has he done it? He pulls back the curtain here to let us have a peek at what it takes to be a great leader and to have team members not only following you, but growing their own leadership skills at the same time.

Having Billy as part of the Q4iNetwork gives everyone ample opportunity to step up their own leadership game from the excellent example he sets and the ideas and lessons he is always willing to share.  

Q4i: In an industry with few sales leaders, you stand out as a clear example of someone in it for the team. What led you to this agency leadership position and what has been the most noticeable change for you and the organization as a result?

BB: This is a very good question, and one I truly believe can’t be answered with a single point of perspective. Meaning, 23 years ago I began this journey in the insurance business with the energy and drive to prove to myself, and to everyone who knows me, that I can sell.

Starting at age 18 and selling group benefits to employers was interesting! With early success I experienced the feeling of a great deal of accomplishment and thankfulness. As I got a little older and continued to grow in the business, my perspective of success began to change. I became very interested in leadership and more specifically, what successful leaders do to reach the top of their game and sustain winning over a long period of time.

This is where the perspective comes into play. There isn’t one thing, one tactic, one moment where it happens. It comes from reading leadership books, watching great leaders whom I knew personally, as well as leaders I did not know personally, but could watch from a distance. It’s leadership classes I took, going to seminars, watching business owners influence their teams, Pastors leading their churches, good fathers leading their families, and other people who are successful impacting, enhancing, and leading others to be all they can be and more.

Part of this perspective happened at some point in this informal research study I was living where it stopped being all about me and my success and became about the success of others. A changed happened in my mind as a result of all the information I was putting in my brain, where I realized the success of my team doesn’t depend on me selling, it depends on me raising the tide of everyone around me so they can sell more.

Since this mindset shift, my goal is to truly impact every member of my team to be the best version of themselves they can be in every aspect of life. Let’s face it, there is no business and personal, there is just life. This is an absolute truth I realized as I have continued on this 23 year journey. That is, I am just me whether in the office, at home with my kids, on a client meeting, or sitting at church on Sunday. It’s just life. All this to say, my journey to this leadership position has been a series of moments stacked up over a bunch of great years.

The most noticeable change for me and the organization, Keystone, has been that everyone around me is wired much like me. That is, when you treat people with respect and are constantly giving them the chance to be leaders, what do they do? They lead.

I am surrounded be 36 other colleagues here at the Keystone benefits division who are all empowered to be the best they can be, which is one of the biggest drivers of our growth over the past 10 years.

One more note: Funny thing about leadership and the success of leadership. It’s not a title, it’s just who you are. If someone says you are a great leader and you look around to the emptiness and there is no one following you, you ain’t no leader!! But, if you are impacting others in a positive way and they are, in turn, impacting others in their own world in a positive way, no one has to give you a title, you just is the leader!! (Those are not typos, I typed it like I would have said it ;‐)

Q4i: Over the last couple of years, you have been systematically organizing how you are operating and growing as an agency. What has your peer group in Q4i meant for your development?

BB: The leadership at Q4, as well as the Q4iNetwork, has opened my eyes to see a world bigger than I knew was out there as it relates to the insurance / healthcare / benefits industry space. It has plugged me into the middle of a group of professionals and introduced me to fellow leaders and colleagues who are at the top in our industry.

Q4 has put me and my Keystone colleagues on a team of pioneers who are all hacking through this healthcare / benefits jungle in search for a land we know exists. A land where ingenuity, strategy and ultimate control can be given back to the employers and their employees and shifted away from ‘the system’ that has been broken and in a ‘death spiral’ for many years. Ultimately, joining Q4 has opened my mind to new possibilities and new ways of leading my team. I am thankful to be a part of this movement and can’t wait to continue the journey!!

Q4i: What has been the biggest obstacle you’ve encountered as you work through the process?

BB: This is a good question as well. First, the biggest challenge has been trying to implement it all at once. The sales system, the solutions pages, the marketing pieces, The Challenger Sale methodology and really just the whole process at once. It’s a lot! It’s all good, just a lot!

Secondly, it’s been tough to find the right folks for our team. The right VPs for sales, Account Managers, as well as Operations-minded people to help with organizing the tactical. Probably a fairly standard answer most would give, but when you are in the trenches, the reality is these two obstacles / challenges are real. They require consistent attention in order to achieve the highest success rates.

Q4i: What has kept you persevering?

BB: This is simple, I don’t have any quit in me. Also, we recognize all our problems are growth problems. We are having a great run and it’s fun trying to figure all of it out. It’s also fun pushing past any barrier I once thought may have existed within myself or within my team. All in all, I have learned the journey really is where the fun happens.

When you talk with veterans of our industry, and really any industry for that matter, and they look back over their career and begin to share the memories, it’s always an interesting glimpse into what is really important.

They begin to recount the people they went into battle with, the challenges they had and how they pushed through to victory, the good times and the laughs, the difficult times and how this shaped them, their company and their bonds with God, family, friends and their fellow coworkers who were all on the journey together. Having noticed this several years ago, I determined to truly find the joy in the journey, even when it’s a hot‐mess of challenges.

Because really, in a few years when we all look back, the realization sets in that it’s all small stuff, so don’t sweat the small stuff!!

Q4i: What has been your biggest surprise throughout the process?

BB: The biggest surprise I did not see coming are all the friendships made along the way that continue and thrive today. Growing up in a rather small town, I had friends I would hang out with all the time and we all did stuff together. But with the geographic reach Keystone has and the amount of good people I come into contact with and work with and do life with, it has allowed for some very good friendships and lifelong relationships!

I truly enjoy everyone I work with and I view them as a huge part of my life. Not my business life, but my life. Our families hang out together and we all just do life together. Remember, there is no business and personal in my world, there is just life!!!

Q4i: What piece of advice would you share with other agency owners and advisers about making the change from a wild west approach to following processes with a consistent standard?

BB: Easy… What got you here won’t get you there. In order to grow, continue to accomplish, and to achieve your goals, you must refine and progress from where you are now. If you have no process or intended plan of action for getting you from where you are to where you want to go, you will remain closer to where you currently are.

You need to have a process in place and then work the process. Hope is not a strategy! Being intentional is a must!

Also, I have learned everyone in life needs a coach, someone pulling them forward and challenging them to do just a little more. Think about it, the best golfers in the world all have multiple coaches: for their swing, their mind, their body, their putting stroke, their short game, their finances… and the list goes on.

We too are professionals and the best at what we do. Getting the right coaching staff is essential to get us from here to there!!


Bridwell Billy Keystone Insurers GroupBilly Bridwell, Vice President, Keystone Insurers Group
Billy Bridwell is the Vice President of the Keystone Insurers Group Employee Benefits Division, where he is responsible for growth in the eleven Keystone states. He builds infrastructure across a multi-state platform, leads a dynamic sales team focused on new business production, enhances the account management team responsible for client retention, and works with key accounts in the mid-market and large market sector. Connect with Billy on LinkedIn

Blog photo by Geralt.

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