Charles Hollander

Founder of Red Flag Advantage and Creator of the Compass Framework

Chuck is a life insurance industry insider and knows what it takes to challenge and inspire change in growth-minded life insurance professionals and sales teams.

Twenty-five years ago, Chuck entered the competitive field of selling complex life insurance solutions to select families and business owners.

He has competed and won against almost every type of distribution channel in the life insurance industry.

Twelve years ago he formed Red Flag Advantage. His background as a pioneer, entrepreneur and industry insider combined with his late partner’s unparalleled background as a retired Admiral with 32-years as a Navy SEAL and former commander of all SEAL Teams positions the firm with the unique discipline of helping sales teams unlock their hidden potential.

Chuck Hollander’s Keynote Presentations


Taking the Mystery Out of Stalled Deals – 3 Steps to Winning More Clients.

There’s a Hidden Source of Revenue You’re Missing.

The Secret is Knowing Where to Look!

Tap into It and Convert $50K-100K More in Deals – THIS YEAR!

The age-old problem of getting clients to take action has become an epidemic. In fact, it is the single biggest roadblock to advisor growth. This session will show you that your stalled deals can be a new source of added revenue and Chuck will reveal how you can harvest them immediately!

Attend this session and you will learn:

  • There is a single point in time in every sale where the probability of a successful engagement is at its absolute highest. The session will show you how to spot it and quickly position for it.
  • The 2 reasons why stalled deals happen and how to avoid them.
  • The 3 Fundamental Truths behind every client’s decision to buy and how to leverage them to create urgency, avoid client procrastination and win more clients.

If you’re frustrated by the stalled deals in your pipeline or you have prospects procrastinating around your advice, then you can benefit by attending this upcoming session.

Rethinking Your Recruiting Process

Six Trends You Need to Understand to Improve Your Advisor Recruiting


Great sales organizations don’t rely on the quality of their product portfolio –they rely on exceptional sales talent. But here’s the challenge –it’s not easy recruiting top talent. it’s a crowded market and it’s an unfair game!

Here’s the good news – you can double the number of A-Players inside your firm! However, in order to do this, you need to change the way you are playing. Recruiting is not a numbers game where we win some lose some. This type of thinking leads to the game being played at severe disadvantage.

Chuck has created this specialized session to help leadership teams take the guesswork out of recruiting top sales talent. You will be learning from an industry insider on how to structure authentic and compelling recruiting conversations around Six Industry Trends that are keeping top advisors from unlocking their full potential. He will also teach you how to communicate how your firm can play a vital role in helping select advisors overcome these trends and begin growing their practices in ways they never have done before.

If you’re frustrated with your recruiting efforts and want to faster way to build a consistently top performing sales team then you can benefit by attending this upcoming session.

Branded Messaging: Giving Your Company A Voice

How to Create Clear and Compelling Client Building Conversations 



Here’s why…the natural tendency is to begin initial conversations with discussions around your company and the benefits of your products, services, and advice. Effective client building begins with a different approach – it always begins by introducing your firm through the problems you solve not the benefits of your products and services and the benefits of becoming a client.  Initial client building conversations that are not clear and compelling lead to a smaller pipeline and this constrains growth. That’s why messaging matters.

What Is It

The Branded Messaging module is a unique approach to unifying your team’s sales conversations around your firm’s Distinct Point Of View. This becomes your team’s Signature DNA, the heart of your client building strategy. It’s centered on the strategic decision on how you intend to make a difference with the select clients [and strategic partners] you wish to serve. It also becomes your way to link your firm’s brand identity to three vital conversations. The module concludes by putting written standards around your sales, marketing & client building conversations, so they remain clear, compelling, collectively understood, and consistently communicated.

We Do-It-With-You Session

Red Flag will work with your team to develop a set of clear and differentiated client-based messages. In this module you will leverage Red Flag’s industry research and insight to find clarity around your competitive advantage, what makes your services different, and how you intend to bring value to your target client in ways your competition is not. Your message is aligned to solving client’s challenges and then compelling conversations are built around your difference. 

Conversation Value Creation

Your new messaging is part of a core story that is then linked to three vital client building conversations deliberately answering three key questions – Why Change, Why Change Now, and Why Change With Your Firm.