November 1, 2021

The Top Challenges CEOs Face & Why High Growth CEOs Should Join Our CEO Mastermind


If you’re the leader or chief executive officer of a large, fast-growing business, you might have been featured on the Inc 5000! You know just how difficult it can be to captain the ship. Especially now after going through a pandemic, dealing with the internal and external factors that make leading a business hard is more topical than ever.

At Ajax Union, we understand the unique challenges of CEOs of fast-growing companies, because we are one; we were featured on the Inc 500 in 2013.

Here are the top 8 challenges high-growth CEOs face today.


1. Taking a step back

As a leader, the rush of day-to-day work tends to consume your energy in your personal life, too. Today, CEOs are finding it more and more difficult to find the time and space to take a step back and reflect. 

Why reflect? It’s important for mental health, but it can also help CEOs get clarity on key strategic initiatives. CEOs today need to schedule time for reflection just as much as they need to join meetings. 

2. Dealing with transitional periods

Leaders and employees alike know just how difficult it is to navigate change at a company. CEOs, most of all, bear the burden of deciding what the best possible way to navigate company change is. 

How do you make sure the culture is defined by trust and communication? How do you make it easy for your teams to navigate growth? High-growth CEOs are plagued by how to make a transitional period at a company a seamless and effective one.

3. Standing out in a saturated market

In today’s day and age, there are immense amounts of competition in the market and due to the nature of the internet, brand awareness has become a slippery slope to tread. 

CEOs today are wondering how they can stay ahead of the competition in a saturated market. CEOs are looking for support in uncovering their unique value and how to properly market it.

4. Finding and retaining talent

One of the largest issues CEOs, not just recruiters, face is finding the best talent for your company. If your business is navigating high-growth, it may be especially difficult to find talent with not only the right skill set but the right cultural fit for your company. 

Talent Optimization CEO Struggles

How are other companies doing it? CEOs spend plenty of time trying to uncover the best ways to find talent when some of the best talent is already working for a competitor!

CEOs Need Help With Their Talent Strategy

5. Getting overwhelmed

As you can probably imagine, CEOs are very prone to feelings of overwhelm. By having to deal with several, sometimes hundreds of problems daily, CEOs need help navigating immense stress during their workweek. 

CEOs 1 Priorities

6. Navigating social issues

It’s no secret that politics and business don’t mix. But in today’s politically charged climate, CEOs are learning how to navigate social issues as a company. 

Stakeholders and employees are demanding that their companies take a stand on key political issues that face our nation today. It’s no wonder CEOs need support with this.

7. Nurturing a strong and supportive work culture

Is having a successful company the same as having a positive and healthy work culture? Not necessarily. CEOs today need support creating a work environment and company culture that employees want to work in for the long haul. 

8. Creating something that lasts

Is high-growth always sustainable? Not always. In a fast-moving economy, CEOs are finding it more and more difficult to navigate growth opportunities that align with their company’s mission. CEOs need trusted advisors, colleagues, and confidants to rely on to make sure they’re taking actions that don’t only allow the company to grow, but to grow with integrity.

What Keeps CEOs Up At Night

All in all, being a leader comes with a unique set of challenges that only other leaders can understand. The list of challenges above gives only a small peek into the world of entrepreneurship and fast growth. CEOs, now more than ever, need support to tackle and navigate the challenges they face in their day-to-day lives. 

Luckily, there is a community of like-minded CEOs — CEO Mastermind — that does just that!

What is the CEO Mastermind and why should high-growth CEOs join?

The CEO Mastermind is a community of the fastest-growing companies including CEOs and business owners that were featured on the Inc. 5000 and other fast-growing company lists over the past decades. 

This community is designed specifically for high-growth CEOs that want to exchange insights, engage in networking opportunities, share resources, and discuss the unique challenges associated with fast growth.

Some of the top challenges high-growth CEOs face include:

  • Team agility
  • Compliance
  • Revenue management
  • Talent acquisition & retention
  • Company development
  • Strategy alignment
  • And much more…

If you want to meet like-minded, successful, high-growth professionals, join our vetted community for much-needed insights and opportunities—especially during this time of uncertainty.

What will you gain?

  • Insights
  • Advice
  • Exposure
  • Strategy-coaching
  • Group support
  • Social events
  • Connections
  • Relationships
  • & more!

How can CEOs join? What should they expect?

To join the CEO Mastermind, CEOs will need to apply here. Once approved, we will send you more information about membership and costs.

As a member, CEOs can expect to spend 2-3 hours per month engaging with other members of the CEO Mastermind through virtual meetings. 

Upon initiation, each member will:

  • Be interviewed by the moderator and host of the CEO Mastermind, Joe Apfelbaum
  • Gain access to the CEO Mastermind directory, a vault of company-related and contact information for CEO Mastermind members to get in touch with other CEOs strategically

Why was the CEO Mastermind created?

Moderator and host Joe Apfelbaum created the CEO Mastermind because he realized there were no other communities designed specifically for high-growth CEOs. As the CEO & Founder of Ajax Union, an Inc 5000 company, and a longtime member of other entrepreneurial communities such as Vistage, EO, YEC, YJP, EANYC, NSA and beyond, Joe wanted to create a more strategic and thoughtful opportunity for high-growth CEOs to engage and learn from one another. 

Joe’s vision is to make the CEO Mastermind the most trusted resource for high-growth CEOs in the country. Using his years of experience as a trusted advisor and professional speaker, Joe intends for this forum to be a tightly moderated, success-driven renaissance-of-sorts for CEOs to become the best versions of themselves.

As the owner of two fast-growing companies, Joe Apfelbaum is uniquely positioned to serve CEOs of the CEO Mastermind because he is one.

Many of Joe’s clients have been featured on the lists of the fastest-growing companies, and those companies have seen success because of his team’s strategic insights. He is proud to be associated with companies that have made the list and remain on the list, like Sullivan Engineering, a long-time client of his that has been on the list 5 years in a row and was recently acquired by Rimkus Consulting Group. Listen to what he has to say about working with Ajax Union here!

Joe has also spent hours interviewing fellow CEOs and executives to share valuable information on having a successful, growing business — you can listen to interviews with Joe and the CEOs HERE! Joe will continue to interview CEOs so keep checking back for more content!

If you’re looking to join a community of other high-growth CEOs that understand your unique challenges as a leader of one of the largest and fastest-growing companies in America, apply to join the CEO Mastermind TODAY

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