In technology, change is steady and unrelenting. To remain successful and grow amidst constant and rapid change, we must adapt to our environment while retaining our core values, always remember where we came from, and stay true to our identity. Every day brings new challenges, and if we can see these challenges as opportunities to differentiate and improve ourselves, we can proceed in a positive direction.

I have been thinking about these concepts while reflecting on the trajectory of IT Ally, a business and technology advisory firm I founded in 2017. Serving small and medium-size businesses (SMBs) is central to IT Ally’s identity as is our virtual company and independent contractor business model and culture that has attracted highly experienced, executive-level talent.

It has been advantageous for us to focus on our mission of serving SMBs, but also to evolve in exciting ways, as we have reacted to the needs of our clients and the challenges of an ever-changing world.

Turning Challenges into Opportunities

Growing up in the Bronx, New York in the late seventies and eighties, I met my fair share of challenges and became street-smart at a young age to navigate the precarious situations developing around me. As a teenager, it became clear to me that many of my peers were on a path that led to drugs, crime, or dead-end careers.

Drawing on a rigorous work ethic and a strong spirit of entrepreneurialism instilled by my father, I chose a path toward achieving a better life for myself and my future family. I decided to attend an all-boys Catholic high school rather than the local public school and I also worked in the restaurant business to earn money and contribute to the cost of the tuition.

This turned out to be a key life-changing decision that helped lead me to the position that I am in today. In my professional career, the work ethic and entrepreneurialism I learned from my father remained important facets of my identity. I worked hard to climb the corporate ladder to become a Fortune 500 global CIO, a small business CFO, and a technology entrepreneur and management consultant.

These positions were all challenging and the experience I gained facing, overcoming, and learning from these challenges helped pave the way for the next chapter in my career.

Identifying Key Areas of Differentiation

Mindful of the critical role that SMBs play in our economy and fueled by a desire to help SMBs prosper, I founded IT Ally in 2017 with the fundamental purpose of being an ‘ally’ to SMBs on a variety of technology IT advisory needs. I realized that several companies had attempted to provide IT consulting services in the SMB market, but I also felt that these companies were already established businesses servicing much larger clients. They had entered the SMB market to grow their existing business, but the infrastructure, overhead, and complexity of larger companies are not typically compatible with smaller businesses.

IT Ally was conceived and deliberately built to serve SMBs from day one. These differentiating aspects of our business model have enabled us to provide enterprise-level experienced talent and capabilities that are tailored for the SMB market in terms of pricing and service delivery.

Another important differentiator for IT Ally is that from its inception, it was designed to be a virtual company not bound by physical location or geography. This was years before the COVID-19 pandemic when many companies scrambled to implement work-from-home capabilities. There is no IT Ally corporate office, and we will likely never need one. This has enabled access to a nationwide talent pool and has kept us agile and efficient in terms of servicing our clients.

Further, we have a company culture that promotes quality of life and encourages thought leadership while operating with a level of flexibility. This has helped to attract highly experienced talent to our team, all to our clients’ benefit. “We bring talent to these organizations that they never dreamed would be possible given their size,” says Mary Ann Burr, IT Ally Senior IT Advisor, Transaction Advisory Services Practice. Adding, “The team is high caliber with an amazing work ethic, and it shows when we see our clients so delighted.”

Our business model has a fractional component that makes us somewhat unique as our entire advisory team is composed of independent contractors. Some of the people on our team are full-time while others operate in an on-demand capacity, and unlike some of the other advisory firms, we don’t have a handful of experienced people at the top and a base of recent MBAs. On our team, everyone has twenty to forty years of experience, because, to serve our clients, we need to be comfortable working with business owners and C-suite executives.

There is a level of experience and credibility required to work in those circles. We have had a great deal of success finding an experienced pool of talent, and in fact, I have found that IT Ally has become a destination for many executives entering the second half of their careers. 

According to Tony Bezilla, IT Ally Senior IT Advisor, Technology Advisory Services Practice, "We’ve all arrived from the other side of the mountains we felt we had to climb earlier in our careers, and we are received as proven, tested, highly valued people. At IT Ally, there are no corporate ladders to climb, no colleagues trying to outshine you for that coveted rung on the ladder, and no games or gamesmanship. Our colleagues are all impressive, accomplished pros and each of them could be anywhere else. We’re here because we choose to be.”

Growing Without Losing Focus

As IT Ally has grown, SMBs continue to be central to our mission. We offer a comprehensive suite of technology advisory services to address a wide range of SMB needs including:

• Growth and Value Creation

• Technology Modernization

• Cybersecurity

• Data Analytics

• Talent

These efforts are focused on preserving the value of SMBs in addition to enabling value creation and future-proofing SMBs.

IT Ally has also added business advisory services to help SMBs with growth strategies. This is a departure from some of the technology advisory services we have traditionally provided, but we see it as a natural extension because technology is an enabler for growth, though the growth strategies are not limited to technology. We are focusing on growth and value creation in addition to technology.

Often, as advisory organizations grow, they get so big that they eventually need to take on larger clients and projects. At IT Ally we feel differently and have found a way to evolve as a company without losing focus on SMBs. We have developed a relationship with private equity firms because we have so much experience working with the type of companies they invest in, particularly in the lower-middle market (LMM) segment of private equity. These firms are more likely to show interest in companies that are in the size demographic that we have traditionally served.

As SMBs grow, they often reach the point of needing to raise capital to further enable their expansion. Private equity becomes a vehicle for accomplishing that, as they typically buy small businesses with the intention of making an investment, increasing the value of the business, and ultimately selling for a profit. Over the past ten years, IT has become a focal point for private equity due diligence.

With our many years of experience providing IT and business advisory services and thought leadership in the SMB space, we have become invaluable partners to private equity firms in their buy-and-sell side due diligence. We help private equity firms validate what they are buying from a technology perspective. We ensure they know where the potential risks are and the types of investments they will need to make, to bring the company to a more contemporary grade.

Our services extend to the full lifecycle, so when private equity buys an SMB, we work with them to address any issues and deficiencies. When it is time to sell, we work to highlight the key capabilities of that company’s technology portfolio that drive differentiation and value creation.

This technology-based value creation is what we call Tech Equity and is the subject of my most recent book, Tech Equity, How to Future Ready Your Small Business and Outperform Your Competition.

Thought leadership comes into play in everything we do at IT Ally, and this is clearly seen as we help our clients identify and focus on “Alpha” components while balancing them with “Beta” components:

• Alpha – Tech Equity components that create value by enabling SMBs to outperform their competition and increase company valuation.

• Beta – Tech Equity components that are essential for managing risk and volatility in an SMB.

Now in our sixth year at IT Ally, we continue to forge ahead and have become an “ally” to dozens of SMBs nationwide helping them to maximize their value from technology investments. As we move forward, we remain ever mindful of our core values, the path we took to where we are now, the challenges we met and overcame, and the clients we serve and will continue to serve for years to come.

About the Author

Michael Fillios is the founder and CEO of IT Ally, a business and technology advisory firm for family-owned and private equity-backed small and medium size businesses (SMBs). He is a former Fortune 500 global CIO, small business CFO, technology entrepreneur, and management consultant with more than 25 years of experience. His first book, Tech Debt 2.0®: How to Future Proof Your Small Business and Improve Your Tech Bottom Line, was published by the IT Ally Institute in April 2020. His next book, Tech Equity, How to Future Ready Your Small Business and Outperform Your Competition was published in May 2023.