Running a middle market information technology or cybersecurity company has never been easy, but in today’s unpredictable climate, it is a full-on contact sport. For founders and CEOs leading companies with $30 million to $500 million in revenue, the current environment demands something beyond vision or charisma. It demands grit, capital discipline, a dealmaker’s instincts and the judgment to prioritize what truly moves the needle, while navigating the uncontrollable effects of tariffs, shifting government incentives, budget cuts at the Department of Governmental Efficiency, AI’s impact and broader geopolitical uncertainty driven by fluctuating peace prospects in the Middle East and the ongoing war in Ukraine.
I have personally lived this reality for over a decade, leading three private equity-backed companies through mergers, pivots, growth phases, refinancing and downturns. What I offer here is not theory. It is field-tested guidance for fellow operators trying to survive and thrive when the room gets hot and the margin for error disappears.
Capital Efficiency Is Not Optional Anymore
For more than a decade, roughly from 2009 through early 2022, the technology sector operated under a zero interest rate policy, known as ZIRP. This approach, used by central banks such as the U.S. Federal Reserve, kept interest rates near zero to stimulate borrowing and economic activity. With capital so cheap, investors and companies took aggressive risks. They flooded startups with cash, inflated valuations and prioritized growth at all costs, even without a path to profitability.
That era of easy money created artificial momentum for many technology companies, enabling unsustainable business models and bad habits that are now being painfully unwound. In the ZIRP environment, companies often grew on the back of cheap capital and vanity metrics. That game is over.
Today, whether you are backed by private equity or self-funded, capital efficiency is the new scoreboard. Growth without margin — also known as unprofitable growth — is no longer acceptable. Profitable growth is, and always should have been, the mantra. That starts with tracking customer acquisition cost, or CAC, payback periods closely. Cut vanity spend. Push pricing. Drive customer lifetime value, or LTV, through services, renewals and loyalty. If a dollar leaves your bank account, it should generate at least two dollars in pipeline or value. Every department must earn its budget by proving return on investment through a zero-based budgeting approach.
A Mergers And Acquisitions Mindset Could Be A Lifeline
You do not need to be in market to act like you are. Operate like a company that is always six months away from a transaction. Why? Because valuation discipline, process hygiene and strategic clarity are not just good for buyers. They are good for operators.
Even if you are not actively engaged in a process, behave like you are. Build your data room in real time. Know your customer churn and cohort metrics cold. Track earnings before interest, taxes, depreciation and amortization quality, recurring revenue mix and gross margin by segment. Do not wait until you are under pressure to get your house in order.
And remember, the best time to sell is before you need to. When you start getting a lot of inbound interest, that may be the clearest signal it is time to consider your options. Markets are not rational. They are cyclical and often maniacal. They go up, then suddenly down when lower-quality assets flood the field and drag everyone’s value down with them. Timing matters.
If you are not thinking of selling, start thinking about buying. Acquisitions are not just for the giants. In the middle market, they are often the most efficient way to grow revenue, acquire talent, expand geography or eliminate a competitor. You can spend 18 months building a new service line, or you can buy it in 60 days. You can overpay for customer acquisition through marketing, or you can buy customers profitably through acquisition.
Some of the best deals I have seen were not reactive. They were made by CEOs with a running list of targets, ready to pounce when market conditions turned or a competitor stumbled. This is where the real discipline kicks in. Build relationships in advance. Know what a good deal looks like. Have your financing strategy lined up, whether it is seller notes, debt, earn-outs or equity. And most important, only pursue targets that fit your strategic blueprint. Buying the wrong company is worse than not buying at all.
Acquisitions can create leverage, but they also expose cracks in your operations, culture and integration capacity. That is why companies that prepare for transactions, even when they are not in one, tend to outperform. They are sharper, more focused and better equipped to seize opportunity while others are still debating.
Go-To-Market Discipline Beats Product Brilliance Every Day
Your go-to-market motion is the engine of your company. Without a disciplined strategy, even the most innovative technology gets lost in the noise. I have seen too many companies overbuild and under-market. The better play is to underbuild and oversell, with discipline.
As chief executive officer, you are the rainmaker and the face of the company. If your persona is not driving the commercial engine, you need to figure out who or what is. Practice makes perfect. Whether on stage, in a boardroom or on a podcast, you need to be the mastermind behind the narrative.
Thought leadership is not a vanity exercise. It is air cover. It is differentiation. It is demand creation. And it absolutely can be ghostwritten, but do not go cheap or generic. Invest in marketing that can clearly articulate your value proposition. You own that message, not the product marketing manager you just hired. If you cannot explain what you do and why it matters in three sentences, nobody else can either.
Segment your customers. Align sales and marketing against real ideal customer profiles, not imaginary ones built in a vacuum. Focus on fewer plays, not more features. Build repeatable motion. Get serious about pipeline velocity, win rates and quota attainment. Track it weekly. Share it widely.
Your board does not care about activity. They care about bookings, renewals and predictability. That is how companies get valued and how CEOs earn trust.
Case Study: Canva’s Go-To-Market Strategy Beats Product Complexity
Canva entered a market dominated by Adobe, whose tools were powerful but complex and designed for professionals. Canva saw an opportunity with non-designers who needed a simple, accessible way to create high-quality visuals.
Canva’s success came from a few core moves:
- Ease of Use: A drag-and-drop interface made design simple for anyone.
- Freemium Model: A free version drove adoption, with paid upgrades as needs grew.
- Community and Content: Tutorials and user-generated content fueled engagement.
- Smart Partnerships: Deals with schools and nonprofits expanded reach and trust.
The result: over 10 million users in five years, all without targeting enterprise buyers with fancy and complex features. Canva proved that a focused, user-first go-to-market strategy can outperform even the most advanced product if that product fails to resonate.
Hire Slow. Fire Faster.
Talent is leverage, but only if you get it right. In middle market companies, every hire matters. One wrong vice president can burn a year. One mediocre sales rep can poison a region. One distracted engineer can stall a roadmap.
Get involved in hiring at every level that matters. Vet for cultural alignment, not just resumes. Hire utility players who can flex across functions, especially in turbulent markets. And when someone is not working out, act fast. You owe it to the rest of the team. The market is full of available great talent right now.
Do Not Outsource Your Value Proposition Or Your Backbone
You cannot outsource your value proposition. First, define what your company is known for—what customers actually pay a premium for—and hold that close to the vest. If your brand is built on world-class customer support, do not offshore that function in the name of efficiency. If your edge is product innovation and development speed, do not hand engineering off to the lowest bidder overseas. If you are a cybersecurity services company, outsourcing you Security Operating Center is a mistake. Cost savings today often come at the expense of long-term enterprise value. The very thing that differentiates you in a crowded market cannot be treated like a commodity. Protect it, invest in it and make sure it stays under your control.
Here is the other truth no one wants to say out loud: in middle market tech, you cannot delegate survival. You, as CEO, are the final backstop on cash, culture, strategy and execution. Consultants can help. Boards can advise. But when the pressure is on, only the chief executive officer bleeds.
That means you must master your numbers, own your narrative and lead from the front. Walk the floor. Sell the top deals. Mediate the team conflicts. Get your hands dirty. You are not just the strategist. You are the shock absorber.
Zero Breaches Is The Standard
If you are in cybersecurity or technology, you must be right every time. The attackers only need to be right once. In this threat environment, your company is not just a provider. It is a target.
Security can no longer be someone else’s job. It must be embedded in leadership, in culture and in daily decision-making. Anything less is an invitation for disaster.
CEO Scoreboard: Metrics That Matter Now
Bottom Line
You do not need to be just a visionary to be a successful middle market chief executive officer. You also need to be relentless, grounded and allergic to delusion. You must know where every dollar goes, what every customer needs and where your team needs to be pushed or protected.
In today’s volatile landscape shaped by tariffs, policy swings and the realities of the Trump economy, survival is a win. But if you stay focused on fundamentals, lead with discipline and execute with clarity, survival becomes the foundation for thriving. Regardless of who is in the White House or what happens in the next election cycle, the companies that double down on operational excellence will not only endure but set themselves apart.