Both Sides of the Table: What Leading Finance Through Two Acquisitions in One Year Taught Me

In five months this year, I sat on both sides of the mergers and acquisitions table. In February, I was on the buy side when our company made the first acquisition in its history. By June, I was on the sell side, when Cognizant acquired Astreya in a deal reported at roughly 600 million dollars. It changed how I think about leading through an acquisition.

Most finance leaders see one side of that table in an entire career. I lived both in a single spring. It is the kind of career inflection Recruiter Hustle tracks every week in its executive People Moves coverage, and living it taught me more than two decades of clean closes ever did.

I have spent more than 20 years in corporate finance. I started at Genpact, spent 13 years at NTT Data working across FP&A, corporate strategy, and M&A, and most recently served as Senior Vice President of Finance at Astreya, a global managed services company operating in more than 30 countries. I have built budgets, closed countless books, implemented Workday in nine months, and sat beside sales teams to structure the deals that grew the business. I am a chartered accountant and a CPA. Numbers are my native language.

And here is the truth that surprises people: the numbers are the easiest part of any deal.

The Spreadsheet Is the Easy Part

When people imagine an acquisition, they imagine the models. Valuation, quality of earnings, working capital adjustments, synergy targets. Those matter, and getting them wrong is expensive. But models behave. They do what you tell them to do.

People do not. Every acquisition is really thousands of small human decisions made by people who are uncertain about their own futures. The controller deciding whether to stay through integration. The payroll manager wondering if her job survives the synergy plan. The client asking quietly whether service will slip. No spreadsheet captures any of that, and all of it determines whether the deal you modeled becomes the deal you get.

Finance That Helps Close the Deal

Long before this year of acquisitions, I learned the most valuable lesson of my career: finance creates the most value when it leaves the back office. In business finance and FP&A roles, I spent as much time with clients and sales teams as I did with spreadsheets. In managed services, the contract is the product. How you structure pricing, service levels, and renewal terms determines whether a deal creates value for both parties or slowly erodes the relationship.

Some of my proudest work happened hand in hand with sales and delivery: structuring managed services contracts to capture upside for us while giving the client economics they could defend to their own CFO. When finance helps design the deal instead of just approving it at the end, three things happen. Deals close faster, because the pricing has already survived scrutiny. Margins hold through delivery, because the value drivers were built in, not bolted on. And clients trust the numbers, because the person who built them is sitting at the table.

That same muscle is exactly what a merger tests, just on a larger scale.

What the Buy Side Taught Me

In February, Astreya acquired Reliant Information Services. It was our first acquisition, and I worked on the finance side of diligence and integration planning. Here is what I learned sitting in the buyer’s chair: the other side is reading you from the first meeting.

If your diligence feels like an interrogation, you may win the asset and lose the people who make the asset worth buying. In services businesses especially, you are not acquiring buildings and inventory. You are acquiring relationships, institutional knowledge, and trust that took years to build. Treat the seller’s team like suspects and watch that value walk out the door before the ink dries.

So we asked questions like partners, not prosecutors. We explained why we were asking. We moved fast, because slow diligence tells the other side you are either disorganized or having doubts, and both make good people update their resumes.

What the Sell Side Taught Me

Two months later, the chairs flipped. When the Cognizant announcement came in April, I was no longer the one asking the questions. My team was looking at me for answers I did not have.

That is the loneliest moment in executive leadership, and it is exactly the moment your leadership matters most. I learned quickly that your people do not actually need you to have all the answers. They need three things: honesty about what you know, honesty about what you do not know, and proof that the work still matters.

So we kept the basics boring. Payroll went out on time in every country, every cycle. The books closed on schedule. Reporting stayed clean through diligence, announcement, and close. It sounds unglamorous, but in a period of uncertainty, flawless execution is the most reassuring message a leader can send. Chaos in the numbers reads as chaos in the company. Calm in the numbers gives everyone, including the buyer, a reason to believe.

Five Takeaways for Any Leader Facing a Deal

1. Run toward the deal, not away from it. The leaders who add value in an acquisition are the ones who engage early, learn the buyer’s language, and make themselves useful to the outcome, whatever it means for them personally.

2. Overcommunicate, especially when there is nothing new to say. Silence gets filled with fear. A weekly ten-minute update with “no news yet, here is what happens next” beats a perfect announcement delivered too late.

3. Keep the basics boring. On-time payroll and clean closes are leadership statements during uncertainty, not back-office chores.

4. Structure deals so both sides win. Whether it is a managed services contract or diligence across the table, the people you negotiate with today may be your partners in six months.

5. Separate your identity from your title. Titles are granted by org charts. Reputation, judgment, and relationships belong to you, and they are fully portable into your next executive chapter.

What Remains After the Ink Dries

When the deal closed in June, my own role at Astreya closed with it. I say that without bitterness, because that is how acquisitions work, and any executive who has sat on the buy side understands it. Deals restructure org charts. That is their job.

But here is what a deal cannot do. It cannot take the team you developed, the processes you built, the trust you earned with auditors and bankers and clients, or the judgment you sharpened under pressure. A transaction can eliminate a position. It cannot eliminate what you built.

If you lead long enough, you will eventually sit on one side of the table or the other. When you do, remember that the models will take care of themselves. Take care of the people, tell the truth early and often, and keep the trains running. That is what both sides of the table are really buying.

Neeraj Gupta, CA, CPA, is a global finance executive with more than 20 years of experience across Genpact, NTT Data, and Astreya, where he served as Senior Vice President of Finance and led global finance, accounting, and payroll through the company’s acquisition by Cognizant in 2026. This article is part of the Recruiter Hustle Executive Voices contributor series, edited by Cathy Trinh.

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