Should I Hire an Investment Bank or a Boutique M&A Advisor to Sell My Company?

If your company is worth $500M or more, hire the investment bank. You will be a priority client and the machine works. If your company is worth between $5M and $350M, a specialized boutique advisor will usually get you a better outcome, because at that size the single biggest risk to your deal is not the market. It is who actually does the work.

Founders ask me this question every week, and the standard answer they get is useless. So here is the real one, from 25 years of selling payments and software companies. A version of this answer reached more than 130,000 readers when I shared it on LinkedIn, which tells you how many founders are quietly asking it.

What happens to a mid-market deal inside a large investment bank

Large banks are built to serve their largest clients, and the economics are unforgiving. If your company is worth $5M, $50M, or even $250M, you are the smallest deal on the sheet. The pattern is predictable: you meet the managing director at the pitch, you are impressed, you sign. Then you never see that person again. Your deal gets handed to an associate who has never sold a payments company, does not know the strategic buyers in your niche, and is running four other deals at the same time.

None of this makes big banks bad at their job. It makes them bad at your job. Their model is calibrated for $500M and up, and below that line the incentives stop working in your favor.

What a boutique M&A advisor does differently

At a boutique, the person who pitched you is the person who calls the buyers. Every conversation, every negotiation, every 11pm call when the deal wobbles. That continuity is not a nice-to-have. Deals in the $5M to $350M range die from small things: a diligence finding that gets framed badly, a buyer who goes quiet for two weeks, a retrade attempt at week fourteen. Catching those moments takes someone senior who knows the file cold because they built it.

Specialization compounds the advantage. A boutique that lives in payments, fintech, and SaaS already knows which strategic acquirers are actively buying, which private equity groups have dry powder allocated to your category, and what comparable companies have actually traded for. That is the difference between a curated list of forty real buyers and a database blast to four hundred names.

Why fewer deals means better outcomes

We take fewer deals than a bank ever would, and that is deliberate. Selectivity means every engagement gets senior attention, and it means we do not take companies to market with a story we cannot defend in diligence. A bank measures success across a portfolio of fees. A boutique lives and dies on each closing, so the incentive to pick the right deals and finish them runs through everything we do.

The one question to ask before you sign an engagement letter

Who actually runs my deal? Not who pitches it, not whose name is on the letterhead. Who calls the buyers, who negotiates the letter of intent, who defends the price in diligence. Ask it directly and watch the answer. If the honest answer is an associate you have not met, keep looking. The answer to that one question tells you everything about the next six months of your life.

If you want to see what those six months look like when they are run properly, I walked through the whole sequence here: how the M&A process works when selling a tech company.

Where 733Park fits

733Park is a boutique M&A advisory firm focused on payments, fintech, AI, and SaaS companies with enterprise values from $5M to $350M. Twenty-five years in this market and more than $10 billion in transaction volume. When you work with 733Park, you work with me directly, on every call, from pitch to close. If you are weighing an exit, start with a confidential conversation at 733park.com/contact.