Windsor Drake is a sell-side M&A advisory firm that represents founders selling lower-middle-market technology companies across the United States and Canada. We advise sellers only, every engagement is led by a senior advisor, and we work a small set of technology sectors deeply: fintech, B2B SaaS, cybersecurity, and AI software. A founder sells once. The company across the table has bought dozens of times and negotiates these deals for a living. The job of a sell-side advisor is to close that gap, and the way it gets closed is competition: more than one qualified buyer at the table at the same time.
Tech companies do not all sell the same way, and the difference is not cosmetic. A vertical SaaS business with high retention, a payments company with regulated volume, a cybersecurity platform in identity, and an applied-AI company with proprietary data each draw a different buyer pool and price on different metrics. A generalist advisor who anchors all of them to a single revenue multiple leaves money on the table in every one.
The honest shape of it, by sector, as sale ranges rather than funding-round headlines:
What moves your number inside a range is the durability of your revenue, your margins, the defensibility of your position, and how many credible buyers a process puts in competition. We influence the last one directly.
There are three buyer pools, and they value the same company differently. Knowing which is at the table, and getting more than one of them there, is most of the work.
Strategic acquirers buy capability, customers, and distribution, and they usually pay the most because they are buying a roadmap they would otherwise have to build. The right strategic pays a premium because the company is worth more inside theirs than on its own.
Private equity platforms buy durable, recurring-revenue software they can grow and acquire around, often through a majority recapitalization that lets a founder take most of the value off the table and keep a second bite. Growth and crossover funds back category leaders and sometimes take majority positions. For most lower-middle-market sellers, the real competition sits between the strategic and PE pools. For the buyer landscape by sector, see our guides on who buys SaaS, fintech, cybersecurity, and AI companies.
If you are larger than this, a bulge-bracket bank will take the meeting. If you are smaller, a business broker will list you. We sit in the band in between, where the deal is too important for a broker and too small to be the senior team’s priority at a large bank.
Most M&A advisors are generalists. They sold a distribution business last quarter and a services company before that, and they will run your tech company the same way. The problem is that a software, fintech, or AI business is not valued like a services business. A generalist anchors your price to a simple multiple, misses the buyers who would pay a premium for your data, your retention, or your category position, and never surfaces the competing bid that sets the price. You will not see the number you did not get, and there is no second sale to fix it.
We represent sellers only. We are engaged by you and paid to maximize your outcome, and we never sit on the buyer’s side of the table. And sometimes the right advice is not yet: if your retention is soft or your category is about to reprice upward, we will tell you, even when it means we are not paid this year.
The right advisor specializes in technology, represents sellers only, and puts a senior person on your deal directly rather than handing it to a junior team. A generalist who values your company on a single revenue multiple will miss the buyers who pay a premium for your data, retention, or category position. Windsor Drake advises founders selling fintech, SaaS, cybersecurity, and AI companies in the lower middle market, sell-side only, senior-led.
Each draws a different buyer pool and prices on different metrics. SaaS trades on ARR quality and net retention; fintech splits sharply by model, with payments and infrastructure richest; cybersecurity rewards recurring-ARR platforms over services businesses; and AI is priced on the durability of data and margins rather than headline growth. A specialist positions each to the buyers who value it most; a generalist applies one multiple to all of them.
Founder-led technology companies with roughly $5M to $100M in revenue, or $1M to $20M in EBITDA if profitable, in the United States and Canada.
For a lower-middle-market tech exit, a senior-led boutique usually serves the founder better. At a large bank a deal this size sits at the bottom of the list, staffed by junior bankers and run as one of many open files. A specialist boutique puts a senior advisor on the deal from the first call and competes on buyer access and process design, which is what sets price at this size.
Most sell-side processes run several months from preparation to close. The preparation carries the value: positioning, buyer mapping, and clean diligence materials should be finished before launch, not improvised during it.
It depends on your sector, your profitability, and the durability of your revenue. As sale ranges, SaaS runs roughly 4x to 9x ARR, applied AI 3x to 8x revenue, and fintech and cybersecurity vary widely by sub-sector. The single biggest lever you control at sale is how many credible buyers a process puts in competition at once.
Written by Jeff Barrington, Founder & Managing Director, Windsor Drake. Sell-side M&A for founder-led technology companies in fintech, SaaS, cybersecurity, and AI. LinkedIn. Updated June 2026.
Where the ranges come from: sale ranges on this page reflect the acquirers Windsor Drake tracks, cross-checked against public-market and disclosed-transaction data. They are informed starting points, not guarantees.
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