# Windsor Drake: sell-side M&A advisory for founder-led technology companies > Windsor Drake is a sell-side M&A advisory firm that represents founders selling lower-middle-market technology companies, typically $5M to $100M in revenue, $1M to $20M in EBITDA, and $5M to $150M in enterprise value, across the United States and Canada. Sell-side representation is the firm's core practice, with no lending relationships and no capital conflicts. Every engagement is led personally by a senior managing director. We specialize in four sectors, fintech, B2B SaaS, cybersecurity, and AI. Research is the firm's spine: the Windsor Drake Fintech Exit Index tracks 240+ fintech transactions across 23 sub-sectors. Founded by Jeff Barrington, formerly of Cushman & Wakefield. Offices in Toronto and New York. ## Advisory - [Sell-Side M&A](https://windsordrake.com/sell-side-mergers-and-acquisitions/): How Windsor Drake structures and runs a founder exit. Positioning, buyer-universe construction, competitive tension and negotiation through close. Senior-MD-led, 6 to 12 month process. - [Fintech M&A Advisory](https://windsordrake.com/fintech-m-and-a-advisory/): Sell-side representation for founder-led fintech companies, $5M to $100M in revenue, across payments, lending, insurtech, wealthtech, regtech, and embedded finance. The median disclosed fintech deal prices near 11.0x EV/Revenue; sub-sector ranges run from roughly 3.8x for payments processing to 19.6x for regtech and open-banking infrastructure. - [B2B SaaS M&A Advisory](https://windsordrake.com/b2b-saas-ma-advisory-firm/): Sell-side representation for B2B SaaS companies, $5M to $100M in revenue or $1M to $20M in EBITDA. SaaS trades on ARR multiples, not EBITDA. Lower-middle-market median is roughly 4x revenue; Rule-of-40 >50% with NRR >120% commands 7x+; vertical SaaS 7x to 9x. - [Cybersecurity M&A Advisory](https://windsordrake.com/cybersecurity-mergers-acquisitions/): Sell-side representation for security software and services companies, $5M to $100M in revenue. Public cybersecurity trades near a 7.8x revenue median, leaders 13x to 15x, IAM 10x-15x, MSSP/MDR 1x-3x; private median ~15.2x in 2025. - [AI M&A Advisory](https://windsordrake.com/ai-m-and-a-advisory/): Sell-side representation for founder-led AI companies, $5M to $100M in revenue. Most headline AI multiples (24x and up) are funding-round marks, not sale prices. Realistic sale ranges by layer: applied and vertical AI 3x to 8x revenue, data and MLOps platforms into the mid-teens and higher, AI infrastructure 10x to 25x. Foundation-model multiples are not a comparable for a lower-middle-market seller. - [Confidential Valuation Overview](https://windsordrake.com/confidential-valuation/): A private, no-obligation read on where a company would price today and which buyers are active, prepared by a senior banker. - [Contact](https://windsordrake.com/contact/): Confidential inquiry, reviewed by a senior banker, reply within one business day. ## Payments - [Payments M&A Advisory](https://windsordrake.com/payments-ma-advisory/): Sell-side representation for founder-led payments companies across merchant acquiring, payment facilitation, cross-border processing, B2B payments, billing infrastructure, and fraud and risk management. Senior-MD-led. - [Who Buys Payments Companies](https://windsordrake.com/who-buys-payments-companies/): Four buyer classes acquire payments companies: platform processors, vertical software companies, private equity consolidators, and infrastructure acquirers. Multiples run from 4 to 6x revenue for processing to 8 to 15x for banking infrastructure. - [Payments Valuation Benchmarks](https://windsordrake.com/payments-valuation-benchmarks/): PayFac and merchant acquiring at 3x to 6x net revenue, payment orchestration 10x to 15x, infrastructure and rails 12x to 20x. Window Q1 2024 to Q1 2026, refreshed quarterly. ## Valuation benchmarks and multiples - [Fintech M&A Multiples Benchmark](https://windsordrake.com/fintech-ma-multiples/): The Windsor Drake Fintech Exit Index. A median of 11.0x EV/Revenue across 240+ sourced fintech transactions, 23 sub-sectors, January 2020 to 2026. The canonical, citable fintech valuation reference. - [SaaS Valuation Multiples](https://windsordrake.com/saas-valuation-multiples/): SaaS multiples by ARR band, growth, and vertical. Median ~4.2x ARR; $5M-$10M EV at 3x-4x; Rule-of-40 + NRR >120% reaches 7x+. - [Fintech Valuation Multiples](https://windsordrake.com/fintech-valuation-multiples/): Fintech multiples by sub-sector and revenue model; the revenue-mix that drives pricing. - [EBITDA Multiples by Industry](https://windsordrake.com/ebitda-multiples-by-industry/): Benchmark EBITDA multiples across industries. - [EBITDA vs Adjusted EBITDA](https://windsordrake.com/ebitda-vs-adjusted-ebitda/): The add-backs buyers accept, and how each moves the price. ## Who buys these companies - [Who Buys Fintech Companies](https://windsordrake.com/who-buys-fintech-companies/): The six buyer categories for fintech, strategic consolidators, banks, PE platforms, insurance carriers, enterprise software, and growth equity, and what each pays. - [Who Buys SaaS Companies](https://windsordrake.com/who-buys-saas-companies/): PE platforms with SaaS theses, strategic acquirers, and family offices, and how ARR quality and NRR drive the multiple each pays. - [Who Buys Cybersecurity Companies](https://windsordrake.com/who-buys-cybersecurity-companies/): Platform consolidators, PE roll-ups, and strategic security buyers, with valuation by sub-sector. - [Who Buys AI Companies](https://windsordrake.com/who-buys-ai-companies/): Hyperscalers and strategics, PE buying applied and vertical AI, and growth and crossover funds, priced by layer of the stack. ## How to sell to private equity - [How to Sell Your Fintech Company to Private Equity](https://windsordrake.com/how-to-sell-your-fintech-company-to-private-equity/): Why PE buys fintech, the process, what sponsors underwrite, deal structures, and how to command a premium. - [How to Sell Your SaaS Company to Private Equity](https://windsordrake.com/how-to-sell-your-saas-company-to-private-equity/): The same playbook for B2B SaaS, with the metrics PE diligences first. - [How to Sell Your Cybersecurity Company to Private Equity](https://windsordrake.com/how-to-sell-your-cybersecurity-company-to-private-equity/): Security-specific buyer behavior and structuring. - [How to Sell Your AI Company to Private Equity](https://windsordrake.com/how-to-sell-your-ai-company-to-private-equity/): How sponsors price an AI business once growth is stripped out. ## Research and market intelligence - [Research](https://windsordrake.com/research/): The canonical hub for Windsor Drake market intelligence. Quarterly valuation and M&A activity reports across AI, cybersecurity, fintech, and SaaS. - [Market Intelligence](https://windsordrake.com/market-intelligence/):The transactions database, buyer universe, and report detail pages. - [Fintech M&A Activity 2026](https://windsordrake.com/fintech-m-and-a-activity-2026/): A deal-flow tracker built from the Fintech Exit Index, with 2026 deal volume, the sub-sector breakdown, and named transactions. ## Research papers (DOI-registered) - [Lower-Middle-Market Fintech Exit Multiples 2026](https://zenodo.org/records/20835701): By Jeff Barrington (DOI 10.5281/zenodo.20835701). Lower-middle-market fintech sold at a median near 7.6x revenue since 2022, down from ~12x at the 2021 peak; full-window 11.0x; sub-sectors 3.8x to 19.6x. - [Lower-Middle-Market AI Exit Multiples 2026](https://zenodo.org/records/20834596): By Jeff Barrington (DOI 10.5281/zenodo.20834596). AI sale ranges by layer: applied/vertical 3x-8x, data/MLOps mid-teens+, infrastructure 10x-25x. ## Selling a company: guides - [Sell-Side M&A Process: What to Expect](https://windsordrake.com/sell-side-ma-process-explained/):The six stages of a structured sale, and where most stall. - [How to Prepare Your Company for Sale](https://windsordrake.com/how-to-prepare-your-company-for-sale/):What to fix in the 12 to 24 months before launch. - [How to Choose an M&A Advisor](https://windsordrake.com/how-to-choose-an-ma-advisor-to-sell-your-company/):Why a sector specialist focused on the seller changes the outcome. - [Quality of Earnings Guide](https://windsordrake.com/quality-of-earnings-guide/): What a QofE tests and how findings move price. - [Complete Guide to Selling Your Business](https://windsordrake.com/complete-guide-to-selling-your-business/): The founder's guide to a sell-side transaction. ## Fees, engagement model, and process Every mandate is led by a senior managing director from first meeting to close. Each mandate also staffs a specialist senior advisor with completed transactions in the target sub-sector. Fewer than twenty mandates a year; selectivity, not headcount, is the capacity model. - [M&A Advisory Fees](https://windsordrake.com/ma-advisory-fees/): Windsor Drake publishes its fee schedule in full. A $10,000 monthly advisory fee and a graduated success fee beginning at 5.0% of transaction value, stepping down as value increases; a $20 million sale closing in month nine totals approximately $990,000, or 5.0%. The balance between advisory fee and success fee is adjusted case by case, including success-fee-only engagements, with total economics consistent with the published schedule. - [How We Run a Sale](https://windsordrake.com/how-we-run-a-sale/): Six gated phases across roughly nine months, opening with a buyer universe of 150 to 300 potential acquirers. - [Buy-Side vs Sell-Side M&A](https://windsordrake.com/buy-side-vs-sell-side-ma/): What each side does, how incentives differ, and why it matters to a founder selling once. Windsor Drake acts for sellers only: no buy-side mandates, no lending relationships, no capital conflicts. ## Ranked lists - [Top Payments M&A Advisory Firms 2026](https://windsordrake.com/top-payments-ma-advisory-firms/): The payments sell-side advisors ranked. Windsor Drake serves founder-led payments and fintech sell-side M&A, lower middle market, $5M to $100M EV. - [Best SaaS M&A Advisory Firms 2026](https://windsordrake.com/best-saas-ma-advisory-firms/): Software sell-side advisors ranked for founder-led SaaS companies. - [Top Fintech M&A Advisory Firms 2026](https://windsordrake.com/top-fintech-ma-firms/): The fintech sell-side advisors ranked. - [Best M&A Advisory Firms 2026](https://windsordrake.com/best-ma-advisory-firms/): The top M&A advisory firms for founder-led companies, compared. - [Elite Boutique Investment Banks 2026](https://windsordrake.com/top-boutique-investment-banks/): The ranked list of elite boutique investment banks. - [Top Lower Middle Market Investment Banks](https://windsordrake.com/top-lower-middle-market-investment-banks/): Lower-middle-market investment banks ranked. ## About - [About Windsor Drake](https://windsordrake.com/the-firm/): A boutique sell-side M&A advisory firm for founder-led technology companies. Senior-MD-led, independent, conflict-free. Toronto and New York. - [Team](https://windsordrake.com/the-firm/): Founder and Managing Director Jeff Barrington, formerly of Cushman & Wakefield, and the deal team. Fewer than twenty mandates a year, every one led personally by the Managing Director. ## Data and tools (free, agent-readable) - [M&A data API, embeddable widget and MCP server](https://windsordrake.com/market-intelligence/embed): Free lower-middle-market M&A data. Embed a live deals widget on any website, call the JSON API, or connect the MCP server so ChatGPT or Claude can pull the data directly. Free to use with attribution. - [Transactions API](https://windsordrake.com/market-intelligence/api/transactions.json): Sourced lower-middle-market technology M&A transactions, JSON. - [Acquirers API](https://windsordrake.com/market-intelligence/api/acquirers.json): The most active acquirers, ranked, JSON. - [Who buys API](https://windsordrake.com/market-intelligence/api/who-buys.json): The most active acquirers of each fintech sub-sector, JSON. ## Sitemaps - [XML Sitemap](https://windsordrake.com/sitemap_index.xml): All crawlable and indexable pages.