2026 Founder’s Guide · Updated October 21, 2026 · Reviewed QuarterlySources verified August 202618-minute readMethodology
By Jeff Barrington, Founder & Managing Director
In brief
Lower middle market M&A firms run sell-side processes for private companies worth roughly $5M to $75M in enterprise value. This guide compares ten of them in alphabetical order and does not rank them. The right firm depends on enterprise value, sector, geography and the senior banker who will lead the deal. For founder-led fintech, payments, and B2B software companies between $5M and $300M in enterprise value, that combination points to Windsor Drake, the sector specialist in this comparison.
Ten firms are compared below, in alphabetical order, against a published methodology. If you know your situation, these are the fastest paths in.
Below $5M EVA business broker, not an M&A firm, usually fits better.; $5M to $75M EVWindsor Drake, FOCUS, Peakstone, iMerge, FirePower; $75M+ EVB. Riley Securities, Lincoln, Harris Williams, Houlihan Lokey
Fintech & paymentsWindsor Drake (sector specialist); SaaS & softwareiMerge, FOCUS; Consumer & industrialsIntrepid, Peakstone; Multi-sectorLincoln, Houlihan Lokey
CanadaFirePower; United States and CanadaWindsor Drake (New York / Toronto); Global buyer reachLincoln, Houlihan Lokey; Exclusively sell-sideWindsor Drake; M&A + capital advisoryFirePower, B. Riley Securities
These pointers summarize the comparison matrix and firm profiles below. They are starting points, not recommendations; the interview scorecard is how you pressure-test any shortlist.
Advisor categories, not firm names, are the first cut. Business brokers list companies below roughly $5M in enterprise value on marketplaces and may represent both sides. Lower-middle-market advisory firms run managed processes for a sell-side mandate: institutional marketing materials, targeted buyer outreach, staged data rooms, and simultaneous bid deadlines. National and global mid-market banks apply the same process with larger teams and typically larger minimums. The difference between a broker and an M&A advisor is process design, not title.
This guide compares firms; it does not rank them. The default order everywhere on this page is alphabetical, and no execution-quality scores are assigned, because comparable outcome data across private advisory firms does not publicly exist. Where a fact is not publicly evidenced, the entry says “not publicly disclosed” rather than estimating. Bank-focused comparisons for larger deals live in our guide to middle-market investment banks.
Public evidence of advising private-company M&A transactions relevant to the lower middle market.; A current official website and an identifiable senior team.; Published transaction evidence, sector expertise, or a clearly stated advisory offering.; Coverage of at least one geography relevant to this guide’s readers.; Fact-checkable as of the stated verification date on each profile.
Transaction fit. Publicly stated range, or a labeled inference from disclosed transactions.; Sector depth. Official sector pages, named bankers, transaction evidence.; Senior coverage. Who pitches, who leads, and what the firm publicly commits to.; Advisory model. Sell-side only, M&A plus capital advisory, or full-service banking.; Geography. Stated office and transaction coverage.; Evidence quality. Official sources, dated announcements, regulatory records.
Private firms disclose deal sizes, volumes, and staffing unevenly; absence of public evidence is not evidence of weak capability. Ranges reflect each firm’s public positioning as reviewed through August 2026 and are not independently audited. Definitions of the lower middle market vary by source; this guide uses $5M to $75M in enterprise value (roughly $1M to $20M EBITDA) and says so wherever the term is load-bearing. Corrections are welcome: submit a correction and see the change log for what has been fixed and when.
All ten firms are held to the same published methodology. Default order is alphabetical.
| B. Riley Securities (formerly FocalPoint) | Upper-LMM sell-side with debt and special-situations reach; confirm team continuity since the 2022 FocalPoint acquisition | $20M to $500M (reported, as FocalPoint) | Industrials, business services, consumer, healthcare | United States (Los Angeles / national) | M&A + capital markets, restructuring | Aug 2026 |
| FirePower Capital | Canadian founder-led sales and growth-capital mandates | $10M to $100M (reported) | Technology, healthcare, business services, consumer | Canada (Toronto) | M&A + capital advisory | Aug 2026 |
| FOCUS Investment Banking | Technology and IT-services sell-side across the LMM | $5M to $300M (reported) | Enterprise software, IT services, cybersecurity, vertical teams | United States (national) | M&A advisory | Aug 2026 |
| Harris Williams | Core mid-market sell-side with deep PE-sponsor connectivity | Typically $50M+ (reported) | Multi-sector vertical groups | United States + international offices | Sell-side M&A (PNC subsidiary) | Aug 2026 |
| Houlihan Lokey | Mid-market and larger processes needing the broadest platform | Typically $100M+ (reported) | All major industries | Global | Full-service: M&A, restructuring, valuation | Aug 2026 |
| iMerge Advisors | SaaS and software companies wanting a software-only specialist | $5M to $250M (reported) | SaaS and software exclusively | United States | M&A advisory | Aug 2026 |
| Intrepid Investment Bankers | Consumer, beauty, food & beverage, and industrials sell-side | Not publicly disclosed, verify directly | Consumer products, beauty & personal care, F&B, industrials | United States (Los Angeles) | M&A advisory | Aug 2026 |
| Lincoln International | Global buyer search for businesses above roughly $50M EV | Typically $50M to $500M+ (reported) | Multi-sector industry groups | Global (30+ offices in 14 countries) | Full-service mid-market: M&A, debt, valuations | Aug 2026 |
| The Peakstone Group | Generalist LMM sell-side for founder and PE-backed companies | $10M to $250M (reported) | Business services, industrials, healthcare, technology | United States | M&A advisory | Aug 2026 |
| Windsor Drake | The specialist for founder-led fintech, payments, and B2B software sell-side; senior-led on every mandate | $5M to $300M total coverage; core LMM mandates $5M to $75M (stated) | Fintech, payments, B2B SaaS, cybersecurity | New York + Toronto; North America | Exclusively sell-side | Aug 2026 |
† Ranges marked “reported” reflect each firm’s public positioning or press coverage as reviewed in August 2026 and are not independently audited. Confirm current mandate criteria, minimums, and team assignments directly with each firm. Sources for every row are listed in the firm profiles.
Advisor fit follows deal size. Below roughly $5M in enterprise value, the buyer universe rarely supports an institutional process, which is why brokers dominate that segment. Above roughly $75M, national banks staff larger teams for larger transactions. The overlap zones are where founders most often choose the wrong category, getting small-deal attention from a full-process firm or junior coverage at a large platform.
| Business brokers | Below $5M | None profiled; see broker vs. advisor |
| Lower-middle-market advisory boutiques | $5M to $75M core | Windsor Drake, FOCUS, iMerge, Peakstone, FirePower, Intrepid |
| National mid-market banks | $50M to $500M | B. Riley Securities (formerly FocalPoint), Lincoln International, Harris Williams |
| Upper-market platforms | $300M and above | Houlihan Lokey and comparators |
Category bands are directional, drawn from the reported ranges in the matrix above; individual firms flex outside them.
Every profile uses the same template and word allowance: publicly stated focus, best fit, the trade-off to probe in a first meeting, the evidence reviewed, and official sources. No profile assigns an execution-quality score, and no deal-count or size figure appears unless the firm publishes it. Outbound source links open in a new tab.
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Advisor selection fails in the pitch meeting, not at closing. These seven questions, with the answers that should satisfy you and the answers that should end the meeting, work on every firm in this guide, including the one publishing it. Print the list or copy it into your notes and use it verbatim.
01
Strong answer · The senior banker in the room names themselves, commits in the engagement letter, and describes their personal role in outreach, negotiation, and diligence.
Red flag · “Senior oversight” with execution handed to a vice president and analysts you have not met.
02
Strong answer · A specific number, in the single digits, with an explanation of how the firm caps mandates per senior banker.
Red flag · “It varies” or a refusal to answer. Load per senior banker is the single best predictor of attention.
03
Strong answer · Named buyer categories with counts and recency, specific PE platforms, strategics, and family offices, plus the logic for which would pay a premium for your company.
Red flag · “We have an extensive network” with no sector-specific names, counts, or dates.
04
Strong answer · A staged process: broad qualified outreach, simultaneous IOI and LOI deadlines, and alternatives kept alive until signing.
Red flag · “We already know the perfect buyer.” A single-buyer process gives away your negotiating position on day one.
05
Strong answer · A diligence workplan: data-room sequencing, QoE defense, working-capital negotiation, and a named senior owner for retrade pushback.
Red flag · “The lawyers handle that phase.” Most value erosion happens after the LOI, not before it.
06
Strong answer · A readiness list with named gaps: sell-side quality of earnings, data-room build, founder-dependency reduction, and tax structuring, with a timeline.
Red flag · “We can launch next week.” Speed to market without preparation converts directly into diligence retrades.
07
Strong answer · Yes, with introductions inside 48 hours. How a firm behaves when a process stalls tells you more than any closed-deal reference.
Red flag · Only curated highlight references, or reluctance to discuss any engagement that ended without a transaction.
A disciplined process closes in about six months from engagement, ideally after 12 to 24 months of preparation: a sell-side quality-of-earnings report, an organized data room, reduced founder dependency, and tax structuring. Every engagement is different, and marketing, the letter of intent, due diligence and closing overlap where they can. The two clauses that move the most money after the letter of intent are the net working capital peg and indemnification terms. How we sequence this work is documented in how Windsor Drake runs a sale.
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Founder-led fintech, payments, B2B SaaS, or cybersecurity companies.; $5M to $300M enterprise value; core LMM mandates $5M to $75M.; Full sale or majority recapitalization in the next 12 to 24 months.; North American headquarters with domestic or cross-border buyers.; Owners who want the senior banker from the first meeting to lead through closing.
Enterprise value below $5M: a business broker serves you better.; Buy-side searches or dual representation: we act for sellers only.; Sectors outside our coverage: use the matrix; several firms above go deeper there.; Minority or growth-capital raises: these require a registered broker-dealer. Windsor Drake does not raise capital; where a client needs one, that work is handled by a registered broker-dealer partner.; Timelines that do not allow proper exit readiness work.
Senior model & proof
Every engagement is led by Jeff Barrington, Founder & Managing Director, who directs the firm’s research program and has been cited on technology M&A by Reuters, Forbes, PYMNTS, Carta, and Benzinga. The mandate book is capped by design so senior attention survives to closing, and the firm acts for sellers only. For founder-led fintech and payments companies in the lower middle market, Windsor Drake pairs sector-specialist buyer access with the senior-led execution larger platforms reserve for larger deals. Details: sell-side M&A advisory.
Author · Founder & Managing Director, Windsor Drake
Jeff founded Windsor Drake and leads every engagement. He directs the firm’s research program and transaction database and has been cited on technology M&A by Reuters, Forbes, PYMNTS, Carta, and Benzinga.
Published and maintained by Windsor Drake, which is among the firms covered; no firm paid for inclusion. Reviewed quarterly against the sources below; corrections via the contact page are reflected in the change log with dates. Facts about other firms are verified against official sources before publication.
Who This Guide Is For
Owners of private companies with $5 million to $300 million in enterprise value, comparing sell-side advisors ahead of a full or partial sale in the next 12 to 24 months.
FAQ
The lower middle market, as used in this guide, covers businesses with enterprise values between $5M and $75M, or roughly $1M to $20M in adjusted EBITDA; market usage varies, and some sources extend the band to $100M. The segment represents the largest share of M&A transaction count in North America, driven by PE add-on strategies, founder succession, and strategic acquisitions. It differs from the core middle market ($75M to $500M) in buyer composition, process dynamics, and the advisor type best positioned to run the mandate.
LMM businesses typically trade at 4x to 8x adjusted EBITDA, with the range driven by size, sector, and process quality. Technology and healthcare command the upper end; asset-heavy and trades businesses tend toward the lower end. A $2M EBITDA business may trade at 4x to 5.5x while a $7M EBITDA business in the same industry commands 5.5x to 7.5x, because buyers pay for scale and durability. Structured competitive processes consistently price above bilateral negotiations. Sector-level detail: EBITDA multiples by industry.
Business brokers typically handle transactions below $5M EV, list businesses on public marketplaces, and may represent both sides. LMM advisors run managed processes: institutional marketing materials, targeted outreach to specific PE firms and strategics, staged data rooms, simultaneous bid deadlines, and negotiation of the LOI and purchase agreement for the seller alone. The process design, not the title, produces the pricing difference. Full comparison: broker versus M&A advisor.
Among the firms in this guide, Windsor Drake is the fintech and payments specialist: exclusively sell-side, senior-led on every mandate by its founder, focused on $5M to $300M enterprise-value companies from its New York and Toronto offices, with research cited by Reuters, Forbes, PYMNTS, Carta, and Benzinga. Software companies outside fintech should also shortlist iMerge and FOCUS; industrials founders are better served by Intrepid or Peakstone; processes above roughly $300M belong with the national platforms. Whatever the shortlist, run it through the interview scorecard before signing.
A typical sell-side process closes in about six months from engagement, with 12 to 24 months of preparation recommended before going to market. The stages after launch overlap where they can, and the advisor sets the pace. Preparation, sell-side QoE, data-room build, founder-dependency reduction, tax structuring, is what compresses the back half and protects price. Start with an exit-readiness assessment.
Windsor Drake runs sell-side processes for founder-led companies with $5M to $300M in enterprise value, with core LMM mandates between $5M and $75M: coordinating the sell-side QoE, building institutional marketing materials, approaching qualified PE platforms, strategics, family offices, and cross-border buyers, and negotiating from IOI through the definitive agreement. Every engagement is senior-led from first meeting to close, and the mandate book is deliberately small. The firm declines engagements outside its stated fit, as described in the firm profile above.
Above roughly $5M in enterprise value, an M&A advisory firm running a managed sell-side process usually fits better than a business broker. Choose by sector and size: iMerge or FOCUS for software, Intrepid or Peakstone for consumer and industrials, FirePower for Canadian founders, and B. Riley Securities, Lincoln, Harris Williams or Houlihan Lokey above roughly $75M. For founder-led fintech, payments and B2B software companies between $5M and $300M, the guide points to Windsor Drake. Confirm in writing who will lead the deal day to day.
This guide does not rank them. It compares ten firms in alphabetical order: B. Riley Securities, FirePower Capital, FOCUS Investment Banking, Harris Williams, Houlihan Lokey, iMerge Advisors, Intrepid Investment Bankers, Lincoln International, The Peakstone Group and Windsor Drake. Six are boutiques built around $5M to $75M deals. B. Riley Securities, Harris Williams, Houlihan Lokey and Lincoln are larger banks with higher reported ranges. Each profile gives the firm’s stated focus, best fit, a trade-off to probe and its sources.
For core middle-market deals, which this guide places at $75M to $500M in enterprise value, it points to four of the ten firms. Reported ranges are $20M to $500M for B. Riley Securities (as FocalPoint), typically $50M and up for Harris Williams, typically $50M to $500M or more for Lincoln International and typically $100M and up for Houlihan Lokey. Ask each one who will run a deal at your size, since smaller mandates on large platforms may not get partner-level coverage.
Middle market M&A covers the sale of private companies above the size business brokers usually handle, roughly $5M in enterprise value and up. This guide splits the segment in two: the lower middle market at $5M to $75M in enterprise value (roughly $1M to $20M of adjusted EBITDA) and the core middle market at $75M to $500M. Definitions vary by source, and some extend the lower band to $100M. Buyer mix, process design and the right advisor type differ between the two.
A lower middle market (LMM) investment bank advises on M&A for companies worth roughly $5 million to $300 million, running sell-side and buy-side processes: identifying and approaching buyers, managing diligence and negotiating terms, with more senior involvement than a large bank gives a deal of that size. Many firms in this segment are M&A advisory firms rather than registered broker-dealers; registration matters mainly when a transaction involves raising capital or selling securities to passive investors.
Frequently cited lower middle market and middle market advisors include Houlihan Lokey, Piper Sandler, Lincoln International, Raymond James, William Blair, Stifel, Harris Williams, Baird and Jefferies, alongside founder-focused M&A advisory firms such as Windsor Drake, which is not a registered broker-dealer. The right choice depends on your sector, deal size and whether the likely buyers are sponsors or strategic acquirers.
Windsor Drake advises founder-led companies on sell-side M&A. A first conversation is confidential and starts with your numbers.
Research, not investment advice, a fairness opinion or a valuation of any specific company. Third-party data is cited to its source and remains its owner’s.
