Cherry Tree Companies vs Headwaters SC
Comparing two boutique M&A advisors · Last updated April 25, 2025
| Attribute | Cherry Tree Companies | Headwaters SC |
|---|---|---|
| Type | Boutique | Boutique |
| HQ | Minneapolis, MN | San Diego, CA |
| Founded | 1980 | 2008 |
| Sector focus | Generalist | Generalist, Tech-Services |
| Deal size | $10M-$100M | $10M-$150M |
| Senior team |
|
|
| Rating | Locked | Locked |
| Reviews | 0 verified | 0 verified |
Choosing between Cherry Tree Companies and Headwaters SC
Cherry Tree Companies and Headwaters SC both work in Generalist. Founders running a sell-side process in those categories often see both names on their advisor longlist, which is why this comparison comes up. Both firms position themselves as boutique advisors, so the choice is less about category and more about pattern recognition, senior attention, and process fit.
Cherry Tree Companies is headquartered in Minneapolis, MN and was founded in 1980, while Headwaters SC operates out of San Diego, CA and was founded in 2008. Geography matters here: Cherry Tree Companies's Minneapolis relationships and Headwaters SC's San Diego relationships will overlap on national strategics but diverge on the regional private equity buyer set most likely to push price. On deal-size focus, Cherry Tree Companies states $10M-$100M while Headwaters SC states $10M-$150M. Beyond shared coverage, Cherry Tree Companies also reaches into adjacent categories, while Headwaters SC extends into Tech-Services.
For founders deciding between Cherry Tree Companies and Headwaters SC, the honest recommendation is to take a working session with each named partner before signing. Read the firm-level reviews on BankerNotes for the pattern that matters most: did the partner who pitched the mandate run the buyer calls and final negotiations, or did the work slide down the org chart by week six. That pattern, more than league-table position, is what separates a good outcome from a mediocre one.
Cherry Tree Companies is a boutique headquartered in Minneapolis, MN and founded in 1980. The firm focuses on Generalist and typically advises on transactions in the $10M-$100M range. Key dealmakers include Tony Christia...
Headwaters SC is a boutique headquartered in San Diego, CA and founded in 2008. The firm focuses on Generalist, Tech-Services and typically advises on transactions in the $10M-$150M range. Key dealmakers include Mike Pel...
Frequently asked questions
- What is the main difference between Cherry Tree Companies and Headwaters SC?
- Cherry Tree Companies is a boutique HQ'd in Minneapolis, MN (founded 1980), focused on Generalist, with a typical deal range of $10M-$100M. Headwaters SC is a boutique HQ'd in San Diego, CA (founded 2008), focused on Generalist, Tech-Services, with a typical deal range of $10M-$150M. Beyond those facts, the most reliable differentiator is senior banker attention, which BankerNotes reviews are designed to surface.
- Which firm has better founder reviews, Cherry Tree Companies or Headwaters SC?
- Cherry Tree Companies's current rating is Locked (reviews unlock after five verified founders submit ratings). Headwaters SC's current rating is Locked (reviews unlock after five verified founders submit ratings). Read the individual firm profiles for the full review breakdown.
- Should I shortlist both Cherry Tree Companies and Headwaters SC?
- For most founders evaluating sell-side advisors with overlapping sector and deal-size fit, putting both on a shortlist is reasonable. The point of a bake-off is to test how the senior team behaves under pressure, how the firm shapes the buyer universe, and how it handles a difficult diligence question. Treat the shortlist as an interview, not a beauty contest.
- How does BankerNotes verify reviews of Cherry Tree Companies and Headwaters SC?
- Every review is submitted by a founder who confirms they hired the firm as their sell-side advisor. We verify the reviewer privately using work email, LinkedIn, and approximate engagement timing. The verified identity is never published. Only the rating, written review, and a generic sector label appear on the public page.
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Last updated: April 25, 2025