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Chrysalis Ventures

chrysalisventures.com · Louisville, KY

Investment thesis

Apply technology and operating expertise to established, profitable businesses led by proven management teams in underserved markets, often as platforms for roll-up acquisitions, plus selective earlier-stage technology investments.

$400M
AUM
01Investment Thesis

Apply technology and operating expertise to established, profitable businesses led by proven management teams in underserved markets, often as platforms for roll-up acquisitions, plus selective earlier-stage technology investments.

Exclusion Criteria

Rarely invests at seed; prefers companies with at least $1M revenue.

02Investment Team
DA
David A. Jones
Chairman & Managing Partner
IB
Irv Bailey
Managing Director
WS
Wright Steenrod
Partner
CC
Charlie Crawford
Vice President
03F4 Research Brief

Chrysalis Ventures Research

Investment Thesis

Chrysalis Ventures (branded Chrysalis Capital on its site) is a Louisville, Kentucky firm founded in 1993 by David A. Jones. It was started on the observation that Mid-America had almost no resident venture capital managers, which left promising regional growth companies underserved. The firm says it invests where technology and its own expertise can be applied to businesses run by talented management teams, to build enduring value. It describes a particular strength in predictive analytics and technologies that empower workforces. It says it has invested in or built more than 70 technology-enabled businesses over roughly 25 years.

The firm leans toward established, profitable businesses that can be optimized with technology and used as platforms for rolling up smaller, less efficient competitors. It also makes highly selective investments in earlier-stage technology companies led by visionary, experienced leaders. This is a growth and lower-middle-market profile more than a classic seed venture profile.

Stage Focus

The strategy page says the firm rarely invests at seed and prefers companies already generating at least $1 million in revenue. It targets established businesses with $1 to 10 million of EBITDA, plus expansion-stage companies and occasional select opportunities such as roll-ups. Stage fit is therefore Series A and later growth, not pre-seed or seed.

Check Size

The firm does not publish a check size range. The only stated financial screen is $1 to 10 million of EBITDA and at least $1 million of revenue. Check size fields are left empty rather than guessed.

Lead Tendency

Not stated publicly. The firm describes itself as a hands-on partner that helps with acquisitions, business development, operations, strategy and applying technology, and says it invests only where it can add value beyond capital. Lead tendency is recorded as unknown.

Recent Activity

The firm's site and third-party profiles show no dated recent deal announcements that could be verified. A LinkedIn search snippet puts assets under management at about $400 million. Press coverage shows a fourth fund closed on $163 million after 18 months of fundraising, and a 2008 Venture Capital Journal piece reports a $175 million fourth fund close, so fund history is inconsistent across sources. Fund status is recorded as unknown. An Altss profile appears to conflate this firm with a different Chrysalis Capital acquisition fund in Western Canada and was not used.

Portfolio Highlights

Current portfolio page names AlayaCare, Appriss, AmeriPath, AfterBOT, Advanced Academics, Allscripts and Aperture. About 12 further logos on the page carry no readable caption. Team bios name current investments including BehaVR, Confluent Health, Edj Analytics, Fit For Work, GoNoodle, meQuilibrium and Regent Education. Named exits and graduates include Appriss (sold to Bain Capital), Advanced Academics (sold to DeVry), Tritel (merged with Telecorp, sold to AT&T Wireless), Regent Communications, ActaMed (merged with Healtheon, then WebMD), TechRepublic (sold to Gartner), High Speed Access Corp (IPO, sold to Charter), Digitalsmiths (sold to TiVo), MyHealthDirect (sold to Experian Health), StraighterLine and Sanovia (sold to BV Investment Partners), XLerant (sold to Constellation Software), Genscape (sold to GFI), iSqFt (sold to Genstar Capital) and Continuum (sold to T-Mobile).

Team

  • David A. Jones, Chairman & Managing Partner: Founded Chrysalis in 1993. Focuses mainly on healthcare and chairs the investment committees. Humana board member from 1993 to April 2023 (Chairman 2005 to 2010). Yale BA and JD, former State Department legal office lawyer and Bank of Boston banker.
  • Irv Bailey, Managing Director: Former Chairman and CEO of Providian Corporation (sold to AEGON in 1997), with about 40 years of portfolio management experience.
  • Wright Steenrod, Partner: Joined in 2001. Focuses on data-driven innovation in healthcare and training. Sits on boards including Regent Education, GoNoodle, Lucina Health and Edj Analytics. Princeton BA, former US Marine Corps captain.
  • Charlie Crawford, Vice President: Joined in 2012 from Innova Memphis. Sources new investments and works with BehaVR, Confluent Health, Edj Analytics, Fit For Work, GoNoodle, meQuilibrium and Regent Education. Williams College BA.

Decision Process

The investment committees are chaired by David Jones. The firm does not describe a formal process publicly, so this is recorded as a partnership.

Founder Preferences

Proven operators with relevant industry expertise and experience scaling businesses. Where founders want to exit, the firm looks for rising executives ready to take bigger roles. It values management teams that want a hands-on thought partner.

Geographic Focus

Mid-America, the Midwest and the Southeast. The firm says it will invest anywhere it can add value but has a particular interest in the middle of the country.

Sectors

Business services, communications, construction, education and corporate training, energy, government services, healthcare, human capital management, logistics, and media and entertainment. Healthcare and workforce or training technology recur most in the partner bios.

Gaps

No published check size, no verified recent dated investments, no confirmed current fund size, and about 12 uncaptioned portfolio logos. Portfolio domains were left empty on purpose.

04Selected Portfolio
EdTech
Advanced Academics·GoNoodle·Regent Education
Enterprise Software
Appriss·AfterBOT·Aperture·Edj Analytics
Healthcare & Digital Health
AlayaCare·AmeriPath·Allscripts·BehaVR·Confluent Health·Fit For Work
HR Tech & Future of Work
meQuilibrium
Open the full portfolio→
05Recent Updates

Fresh signals from public announcements, essays, and portfolio activity.

Portfolio company Advanced Academics was sold to DeVry.
EXIT·chrysalisventures.com
Added recently
Portfolio company Appriss was sold to Bain Capital.
EXIT·chrysalisventures.com
Added recently
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Quick Reference
Stages
Series A · Series B · Growth
AUM
$400M
Decision
Partnership
Location
Louisville, KY
Sector Focus
EdTechEnterprise SoftwareHR Tech & Future Of WorkHealthcare & Digital Health
Models
Technology-Enabled ServicesRoll-UpsB2B
Technology
Predictive AnalyticsWorkforce Technology
See all EdTech investors →See all Enterprise Software investors →See all HR Tech & Future of Work investors →
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Focus Areas
EdTechEnterprise SoftwareHR Tech & Future Of WorkHealthcare & Digital Health

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F4 Intelligence Report · Last Researched November 6, 2026F4 Research Engine