Single Family Office

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FieldWare

FieldWare is a software solutions provider founded in 2001 and based in Chicago, Illinois, serving judiciary and supervision agencies.

FieldWare

FieldWare is a software solutions provider founded in 2001 and based in Chicago, Illinois, serving judiciary and supervision agencies.

General information

Firm type

Single Family Office

Year founded

1997

AUM

$500M – $1B (Altss estimate)

Location

Region

North America

Country

United States

City

Chicago

Corporate office

Chicago, IL, United States

Principals

Robert G. Romasco

Managing Principal

Sector focus

Enterprise SoftwareFinancial ServicesDigital HealthReal Estate

Frequently asked questions

What is the origin of the wealth behind FieldWare?

The capital originated from the 1997 sale of CCC Information Services Group, a provider of software and data to the automotive claims and collision-repair industry, to a private equity consortium. Bob Romasco was the CEO of CCC at the time of the sale and used the proceeds to establish FieldWare as a single-family office.

How does FieldWare make investment decisions?

Bob Romasco serves as the managing principal and primary decision-maker. The office does not employ an institutional investment committee layer common in larger family offices. Decisions are shaped by Romasco’s operating background as a former public-company CEO and his longstanding relationships with venture and growth-stage general partners.

Does FieldWare invest directly in private companies or only through funds?

FieldWare primarily invests as a limited partner in venture capital and growth equity funds, but it also makes direct real estate acquisitions. There is no public evidence that it regularly leads or prices direct minority or control investments in operating companies, placing its posture closer to an allocator than a direct-investment shop in the private markets.

Is FieldWare open to co-investment opportunities alongside its fund managers?

The office does not publicly solicit co-investment opportunities and does not operate a formal co-investment program. Its typical posture in venture funds is that of a passive limited partner, which suggests that co-investment participation, if it occurs, is episodic and relationship-driven rather than systematic.

What is FieldWare's position on the succession of the office?

Publicly available materials do not describe a formal succession plan or a transition to a next-generation family member. The office’s existence is tied to first-generation wealth from the CCC sale, and there is no indication that it has been structured as a multi-generational institution or is in the process of professionalizing beyond its current lean configuration.

Profile maintained by using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.

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