Chesapeake Corporate Advisors

What Chesapeake Corporate Advisors does

Chesapeake Corporate Advisors (CCA) is a privately held, boutique investment banking and corporate advisory firm founded in 2005 and headquartered in Baltimore, Maryland. The firm serves investor-owned and closely held lower middle market companies in the Mid-Atlantic region, with a target client profile of businesses generating $20 million to $200 million in annual revenue. Over its 20-year operating history CCA has completed more than 150 transactions representing in excess of $4.7 billion in cumulative deal value across verticals including government contracting and IT, engineering and construction, healthcare, business and financial services, logistics/transportation/distribution, and manufacturing/distribution.

CCA operates two integrated service lines. Corporate Advisory Services delivers strategic assessments, business valuations, ownership continuity planning, transaction readiness preparation, succession strategy, financial modeling, and value creation advisory on an ongoing engagement basis. Investment Banking Services provides sell-side and buy-side M&A representation, merger advisory, recapitalization, growth capital raises, and management buy-outs on a success-based fee model. The firm's primary proprietary asset is the Shareholder Value Maturity Model, a diagnostic framework that evaluates nine complementary categories affecting business valuation and maps them to a company's stage of life to tailor advisory recommendations.

The firm distributes services through direct senior-banker engagement and network referrals rather than intermediaries, supported by a content marketing program that includes quarterly industry updates, macroeconomic commentary, and a blog. CCA is led by founder and Managing Partner Charlie Maskell alongside six additional managing directors and a team of directors, vice presidents, analysts, and operations staff. Revenue is generated primarily through success-based transaction fees tied to deal closings, supplemented by advisory retainers and valuation engagements; specific revenue figures are not publicly disclosed.

Name

Chesapeake Corporate Advisors

Legal name

Chesapeake Corporate Advisors

Website

https://ccabalt.com

Company type

Private

Founded year

2005

Operating status

Operating

Headcount range

11–50 employees

Short description

Chesapeake Corporate Advisors is a Baltimore-based boutique investment banking and corporate advisory firm serving lower middle market companies ($20M-$200M revenue) across the Mid-Atlantic. It delivers M&A advisory, recapitalization, valuations, and value-creation advisory across six industry verticals.

Ownership category

akta.pro rank

Product category

Investment Banking & Corporate Advisory

NAICS

Management Consulting Services (54161), Portfolio Management and Investment Advice (523940)

SIC

Services-Management Consulting Services (8742), Investment Advice (6282)

akta.pro primary industry

Corporate Finance Advisory (Strategic Finance, Capital Structure & Recaps) (FSAEAGAE)

Keywords

• Investment banking
• M&A advisory
• Corporate advisory
• Business valuation
• Middle market advisory

Headquarters

HQ city

Baltimore

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Investment Banking Advisory Fees: Success-based fees aligned with transaction outcomes. Fee structures vary based on transaction size, complexity, and scope. The firm guides owners through valuation, preparation, marketing to qualified buyers, managing due diligence, negotiating terms, and closing.
2. Corporate Advisory Services: Ongoing advisory engagements providing strategic assessments, financial planning and analysis, transaction advisory, value creation strategy, and business valuations. Services include ownership continuity assessment, transaction readiness preparation, business planning, financial modeling, and M&A advisory support.

Pricing tiers

Go-to-market motion2 records

Distribution channels2 records

Marketing channels7 records

Core offering

Chesapeake Corporate Advisors is a boutique investment banking and corporate advisory firm that serves lower middle market companies (typically $20 million to $200 million in annual revenue) in the Mid-Atlantic region. It delivers two integrated service lines: Corporate Advisory (business valuations, transaction readiness assessments, ownership continuity and succession planning) and Investment Banking (sell-side and buy-side M&A representation, recapitalizations, growth capital, and management buy-outs). Engagements are led personally by senior bankers using the firm's proprietary Shareholder Value Maturity Model.

Product overview

Chesapeake Corporate Advisors (CCA) is a boutique investment banking and corporate advisory firm offering two integrated service lines: Corporate Advisory Services and Investment Banking Services. Corporate Advisory Services provides strategic advisory including business valuations, transaction readiness assessments, and succession planning using the proprietary Shareholder Value Maturity Model. Investment Banking Services encompasses sell-side and buy-side M&A representation, recapitalization, and growth capital advisory. The firm specializes in six industry verticals: Business Services, Engineering & Construction, Government Contracting & IT, Healthcare, and Logistics/Transportation/Distribution/Supply Chain Management.

Differentiator

Problem solved

Functional benefit

Products and services

• Corporate Advisory Services Strategic advisory services for middle market companies including business valuations, value and marketability assessments, ownership continuity planning, transaction readiness preparation, strategic planning, and exit/succession strategy development. Provided on an engagement basis using the firm's proprietary Shareholder Value Maturity Model.
• Investment Banking Services M&A advisory services for middle market companies including sell-side representation, buy-side representation, merger advisory, recapitalization, growth capital, and management buy-out services. Fees are success-based and aligned with transaction outcomes; structure varies with transaction size, complexity, and scope.

Quantifiable outcome

• 150+ successful deals completed since inception
• +2 more outcomes

Named customers8 records

Segments8 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature1 record

Partnerships

Two partnerships are on record, tiered core.

• Private Equity Firms (Network)coreOthersCCA maintains relationships with private equity firms throughout the Mid-Atlantic region as part of their buyer network for client transactions. These relationships enable finding the right private equity partner for each transaction.
• Strategic Buyers (Network)coreOthersExtensive network of strategic acquirers throughout the Mid-Atlantic region that CCA leverages to identify optimal buyers for client businesses being sold.

Scale indicators8 records

Recent moves6 records

Expansion highlights4 records

Broad incumbents

• Stout: Larger global advisory firm with a dedicated middle-market M&A and valuation practice. Broader service portfolio and international reach, but overlaps with CCA on lower middle market sell-side and valuation engagements.
• Houlihan Lokey: Global investment bank with a substantial middle-market M&A practice. Larger scale and broader capabilities, but routinely competes with CCA for sell-side mandates in the lower middle market and across CCA's core sectors.

Direct peers

• Clearsight Advisors: Boutique M&A advisory firm focused on technology and tech-enabled services within the middle market. Comparable boutique positioning and lower middle market focus, with sector overlap in CCA's technology and government contracting verticals.
• Cascadia Capital: Middle-market investment bank providing M&A and capital advisory to emerging growth and lower middle market companies. Comparable in target client profile, deal size, and senior-led engagement model.
• Capstone Partners: Middle-market M&A advisory firm serving companies typically in the $20M-$500M revenue range across multiple verticals. Direct competitor for sell-side mandates within CCA's target segment and sector mix.
• Brown Gibbons Lang & Company: Boutique middle-market M&A advisory firm with sector-specialized practices serving lower middle market companies in similar revenue ranges. Closely comparable in target client size, transaction model, and senior-banker-led engagement style.
• Marsh Berry & Company: M&A and growth advisory firm focused on financial services and insurance distribution, with lower middle market positioning. Comparable boutique advisory model, though more concentrated in financial services verticals.

Regional players

• Boenning & Scattergood: Mid-Atlantic-based investment bank and wealth manager with middle-market advisory capabilities. Operates in CCA's geographic footprint, competing for regional lower middle market mandates.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks5 records

Key highlights6 records

Customer concentration

• YouTubeyoutube.com/@chesapeakecorporateadvisors
• LinkedInlinkedin.com/company/chesapeake-corporate-advisors

Revenue estimate

Valuation estimate

Number of profiles

Profiles9 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Chesapeake Corporate Advisors