Real transactions. Confidentially told.
Each story explains the client situation and the CEOSSI role without exposing confidential information.
Founder Succession & Strategic Sale for Specialty Contractor
The Situation
The founder of a 28-year-old specialty commercial contracting firm with $14M in revenue wanted to retire within 18 months, but the company was heavily dependent on his personal relationships.
The Challenge
No formal financial reporting was prepared for buyers; customer concentration in the top three accounts represented 54% of revenue, and the founder had never been through an M&A transaction.
The CEOSSI Role
CEOSSI acted as transaction advisor to the founder, establishing a sell-side roadmap, preparing the documentation, and guiding negotiations through closing.
The Process & Advisory Milestones
- Conducted a thorough M&A readiness assessment and normalized 3 years of financial records with the company CPA.
- Designed an operational handover plan shifting key accounts to senior project managers 9 months prior to marketing.
- Structured a detailed Letter of Intent establishing working capital definitions, a 20% seller note, and an 80% cash-at-close requirement.
- Coordinated legal counsel, due diligence data rooms, and insurance requirements through closing.
The Outcome
Closed a transaction at 4.8x adjusted EBITDA with a regional strategic buyer. Founder completed a smooth 6-month consulting transition and achieved full liquidity.
The Lesson for Owners
Early preparation transforms an owner-dependent business into an institutional asset that buyers are willing to pay top dollar for.
First-Time Corporate Executive Acquiring IT Managed Services Provider
The Situation
A former technology executive with $400k in personal equity sought to acquire a profitable B2B recurring revenue service provider using SBA 7(a) financing.
The Challenge
The buyer was overwhelmed by conflicting broker listings, ambiguous seller add-backs, and aggressive LOI deadlines requiring non-refundable earnest deposits.
The CEOSSI Role
CEOSSI served as the buyer’s independent buy-side advisor, analyzing target financials, structuring the offer, and orchestrating diligence and lending specialists.
The Process & Advisory Milestones
- Evaluated three prospective target companies and identified severe unrecorded customer churn in two broker-marketed businesses.
- Focused on an off-market $3.2M revenue MSP with 82% recurring contract revenue and verified financial records.
- Drafted a protective LOI with clear financing contingencies, inventory reconciliation rules, and key-technician retention bonuses.
- Liaised with the SBA lender, Quality of Earnings accountant, and legal counsel to complete due diligence in 65 days.
The Outcome
Successfully acquired the business with 10% equity down, 80% SBA loan, and 10% on a seller standby note. The company grew revenue by 18% in year one.
The Lesson for Owners
Disciplined financial vetting prevents buyers from overpaying or taking on hidden liabilities.
Navigating a Pre-Arranged Buyout Between Engineering Partners
The Situation
Two founding partners of a 45-person civil engineering firm reached an impasse regarding the retirement and buyout terms of the senior partner.
The Challenge
Neither partner wanted to pay huge broker commissions, but direct discussions were becoming emotionally tense, threatening the ongoing stability of client projects.
The CEOSSI Role
CEOSSI was engaged as an independent transaction advisor to both shareholders to establish a neutral valuation methodology, structure terms, and coordinate execution.
The Process & Advisory Milestones
- Reviewed 5 years of billings, backlog, work-in-progress (WIP), and shareholder distribution history.
- Constructed a phased 3-year buyout model using internal company cash flow that preserved bonding capacity and bank covenants.
- Facilitated weekly commercial terms sessions to agree on non-compete boundaries, client transition protocols, and equity transfer schedules.
- Worked alongside the firm’s CPA and corporate attorney to translate business terms into definitive stock redemption agreements.
The Outcome
Agreement executed without litigation or team disruption. Junior partners stepped into equity ownership while the senior partner received guaranteed payouts.
The Lesson for Owners
When buyers and sellers have already found each other, an experienced independent transaction guide provides the objectivity needed to close without conflict.