Acquisition & Investment Lead

Bristlecone Companies; Chicago (IL); On-site; USD 120,000 - 210,000; Full time

Benefits offered by this job

Base salary

Uncapped bonus

Equity participation

Job summary

Bristlecone Companies in Chicago seeks an Investment Lead to help build our acquisition engine. You will partner directly with the CEO to source deals and shape the investment function from the ground up.

The role emphasizes building durable businesses with time, strong judgment, and the ability to develop relationships with owners and brokers. Travel is frequent; compensation includes base salary, uncapped bonus potential, and meaningful equity participation.

Qualifications

• Sourcing 1–3 proprietary acquisitions per year, ideally platform investments in lower middle market valued on cash flow/EBITDA
• Strong ability to assess business quality, financial performance, and market structure
• Clear, credible communicator who builds trust quickly
• Thrives in fast-paced, entrepreneurial sourcing environments

Responsibilities

• Develop investment theses and proactively source businesses through research, referrals, and outreach
• Cultivate long-term relationships with business owners, brokers, and intermediaries
• Evaluate businesses with strong judgment and advance the strongest to actionable opportunities
• Support transaction structuring, negotiation, and execution with the CEO
• Collaborate with operating company leadership on post-acquisition strategy and add-on acquisitions
• Build and improve sourcing/diligence processes to scale the engine

Skills

Originator

Investment judgment

Relationship building

Communication

Resilience

Job description

Bristlecone Companies in Chicago seeks an Investment Lead to help build our acquisition engine. You will partner directly with the CEO to source deals and shape the investment function from the ground up.

The role emphasizes building durable businesses with time, strong judgment, and the ability to develop relationships with owners and brokers. Travel is frequent; compensation includes base salary, uncapped bonus potential, and meaningful equity participation.