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

Who We Are

Bristlecone Companies is a permanent capital holding company that acquires and builds mission-critical businesses with one defining characteristic: customers who don't leave. We are company builders at heart, committed to deepening customer relationships, creating environments where talented people thrive, and amplifying the legacies of founders who have entrusted us with their life's work.

While our mandate is broad, our approach is focused: we develop deep domain expertise and partner with management teams to build enduring market leaders through both organic and inorganic growth. We seek essential businesses with predictable cash flow, exceptional retention, and leading positions in specialized markets. Our investment discipline is grounded in deep fundamental research, and our ownership philosophy is defined by decentralization, continuous improvement, and an indefinite time horizon.

Rooted in an ethos of stewardship, we find meaning in the work itself, in the pride of ownership, and in the quiet rigor of doing things the right way. Our team is lean by design: autonomy is given early, standards are high, and the reward for great work is more responsibility. If you are driven, deeply curious, and energized by the opportunity to build alongside people who share your standards and ambition, you will thrive here.

What You’ll Do

We’ve established a quality foundation through our first acquisitions. In this next chapter, we’re hiring an Investment Lead to help build our acquisition engine - a core competency that will compound over time and determine the quality of businesses we own. Joining at a formative stage, you’ll partner directly with the CEO to build the investment function from the ground up, serve as the first layer of judgment in our investment process, and drive opportunities through close with full ownership pre-LOI. More specifically, you will:

• Develop investment theses and proactively source businesses through research, referrals, and persistent outreach to owners and industry participants.

• Cultivate long-term, trust-based relationships with business owners and with the brokers and intermediaries who represent them.

• Evaluate businesses with your own investment judgment and advance the strongest to actionable opportunities.

• Support transaction structuring, negotiation, and execution in partnership with the CEO.

• Collaborate with operating company leadership on post-acquisition strategy and add-on acquisitions.

• Build and continuously improve the systems that make sourcing and diligence repeatable and scalable.

Success will be measured by the quality and consistency of deal flow and, ultimately, closed acquisitions. Over time, you will have the opportunity to become a key partner in building and scaling Bristlecone.

Who You Are

While we care far more about who you are than where you've been, the role is best suited for someone with 1-5 years of investing experience in private equity, growth equity, or serial acquirors. More importantly:

• A proven originator - you've sourced 1-3 proprietary acquisitions per year, ideally platform investments in the lower middle market valued on cash flow or EBITDA

• Strong investment judgment with commercial fluency across business quality, financial performance, and market structure

• Clear, crisp, and thoughtful communicator who establishes trust and credibility quickly through authenticity, humility, and reliability

• Relentless and resilient, thriving in a fast-paced, entrepreneurial environment

• Insatiably curious, actively reflective, and quick to update your beliefs and approach based on feedback and outcomes

• A builder at heart - energized by shaping something from the ground up and genuinely motivated by building a sourcing engine and durable businesses that compound with time

• This role is based in Chicago with frequent travel to build differentiated relationships with owners in person. Compensation includes a competitive base salary, uncapped bonus potential, and meaningful equity participation structured for long-term compounding.