Investment Lead

Who We Are

Bristlecone Companies is a long-term holding company backed by permanent capital from a select group of aligned investors and operators. We acquire mission-critical businesses that quietly keep our economy running and build them for decades.

We are owner-operators focused on companies with one defining characteristic: customers who don’t leave. We seek predictable cash flow, exceptional retention, and niche market leadership across business services, industrial services, and tech-enabled services. Our investment discipline is grounded in deep fundamental research, and our ownership philosophy is defined by decentralization and continuous improvement.

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. Autonomy is given early, standards are high, and the reward for great work is more responsibility. If you are talented, tenacious, and determined to find out how good you can be over the long arc of a career, 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 own the back half of our acquisition process from signed LOI through close and into the first 90 days of ownership. You should expect to spend roughly 10% of your time sourcing, 70% leading diligence and execution, and 20% supporting operating companies. Joining at a formative stage, you’ll partner directly with the CEO to shape our investment process, philosophy, theses, and capital allocation plan. More specifically, you will:

• Own the Process: Drive every deal from signed LOI through close, managing timelines, workstreams, and counterparties with discipline, urgency, and care.

• Manage Relationships: Lead conversations with sellers, advisors, and intermediaries throughout diligence, building trust and lasting relationships through a stressful process.

• Lead Diligence: Execute financial, commercial, operational, and organizational diligence, translating learnings to valuation and operating models.

• Synthesize & Recommend: Synthesize complex information into clear investment decisions, articulating what matters, key risks, and a coherent value creation plan.

• Steward Integration: Execute post-close transition and support new companies in the first 30-90 days with early strategic planning, leadership alignment, and operational priorities.

• Build the Engine: Continuously improve the processes and infrastructure that make disciplined deal execution repeatable at scale.

Success will be measured by closed acquisitions on disciplined timelines and terms, no material surprises in the first year of ownership, and CEOs who feel set up to win from day one. 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 4-7 years of direct deal execution experience at a private equity firm, independent sponsor, or search fund. More importantly, you are:

• Proven Closer: Led or co-led multiple transactions from LOI through close, managing diligence workstreams, advisors, and timelines with increasing independence.

• Commercially Judicious: You consistently distinguish great businesses from good ones and understand why a deal works, where it breaks, and when to walk away.

• Analytically Rigorous: Comfortable evaluating financials, building structured models and analyses, and synthesizing complex systems.

• Composed Operator: Stoic, organized, and detail-oriented in high-stakes situations, able to manage multiple workstreams on compressed timelines without sacrificing judgment.

• Trustworthy: You earn trust quickly through humility, authenticity, and reliability.

• Effective Communicator: Write and speak clearly, crisply, and thoughtfully, engaging founders and counterparties with credibility and professionalism.

• Ownership-Oriented: You take pride in your work, operate with urgency, and thrive in environments where autonomy and accountability go hand in hand.

• Learning Machine: Insatiably curious, actively reflective, and rapidly update beliefs, actions, and systems based on feedback and outcomes.

• Long-Term Oriented: Motivated by building durable businesses and compounding long-term equity value rather than simply executing transactions.

Why This Will Be Challenging

• Deals Die Late: At our stage, every deal in diligence is a significant investment of time. When they fall apart (and some will), it can be disheartening. You must be able to reset quickly and maintain conviction in the process.

• No Steady State: There is no quiet season. Each deal is intense and demands full presence. You will need to manage energy and judgment across compressed timelines and irregular deal flow.

• Discipline is Structural: Our ‘Rule of 10’—a simple guardrail linking customer churn and entry multiple—enforces quality and price discipline. Many deals will be good but not good enough.

• Uncommon Commitment: We’re in pursuit of excellence, which requires intense focus, high standards, and obsession with the craft.

This role rewards judgment, rigor, and composure.

Why It’s Worth It

• Foundational Impact: You’re joining early. The deals we close, and the discipline with which we close them, will define Bristlecone for decades. That starts with you.

• Compounding Upside: Most acquisition roles operate inside structures that eventually force exits. Ours doesn’t. The equity you earn today compounds alongside the businesses we own for decades.

• Hidden Gems: You’ll spend your time deeply understanding the hidden gems of American business. If you genuinely enjoy exploring overlooked corners of the economy, you’ll be in good company.

• Aligned, Engaged Backing: We’re backed by investors and operators who are active, opinionated, and committed to building alongside us. You'll be challenged and supported in equal measure.

This role is based in Chicago with periodic travel for diligence and site visits. Compensation includes a competitive base salary, performance-based bonus tied to closed acquisitions, and meaningful equity participation structured for long-term compounding.