Investment Lead (Execution)

Bristlecone Companies•Chicago, IL

4d•Onsite

About The Position

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. 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.

Requirements

4-7 years of direct deal execution experience at a private equity firm, independent sponsor, or search fund.
Proven ability to lead or co-lead multiple transactions from LOI through close, managing diligence workstreams, advisors, and timelines with increasing independence.
Ability to distinguish great businesses from good ones and understand why a deal works, where it breaks, and when to walk away.
Comfort evaluating financials, building structured models and analyses, and synthesizing complex systems.
Stoic, organized, and detail-oriented in high-stakes situations, able to manage multiple workstreams on compressed timelines without sacrificing judgment.
Ability to earn trust quickly through humility, authenticity, and reliability.
Ability to write and speak clearly, crisply, and thoughtfully, engaging founders and counterparties with credibility and professionalism.
Takes pride in work, operates with urgency, and thrives in environments where autonomy and accountability go hand in hand.
Insatiably curious, actively reflective, and rapidly updates beliefs, actions, and systems based on feedback and outcomes.
Motivated by building durable businesses and compounding long-term equity value rather than simply executing transactions.

Responsibilities

Drive every deal from signed LOI through close, managing timelines, workstreams, and counterparties with discipline, urgency, and care.
Lead conversations with sellers, advisors, and intermediaries throughout diligence, building trust and lasting relationships through a stressful process.
Execute financial, commercial, operational, and organizational diligence, translating learnings to valuation and operating models.
Synthesize complex information into clear investment decisions, articulating what matters, key risks, and a coherent value creation plan.
Execute post-close transition and support new companies in the first 30-90 days with early strategic planning, leadership alignment, and operational priorities.
Continuously improve the processes and infrastructure that make disciplined deal execution repeatable at scale.