Investment Lead (Origination)

Bristlecone Companies•Chicago, IL

1d•Hybrid

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 help build our origination capability—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 develop investment theses, discover exceptional businesses, build lasting relationships with entrepreneurs, and drive opportunities from first conversation through LOI. More specifically, you will: Develop Theses: Conduct primary market research to identify fragmented industries where durable, high retention businesses are likely to exist. Discover Businesses: Proactively surface companies through research, referrals, and persistent outreach to founders and industry participants. Engage Owners: Engage entrepreneurs through thoughtful outreach and introductions across email, phone, LinkedIn, industry networks, and events. Build Relationships: Cultivate authentic, long-term relationships with owners, understanding their business challenges, long-term objectives, and catalysts for a sale. Qualify Opportunities: Evaluate financial profile, customer retention, and market position to determine which opportunities merit deeper diligence. Win LOIs: Position Bristlecone as the best long-term partner and convert promising opportunities to signed Letters of Intent, defining valuation and structure alongside the CEO. Build the Engine: Help design and refine the systems that make proprietary origination repeatable, maintaining CRM discipline and improving research, outreach, and pipeline management processes. Success in this role 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.

Requirements

3-5+ years of M&A origination experience at a private equity firm or a serial acquirer
Prior background in investment banking, sales, recruiting, or expert networks
Proven ability to source 1-3 proprietary acquisition opportunities per year, ideally platform investments across multiple verticals valued based on cash flow (or EBITDA).
Earns trust quickly through humility, authenticity, and reliability.
Disciplined, persistent, and resilient in the face of long odds—comfortable hearing “no” (or nothing!) many times before hearing “yes.”
Writes and speaks clearly, crisply, and thoughtfully. Can engage founders with credibility and professionalism.
Comfortable evaluating business quality, market structure, and financial performance with the commercial judgment to identify opportunities worth deeper diligence.
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 update beliefs, actions, and systems based on feedback and outcomes.
Motivated by building an origination engine and durable businesses that compound long-term equity value rather than simply executing transactional deal flow.
Thoughtful, observant, and mature beyond years, naturally drawn to meaningful conversations, enduring businesses, and relationships that compound over time.

Responsibilities

Conduct primary market research to identify fragmented industries where durable, high retention businesses are likely to exist.
Proactively surface companies through research, referrals, and persistent outreach to founders and industry participants.
Engage entrepreneurs through thoughtful outreach and introductions across email, phone, LinkedIn, industry networks, and events.
Cultivate authentic, long-term relationships with owners, understanding their business challenges, long-term objectives, and catalysts for a sale.
Evaluate financial profile, customer retention, and market position to determine which opportunities merit deeper diligence.
Position Bristlecone as the best long-term partner and convert promising opportunities to signed Letters of Intent, defining valuation and structure alongside the CEO.
Help design and refine the systems that make proprietary origination repeatable, maintaining CRM discipline and improving research, outreach, and pipeline management processes.