Investment Lead (Origination)

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 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 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 3-6 years of M&A origination experience at a private equity firm or a serial acquirer and a prior background in investment banking, sales, recruiting, or expert networks. More importantly, you are:

• Proven Originator: Demonstrated ability to source 1-3 proprietary acquisitions per year, ideally platform investments in the lower middle market valued on cash flow (or EBITDA).
• Trustworthy: Earns trust quickly through humility, authenticity, and reliability.
• Relentless: Disciplined, persistent, and resilient in the face of long odds-comfortable hearing "no" (or nothing!) many times before hearing "yes."
• Effective Communicator: You write and speak clearly, crisply, and thoughtfully. You can engage founders with credibility and professionalism.
• Analytically Fluent: Comfortable evaluating business quality, market structure, and financial performance with the commercial judgment to identify opportunities worth deeper diligence.
• 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 an origination engine and durable businesses that compound long-term equity value rather than simply executing transactional deal flow.
• Old Soul: Thoughtful, observant, and mature beyond your years, naturally drawn to meaningful conversations, enduring businesses, and relationships that compound over time.

Why This Will Be Challenging

• Building the Engine in Flight: Pipeline, infrastructure, and process are still early. You'll operate with real autonomy in an unstructured environment, hustling for the next acquisition while building the systems that make proprietary deal flow repeatable.
• No Shortcuts: Building differentiated access to great businesses takes time. In a competitive market, our edge comes from disciplined sourcing, authentic relationships, and a reputation built over many years. You must find joy in the work itself, not just the close.
• 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 curiosity, persistence, and craftsmanship.

Why It's Worth It

• Foundational Impact: You're joining early. Where we play, how we source, and what we become will have your fingerprints for decades.
• 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 uncovering 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 frequent travel to build differentiated relationships with owners in person. Compensation includes a competitive base salary, performance-based bonus tied to closed acquisitions, and meaningful equity participation structured for long-term compounding.