First Hire - Deal Sourcing & Diligence Associate

Overview

You're employee #1 at a search fund. Your job is to help Julia Huebner source, diligence, and close the acquisition of a small American B2B services business (likely $1-10M revenue). You'll cold-call business owners, build financial models, coordinate lawyers and accountants, and do whatever needs doing to get a deal done. Post-acquisition, you'll likely move into an operating leadership role at the company you helped buy.

Role Snapshot

Company Context

Stage: Pre-acquisition search fund (essentially a startup)

Size: 2 people total (you + Julia)

Growth: Not hiring beyond this role until post-acquisition

Market Position: One of thousands of search funds competing for the same small pool of quality, owner-operated businesses for sale

GTM Reality

Pipeline Sources:

• 90% Cold outreach to business owners (calls, emails, LinkedIn)
• 10% Broker relationships, referrals from your network

Support Structure: None. You and Julia are the entire team. No admins, no analysts, no support staff.

Tools: You'll use whatever CRM Julia has set up (probably something simple), basic financial modeling in Excel, and a lot of phone/email.

Competitive Landscape

Main Competitors: Other search funds, traditional PE firms, strategic buyers, family offices, competitors trying to roll up the same industry

How They Differentiate: Hudson Street pitches a "clean, no-B.S. process" and promises to treat employees/customers well (vs. PE firms that gut companies)

Common Objections:

• "I'm not ready to sell yet"
• "I want to keep this in the family"
• "Your price is too low"
• "I don't trust private equity types"

Win Themes: Personal relationship with Julia, commitment to preserving company culture, speed of process

What You'll Actually Do

Time Breakdown

Sourcing (40%) | Diligence (30%) | Deal Coordination (20%) | Everything Else (10%)

Key Activities

• Cold Outreach: Make 30-50 calls/day to small business owners. Most won't answer. Of those who do, most will say "not interested." You're looking for the 1-2% who might be open to a conversation in the next 1-3 years.
• Relationship Building: Follow up with warm leads over months/years. Send quarterly check-ins. Build trust slowly. This is a long-game sales motion.
• Financial Analysis: Build models to value businesses. Pull tax returns, P&Ls, balance sheets. Identify red flags. Determine what you can afford to pay.
• Diligence Coordination: Once a deal gets serious, you're scheduling calls with customers, employees, suppliers. You're chasing down documents. You're managing lawyers, accountants, and lenders.
• Everything Else: Update the CRM. Write email sequences. Research industries. Book Julia's travel. Order lunch for diligence meetings. This is a startup—you do what needs doing.

The Honest Reality

What's Hard

• Rejection is constant: You'll call hundreds of business owners. Most won't want to talk. Of those who do, most won't want to sell. You need extreme patience and thick skin.
• Deals fall apart: You'll get 6 months into diligence and discover a major problem (customer concentration, messy financials, owner dishonesty). Months of work evaporate.
• Uncertainty: There's no guarantee you close a deal in year one. Or year two. Search funds sometimes take 3+ years to find the right company.
• Loneliness: It's you and Julia. No peers, no mentors beyond her, no team to bounce ideas off.
• Ambiguity: There's no playbook. You figure out what works through trial and error.

What Success Looks Like

• You build a pipeline of 50+ business owners you're actively nurturing relationships with
• You generate 2-3 serious LOIs (letters of intent) per year
• You close 1 acquisition within 12-24 months
• Post-acquisition, you successfully transition into a leadership role (e.g., VP of Ops, GM of a division)

Who You're Selling To

Primary Buyers (actually sellers in this case):

• Business owners of small B2B services companies ($1-10M revenue)
• Typically 55-70 years old, no succession plan, thinking about retirement
• Skeptical of private equity, protective of their employees and legacy

What They Care About:

• Will you preserve what they built? They want assurance you won't fire everyone and gut the company
• Price: Fair market value, but relationship matters more than an extra $500K
• Confidentiality: They don't want employees/customers to know they're exploring a sale
• Speed and certainty: They've talked to buyers before who wasted their time

Requirements

• College senior or 1-2 years professional experience (consulting, banking, startups, ops roles)
• Strong financial modeling skills (you need to build LBO models, comps, DCF analyses)
• Comfort with cold outreach and rejection (this is a sales role, even though you're buying not selling)
• High ownership mindset (there's no one to delegate to—if you don't do it, it doesn't get done)
• Genuine interest in running a business long-term (not just doing M&A for 2 years then leaving)
• Integrity (you'll handle sensitive financials and have access to confidential info)
• Willingness to relocate post-acquisition (the company you buy might not be in your current city)