Execute daily outbound prospecting via cold calls, email sequences, and LinkedIn to business owners in the community management industry
Manage an outsourced data sourcing team to continuously find and enrich target contact lists
Conduct introductory seller meetings — qualify fit, collect key financial and operational information, and determine timing
Maintain a disciplined CRM pipeline (HubSpot) across hundreds of active prospects at varying stages of readiness
Build and sustain relationships with business brokers, M&A intermediaries, and referral partners through regular check-ins and conference attendance
Organize and host local gatherings with prospective sellers and TCC Member Company leaders to advance relationships
Work directly with co-founders to structure transactions and negotiate letters of intent through to close
Identify and implement improvements to TCC's AI-enabled outreach automation stack on an ongoing basis

2–4 years of experience in a business development, outbound sales, or deal origination role
Proven track record of cold calling and outbound prospecting in a B2B environment
CRM proficiency — HubSpot or Salesforce; consistent, accurate pipeline management
Experience building and delivering presentations to senior decision-makers (PowerPoint or Google Slides)
Comfort with sales automation and AI-enabled outreach tools (e.g., Apollo, Outreach, Salesloft, or similar)
Strong verbal and written communication skills — ability to build trust with business owners quickly
Self-directed and organized — able to manage a high volume of simultaneous prospect relationships without oversight
Bachelor's degree
Nice to Have
Background in M&A advisory, private equity, commercial banking, financial advisory, or insurance — any role where calling on business owners was the job
Experience managing an outsourced or offshore research/data team
Familiarity with the community association management (HOA/CAM) industry
MBA

$110,000 OTE — $55,000 base salary plus commission
$1,500/month in guaranteed commissions for the first three months (ramp protection)
Fully remote with high autonomy — you own your schedule and your pipeline
Direct mentorship from TCC's co-founders on live acquisition deals
Clear career path into a senior origination or deal execution role as TCC scales nationally
Quarterly in-person team gatherings in Chicago

Business Development Associate – Acquisitions

Key skills