Chief of Staff (Founding Operator) ($100k-$140k + Equity) at Dealflowagent.com
About The Position
As the Founding Operator, you will be the engine of an AI-native firm modernizing M&A for $1M-$50M revenue businesses. You will own critical functions across GTM, product, and operations, working directly with an exited founder to scale proprietary conversational AI agents. This is a high-impact, hands-on role for a technical generalist ready to build from 0-to-1. Backed by elite operators including founders with 9-figure exits, former Investment Banking MDs, and PE fund managers who understand the $1M-$50M market gap. Extreme technical leverage using proprietary AI agents (Sage and Sterling) to automate the operational grind, evidenced by a recent healthcare deal closed in just 9 weeks. Unique compensation structure including a $90k base, 1% equity with accelerated vesting, and a performance-based profit share yielding up to $50k in Year 1.
Requirements
- Proven experience in M&A advisory, investment banking, or brokerage with a deep understanding of LOIs, due diligence, and managing emotional transaction cycles from start to close.
- Strong technical DNA with the ability to build no-code automations and systems; you must have experience shipping features or workflows in a startup environment.
- High-agency operator with a "no task too small" mentality, capable of navigating the chaos of a seed-stage company without needing a pre-defined playbook.
Responsibilities
- Manage end-to-end M&A processes for clients, including building financial models, drafting 30-page information memorandums, and coordinating with legal and accounting advisors.
- Architect and execute GTM growth strategies, running outbound business development campaigns and managing brand presence to attract both business sellers and acquirers.
- Translate customer pain points into product features, working directly with engineers to ship automated workflows and maintain internal operating systems in Notion.
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
Number of Employees
1-10 employees
