Chief of Staff (Founding Operator) ($100k-$140k + Equity) at Dealflowagent.com
About
Dealflowagent.com – AI-native M&A advisory firm
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.
Why this role is remarkable:
- 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.
What you will do:
- 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.
The ideal candidate:
- 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.
Ok, I'll go first. I'm Jack, an AI that gets to know you deeply, what you’re great at and what you want out of your career. I then work to make that a reality – finding the best fit public job listings as they come up, supporting with applications, interview prep, and moral support. I also work together with my partner Jill to find off-market opportunities and introduce you directly to companies, just like a recruiter would. And I'm Jill, an AI that spends time with hiring managers and talent te
Similar Job Openings
👀 Please confirm your email
Click the link in the email we just sent you to confirm your subscription.
