Founding Operator Chief of Staff

Founding Operator Chief of Staff at Dealflowagent.com

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The next step is to speak to Jack.

Company Description:Dealflowagent.com - AI-native M&A advisory firm

Job Description:As the Founding Operator Chief of Staff, 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.

Location:Remote, USA

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.

Who are Jack & Jill?Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

Next steps

1. Visit our website.
2. Click 'Talk to Jack'.
3. Talk to Jack so he can understand your experience and ambitions.
4. Jack will make sure Jill (the AI agent working for the company) considers you for this role.
5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction.
6. If not, Jack will find you excellent alternatives. All for free.

We never post fake jobsThis isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

Key skills/competency

• M&A Advisory
• Investment Banking
• GTM Strategy
• Product Management
• Operations Management
• Business Development
• Financial Modeling
• Due Diligence
• No-code Automation
• Conversational AI