Founding Chief of Staff — Strategy & Operations

Remote, USA • Full-time • Posted 2026-05-31

We are a decision operating system that helps businesses create intelligent workflows to make better decisions. We focus on enabling financial services, fintechs, and insurers to become fully intelligent enterprises — where workflows become intelligent systems across the organization. We are looking for a Founding Operator who thinks fast, moves faster, and builds systems that compound. You will work directly alongside the Founder to run the company.

What You’ll Do

Design and own the operating rhythm of the company — priorities, cadence, and accountability across every function
Build lightweight but durable systems that scale with the team as we grow from 10 to 50
Translate the Founder’s vision into structured weekly execution, ensuring top priorities get executed with excellence

Extend the Founder's capacity across capital, product, and team — providing structured and relentless execution
Prepare, debrief, and follow through on every high-stakes conversation — investor meetings, customer calls, recruiting
Be the person who catches what falls through and closes it without being asked

Partner with engineering and product to track platform stability metrics — uptime, error rates, deployment success across the OS platform
Own the internal product review rhythm — weekly status, flag blockers before they reach the Founder
Coordinate QA processes and ensure quality standards are met before any customer-facing deployment
Build the feedback loop between early customers and the product team — structured, fast, actionable
Maintain a live product roadmap dashboard visible to the full team and investors

Own the operational side of every pilot — onboarding checklist, timeline, stakeholder map, success metrics Coordinate between the GTM team and engineering to ensure pilots launch on time and land well
Build the pilot playbook from scratch — reusable across every new customer
Capture and structure customer feedback into product briefs for the team

Run investment close process with the Founder — investor CRM, outreach sequencing, materials, follow-up cadence
Own the data room — keep it current, organized, and investor-ready at all times
Prepare the Founder for every investor meeting — brief in, debrief out, action items closed
Track every open capital conversation to resolution
Coordinate due diligence requests across legal, finance, and product

Build and own the full recruiting operating system — pipelines, panels, scorecards, offers, onboarding
Own ongoing recruiting ops as headcount scales from 10 to 50+
Develop onboarding playbooks so every new hire is productive and culturally aligned from week one
Build the advisor network ops — equity agreements, engagement cadence, activation for referrals and introductions

3–7 years at a growth startup, MBB, Big4, or Big Tech — you have seen how fast-paced organizations, teams, or client engagements operate
Your friends describe you as the person who always has a plan
You get unreasonably excited about a well-structured agenda
You have strong opinions about how things should run. You are usually right.
No job description has ever fully described your job. You liked it that way.
You are a closer.
You are motivated by ownership and mission — you are tired of making someone else’s vision look good in a deck
You hold yourself to a standard most people find uncomfortable. High ambition, high execution, and high accountability.

Experience supporting or leading an AI strategy or transformation, or complex cross-functional initiative
Experience in fintech, financial services, insurance, or enterprise SaaS
Prior experience supporting early-stage fundraising or technical diligence

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