This Isn't a Normal Bookkeeping Job
Most bookkeeping positions look the same: categorize transactions, run reports, repeat. This one is different.
We're looking for a financial operations partner — not a data entry specialist. Someone who understands the why behind every journal entry, not just the how. Someone who can look at three LLCs with overlapping accounts and see a puzzle worth solving, not a mess to endure. Someone who will co-create the financial systems our growing multi-venture ecosystem needs — and eventually help us offer those systems to other small business owners.
You'll start in QuickBooks Online, because that's where our books live today. But the goal is to move beyond QBO and build something better: an AI-native bookkeeping ecosystem designed for the specific dynamics of small, multi-entity businesses run by real humans with real lives.
You don't need to know AI. We will teach you everything. Your AI education is free — a seat in our nationally recognized AIWE Certification and AI Action Classes, weekly hands-on training, and mentorship from practitioners who are building the future of AI-native accounting right now.
What you do need is the bookkeeping fundamentals, the curiosity to learn something new, and the kind of integrity that makes people trust you with everything.
If you've been looking for a role that values your expertise and your humanity — one that gives you flexibility, education, mentorship, and a genuine growth path — keep reading.
What You'll Do
You'll be managing finances across three distinct LLCs in different industries:
A growing industrial supply company that processes client orders, manages vendor relationships, and handles B2B invoicing. Revenue is strong and growing — this is the entity you'll start with.
A consulting firm that delivers AI training, workshops, and strategic execution services to public-sector and private-sector clients across the U.S. Revenue includes course fees, consulting retainers, and speaking engagements.
A real estate and natural resource entity with property tax, land management, and investment considerations. This entity comes later once you're established in the first two.
Your responsibilities will grow in phases. The work starts hands-on and practical, then expands as you build confidence and AI fluency.
Master the Current State
Take over all financial operations for one established LLC in QuickBooks Online: client order processing, invoicing, accounts receivable and payable, vendor reconciliation, and weekly financial reporting for the CEO. You'll manage the full order-to-cash lifecycle from customer intake through payment collection. Begin 9 hours of AI education through the AIWE Certification — on us.
Expand Across Ventures
Assume responsibility for a second entity's books: expense categorization, chart of accounts cleanup, personal-vs-business separation, and financial reporting. Support tax preparation in coordination with our CPA. Continue weekly AI education and begin applying AI tools to streamline your workflows — every week, your coursework produces real deliverables for the ventures you manage.
Build What Comes Next
Take on a third entity's financials. Co-create the AI-native bookkeeping ecosystem with Katie — a system designed to replace QBO and serve the specific needs of multi-entity small businesses. This is the infrastructure that will eventually become a scalable service offering.
Lead
The ecosystem you helped build becomes the foundation of a bookkeeping agency offering. Your role evolves from financial operations to financial leadership — with a path toward fractional CFO responsibilities, agency leadership, and negotiable financial upside including potential revenue share.
Who You Are
What You'll Get
Compensation is deliverable-based with a flat monthly retainer per entity. As you take on more ventures and co-create the AI ecosystem, your compensation scales. Milestone bonuses are tied to specific deliverables in building the AI-native bookkeeping system. The structure rewards output and initiative, not seat time.
Free AI Education
A full seat in the AIWE Certification (valued at $2,995), AI Action Classes, and ongoing weekly AI training. You'll learn by building real tools for real businesses.
Mentorship
Direct mentorship from Katie Milton Jordan, MBA, CBI, CEPA — and access to a network of practitioners who are building the future of AI-native financial services.
Flexibility
Fully remote. You manage your own schedule. We care about deliverables, not hours logged. You are welcome to maintain other clients and engagements.
Growth Path
This role has a ceiling only if you want one. The path leads to fractional CFO, agency leadership, revenue share, and the opportunity to help build a business from the ground up.
What It's Like to Learn From Katie
Part of this role includes free enrollment in our AI education programs. Here's what past students have said about the experience.
"You took her from intimidated by AI to using it and being curious about more! It has TOTALLY taken me to a new level with AI skills and enthusiasm seeing its potential!"
"Having everything summarized, which used to take me four or five hours, is now down to about 20 minutes. My peers had contracted a company to automate it for $30,000, which we don't have the budget for. So I built the workflows myself."
"Thank you for teaching me how to work with AI and think in ways I never thought possible."
"I wonder if you realize the trail you're blazing. You're the lifeline to a career, not just a helping hand. That's what you're doing."
"Katie was incredible. She walked us through how to build intentional AI workflows — not just prompts, not just tools — but systems that support how we actually think and work."
About Katie Milton Jordan
Katie Milton Jordan, MBA, CBI, CEPA is the Founder and CEO of SimpleEDO.ai and the leading authority on AI execution for economic development organizations. Through the AI Performance School and the AIWE Certification, she has trained dozens of professionals across the country to build AI workflows in their own fields — not with theory, but with real deliverables that produce measurable results.
She manages a multi-venture ecosystem spanning consulting, education, natural resources, and community media. Built across a career that includes buying her first business while living on a Mexican island, running a boutique consultancy through twelve years and three countries, and eventually landing in rural Texas, Katie is a navigator by nature — someone who walks into complex situations and figures out what actually needs to happen.
When she says she'll teach you the future of your profession, she has the curriculum, the tools, and the track record to back it up.
How We Hire
We believe in hiring slow and choosing well. This role requires trust, discretion, and character — so our process is thorough. Here's what to expect.
Written Application
Complete the application form below. It includes scenario-based questions, personality assessments (free, linked in the form), and questions about your values and work style. This is your first impression — take your time with it.
Video Interview
Candidates who pass the written round will be invited to a 30-minute video interview with Katie. We'll dig deeper into your scenario answers, explore how you navigate interpersonal dynamics, and talk about your goals.
Skills Assessment
Finalists will complete a brief, paid skills exercise: a mock reconciliation using sample data (not our live accounts). We'll evaluate accuracy, communication, problem-solving, and initiative.
References and Onboarding
We'll check your professional references, discuss NDA and confidentiality requirements, finalize compensation terms, and begin a structured onboarding that includes immediate AI education alongside hands-on financial operations.