I Asked My AI to Write my Perfect Job Description
For years, my résumé has been a problem. Not because it lacked experience, but because it contained too much of it across categories that are not supposed to overlap.
Real estate operator. Nonprofit executive. Technology architect. CEO. COO. CTO. Author. Systems builder.
Each role made sense on its own. Taken together, they created confusion. People wanted a single lane. Boards wanted a box. Professional bios wanted a headline that fit cleanly into a predefined hierarchy.
Rather than continuing to compress my work into something smaller than it actually was, I tried a different approach. I asked my AI to write the job description I should have been hired into all along.
Not a nonprofit role. Not a pure technology role. Not a traditional real estate role.
A role that assumed the overlap was the point.
What came back was not surprising because it was flattering. It was surprising because it was precise. It is named the work I have been doing for years, but never had a clean language for.
The role it surfaced was simple and specific.
Chief Operating Officer and Head of Digital Infrastructure.
That title ties everything together.
It describes someone responsible for both the physical performance of a business and the systems that make that performance scalable. It assumes the company has real assets, real capital at risk, and real operational complexity. It also assumes that technology is not a support function, but the operating system of the business itself.
This kind of role barely existed a decade ago. Historically, operations leaders ran people, buildings, vendors, and processes. Technology leaders ran tools, integrations, dashboards, and roadmaps. That separation worked when software was optional and scale happened slowly.
It breaks down when portfolios are national, margins are thin, labor is expensive, and AI can replace entire layers of manual coordination. In that environment, the most valuable operator is not the person who manages well. It is the person who designs systems so well that management becomes lighter.
That is what this role is built for.
When you strip the job description down to plain language, it describes someone who builds digital infrastructure that replaces manual workflows instead of decorating them. Someone who turns a sprawl of SaaS tools into a coherent operating system. Someone who uses structured data, automation, and AI agents to reduce dependency on headcount. Someone who oversees real assets and real markets, not abstract products. Someone who prepares a company for diligence, M&A, or exit by making the business legible and defensible.
This is not innovation theater. It is operational gravity.
The work is about making a company run cleaner, faster, and more predictably than competitors who are still duct taping systems together.
When I look at my own background through this lens, the throughline becomes obvious. Nonprofit leadership taught me how to operate under constraints, scrutiny, and mission clarity. Real estate taught me how unforgiving physical assets can be. Technology taught me how leverage actually works. Writing taught me how to explain complex systems to humans who have to make decisions about them.
None of those experiences fit neatly into a single traditional title. Together, they map cleanly to a role that sits between private equity expectations, real assets, and modern digital infrastructure.
It is neither a visionary nor a tactical role. It is architectural.
What struck me most about the job description was not the seniority or the compensation range. It was the assumption underneath it. The assumption that operations and technology are no longer separate disciplines. The future COO must be systems literate. The future CTO must understand the P&L. The companies that win will be the ones whose infrastructure is invisible because it works.
This reflection connects directly to something else I have been writing about recently.
In Collapsing the Skill Stack: How AI Turned a 10-Person Team Into One Operator, I described a quiet shift that most people are still missing. AI did not just make writing, coding, or design faster. It collapsed the distance between them. Writing, research, editing, design, data extraction, automation, SEO, analytics, and customer communication are no longer separate professions. They are functions inside a single interface.
That collapse changes who can build and how fast they can do it. It turns coordination into a non-issue. It shifts leverage from organizations to operators. It rewards clarity over headcount.
Seen together, these two essays are about the same shift viewed from different directions.
Collapsing the Skill Stack explains how one operator can now do the work that once required an entire team. This job description exercise explains who that operator becomes once the stack collapses.
When skills converge into a single interface, roles have to converge as well. You no longer need one person to run operations and another to run technology. You need someone who understands that operations are technology. That systems design is strategy. That leverage comes from architecture, not headcount.
The title Chief Operating Officer and Head of Digital Infrastructure is not aspirational. It is descriptive. It names the role that naturally emerges when a single person can design workflows, build systems, oversee assets, and translate all of it into measurable business outcomes.
This is why small teams suddenly feel dangerous and why traditional organizations feel heavier than they should. The bottleneck has moved. It is no longer tools, talent, or access. It is clarity, judgment, and the ability to orchestrate outcomes across domains.
AI did not simply give us better software. It collapsed the distance between thinking and doing.
Once that happens, the most valuable people are not specialists protecting narrow lanes. They are operators who can hold the whole system in their head and move it forward deliberately.
That is the role I asked the AI to describe.
In a world where the skill stack has already collapsed, it turns out that role has been hiding in plain sight.
Chief Operating Officer & Head of Digital Infrastructure
Organization Type: A mid-market Private Equity-backed firm, a "PropTech" scale-up, or a high-end commercial real estate developer specializing in tech-enabled workspaces (e.g., proworking).
Position Overview
The Chief Operating Officer (COO) and Head of Digital Infrastructure will be the principal architect of the firm’s operational scale and technological superiority. This is a "dual-engine" leadership role. You will be responsible for the physical performance of the organization—overseeing multi-market operations and asset management—while simultaneously building the proprietary digital systems that power those operations. The ideal candidate replaces traditional manual workflows with agentic AI, turning the company into a digital-first leader in its asset class.
Core Responsibilities
Digital-First Scaling: Architect and implement the firm’s enterprise system design, moving beyond standard SaaS integrations to build bespoke, automated workflows that reduce operational friction and headcount dependency.
Proprietary Technology Strategy: Lead the development and deployment of internal technology platforms, focusing on structured data, predictive analytics, and AI-driven marketing systems to maximize asset yield.
National Asset & Market Operations: Manage the operational lifecycle of a national real estate or proworking portfolio. This includes streamlining site acquisition, facility maintenance, and the "proworker" experience through technology.
Growth & Performance Marketing: Oversee the digital marketing engine, utilizing advanced SEO and Generative Engine Optimization (GEO) strategies to drive high-intent lead generation and brand authority.
Operational Governance: Lead the integration of finance, legal, and HR systems into a single source of truth. Ensure that the organization’s digital infrastructure is secure, compliant, and ready for high-level M&A or exit activity.
Qualifications & Experience
Dual C-Suite Background: Demonstrated success in both Chief Executive and Chief Technology roles, with a specific focus on scaling operations from local to national levels.
Advanced Systems Design: Expert-level knowledge of AI-enabled operations, CRM automation (e.g., Salesforce, HubSpot), and bespoke technology infrastructure.
Business Strategy: MBA from an accredited institution with a deep understanding of P&L management, capital allocation, and board-level reporting.
Published Thought Leadership: A track record of producing high-level industry content (books, whitepapers, or strategic blogs) that establishes brand authority and attracts high-value partners.
High-Level Communication: Ability to translate complex technical roadmaps into strategic business outcomes for investors and stakeholders.
The Compensation Opportunity (2026 Projections)
In the commercial and tech-enablement space in Austin, this "unicorn" profile—combining MBA-level business acumen with CTO-level technical depth—commands a premium compensation package:
Base Salary: $325,000 – $415,000
Performance Bonus: 30% – 50% of base, tied to efficiency gains and revenue growth.
Equity / LTI: 1.5% – 2.5% equity stake or long-term incentive plan (LTI) based on exit-oriented milestones.
Total Target Compensation: $450,000 – $700,000+
