Executive Operations Associate to Enterprise-level Chief of Staff: A Corporate Executive Apprenticeship with Personal & Business Support
A structured, hands-on executive apprenticeship for a sharp, driven early-career professional - built with one clear destination: becoming Chief of Staff to a fast-paced CEO across an enterprise of businesses spanning the boardroom, financial markets, property and commercial real estate, software development, and ranch and personal operations.
Position Summary
A fast-paced entrepreneur, CEO, and business owner is seeking a highly capable and adaptable Executive Operations Associate to enter a structured, multi-year apprenticeship with a single defined outcome: Chief of Staff.
This is not a traditional desk-assistant role or a lateral hire. It is a performance-based track in which the successful candidate takes on progressively greater ownership across personal, corporate, real estate, property, financial, and operational responsibilities, alongside the CEO's current Chief of Staff, who is advancing to lead the CEO's suite of AI-based software applications. The candidate learns hands on, building the judgment, relationships, and track record to eventually run the CEO's office as Chief of Staff.
The right candidate will start by supporting corporate initiatives and strategies, preparing for executive meetings, interacting with senior business leaders, assisting with boardroom-level communication, helping execute real estate, ranch, land management, and property development, and assisting on AI-based software projects bound for domestic and international retail distribution. As trust and capability grow, so will responsibility - from execution, to ownership of individual workstreams, to eventually moving into the current Chief of Staff's role as the executive's primary gatekeeper and strategic right hand.
This role is for a sharp, ambitious, dependable early-career professional who wants a defined path to executive leadership - not just exposure to it. Advancement to Chief of Staff is the intended outcome, contingent on demonstrated performance, discretion, and judgment; a rare opportunity for a rare candidate.
About the Opportunity
This position is for someone who wants to learn from direct exposure, not theory, how businesses, leadership, operations, property, land management, real estate development, and entrepreneurship actually work - by doing the job side by side with the CEO, not observing it.
The selected candidate will not watch from the sidelines, but participate, solve problems independently, follow through, and grow deliberately toward the Chief of Staff role over time.
The Apprenticeship Path: Associate to Chief of Staff
This role is a three-phase apprenticeship. Movement between phases is earned through demonstrated ownership, judgment, discretion, and results - not tenure. The timeframes below are targets, not guarantees: an exceptional candidate may move faster, and the pace is always set by readiness, not the calendar.
Phase 1 (Months 1-6) - Executive Operations Associate
- Learn the full scope of the business, ranch, financial, property, real estate, software, and personal operations.
- Execute day-to-day logistics, scheduling, vendor coordination, and supporting ranch/property operations.
- Shadow the executive in meetings and begin handling low-risk correspondence and follow-up independently.
- Build the trust, discretion, and track record to take on larger responsibility within the first six months.
Phase 2 (Months 7-12) - Senior Associate / Deputy Chief of Staff
- Take ownership of specific workstreams - a real estate project, a new business opportunity, a recurring process - start to finish.
- Represent the CEO independently in select vendor, contractor, and business interactions.
- Manage other vendors and coordinate cross-functional priorities without direct supervision.
- Begin sitting in on executive and boardroom discussions in a working capacity, not just note-taking.
Phase 3 (Year 2+) - Chief of Staff
- Own the CEO's operating rhythm across all business and personal priorities.
- Serve as the primary filter and gatekeeper for the CEO's time, priorities, and information flow.
- Represent the executive in boardroom and business settings with authority to act on his behalf.
- Lead special projects and strategic initiatives from concept through execution to completion.
Key Responsibilities
These responsibilities span the full apprenticeship. In Phase 1 the emphasis is on hands-on execution and learning; by Phase 3 it shifts to ownership, delegation, and strategic judgment as Chief of Staff.
Executive & Corporate Support
- Provide direct support to the entrepreneur across multiple businesses, projects, meetings, and priorities.
- Coordinate calendars, appointments, action items, deadlines, commitments, follow-ups, calls, meetings, travel, events, and daily logistics through the Personal Assistant to the CEO.
- Prepare for executive meetings by organizing materials, notes, agendas, documents, and follow-up items.
- Assist with boardroom-level communication, executive presentations, meeting preparation, and business correspondence.
- Interact professionally with executives, business owners, investors, attorneys, consultants, contractors, vendors, and senior contacts.
- Assist with corporate research, vendor communication, document organization, project tracking, and business development.
- Attend meetings when needed, take notes, summarize key points, and help ensure follow-through.
- Help the CEO's Personal Assistant and other executives coordinate corporate events, business meetings, site visits, and executive interactions.
- Handle confidential business and personal information with absolute discretion.
- Assist with special projects, operational initiatives, and problem-solving as they arise.
- Build the relationships and judgment to eventually manage the CEO's calendar, priorities, and information flow independently as Chief of Staff.
Personal & Household Support
- The Executive Operations Associate maintains ultimate responsibility for the following through direct management of the Personal Assistant to the CEO:
- Assist with personal scheduling, errands, appointments, purchases, deliveries, and daily logistics.
- Assist the CEO's Personal Assistant in coordinating household vendors, contractors, repair, landscaping, and maintenance providers.
- Help manage personal projects, family logistics, travel plans, events, and special requests.
- Maintain organization and communication across personal, business, property, and ranch responsibilities.
- Anticipate needs, identify issues early, and take initiative to resolve them.
- Ensure personal and professional commitments are tracked, organized, and completed.
- Reduce unnecessary distractions so the executive can focus on high-value priorities.
Real Estate Development & Property Project Support
The role may also include support for real estate, construction, property improvement, and land development projects. Responsibilities may include:
- Coordinating contractors, architects, engineers, vendors, inspectors, and consultants.
- Helping track project timelines, budgets, bids, estimates, invoices, permits, and punch lists.
- Attending site visits and helping document progress, issues, and next steps.
- Coordinating property improvements, land clearing, access roads, buildings, utility work, barns, gates, fencing, landscaping, and related work.
- Helping manage communication between the CEO, contractors, vendors, and stakeholders in a decision-making capacity.
- Documenting property conditions and tracking development or maintenance priorities.
- Assisting with due diligence, property research, vendor comparison, and project organization.
- Helping move real estate and property projects from idea to completion.
Professional Representation
The candidate must be polished, trustworthy, and able to represent the CEO well across environments - and increasingly, to represent the CEO directly as they advance toward Chief of Staff.
This may include:
- Communicating professionally with executives, investors, vendors, attorneys, contractors, employees, and family members.
- Dressing and presenting appropriately for business meetings, ranch settings, executive environments, property visits, and events.
- Exercising excellent judgment in public and private interactions.
- Maintaining confidentiality, discretion, and loyalty at all times.
- Knowing when to speak, when to listen, when to ask, and when to simply get things done.
- Being positive and professional to be around while maintaining urgency and accountability.
Ideal Candidate Profile
The ideal candidate is early in their career but mature beyond their years: intelligent, hardworking, practical, coachable, physically capable, and hungry for a defined path to meaningful responsibility - someone who wants real-world experience, not the traditional path up the ladder.
A strong candidate may have:
- A business, finance, management, entrepreneurship, agriculture, ranch or construction management, real estate, or related four-year degree, with or without an MBA.
- Recent college graduate or early-career professional experience.
- Executional-level understanding of computer software, AI LLMs, and other IT-related matters.
- Experience with financial matters and willingness to operate independently, with the CEO's portfolio as the ultimate priority.
- Familiarity with ranching, hunting, land management, outdoor work, equipment, trailers, tractors, real estate, or construction.
- Prior firearm experience and a strong respect for firearm safety, responsible handling, and hunting-related safety practices.
- Strong interest in business, finance, entrepreneurship, leadership, operations, real estate, and executive management.
- Comfort moving between corporate, personal, ranch, and property environments.
- A polished, professional presence with strong communication skills.
- Ability to work independently, solve problems, and figure things out.
- A high level of drive, loyalty, humility, and coachability.
- A genuine, long-term commitment to becoming a Chief of Staff - not simply working alongside one.
Required Qualifications
- 4-year bachelor's degree from an accredited college or university.
- Strong organizational and communication skills.
- High level of discretion and confidentiality.
- Professional appearance and demeanor.
- Ability to work in a fast-paced, changing environment.
- Willingness to work flexible hours when needed.
- Strong work ethic and ability to take ownership of tasks.
- Comfortable interacting with senior executives, business leaders, vendors, contractors, service providers, and family members.
- Proficiency with technology, including email, calendars, documents, spreadsheets, phones, and task-management tools.
- Prior firearm experience, with a strong understanding of firearm safety and responsible handling.
- Valid driver's license and clean driving record.
- Clean legal background.
- Must be dependable, punctual, trustworthy, and highly responsive.
- Comfortable with both office-based work and hands-on outdoor responsibilities.
- Willingness to commit to a multi-year apprenticeship track toward the Chief of Staff role.
Preferred Qualifications
- Bachelor's degree in business, management, entrepreneurship, finance, agriculture, ranch or construction management, real estate, or a related field.
- Coding and software development familiarity or experience, LLM integration and programming, and technological acumen for installation, integration, testing, monitoring, maintenance, and replacement of IT-related equipment.
- Experience in financial markets, with broad knowledge of financial vehicles pertaining to lending, financing, budgeting, and portfolio management.
- Formal firearm safety training, hunter education, license to carry, military or law enforcement training, or similar documented safety training.
- Hunting and game management experience: hunting practices, blinds, feeders, game cameras, logistics, season preparation, ranch operations, ranch equipment, trailers, tractors, and outdoor property work.
- Prior experience in ranching, construction, agriculture, logistics, real estate, property management, family business, entrepreneurship, military, or operations.
- Strong understanding of ranch and hunting culture, rural property needs, and land stewardship.
- Ability to communicate confidently with everyone from executives to contractors.
- Experience coordinating vendors, contractors, maintenance teams, or property projects.
- Explicit, demonstrated interest in a multi-year career path to Chief of Staff - candidates chasing a short-term assistant job are not a fit.
Traits That Matter
The right person will be:
- Smart, practical, and resourceful.
- Educated and articulate.
- Loyal, discreet, and trustworthy.
- Driven, ambitious, and coachable.
- Physically capable and not afraid of hands-on work.
- Professional and presentable in executive settings.
- Comfortable in a boardroom, on a ranch, at a construction site, or in a business meeting.
- Responsible and safety-minded around firearms, hunting activities, equipment, vehicles, and property operations.
- Fun to be around.
- Calm under pressure.
- Comfortable with ambiguity.
- Detail-oriented without needing to be micromanaged.
- Able to shift quickly between personal, corporate, ranch, and property responsibilities.
- Willing to do whatever needs doing - preparing for a CEO meeting, coordinating a contractor, checking a deer feeder, hauling a trailer, or organizing business follow-up.
- Genuinely motivated by the Chief of Staff destination, not just the day-to-day work.
What This Role Is Not
This is not a clock-in, clock-out administrative job.
This is not a remote position.
This is not a role for someone who only wants office work.
This is not a role for someone who has little to no understanding of software, computers, and IT.
This is not a role for someone who is uncomfortable outdoors, around ranch equipment, hunting operations, firearms, or physically active work.
This is not a role for someone who needs constant direction or avoids responsibility.
This is not a short-term job - it is a multi-year commitment with Chief of Staff as the defined destination.
This is a role for someone who wants to be trusted, challenged, taught, pushed, and deliberately developed into a CEO's Chief of Staff.
Growth Beyond Chief of Staff
This position offers the chance to work directly with an entrepreneur across multiple businesses, personal operations, finance, ranch and land management, real estate development, executive relationships, AI-based software development, and strategic projects - with Chief of Staff as the milestone, not the ceiling.
Once established as Chief of Staff, the role can expand: broader authority across the executive's businesses and properties, involvement in strategic and investment decisions, and - as with the CEO's existing Chief of Staff - a path toward senior leadership, expanded operating responsibility, or partnership-level involvement in the CEO's ventures.
Work Environment
This role will include a mix of:
- Office and corporate work.
- Executive meeting and boardroom preparation.
- Personal and household support through management of the CEO's Personal Assistant.
- Ranch, land, and property support alongside ranch operational staff.
- Real estate development and construction project support.
- Assistance coordinating software development, programmers, and other IT support efforts.
- Driving, meetings, site visits, and field-based responsibilities.
- Interaction with executives, vendors, contractors, employees, family members, and guests.
- Indoor and outdoor work in varying weather conditions.
This is not a 100% office job or a 100% outdoor job. It is a hybrid role for someone who can move comfortably between both worlds throughout the apprenticeship.
Schedule
This is a full-time position. The schedule may vary based on business, personal, ranch, and property needs, events, travel, hunting season, and special projects.
Flexibility, responsiveness, and availability are important.
Evening or weekend availability may occasionally be needed for travel, events, ranch operations, hunting season, property projects, or business priorities.
Compensation
Compensation is competitive and increases at each phase, based on experience, maturity, capability, education, ranch/outdoor skills, firearm safety experience, professional polish, judgment, reliability, and demonstrated progress toward Chief of Staff.
Phase 1 (Executive Operations Associate) compensation range:
$75,000 to $95,000 base salary, depending on qualifications and experience.
Exceptional candidates with meaningful executive support, operations, financial, ranch, real estate, construction, project management, software, or leadership experience may be considered for more.
Upon advancement to Phase 2 (Senior Associate / Deputy Chief of Staff) and Phase 3 (Chief of Staff), base compensation, bonus targets, and benefits will increase substantially and be benchmarked to market Chief of Staff compensation for a role of this scope - finalized at each promotion based on performance and market data.
Additional compensation and benefits may include:
- Performance-based bonus opportunity: $5,000 to $15,000 annualized (prorated during the six-month Phase 1 period), based on reliability, execution, discretion, initiative, project follow-through, ranch/property readiness, and ability to reduce demands on the executive's time - with targets rising at each phase.
- Vehicle access: Access to a company or ranch vehicle for approved business, ranch, property, and executive-support use.
- Mileage reimbursement: Reimbursement for approved business mileage when a personal vehicle is used.
- Business expense reimbursement: Reimbursement for approved business, ranch, property, and executive-support expenses.
- Structured compensation increases as responsibilities grow through each phase of the apprenticeship.
- Long-term potential for profit-sharing, bonus escalation, or equity-like incentives upon reaching the Chief of Staff role, to be discussed during the promotion process.
- Direct mentorship and executive exposure throughout the apprenticeship, alongside a seasoned Chief of Staff, with the goal of eventually assuming the role.
How to Apply
Qualified candidates should submit:
- Resume.
- Brief cover letter explaining why this role - and specifically the path to Chief of Staff - is the right fit.
- Description of any ranch, hunting, firearm safety, trailer, tractor, outdoor, land management, real estate, construction, operations, business, leadership, software, or executive support experience.
- Three professional or personal references who can speak to work ethic, character, reliability, judgment, safety, and trustworthiness.
Candidates should be prepared to discuss their career goals, business and financial experience, software experience, comfort with ranch and outdoor work, firearm safety and hunting experience, ability to represent an executive professionally, and commitment to a multi-year path to Chief of Staff.
Equal Opportunity Statement
We are an equal opportunity employer and consider qualified applicants without regard to any legally protected status.
Selection will be based on qualifications, experience, character, professionalism, judgment, physical capability for the essential duties, safety-mindedness, and long-term growth potential toward the Chief of Staff role.
Pay: $75,000.00 - $95,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Employee assistance program
- Health insurance
- Paid time off
- Relocation assistance
Work Location: In person
