Hands-On Operations Systems Builder / Fractional COO for Founder-Led Company

ABOUT THE COMPANY We are a growing, founder-led leadership development company that designs and delivers customized, high-touch leadership programs for colleges, corporations, foundations, and other institutional clients. Although we are a small company, our operations are complex. We manage multiple customized client engagements simultaneously, each involving numerous interconnected responsibilities, deadlines, deliverables, people, and approval points. Our programs may include: • Business development and proposals • Contract development and execution • Client onboarding • Program planning and customization • Participant recruitment and registration • Curriculum development • Facilitator and advisor coordination • Program calendars and scheduling • Assessments and evaluations • Client communication • Program delivery • Reporting • Graduation or program closeout • Renewals and follow-up Our current four-person team consists of: • Founder and CEO • Managing Director • Two Program Managers The Founder and CEO is currently the company’s: • Visionary and strategic leader • Sole salesperson and primary business developer • Principal subject-matter expert • Lead program and curriculum designer • Primary facilitator and talent • Senior client relationship leader • Final decision-maker and quality-control authority Although the Managing Director and Program Managers oversee program operations, the team continues to rely on the CEO daily for decisions, approvals, prioritization, clarification, hiring, quality control, and problem-solving. Every hour the CEO spends resolving operational issues is time she cannot dedicate to sales, strategic relationships, intellectual property development, program design, facilitation, and long-term company growth. THE CHALLENGE WE NEED TO SOLVE The CEO wants to step away from daily operations and redirect more of her time toward responsibilities that only she can perform. She has attempted to step away from operations in the past. However, when she does, important details, deadlines, client commitments, communication, or follow-up can fall through the cracks. This requires her to step back into daily operational management. We have already invested significant time and effort in creating: • Detailed program blueprints • Project spreadsheets • Procedures • Training materials • Accountability tools • Calendars • Templates • Some standard operating procedures However, the systems remain fragmented, highly dependent on individual employees, and potentially unsustainable as the company grows. Our challenge is not a lack of effort or commitment. The team works hard. However, no one currently has the combination of operational systems expertise, implementation experience, cross-functional perspective, and protected capacity required to build a fully integrated company operating system. We do not want to transfer operational dependence from the founder to the Managing Director or another employee. We want to build institutional infrastructure so the business does not depend on one person holding all the systems, knowledge, relationships, or processes. Our goal is to create operations where, if an employee is absent, changes roles, or leaves the company, another qualified person can step in with minimal disruption. THE PERSON WE ARE SEEKING We are seeking an experienced, hands-on Operations Systems Builder with fractional COO-level judgment. This is not a purely strategic, advisory, coaching, or delegation-based fractional COO role. We need someone who will personally: • Assess our current operations • Identify the most important operational risks and gaps • Design the appropriate systems • Build and configure the systems • Document the processes • Implement the systems with the team • Test the systems during active operations • Correct breakdowns • Train the team • Stabilize the infrastructure • Transfer ownership after the systems have been proven to work We are not looking for someone who will only deliver a diagnostic report, strategic roadmap, presentation, or list of recommendations for our existing team to implement independently. The selected contractor must be willing to work directly inside our documents, spreadsheets, program blueprints, calendars, project-management tools, workflows, SOPs, and reporting systems. You should be comfortable opening the spreadsheet, mapping the process, configuring the workflow, creating the template, drafting the SOP, establishing accountability, running the operating cadence, and testing whether the system works under real business conditions. PRIMARY OBJECTIVE The primary objective of this engagement is to replace founder-dependent operations with a centralized operating system spanning sales, hiring, client delivery, finance, accountability, institutional knowledge, and AI governance. The system must reduce the team’s daily reliance on the CEO while protecting quality, client relationships, accountability, and business continuity. SCOPE OF WORK 1. CONDUCT A COMPANY-WIDE OPERATIONAL ASSESSMENT The selected contractor will: • Review the current organizational structure • Review the responsibilities of the CEO, Managing Director, and Program Managers • Review current workflows, calendars, tools, systems, and decision-making processes • Review existing program blueprints, spreadsheets, SOPs, training materials, and accountability tools • Identify bottlenecks, duplication, missing processes, weak handoffs, and execution risks • Identify why employees continue to rely on the CEO for routine decisions • Identify where institutional knowledge is concentrated in one person • Identify where responsibilities are unclear, duplicated, or falling between roles • Evaluate whether the current systems can support future growth • Prioritize the systems that must be corrected or built first The assessment must lead quickly into implementation. We are not seeking a lengthy diagnostic process that ends with recommendations alone. 2. BUILD A CENTRALIZED COMPANY OPERATING SYSTEM The contractor will personally help us create a centralized operating infrastructure that connects: • Sales • Hiring • Client onboarding • Program planning • Program delivery • Team accountability • Financial administration • SOPs • Knowledge management • Quality control • AI-supported workflows The operating system should include: • One centralized operational command center • A company-wide master calendar • Visibility into all active programs and client commitments • Clear ownership of tasks and deliverables • Deadline and dependency tracking • Risk and escalation tracking • Capacity and workload visibility • A consistent system for documenting decisions • A clear system of record for tasks, documents, deadlines, and responsibilities • Reduced duplication across spreadsheets, documents, email, and project-management tools The contractor should evaluate our existing tools and recommend whether they should be improved, simplified, replaced, or integrated. 3. STANDARDIZE THE CLIENT LIFECYCLE The contractor will map and standardize the complete client lifecycle, including: • Lead generation • Opportunity qualification • Initial client conversations • Proposal development • Proposal follow-up • Contract development and execution • Internal sales-to-operations handoff • Client onboarding • Program customization • Program planning • Program implementation • Client communication • Quality control • Reporting • Invoicing coordination • Graduation or closeout • Renewal and follow-up We need a reusable task-delivery template that can be adapted for different leadership development programs and institutional clients. The standardized client lifecycle must include: • Clear phases • Required tasks • Assigned owners • Due dates • Dependencies • Approval points • Quality-control checkpoints • Communication expectations • Escalation criteria • Required documents • Completion standards The system must prevent client commitments from depending on the CEO remembering, monitoring, or personally following up on every detail. 4. BUILD SALES OPERATIONS AROUND THE CEO The CEO is currently the company’s sole salesperson and primary business developer. This engagement is not intended to replace the CEO as the salesperson. It is intended to build the operational infrastructure that supports her sales efforts and protects her selling time. The contractor will help us: • Create a centralized sales pipeline • Track leads, opportunities, proposals, follow-up, contracts, and next steps • Establish a consistent proposal-development process • Establish a process for preparing the CEO for sales meetings • Create a process for capturing decisions and action items after client meetings • Clarify what the CEO must personally complete • Clarify what the team can prepare, manage, or follow up on • Establish clear handoffs from sales into contracting, onboarding, and delivery • Ensure opportunities are not lost because follow-up is delayed or unclear • Reduce administrative work that pulls the CEO away from revenue-generating activity • Create visibility into the value and status of the sales pipeline 5. BUILD A STRUCTURED HIRING PIPELINE The CEO is currently involved in too many stages of hiring. We need a structured hiring process that reduces the CEO’s involvement to a clearly defined final approval point whenever possible. The contractor will help us create: • A workforce-planning and role-identification process • Standard job-description templates • Role scorecards • Candidate-screening criteria • Application-review procedures • Structured interview processes • Interview questions and evaluation rubrics • Reference-check procedures • Candidate-selection workflows • Offer and acceptance processes • Pre-onboarding checklists • Employee onboarding systems • Training plans • Knowledge testing • Early performance-monitoring processes • 30-, 60-, and 90-day employee review processes Hiring knowledge and decisions must be documented and not dependent on one person. 6. CLARIFY ROLES, RESPONSIBILITIES, AND DECISION RIGHTS The contractor will help us: • Clarify the responsibilities of the CEO, Managing Director, and Program Managers • Define who owns each recurring responsibility • Clarify what employees can decide independently • Clarify what requires Managing Director approval • Clarify what genuinely requires CEO involvement • Create clear escalation criteria • Reduce unnecessary approvals • Prevent responsibilities from falling between roles • Establish backup ownership for essential responsibilities • Develop role scorecards and measurable performance expectations • Establish accountability for deadlines, quality, communication, and follow-through • Recommend whether responsibilities should be reassigned, automated, outsourced, eliminated, or added to a future position The goal is not to remove the CEO from important decisions. The goal is to ensure the CEO is involved only where her judgment, authority, relationships, or expertise are truly required. 7. BUILD ACCOUNTABILITY AND MANAGEMENT RHYTHMS The company needs a clear operating cadence that allows leadership to identify problems before deadlines are missed. The contractor will help establish: • Weekly operations meetings • Standard meeting agendas • Weekly priorities • Employee commitments • Status reporting • Risk reporting • Decision logs • Escalation processes • Follow-up procedures • Deliverable tracking • Leadership dashboards • Monthly operational reviews • Documentation of decisions and ownership • Processes for addressing missed deadlines and repeated performance problems The CEO should be able to see the status of the company without gathering updates manually from multiple employees, spreadsheets, emails, and documents. 8. DEVELOP SOPS AND PROTECT INSTITUTIONAL KNOWLEDGE We need a practical SOP architecture that protects the company from employee turnover and inconsistent execution. The contractor will help us: • Establish standards for creating, naming, storing, updating, and approving SOPs • Identify the SOPs most critical to business continuity • Develop or improve priority SOPs • Create recurring-task checklists • Develop process maps • Create decision guides • Create reusable templates • Establish document ownership • Establish review and update schedules • Create cross-training processes • Create backup coverage • Create knowledge-transfer expectations • Ensure employees can locate and use the documentation • Test whether the SOPs are sufficiently clear for another qualified person to follow The systems should not reside solely in the CEO’s, Managing Director’s, or Program Managers’ heads. 9. BUILD FINANCIAL AND OPERATIONAL VISIBILITY This contractor will not serve as our accountant or CFO. However, we need stronger operational processes and visibility around financial responsibilities. The contractor will help us build systems for tracking: • Signed contracts • Proposals and pending opportunities • Client payment schedules • Invoices • Accounts receivable follow-up • Program budgets • Vendor and contractor commitments • Program delivery costs • Upcoming financial obligations • Capacity • Profitability indicators when reliable data is available The contractor will also help clarify responsibility for: • Invoice preparation and submission • Payment follow-up • Expense documentation • Budget monitoring • Contract payment schedules • Financial reporting to the CEO We need one executive-level view of the company’s financial and operational health. The CEO should not have to collect information manually from multiple employees, spreadsheets, or systems to understand what is happening in the business. 10. ESTABLISH AI WORKFLOWS AND GOVERNANCE We are actively exploring ways to use AI responsibly to improve efficiency, documentation, communication, and operational execution. The contractor will help us: • Identify appropriate uses of AI across operations, sales support, hiring, documentation, and client delivery • Identify processes that should not use AI • Establish standards for AI-generated work • Define required human review and approval • Establish confidentiality and data-handling standards • Protect client information and company intellectual property • Document approved tools and use cases • Create clear accountability for AI-assisted outputs • Establish quality-control standards • Build AI-supported workflows where they create meaningful value • Prevent employees from independently adopting tools or practices that create confidentiality, quality, or intellectual-property risks The objective is not to automate everything. The objective is to use AI intentionally, responsibly, and only where it strengthens the operation. 11. IMPLEMENT, TEST, AND STABILIZE THE SYSTEMS The selected contractor will: • Personally build and configure the initial systems • Lead implementation rather than only making recommendations • Run the systems with the team during active operations • Test whether the systems work under actual business conditions • Identify and correct breakdowns • Train the Managing Director and Program Managers • Evaluate whether employees can operate the systems independently • Refine the systems based on actual use • Create documentation and training materials • Establish clear ownership after implementation • Transfer responsibility only after the systems are functioning consistently We expect the contractor to remain involved long enough to determine whether the systems actually work. A system will not be considered complete simply because a document, spreadsheet, workflow, or platform has been created. It must be usable, adopted, tested, and producing greater clarity and reliability. EXPECTED OUTCOMES By the conclusion of the initial engagement, we expect to have: • One centralized company operating system • One reliable source of truth for tasks, deadlines, deliverables, decisions, and responsibilities • Clear ownership of every major recurring responsibility • Defined decision rights and escalation protocols • Greater visibility into deadlines, deliverables, risks, capacity, and financial responsibilities • A structured sales operations process that protects the CEO’s selling time • Clear handoffs between sales and client delivery • A standardized client lifecycle • A reusable program and task-delivery template • A structured hiring pipeline that reduces the CEO’s role to clearly defined approval points • Documented and accessible priority SOPs • Stronger employee accountability and follow-through • Business continuity and cross-training systems • Centralized operational and financial reporting • Documented AI governance and approved AI-supported workflows • Reduced dependence on the CEO • Reduced dependence on any single employee • More CEO capacity for sales, strategic relationships, intellectual property development, facilitation, and long-term growth REQUIRED EXPERIENCE Please apply only if you have: • At least five years of relevant operations leadership, business systems, process improvement, or operational implementation experience • Direct experience working with founder-led companies • Experience building operations for a small company with limited internal infrastructure • Experience supporting a company with multiple simultaneous clients, projects, or customized service engagements • Experience reducing employee dependence on a founder • Experience building systems that protect business continuity • Personally built workflows, SOPs, dashboards, hiring systems, accountability structures, and project-management systems • Experience connecting multiple business functions into one operating system • Experience implementing systems rather than only recommending them • Strong process-mapping, project-management, and documentation skills • Experience clarifying roles, responsibilities, handoffs, and decision rights • The ability to balance company-wide strategic thinking with detailed implementation • The confidence to challenge inefficient practices respectfully • The ability to work directly with a visionary founder and translate ideas into organized execution • Excellent written and verbal English communication • Strong follow-through, judgment, and attention to detail Experience with professional services, consulting, education, leadership development, coaching, agencies, or other high-touch service businesses is strongly preferred. Experience working with a company of fewer than 20 employees is strongly preferred. Experience with ClickUp, Asana, Monday.com, Airtable, Smartsheet, Notion, Google Workspace, Microsoft 365, CRM systems, automation tools, or similar platforms is helpful. We are more interested in your ability to design and implement the right operating system than in expertise with one specific software platform. THE IDEAL CANDIDATE The ideal candidate combines three distinct capabilities: EXECUTIVE-LEVEL JUDGMENT You can assess the company as a whole, identify root causes, prioritize the most important risks, and make sound recommendations about roles, systems, people, and execution. OPERATIONS SYSTEMS ARCHITECTURE You understand how sales, hiring, client delivery, financial administration, accountability, documentation, technology, and decision-making connect. HANDS-ON IMPLEMENTATION You are willing and able to personally build the first working version of the systems, implement them with the team, and correct them until they work. You should be able to say: “I have entered a founder-led company where operations were dependent on the founder, information was fragmented, responsibilities were unclear, and systems were not scalable. I personally built the operational infrastructure, implemented it with the team, tested it, and transferred ownership after it was stable.” THIS ROLE IS NOT A FIT IF YOU: • Primarily provide advice, coaching, or high-level recommendations • Expect our team to build all systems after you provide a roadmap • Prefer to delegate detailed implementation work • Are uncomfortable opening spreadsheets, reorganizing workflows, writing SOPs, or configuring project-management systems • Have only operated inside large companies with established departments and support teams • Primarily implement one software platform without addressing the larger operating model • Want to provide generic templates without learning the complexity of our business • Believe the solution is simply to hire more employees before correcting the underlying systems • Are seeking a board-level advisory position rather than a hands-on implementation engagement • Are uncomfortable working closely with a visionary founder • Do not have examples of systems you personally built • Cannot distinguish between work you performed and work completed by your team or subcontractors ENGAGEMENT STRUCTURE • Engagement type: Contract • Initial duration: Four months • Possible extension: Up to six months or an ongoing reduced fractional arrangement • Estimated commitment: Approximately 15–25 hours per week • Work arrangement: Remote • Required availability: Regular overlap with Pacific Time business hours • Start date: As soon as the right candidate is identified • Hourly range: $35–$60 per hour, depending on directly relevant experience and demonstrated implementation ability We anticipate that the strongest fit will likely fall within the $40–$50 per hour range. Higher proposals may be considered when supported by exceptional, directly relevant experience and evidence of measurable results. We expect to begin with a four-week paid assessment and implementation sprint. Continued engagement will depend on: • Quality of the operational diagnosis • Quality of the work product • Demonstrated implementation ability • Communication • Responsiveness • Ability to work with the team • Ability to reduce founder dependence • Ability to create usable systems rather than theoretical recommendations The full engagement should include defined 30-, 60-, 90-, and 120-day outcomes. We are open to an hourly or milestone-based structure, but the engagement must include sufficient working time for direct implementation. WHAT WE EXPECT DURING THE FIRST 30 DAYS During the first 30 days, we expect the contractor to: • Review the organizational structure and current responsibilities • Review existing operational tools, documents, blueprints, spreadsheets, and SOPs • Interview the CEO, Managing Director, and Program Managers • Identify the most serious operational risks and bottlenecks • Identify why the team remains dependent on the CEO • Identify what is working and should be preserved • Identify duplicate, fragmented, or unnecessary systems • Establish immediate priorities • Recommend the company’s system of record • Create an initial operating dashboard or command center • Establish a weekly operating cadence • Clarify immediate roles, ownership, and escalation rules • Begin implementing at least one high-priority workflow • Present a practical 60- to 120-day implementation roadmap The first month should produce visible operational improvements, not only analysis. HOW TO APPLY Please begin your proposal with the words: FOUNDER-LED OPERATIONS This confirms that you have read the complete posting. Please answer the following questions: 1. Describe a founder-led company with fewer than 20 employees where you personally built or rebuilt the operational infrastructure. 2. What was the company’s approximate stage, team size, and business model? 3. What operational problems did you inherit? 4. How dependent was the company on the founder when you began? 5. What systems, workflows, SOPs, dashboards, hiring processes, or tools did you personally create? 6. What work did you personally complete versus delegate to employees or subcontractors? 7. What measurable improvements resulted from your work? 8. Provide an example of how you reduced a company’s daily dependence on its founder. 9. How would you prevent operational dependence from simply transferring from the founder to the Managing Director? 10. What would you expect to complete during the first 30 days of this engagement? 11. What percentage of your time would be spent on direct implementation versus strategy, meetings, coaching, and delegation? 12. How would you determine which systems should be built first? 13. How would you confirm that a system is working before transferring ownership to the internal team? 14. How many hours per week would you recommend for the first four months, and why? 15. What is your hourly rate or proposed engagement fee? 16. What is your current availability? 17. How much overlap can you provide with Pacific Time business hours? 18. Are you applying as an independent professional or through an agency? 19. Will you personally perform the work described in your proposal? 20. Do you currently serve other clients, and how will you protect availability for this engagement? Please attach or describe an example of an SOP, dashboard, workflow, process map, project-management architecture, hiring system, accountability system, or operating cadence that you personally designed. Confidential information may be removed. Please clearly distinguish between work you personally performed and work completed by another employee, subcontractor, agency, or implementation team. Generic proposals will not be considered.