Inspector/ Fractional COO

Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered. WHO WE ARE Spyglass Ops helps founders scale themselves and their visions through operations. We partner with 7-8 figure digital entrepreneurs who are scaling with purpose: leaders who value impact, and a people-first approach to growth. Our mission is to transform operations from a bottleneck into the highest leverage point for business impact, growth, profit & freedom. We don't do cookie-cutter solutions. We dive deep to understand our client’s businesses, goals, and them as a person, then we level up their team & Ops foundation so they can scale toward their version of business and life that matters most. Founded by Jhana Li almost 5 years ago, after serving as COO at two successful startups, Spyglass has evolved from operator coaching to full-service, high-ticket operations transformation, including Fractional COO consulting, "done for you" operations recruitment, and Operations + leadership coaching. Our Core Values are: • Play Like A Nerd: We are a team of nerds, each hopelessly passionate and excited about our area of expertise. We believe that if you are an absolute nerd for what you do, then work is play. And we play hard. • Own Your Opportunities: Every mistake and failure is an opportunity. See it and use it as such. Take as much ownership as you possibly can, and use it as feedback to improve. The only two words you'll never hear at this company: fault and blame. • Commit to Your Own Potential: We expect this of ourselves, each other, and our clients: to relentlessly, critically be redefining and growing into the most potent version of ourselves and the impact we can have. • Van Talk: Discovered while Jhana was traveling full-time in a van through South America, Van Talk is not just a willingness and ability to speak honestly. It is a way of receiving crucial communication, not as a personal affront, but as a genuine and necessary act of service to accomplish our shared goals and highest potential. If our culture and mission does not resonate with you, please do not bother applying. JOB DESCRIPTION SpyGlass Ops is looking for a seasoned COO turned strategic advisor to join our team as an Inspector / Fractional COO. This is not a traditional operations role — and it's not a traditional consulting role either. This is the primary client-facing delivery position at SpyGlass Ops, and it sits at the intersection of deep business diagnostics, executive coaching, and operational transformation. You will lead our signature deep-dive business inspections — analyzing data, conducting interviews, identifying root causes, and delivering comprehensive reports of findings that change how founders see their own companies. From there, you'll transition into ongoing fractional COO work with a portfolio of clients, serving as their strategic advisor and transformation coach. Your job is to untangle the human webs that prevent organizations from scaling — management gaps, delegation failures, role confusion, founder bottlenecks, cultural drift, and strategic misalignment — and coach leaders through the messy middle of building something better. The application code word is CATALYST. You will not be asked to sell, handle billing, lead recruitment execution, or build systems inside client businesses. Your focus is entirely on diagnostics, strategy, and the human side of operations — supported by a team that handles everything else. This is a full-time, remote, 1099 contractor position. Given the critical nature of this role, we host a rigorous, multi-part application process. WHAT MAKES THIS ROLE UNIQUE This is not a fractional COO engagement where you're embedded in one company part-time. At SpyGlass, you are the diagnostic engine and transformation coach for a portfolio of purpose-driven businesses, each at a different stage of their operational evolution. Your work begins with the inspection — a deep-dive analysis across every dimension of a client's business. You'll review financial data, conduct team interviews, assess systems and processes, evaluate leadership dynamics, and synthesize everything into a clear picture of what's really going on beneath the surface. Then you'll present those findings, build an operator profile for the recruitment team, and transition into the ongoing advisory relationship. The fractional COO work is where the real transformation happens. You'll coach founders through extracting themselves from day-to-day operations. You'll help build strategic vision, establish role clarity, create job scorecards, roll out OKRs, and navigate the conversations that nobody else in the organization is willing to have. Some weeks that means helping a CEO see that they're the bottleneck. Other weeks it means mediating a leadership conflict or walking a founder through a difficult termination decision. You are supported by SpyGlass's product team, account management team, and recruitment team — so you can focus entirely on what you do best: seeing what others can't, saying what others won't, and helping leaders build organizations worthy of their vision. At full capacity, you'll manage approximately 3 inspections per month alongside a portfolio of 10–15 active fractional COO clients. RESPONSIBILITIES Business Inspection & Diagnostics • Conduct deep-dive business inspections across SpyGlass's Six Pillars: Team, Leadership, Mindset, Strategy, Systems, and Data • Review all client-submitted data — financials, org charts, survey results, CRM data, meeting recordings — and identify patterns, gaps, and root causes • Conduct structured interviews with team members, department heads, and CEOs to surface operational realities beneath the surface narrative • Synthesize findings into a comprehensive inspection report with clear root cause identification, financial impact analysis, and prioritized recommendations • Build and deliver the report of findings presentation to clients • Construct detailed operator profiles when a hire is necessary — calibrated to the specific needs, dynamics, and growth stage of each client organization Fractional COO & Strategic Advisory • Serve as the ongoing strategic advisor and transformation coach for an assigned portfolio of clients • Lead strategic vision development — helping founders articulate a grounded North Star and reverse-engineer it into actionable roadmaps, quarterly priorities, and departmental goals • Conduct role clarity exercises, build job scorecards with lever-based KPIs, and redesign org structures for scalability • Perform time analysis and EHV (Entrepreneurial Highest Value) work to help founders focus on their highest-leverage activities and delegate effectively • Roll out OKRs and accountability frameworks that connect individual performance to company-level objectives • Lead operator onboarding alongside the client to set placed candidates up for success Founder Coaching & Change Management • Coach founders through the transformation process — holding accountability, calling out blind spots, and navigating resistance to change with diplomacy and directness • Facilitate hard conversations within client organizations including performance issues, leadership dynamics, and personnel decisions • Serve as a stabilizing, clarifying force for leadership teams experiencing the discomfort of meaningful organizational change • Manage the human side of transformation — helping teams adapt to new standards, structures, and expectations without losing momentum or trust Internal Collaboration • Collaborate with SpyGlass's product team on execution support and process improvement • Hand off operator profiles and hiring context to the recruitment team with clear, actionable documentation • Coordinate with account management on client onboarding, scheduling, and engagement continuity REQUIREMENTS Experience (Non-Negotiable) • Senior operations leadership experience — you have held a Head of Operations, Director of Operations, VP of Operations, or COO title inside a growing business and have real experience managing teams, building infrastructure, and driving organizational change • Direct experience coaching or advising founders and CEOs — you have navigated strong personalities, held accountability conversations, managed up, and helped visionaries extract themselves from day-to-day operations • Track record leading organizations through operational transformation and change management — you have implemented new standards, restructured teams, shifted cultural norms, and managed the human resistance that accompanies meaningful change • Cross-functional business acumen — you have operated across or overseen multiple departments (sales, marketing, operations, finance, fulfillment) and understand how they interconnect • Financial literacy — you can read a P&L, spot red flags, assess whether a business model can achieve its stated goals, and use financial data to inform strategic decisions • Experience with organizational design — you have built or restructured org charts, defined role clarity, and created accountability frameworks tied to measurable outcomes Core Competencies • Diagnostic and analytical thinking — the ability to take a mountain of raw information and synthesize it into a clear, prioritized picture of root causes and recommended actions • Strategic planning and execution — translating vision into actionable roadmaps, OKRs, quarterly priorities, and departmental goals • Communication architecture — evaluating and redesigning how companies communicate, meet, and cascade information across levels • Systems and process assessment — evaluating CRM usage, project management architecture, workflow design, and automation opportunities (you assess and advise; you don't build) • Data and KPI strategy — understanding how metrics should be collected, displayed, and used for decision-making at every level of an organization • Cultural auditing — discerning whether core values are actively lived or just words on a wall, and identifying toxic patterns or psychological safety gaps Critical Soft Skills (Deal-Breakers) • Accountability and directness — you have the confidence to tell a CEO what nobody else will, respectfully but without flinching • High emotional intelligence — you read rooms, navigate egos, adapt your communication style, and build trust even in high-tension environments • Executive presence — you command respect with founders and C-suite leaders through clarity, confidence, and brevity • Radical curiosity — you ask the questions that peel back layers rather than accepting surface-level answers • Resilience and self-direction — you manage your own schedule, client load, and priorities across multiple businesses without constant oversight • Coaching orientation — you find genuine fulfillment in helping others break through barriers, even when the conversations are uncomfortable Strongly Preferred • Fractional, consulting, or multi-client advisory experience — comfort with context-switching across different businesses, managing competing priorities, and maintaining quality at scale • Experience with EOS (Entrepreneurial Operating System) or similar operating frameworks • Familiarity with common client tech stacks (ClickUp, Go High Level, Monday.com, Zapier, Make) • Background working with digital businesses, education or coaching companies, or service-based organizations in the 7–8 figure range • Experience with personality or behavioral frameworks (DiSC, Myers-Briggs, Enneagram) BENEFITS • Compensation of $8,000 to $12,000+ per month USD, with predictable and transparent pay structure (base salary + hourly inputs + standard inspection fees) • 1099 contractor relationship providing full autonomy in how you structure your work • 100% remote — work from anywhere • Full support infrastructure — you focus on client delivery while our product, account management, and recruitment teams handle everything else • Professional development through SpyGlass's internal training, mentorship, and leadership resources • A portfolio of purpose-driven clients doing meaningful work — you're not optimizing ad spend or shipping widgets, you're helping leaders build organizations that change lives HOW TO APPLY If you are interested in this position, please submit an application at the following link. https://eltiunaqqfh.typeform.com/to/jXlcjb4e Our team will review your application and get back to you shortly. We look forward to hearing from you! Pay: $8,000.00 - $12,000.00 per month Benefits: • Professional development assistance Work Location: Remote