--- title: 'Chief of Staff at Sitreps' canonical: 'https://feeny.ai/job/chief-of-staff-sitreps-portland-bevzjkz40a2n' type: 'job' last_seen: '2026-09-11' --- # Chief of Staff at Sitreps - **Company:** Sitreps - **Location:** Portland, OR - **Work type:** onsite - **Posted:** 2026-09-04 - **Last confirmed live:** 2026-09-11 - **Apply:** https://job-boards.greenhouse.io/sitrepsllc/jobs/4396454009 ## Job description Chief of Staff Company: Aeronautical engineering services · UAS and urban air mobility · Client name disclosed after initial screen Location: Portland, Oregon (onsite, remote not accepted). Relocation is strongly preferred. For the right person we can make an arrangement work where you are on site roughly two weeks out of every month. Fully remote is not a fit for this role. Compensation: $140,000 to $160,000 base, depending on experience, plus a 25% target bonus ## About the Client We are an engineering services firm in Portland, Oregon. We do conceptual design and detailed aerodynamic and aero-structural engineering for other companies' products: large UAVs, urban air mobility platforms, and defense programs. Roughly a third of our work is with eVTOL and air taxi developers, a third is defense UAV programs, and a third is smaller civil work, everything from delivery drones to regional logistics aircraft. We have no products of our own. Clients come to us because they need aircraft designed and, often, physically built. About half our work is design and half is prototype fabrication and assembly, which means we have put first flight and early serial production aircraft into the air for programs you would recognize. We are about 30 full-time engineers plus 15 to 20 subcontractors, running four or five development programs in a given year. We have been doing this for ten years. We are profitable, we are growing, and we have not turned work away. ## About the Role Our engineering capacity has grown faster than the layer that manages it. We can staff more programs than we can currently plan, sequence, and steer. The Chief of Staff is the hire that closes that gap. You would report directly to one of the partners, a former military aviator who runs the programs side of the business. The role is a genuine hybrid: program management, client and account management, some business development, and internal operations. In a firm this size that is not a compromise, it is the job. You are the person who takes a program from a well-planned proposal through the six months of reality that follow it, and keeps the plan, the engineering team, and the client all pointed the same direction. ## Responsibilities - Run development programs end to end. You partner with a Chief Engineer on each program and own the plan, the schedule, the budget, and the client relationship around it. - Steer programs when the plan changes, because it will. Proposals are built on a clean set of assumptions. Two weeks in, the context shifts. Your job is to make the trade deliberately rather than letting it happen by drift. - Manage clients and their expectations. When a program needs more attention or schedule relief, you make the case and frame it in terms of what actually serves the client's aircraft. - Put informed pressure on the engineering side. Not to move faster for its own sake, but to make sure work is scoped and sequenced well. - Pull the numbers and make the call. Get into our program database, pull actuals on aerodynamics hours or mechanical engineering hours from a prior program, compare them against where a current program sits, and come back with a recommendation. The deliverable is the recommendation, not the pivot table. - Support capture and proposal work as you build context, and take more of it over time. - Improve the operating system underneath all of the above. The cadence, the templates, and the SOPs that let the next program manager ramp faster than you did. How the First Year Works The ramp is deliberate. For roughly the first six months you shadow the partner across several key programs. You learn where we put attention, where the real decision points are, and where an experienced team is comfortable improvising. You are doing real work throughout, not observing. After that you start getting peeled off onto your own programs. The target end state is that you run them essentially autonomously, reporting out to the partner in a couple of hours a week. That is the bar this role is measured against. ## Requirements - Roughly four to eight years of professional experience. This is not a senior hire and it is not an entry-level one. - A quantitative background. An engineering undergraduate degree is a plus. So is any graduate work where you were expected to do real analysis and make defensible trades between options with cost consequences. - Enough technical grounding that an undergraduate physics level conversation is comfortable. If an engineer tells you a change is not feasible because of the torsion on the wing, you should not be looking up the word torsion. - Ownership. You move fast, you work independently, and you know the difference between a question worth asking and one you should go answer yourself. - The ability to talk to a business leader like a peer. Our partners advise clients on product development and business strategy, so you will be in front of senior people early. - Strong written and verbal communication. Much of this job is making a case to someone who was not in the room. You will not be doing design work. We are not looking for a practicing engineer, and we are not looking for a career project manager with a PMP and no appetite for ambiguity. We are looking for someone hungry and effective who wants a large scope early. Backgrounds That Fit - A junior military officer coming out of an MBA program who wants an operating role rather than a traditional post-MBA path. - A junior military officer with a business or engineering undergraduate degree going straight into industry. - Someone one to two years into a large company, in strategy, operations, or program management, who has concluded that the scope there is too narrow and the pace too slow. Prior military service is not a requirement. It is a common pattern for this seat and the partner shares that background. Where This Goes Be clear-eyed about what this is. It is not a partner track and it is not a thirty year seat. It is a role where you build a name quickly, in a firm that touches the most interesting aircraft programs in the country, working alongside people who advise those companies at a senior level. Three to five years here should leave you with a real set of options, internally as the firm grows, or at an aircraft or other tech product company. That outcome is a feature of the role, not a risk we are hiding from. ## About Sitreps ## Company Overview - **One-liner**: Sitreps is a veteran-founded recruiting agency and defense technology company that connects elite military talent with high-impact roles and builds software-driven maritime intelligence platforms for the U.S. Department of Defense. - **Entity Type**: Private (startup stage; no public funding rounds disclosed) - **Headquarters**: Arlington, Virginia, USA (multiple job postings list Arlington, VA as primary location; also offices in New York City and Litchfield, VA) - **Founded**: 2019 - **Founders**: Kyle Eberly, Wyatt Frasier, Max Cormier (co-founders) ## Core Business - **Primary Industries**: Defense Technology, Professional Services (Veteran Recruiting & Staffing), Software & Analytics - **Target Customers**: U.S. Department of Defense (DoD) and federal civilian agencies (B2G); defense-focused enterprises and technology companies (B2B) seeking veteran talent - **Mission/Purpose**: Leveraging a deep-rooted community of military veterans to help world-class businesses scale, while also transforming commercial fleets into persistent sensing assets for national security. ## Products & Services - **Sitreps Talent (Recruiting Agency)**: A curated recruiting service that sources, vets, and places high-performing military professionals into roles at partner companies. Serves 10+ industries including defense tech, software, AI, fintech, and private equity. Places roles such as product managers, account executives, engagement managers, and sales directors. - **Maritime Intelligence Platform (Defense Tech Software)**: A next-generation software platform that transforms global commercial fleets into persistent sensing assets for the United States. Used by Navy strategic programs; includes analytics, data integration (SQL/Python/R), and implementation services. - **AI & Agentic Solutions (Emerging)**: Design, prototype, and deploy scalable AI and agentic workflows for defense acquisition challenges, embedding with clients to productionize models. ## Market Standing - **Valuuation / Funding**: Not publicly disclosed. The company appears to be privately funded (no public rounds recorded). A Head of Sales job description references growing revenue from ~$2M to $5M+ (with a path to $30M), suggesting current annual revenue in the low single-digit millions. - **Key Metrics**: 150+ veterans placed, 40+ partner companies, 95% retention rate, serving 10+ industries (source: [sitreps.com/about/clients](https://www.sitreps.com/about/clients)) - **Notable Investors / Partners**: Not listed publicly. Partner companies are not named on the website, but the client portfolio includes defense tech, software, HVAC, real estate, AI, fintech, private equity. - **Growth Signals**: - Scaling sales team from ~$2M to $30M target - Active hiring for senior roles: VP of Engagement, Head of Intelligence, Chief Operating Officer, Forward Deployed Data Scientists - Expanding into AI/agentic solutions for defense acquisition - Multiple office locations and remote/hybrid work options ## Competitive Advantages - **Authentic Veteran Community**: Sitreps began as a viral online community for veterans transitioning to business roles — now the “largest community of veterans in business in the USA,” providing unmatched access to, and credibility with, military talent. - **Dual Capability**: Combines a staffing agency with in-house defense tech software development, allowing cross-pollination of talent insights and mission understanding. - **High Retention**: 95% placement retention rate indicates strong matching and support processes. - **Clearance and Domain Expertise**: Many roles require active security clearances and deep knowledge of naval strategic programs, DoD acquisition, and intelligence — creating a high barrier for competitors. ## Strategic Focus - **Scale Revenue**: Formalizing sales processes (CRM, commissions, segmentation) with a goal of growing from ~$2M to $5M+ in the near term and eventually $30M. - **Productize Defense Tech**: Expand the maritime intelligence platform and AI/agentic solutions for broader DoD adoption. - **Deepen Government Relationships**: Hiring Engagement Directors and Account Executives for each military branch (Air Force, Navy, Army, Coast Guard, Marine Corps). - **Build Internal Infrastructure**: Transitioning from QuickBooks to an audit-ready ERP, adding financial controls and federal contract audit compliance. ## Why Work Here - **Mission-Driven Work**: Directly support national security and veteran employment — two high-impact, purpose-rich areas. - **Hybrid & Remote Flexibility**: Many roles offer remote options (U.S.-based); some positions require on-site presence in Arlington, VA, New York, or Litchfield, VA; a hybrid workspace is the norm. - **Career Growth**: Early-stage company where leaders are expected to build functions from scratch and grow into C-level roles (e.g., Head of Sales → CRO path). - **Diverse Roles**: Opportunities span professional services, engineering (forward deployed, data science), intelligence analysis, sales, and operations — appealing to both veterans and civilians. - **Culture**: Described as “authentic, expertise-driven, and grounded in real connection” — not a typical corporate recruiter but a community-first organization. ## Sources 1. [builtin.com](https://builtin.com/company/sitreps-llc) – Company overview, perks, culture, job listings 2. [job-boards.greenhouse.io](http://job-boards.greenhouse.io/sitrepsllc) – Official careers page with all current openings 3. [sitreps.com/about/team](https://www.sitreps.com/about/team) – Founders and team profiles 4. [sitreps.com/about/clients](https://www.sitreps.com/about/clients) – Client metrics, industries served, roles filled 5. [builtin.com](https://builtin.com/company/sitreps-llc/jobs) – Detailed job descriptions (Head of Sales, Implementation Engineer, etc.) ## Other roles at Sitreps - [Facility Security Officer (TS/SCI with Full Scope Polygraph Required)](https://feeny.ai/job/facility-security-officer-ts-sci-with-full-scope-polygraph-required-sitreps-1cx0btxk19sz) — Arlington, VA - [Defense Tech Talent Pool For Stanford DEFCON Career Fair 2026](https://feeny.ai/job/defense-tech-talent-pool-for-stanford-defcon-career-fair-2026-sitreps-stanford-fm22kzx150em) — Stanford, CA - [General Manager - Aviation Maintenance](https://feeny.ai/job/general-manager-aviation-maintenance-sitreps-santa-monica-y9b88ynzxw5z) — Santa Monica, CA - [Director of Defense Sales](https://feeny.ai/job/director-of-defense-sales-sitreps-washington-mqjtqp8fb779) — Washington, DC - [Director, Strategic Programs](https://feeny.ai/job/director-strategic-programs-sitreps-washington-hyv2076gpey5) — Washington, DC - [AI Product Manager, Public Sector](https://feeny.ai/job/ai-product-manager-public-sector-sitreps-washington-dc-or-san-francisco-k7pwb6nf4jzh) — Washington Dc OR San Francisco, CA - [Senior Forward Deployed Strategist, Public Sector](https://feeny.ai/job/senior-forward-deployed-strategist-public-sector-sitreps-washington-dc-or-san-dkgg0vr1n0qk) — Washington Dc OR San Francisco, CA - [Senior Forward Deployed Engineer, Public Sector](https://feeny.ai/job/senior-forward-deployed-engineer-public-sector-sitreps-washington-dc-or-san-2p8wwrc0mhb3) — Washington Dc OR San Francisco, CA - [Talent Sourcer (LATAM)](https://feeny.ai/job/talent-sourcer-latam-sitreps-latin-america-dybqasqr9346) — Latin America - [Talent Sourcer](https://feeny.ai/job/talent-sourcer-sitreps-argentina-00bg1hz0f31s) — Argentina