# Swooped — Director, Strategic Operations for CEO

- Generated: 2026-09-20 08:47:04 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4469576314/
- Provider: LinkedIn
- Posted: approximately 2026-09-19 10:47 PM EDT (from '10 hours ago')
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp when available
- Applicants: Be among the first 25 applicants
- Work model/location: United States; exact remote/workplace designation is not stated
- Compensation: $174,000-$218,000 base plus possible incentives
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 61%

## Direct-match strengths

Executive advising, cross-functional transformation, annual planning, portfolio prioritization, KPI design, operating rhythms, ambiguity resolution, AI-enabled workflows, budgets, and measurable execution.

## Hard or material gaps

Hard function gap: the central mandate requires significant strategy-consulting-firm experience, CEO-office strategic operations, commercial/financial analysis, and enterprise-wide operating leadership. Keith's central evidence is AI, engineering, product, platform, and technical transformation leadership rather than a dedicated strategy-consulting or CEO-chief-of-staff career.

## Evidence map

1. Significant strategy consulting firm experience (weight 3, evidence 0/3) — Not source-supported.
2. Direct CEO/C-suite strategic advisory (weight 3, evidence 2/3) — Executive advisory is direct; dedicated CEO-office tenure is not.
3. Enterprise strategy through execution (weight 3, evidence 3/3) — Direct technology and transformation strategy with measurable delivery.
4. Commercial and financial acumen (weight 3, evidence 2/3) — Budgets, cases, and KPIs are direct; strategy-finance depth is narrower.
5. Influence across senior executives without authority (weight 2, evidence 3/3) — Direct matrixed and advisory leadership.
6. AI-enabled research and operations (weight 1, evidence 3/3) — Direct production AI and workflow evidence.
7. Core AI/engineering leadership function (weight 3, evidence 0/3) — AI is a supporting tool rather than the role's central function.

## Keyword diagnostic

Executive transformation and KPI strengths are relevant, but the role is not AI leadership and its required strategy-consulting/CEO-office background is unsupported.

## Full normalized job description

About the Opportunity
The
Director, Strategic Operations for CEO
serves as a strategic thought partner and operational leader, working directly with the Chief Executive Officer to operationalize enterprise priorities, pressure-test decisions, and translate high-level strategy into execution. This role bridges strategy consulting rigor with hands-on operational leadership, extending the CEO's reach across the executive leadership team, fostering alignment across cross-functional groups, and maintaining momentum across high-stakes initiatives.
Key Responsibilities
Partner directly with the CEO and senior leadership on annual and quarterly planning, translating enterprise strategy into clear priorities and guiding decisions on what to pursue, pause, or deprioritize.
Structure complex business challenges, pressure-test assumptions, synthesize data and diverse perspectives, and develop actionable recommendations on high-impact decisions and strategic opportunities.
Drive the operating rhythm behind enterprise priorities by establishing clear goals, milestones, ownership, and accountability frameworks to sustain execution momentum.
Represent executive context and decision principles in critical discussions, advancing priorities when direct CEO involvement is not required and delivering a candid, objective assessment of business performance.
Resolve organizational friction and build alignment across senior leaders when perspectives differ, decisions stall, or functional ownership is ambiguous.
Connect operational plans across the organization to identify competing demands on personnel, budgets, and resources, collaborating with leadership to navigate trade-offs.
Establish and maintain essential enterprise key performance indicators (KPIs) to assess strategic progress, identify execution drift, and determine when course corrections are needed.
Direct critical cross-functional initiatives end-to-end, from problem definition and stakeholder alignment through implementation and measurable outcomes.
Synthesize complex strategy, performance data, and organizational decisions into clear executive narratives for leadership, internal teams, and key stakeholders.
Leverage AI and emerging tools to enhance research, data synthesis, analysis, and operational workflows while applying rigorous critical thinking and professional judgment.
Required Qualifications
15+ years of professional experience, including significant experience within a strategy consulting firm solving complex strategic, operational, or business transformation challenges.
Proven experience working directly with CEOs, C-suite executives, or equivalent senior leaders on enterprise strategy, planning, and high-stakes decision-making.
Demonstrated track record of moving from strategy development through operational execution, with concrete examples of driving measurable business results.
Advanced critical thinking and problem-solving capabilities, with proven ability to structure ambiguous challenges, prioritize key levers, and form well-supported perspectives.
Strong commercial and financial acumen, including practical experience utilizing business performance data and KPIs to evaluate trade-offs and drive decisions.
Executive presence and professional judgment to act as a trusted advisor, knowing when to facilitate alignment, when to constructively challenge, and when to assume direct operational ownership.
Demonstrated ability to influence and align senior executives and cross-functional teams without formal authority, especially in scenarios with competing priorities.
Cognitive flexibility and collaborative adaptability to move effectively between strategic planning, advisory support, facilitation, and hands-on operational execution.
High ethical standards, discretion, and the confidence to deliver candid, objective assessments to senior leadership.
Continuous learning orientation, with the agility to absorb context quickly, challenge assumptions, and adapt approaches as conditions evolve.
Practical experience utilizing AI tools to improve efficiency and workflows, combined with the analytical capability to evaluate outputs, identify limitations, and apply appropriate human oversight.
Compensation and Benefits
Annual base salary range:
$174,000 - $218,000,
reflecting the national compensation band. Additional geographic or tiered premium percentages may apply based on location.
Eligibility for discretionary incentive compensation, including bonus and/or commission awards.
Comprehensive benefits package, including employer-sponsored health coverage for employees and dependents, retirement benefits with a company 401(k) match, paid time off, paid parental leave, family support policies, and learning and wellness stipends.
Employment Details
Role Title: Director, Strategic Operations for CEO
Location: United States
Employment Type: Full time
Work Authorization: Visa sponsorship is not available for this position.
Employment Status: Employment is at-will. The organization reserves the right to adjust base compensation, incentive programs, and benefit offerings in accordance with business considerations, market factors, and individual or departmental performance.
Program Participation: The organization participates in the federal E-Verify program.
Equal Opportunity and Accommodations
The hiring organization provides equal employment opportunities to all qualified applicants and employees without regard to age, race, cultural background, sexual orientation, gender identity, disability, veteran status, or any other characteristic protected by law.
Reasonable accommodations are available for applicants with disabilities throughout the recruitment and selection process.

## Artifact metadata

- Resume: Not generated because the fit gate returned FAIL.
- Cover letter: Not generated because the fit gate returned FAIL.
- LinkedIn note: Not generated for a FAIL role.
- Google Drive used: No