# Swooped — Chief Technology Officer

- Generated: 2026-09-19 09:27:30 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4469237536/
- Provider: LinkedIn
- Posted: approximately 2026-09-18 11:27 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: Remote — United States; end employer is unidentified
- Compensation: Not disclosed; Chief title qualifies for missing-compensation review
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: PASS — 88%

## Direct-match strengths

CTO-level product and engineering execution, AI-first architecture, agentic workflows, MCP, RAG, evaluation, guardrails, inference economics, engineering quality, workforce planning, hiring, remote teams, and hands-on technical reviews.

## Hard or material gaps

The end employer is unidentified. The posting asks for demonstrated model fine-tuning and building/fine-tuning models from the ground up; Keith has stronger evidence in applied LLM platforms, RAG, agents, evaluation, routing, and governance than in model training.

## Evidence map

1. AI-first technology and engineering strategy (weight 3, evidence 3/3) — Direct platform, product, and engineering strategy.
2. Agentic workflows, MCP, RAG, context engineering (weight 3, evidence 3/3) — Direct production agent, MCP, RAG, and workflow evidence.
3. Evaluation, guardrails, cost, latency, routing (weight 3, evidence 3/3) — Direct evaluation, observability, model routing, and cost controls.
4. Hands-on code and architecture review (weight 3, evidence 3/3) — Built AssistX core and reviewed architecture/code.
5. Workforce planning, hiring, performance (weight 3, evidence 3/3) — Built teams and managed talent.
6. Foundation-model fine-tuning/training (weight 3, evidence 1/3) — Applied LLM platform depth is direct; model training/fine-tuning is limited.
7. Remote CTO-level eligibility (weight 2, evidence 3/3) — Remote U.S. and Chief title qualifies.

## Keyword diagnostic

Near-direct CTO, AI architecture, agentic workflow, evaluation, operations, and engineering-organization alignment; fine-tuning/model-training depth is the main caveat.

## Full normalized job description

Chief Technology Officer - US-Based
About the Opportunity
The organization is seeking an executive to serve as Chief Technology Officer, driving execution across product and engineering while placing artificial intelligence at the center of the organization's architecture and systems. In this role, the executive will own the entire technical architecture, building it AI-first and utilizing modern practices for agentic engineering.
This is a builder and architect role requiring direct engagement in system design, reviews, and code. The Chief Technology Officer will conceive and execute engineering strategy, guide technical infrastructure to support modular business operations, lead organizational resourcing and workforce planning, and spearhead the deployment of production-grade agentic workflows.
Responsibilities
• Formulate and own the organization's overarching technology and AI strategy, establishing clear architectural standards and driving alignment with executive leadership.
• Own the complete AI architecture, including foundation model selection and fine-tuning, harness design, orchestration, retrieval, context engineering, tool and Model Context Protocol (MCP) integration, guardrails, evaluation, and inference cost control.
• Deploy agentic engineering at scale across core business workflows such as matching, vetting, onboarding, delivery, and internal operations, taking direct ownership of operational outcomes.
• Establish measurable AI quality benchmarks, owning evaluation frameworks, regression suites, and review loops to validate system performance.
• Direct end-to-end platform architecture across services, data pipelines, system boundaries, and interfaces to maintain reliability, high throughput, and secure-by-design standards.
• Manage operational performance across AI-dependent pathways, addressing latency, model drift, and provider outages while balancing build-versus-buy trade-offs and technical debt.
• Modernize engineering practices through AI-assisted development, code review, testing, and operational workflows to increase developer velocity.
• Lead workforce planning and engineering resourcing, including roadmap scoping, team sizing, headcount allocation, role specification, and the hiring of top-tier talent.
• Define and uphold engineering quality standards, mentoring teams on agentic practices and conducting rigorous technical and architectural reviews.
• Guide the organization through defined milestones, moving from initial architectural and organizational assessments to deploying production agentic workflows and establishing an industry-leading engineering organization.
Required Qualifications
• Bachelor’s degree in Computer Science, Engineering, or a related technical field.
• 15+ years of progressive engineering leadership experience, including substantial experience as a Chief Technology Officer, Vice President of Engineering, or as a direct report to one at meaningful scale.
• Deep, hands-on technical command of modern AI engineering, including foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation frameworks, with demonstrated experience building and fine-tuning models from the ground up.
• Proven track record of deploying agentic systems at scale against production business processes with measurable outcomes in cost, cycle time, quality, or revenue.
• Rigorous approach to AI evaluation and evidence-based performance validation for models, prompts, and agentic workflows.
• Strong command of AI operational economics, including model routing, hosted versus self-hosted configurations, inference capacity, latency budgets, token spend, and provider portability.
• Demonstrated ability to write and review code, evaluate architectural design documents, analyze evaluation harnesses, and manage distributed systems, cloud infrastructure, and data-intensive applications at scale.
• Experience modernizing and refactoring large, load-bearing existing codebases in flight without interrupting business operations.
• Experience leading a globally distributed, remote engineering team within a technology or hyper-growth organization.
• Proven ownership of workforce planning, technical recruiting, and performance management.
• Outstanding written and verbal communication skills, with fluency in English for all documentation and communication.
Preferred Qualifications
• An advanced degree in Computer Science, Engineering, or a related technical discipline.
• Leadership experience within a high-volume, two-sided marketplace or multi-tenant platform.
Essential Job Functions
• Regularly and reliably attend scheduled virtual team meetings on camera.
• Work independently with minimal supervision.
• Utilize all required digital collaboration and productivity tools.
• Prioritize and self-manage complex workflows, operational demands, and project deadlines.
Employment Details
• Position Title: Chief Technology Officer - US-Based
• Location: United States (Remote)
• Employment Type: Full time
• FLSA Classification: Exempt

## Artifact metadata

- Resume: https://bit.ly/4rlU065
- Cover letter: https://bit.ly/3V3cXyj
- Validation: PASS — 2-page resume (926 words), 1-page cover letter (195 words); PDF geometry, bounds, annotations, links, and visual pages verified.
- Google Drive used: No