# Rise Technical — Vice President of Artificial Intelligence

- Generated: 2026-09-04 11:36 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4460499824/
- LinkedIn job ID: 4460499824
- Provider: LinkedIn
- Posting company: Rise Technical, recruiting for an undisclosed autonomous-security and defense-technology startup
- LinkedIn title: Vice President of Artificial Intelligence
- Internal JD title: VP of Engineering (Federal)
- Employment type / listed seniority: Full-time / Director
- Work model/location: Boston, MA — Hybrid / Remote
- Posting age at retrieval: 1 day ago
- Applicants at retrieval: 49 applicants
- Compensation: $250,000-$330,000 base salary plus equity and benefits
- Travel: Based in Boston or comfortable with travel; percentage not disclosed
- Citizenship: U.S. citizenship required
- Positioning track: Executive leader
- Capability fit score: 40.6%
- Fit outcome: FAIL

## Central mandate

Build and lead a federal engineering organization for an autonomous-security and defense-technology startup. Own architecture through deployment of production LLM and multi-agent systems in high-security government environments, including FedRAMP and GovCloud constraints, and align research, engineering, federal stakeholders, enterprise operators, product roadmaps, and go-to-market execution.

## Fit decision

FAIL. The role is explicitly centered on federal and defense operations, which conflicts with Keith's standing no-defense constraint. It also requires U.S. citizenship, while Keith's source materials document permanent-resident status and an ongoing citizenship application rather than current U.S. citizenship. Additional hard gaps include no source-supported FedRAMP, GovCloud, federal-compliance, or autonomous-cyber-operations experience. No resume, cover letter, or LinkedIn connection note was generated without an explicit override.

## Weighted evidence map

| Requirement | Weight | Evidence score | Source-supported evidence |
|---|---:|---:|---|
| Build and direct a federal engineering organization from architecture through deployment | 3 | 1 | Keith has repeatedly built and led engineering and AI teams, including an 11-person startup team and a 24-person distributed team, but no federal engineering organization is documented. |
| Build production-grade LLM systems and multi-agent architectures | 3 | 3 | Keith architected and built the production AssistX GenAI platform using LLMs, agents, LangChain, LangGraph, RAG, Python, FastAPI, PostgreSQL/PGVector, and AWS. |
| Design autonomous cyber-operation and continuous-adversarial-validation systems | 3 | 0 | No source-supported autonomous-cyber-operations or adversarial-validation experience. |
| Operate under FedRAMP, GovCloud, and federal-compliance constraints | 3 | 0 | Keith has governance, privacy, IAM, and regulated-software experience, but FedRAMP, GovCloud, and federal security-compliance delivery are not documented. |
| Scale high-performing engineering teams in fast-paced startups | 2 | 3 | Direct evidence from Intelligent DataWorks, SuccessKPI, NorthBay Solutions, and other leadership roles. |
| Design secure, resilient, scalable architectures | 2 | 2 | Strong enterprise AWS, distributed-systems, governance, privacy, IAM, CI/CD, and production-platform evidence, but not in the required defense context. |
| Align research scientists, federal stakeholders, and enterprise operators | 2 | 1 | Keith has scientific-research, enterprise-advisory, and government-customer exposure, but direct ownership of federal stakeholder alignment is not documented. |
| Shape product roadmaps and go-to-market execution | 2 | 2 | Keith has direct product-roadmap and commercialization evidence, although GTM is not his target preference. |
| Be a current U.S. citizen | 3 | 0 | Keith's source materials document permanent-resident status and an ongoing citizenship application, not current citizenship. |

Weighted result: 28 of 69 possible points = 40.6%.

## Direct-match strengths

- Executive and hands-on leadership of production AI, LLM, agentic, cloud, and distributed systems.
- Built AssistX with 70+ AI automations across 20+ workflows and delivered the initial production release in approximately eight months.
- Built and led engineering organizations, including 11-person and 24-person teams, and an 80-person AWS AI/ML technical community.
- Strong executive communication and enterprise architecture experience, including advising 200+ AWS customers.
- Security-adjacent experience in privacy, governance, IAM, auditability, CI/CD, and regulated software.

## Hard and material gaps

- Hard conflict: the role and employer mandate are explicitly federal-defense and autonomous cyber operations; Keith excludes defense roles.
- Hard requirement: current U.S. citizenship is required and is not supported by Keith's source materials.
- No documented FedRAMP, GovCloud, federal accreditation, or high-security government deployment experience.
- No documented autonomous cyber operations, continuous adversarial validation, or automated security-operations expertise.
- GTM execution appears in the mandate, while Keith's stated search preference is AI development rather than GTM.
- Travel percentage is undisclosed; the JD says candidates must be Boston-based or comfortable with travel.

## Keyword diagnostic

Strong source-supported alignment: engineering leadership, AI strategy, AI platforms, production LLM systems, multi-agent systems, agentic AI, LangChain, LangGraph, RAG, Python, FastAPI, AWS, distributed systems, enterprise architecture, startup team scaling, product roadmaps, governance, privacy, IAM, security architecture, CI/CD, executive communication, and enterprise delivery.

Weak or unsupported exact terms: FedRAMP, GovCloud, federal engineering, federal compliance, autonomous cyber operations, continuous adversarial validation, ruggedized federal solutions, high-security government environments, and U.S. citizenship. These were not converted into candidate claims.

## Artifact decision and metadata

- Archived JD capture: https://files.keithsteward.com/Rise_Technical/Rise_Technical_Vice_President_of_Artificial_Intelligence_4460499824_JD_capture.md
- Resume: not generated because the fit gate returned FAIL and no override was supplied.
- Cover letter: not generated because the fit gate returned FAIL and no override was supplied.
- LinkedIn connection note: not generated because the skill prohibits one for FAIL roles.
- Google Drive used: no.

## Full normalized job description

### VP of Engineering (Federal)

Boston, MA (Hybrid / Remote)

$250,000-$330,000 plus equity and benefits

Rise Technical is recruiting an executive engineering leader for a high-growth autonomous-security and defense-technology startup's federal engineering division. The role will build, scale, and lead a specialized federal engineering organization responsible for adapting autonomous multi-agent platforms, continuous self-training loops, and automated execution frameworks for high-security, compliance-heavy government environments.

The role bridges advanced AI research and mission-critical enterprise deployments and owns resilient, scalable architectures operating under modern security constraints. The successful candidate is expected to have worked at the intersection of advanced machine-learning systems and federal compliance and to define how autonomous cyber operations are deployed at scale.

### Responsibilities

- Build and direct the Federal Engineering team from architecture to deployment.
- Design secure, scalable multi-agent frameworks for high-compliance federal and defense environments.
- Translate advanced agentic architectures and planning loops into ruggedized federal solutions.
- Drive technical alignment with strict security standards, FedRAMP, and GovCloud constraints.
- Partner with leadership to shape product roadmaps and go-to-market execution.

### Requirements

- Experience scaling high-performing engineering teams in fast-paced startup environments.
- Experience building production-grade LLM systems and multi-agent architectures.
- Exceptional communication skills aligning research scientists, federal stakeholders, and enterprise operators.
- Based in Boston or comfortable with travel.
- U.S. citizen.