# The Root Ventures — Chief AI Officer

- **Original JD posting:** https://www.linkedin.com/jobs/view/4460848083/
- **Provider:** LinkedIn
- **Canonical job ID:** 4460848083
- **Primary location:** United States
- **Work model:** Full-time remote (explicitly stated in the role description)
- **Seniority / employment:** Executive / Full-time
- **Industry:** Technology, Information and Internet
- **Posted:** August 29, 2026 (LinkedIn displayed “2 days ago” at capture time; exact posting time unavailable)
- **Applicants:** “Be among the first 25 applicants” (below Keith's 90-applicant ceiling)
- **Compensation:** Not disclosed
- **Travel:** Not disclosed
- **Generated:** August 31, 2026 at 5:49 PM EDT
- **Elapsed since posting:** Approximately 2 days

## Normalized job description

### Company description

The Root Ventures is dedicated to building, managing, and scaling digital businesses across property, retail, industry, and commerce. The company provides strategic direction and hands-on operational support, partnering with each venture to strengthen its digital presence and optimize performance. It combines data-driven insight with practical execution to pursue long-term value creation and sustainable growth.

### Role description

The Chief AI Officer is a full-time remote leadership role responsible for defining and executing the company-wide AI vision and strategy across all digital businesses. The role oversees the design, development, and implementation of AI solutions that improve customer experience, operational efficiency, and business performance.

Responsibilities include leading cross-functional AI initiatives; managing data and ML pipelines; prioritizing AI use cases with business leaders; ensuring ethical, secure, and compliant AI practices; building and mentoring AI and data teams; selecting and managing AI technology partners; establishing model-governance and monitoring standards; and communicating roadmaps and results to executives and investors. The role also tracks emerging AI trends and guides adoption of capabilities aligned with long-term strategy.

### Qualifications

1. Proven AI, machine-learning, and data-science expertise, including model development, deployment, and lifecycle management.
2. Strong data architecture, analytics, and engineering background, including robust data pipelines and governance frameworks.
3. Experience building, scaling, and mentoring technical teams and leading inclusive cross-functional work.
4. Strategic and commercial skills, product thinking, digital-business acumen, and the ability to translate AI into measurable business outcomes.
5. Knowledge of AI ethics, Responsible AI, privacy, and regulatory considerations for data and algorithmic decision-making.
6. Excellent communication and stakeholder-management skills, including explaining complex technical topics and influencing executives.
7. Experience with digital businesses in property, retail, industry, or commerce is highly beneficial.
8. Advanced degree in Computer Science, Data Science, Engineering, or a related field, or equivalent senior AI-leadership experience.

## Fit gate

- **Outcome:** PASS
- **Weighted score:** 96%
- **Positioning track:** Executive leader
- **Hard gaps:** None

### Evidence map

| Priority requirement | Weight | Keith's source-supported evidence | Score |
|---|---:|---|---:|
| Define and execute company-wide AI vision and strategy | 3 | Defined IDW's AI strategy, product vision, architecture, roadmap, and operating plan; former VP AI/ML | 3 |
| Deliver AI solutions tied to customer, efficiency, and business outcomes | 3 | AssistX: 70+ automations, 20+ workflows, selected tasks up to 50× faster, initial release in eight months | 3 |
| AI/ML development, deployment, and lifecycle management | 3 | Production GenAI platform; AWS AI/ML specialist; SageMaker, MLOps, model deployment and governance experience | 3 |
| Data architecture, analytics, pipelines, and governance | 3 | TriMark data lake across 11 ERPs; MassMutual data/governance services; 200+ AWS customer engagements | 3 |
| Build, scale, and mentor AI/data teams | 3 | Recruited and led 11 engineers; led teams at SuccessKPI and TriMark; led AWS communities of 80–100 specialists | 3 |
| Responsible AI, privacy, security, and compliance | 3 | MassMutual AI Governance & Ethics advisory; transparency, bias, drift, monitoring, privacy, CCPA/CPRA/GDPR | 3 |
| Cross-functional executive and investor communication | 2 | C-suite advisory, strategy and funding support, executive roadmaps, strategic partnerships, acquisition discussions | 2 |
| Commercial/product thinking and digital-business outcomes | 2 | IDW productization and commercialization; five commercial SaaS products; TriMark retail/commerce transformation | 3 |
| Advanced degree or equivalent senior AI leadership | 2 | Ph.D.; CEO, VP AI/ML, senior AI/data Director, and AWS specialist leadership | 3 |
| Property/retail/industry/commerce exposure (beneficial) | 1 | Direct retail/commerce operating transformation at TriMark; broad AWS customer exposure; no property claim | 2 |

Weighted points: 72 earned of 75 possible = 96%.

### Direct-match strengths

- Executive AI strategy coupled with hands-on platform architecture and production delivery.
- Measured AI and workflow outcomes: 70+ automations, 20+ workflows, up to 50× acceleration.
- Organization building and mentoring across 7-, 11-, 24-, 80-, and 100-person teams or technical communities.
- Deep data-platform and pipeline experience, including an 11-ERP enterprise data lake and 60× reporting improvement.
- Direct Responsible AI, privacy, model-governance, security, monitoring, and auditability work.
- Strong executive, customer, and technical communication developed through 200+ AWS enterprise engagements and 50+ presentations.

### Caveats and gaps

- Compensation is not disclosed; the Chief-level title satisfies Keith's standing inclusion rule when compensation is absent.
- Travel is not disclosed; undisclosed travel is not a fit-gate failure.
- Keith has retail/commerce transformation experience but no property-sector experience is claimed.
- The posting does not specify portfolio scale, budget, reporting line, or current AI-team size.

### Keyword diagnostic

High alignment without keyword stuffing: AI strategy, machine learning, model lifecycle, data architecture, data pipelines, governance, Responsible AI, privacy, compliance, team building, product thinking, executive communication, monitoring, and measurable outcomes are all directly supported. Property-sector expertise is intentionally not claimed.

## Artifact metadata

- **Resume:** `Keith_Steward_The_Root_Ventures_Chief_AI_Officer_4460848083_resume.pdf` — 106,357 bytes, 3 pages, generated August 31, 2026 at 5:46 PM EDT
- **Cover letter:** `Keith_Steward_The_Root_Ventures_Chief_AI_Officer_4460848083_cover_letter.pdf` — 41,187 bytes, 1 page, generated August 31, 2026 at 5:40 PM EDT
- **Resume public URL:** https://files.keithsteward.com/The_Root_Ventures/Keith_Steward_The_Root_Ventures_Chief_AI_Officer_4460848083_resume.pdf
- **Cover-letter public URL:** https://files.keithsteward.com/The_Root_Ventures/Keith_Steward_The_Root_Ventures_Chief_AI_Officer_4460848083_cover_letter.pdf
- **Archived JD public URL:** https://files.keithsteward.com/The_Root_Ventures/The_Root_Ventures_Chief_AI_Officer_4460848083_JD_capture.md
- **Validation:** PASS — content, positioning, ATS text extraction, Letter size, 0.40-inch margin declarations, page bounds, active contact links, pagination, visual layout, and artifact integrity validated locally
- **Publication target:** `/mnt/nfs/wkstation4/The_Root_Ventures/`
- **Google Drive:** Not used