# Arootah — Fractional Chief AI Officer / AI Strategy Leader (Advisor Network)

- Generated: 2026-09-01 10:08:10 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4461735295/
- User-provided LinkedIn posting: https://www.linkedin.com/jobs/view/4461735295/
- Posting time: approximately 2026-09-01 08:47 AM EDT (estimated from LinkedIn's '1 hour ago' at capture)
- Applicants: Be among the first 25 applicants
- Work model/location: Project-based advisor network for United States opportunities; no active engagement is attached; LinkedIn location: United States
- Compensation: Not disclosed; Chief title would otherwise qualify
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 92% evidence coverage; application-material generation explicitly overridden by Keith on 2026-09-01

## Direct-match strengths

AI strategy, governance, transformation roadmaps, workflow automation, vendor evaluation, hands-on implementation, change management, executive advisory, and measurable enterprise outcomes.

## Hard or material gaps

Hard engagement-status gap: this is an application to an advisor network, not a specific active paid opening; placement is explicitly not guaranteed. Engagement location, compensation, travel, duration, and actual client mandate cannot be verified until a future project exists.

## Evidence map

1. Enterprise AI strategy and roadmaps (weight 3, evidence score 3/3) — Direct across IDW, AWS, NorthBay, and MassMutual.
2. Workflow automation and operational efficiency (weight 3, evidence score 3/3) — Direct quantified production outcomes.
3. Governance and responsible AI (weight 2, evidence score 3/3) — Direct AI governance, privacy, auditability, and lifecycle evidence.
4. Executive advisory and stakeholder leadership (weight 3, evidence score 3/3) — Direct advisory to 200+ AWS enterprises and C-level leaders.
5. Hands-on transformation delivery (weight 3, evidence score 3/3) — Direct strategy-through-production accountability.
6. Financial-services or enterprise background (weight 2, evidence score 3/3) — Direct enterprise and financial-services customer experience.
7. Specific active paid engagement (weight 3, evidence score 0/3) — The posting explicitly offers only network membership with no guaranteed placement.

## Full normalized job description

Opportunity Overview
Arootah engages a curated network of senior operators to support clients across the alternative investment industry, including hedge funds, private equity firms, and family offices. Advisors are deployed on project-based engagements when client needs match their expertise. Joining the network does not guarantee placement; it provides access to opportunities as they arise.
Why Join the Arootah Network
Alt-industry-only engagements with hedge funds, private equity firms, and family offices
Project-based work that fits around existing commitments
Client origination and engagement management handled by Arootah; advisors focus on delivery
About Arootah
Arootah is a talent solutions firm purpose-built for the alternative investment industry. We advise and we execute, covering the full talent spectrum from entry to exit across five services: Talent Acquisition, Fractional Leadership, Talent Development, Retention & Compensation, and Transition.
Most talent firms solve one problem. Because we cover the full spectrum, we can help clients identify and solve the right one. We start with diagnosis, then deliver.
Our team has run alternative investment firms at the highest levels as COOs, CFOs, and CCOs. That operator experience, combined with 15+ years of alternatives-specific recruiting and a network of 700+ vetted advisors across 18 functional disciplines, is what makes the advice credible and the execution reliable. We also draw on a network of 600+ coaches, deploying those with specific experience guiding senior executives in the alternatives industry.
One industry. One talent partner. Entry to exit.
Learn more: https://arootah.com/
Who We’re Looking For
Arootah is seeking experienced Chief AI Officers, AI Strategy Leaders, and senior transformation executives to join our advisor network and support clients across the alternative investment landscape.
As part of the network, you may be engaged with hedge funds, private equity firms, and family offices to provide strategic, project-based leadership across AI initiatives, automation, workflow optimization, and digital transformation efforts.
Core Areas of Expertise
Assessing and implementing AI initiatives across investment, operational, and business functions
Identifying opportunities to leverage AI for workflow automation, research enhancement, and operational efficiency
Developing AI strategy, governance frameworks, and implementation roadmaps
Partnering with leadership teams to prioritize and execute high-impact AI use cases
Evaluating AI tools, vendors, and emerging technologies relevant to alternative investment firms
Driving organizational adoption, change management, and cross-functional AI enablement initiatives
What You Bring
Prior experience leading AI, digital transformation, technology strategy, or innovation initiatives within financial services, alternative investments, or enterprise organizations
Deep understanding of AI technologies, automation tools, and organizational implementation strategies
Proven track record of executing technology and transformation initiatives that drive measurable business impact
Strong leadership, communication, and stakeholder management skills
Ability to operate both strategically and hands-on in dynamic environments
Important Note
This opportunity is to join Arootah’s advisor network and is not tied to a specific active engagement. Advisors are engaged on an as-needed basis, based on client demand and fit.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

## Artifact metadata

- Resume: https://bit.ly/464Bqpd
- Cover letter: https://bit.ly/3UyjAbC
- Direct resume: https://files.keithsteward.com/Arootah/Keith_Steward_Fractional_Chief_AI_Officer_Advisor_Network_Resume.pdf
- Direct cover letter: https://files.keithsteward.com/Arootah/Keith_Steward_Fractional_Chief_AI_Officer_Advisor_Network_Cover_Letter.pdf
- Validation: PASS under Keith's explicit override — 2-page resume (953 words), 1-page cover letter (245 words); content, PDF geometry, bounds, annotations, links, text extraction, and visual-layout files validated.
- Archived JD capture: https://files.keithsteward.com/Arootah/Keith_Steward_Fractional_Chief_AI_Officer_Advisor_Network_JD_capture.md
- Google Drive used: No