AI Engineer/Head of AI/Director of AI Strategy and Implementation (open to title)

JRN 2533

Our client is seeking a highly capable AI leader to help transform how a private family office and its portfolio of businesses operate through the practical application of artificial intelligence. Reporting directly to the CEO, this individual will work across legal, finance, operations, marketing, creative, and administrative functions to identify opportunities, build solutions, and optimize workflows.

This is not a strategy-focused role. It is a hands-on builder position for someone who can quickly understand business challenges, identify opportunities for AI-driven improvements, and implement practical solutions that create measurable impact. The ideal candidate combines technical expertise with strong business judgment and thrives in fast-paced, high-trust environments.

The successful hire will play a key role in shaping the organization's long-term AI strategy, systems, and technology stack while building tools, automations, dashboards, and workflows that improve efficiency, visibility, and decision-making across the enterprise.

Requirements

Professional Experience

Proven experience applying AI to real-world business operations and workflows
Strong engineering, systems architecture, or technical development background
Experience building secure systems, automations, integrations, and data pipelines
Ability to work across legal, financial, operational, administrative, and creative business functions
Experience rapidly prototyping and implementing solutions from concept to deployment
Strong understanding of AI tools, models, and emerging technologies

Core Competencies

Builder mentality with the ability to execute independently
Strong product instincts and comfort operating in ambiguous environments
Excellent problem-solving and critical-thinking skills
Ability to identify inefficiencies and translate them into scalable solutions
Exceptional discretion and ability to handle sensitive information
Strong communication and collaboration skills across executive-level stakeholders

Technical Capabilities

Experience building AI-powered tools, workflows, automations, and agents
Knowledge of LLMs, AI platforms, and workflow orchestration tools
Experience creating dashboards, reporting systems, and command-center-style operational tools
Ability to design secure solutions for financial, legal, and operational environments
Familiarity with tools such as ChatGPT, Claude, Notion, Google AI Studio, Adobe Firefly, and related platforms preferred

Demonstrated Success

Candidates should be able to provide examples of:

AI tools, automations, systems, or workflows they have personally built
The problems they identified and the solutions they implemented
Technologies, models, and platforms utilized
Measurable business outcomes and operational improvements achieved
Approaches to security, governance, and responsible AI implementation

Preferred Attributes

Entrepreneurial mindset with a bias toward action
Curiosity and enthusiasm for emerging AI technologies
Ability to move seamlessly between strategic thinking and hands-on execution
High level of professionalism, integrity, and trustworthiness
Passion for building systems that create leverage, efficiency, and scale

Location: Calabasas, CA – fully in office

Compensation: Up to $250,000 DOE. No bonus; base is the full package.

Structure: Consultant to start, to test fit both ways; open to full-time from day one for the right person.

Benefits (on full-time conversion): Medical, dental, vision, 401k.

Dossier is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.

Dossier is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.

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