Leadership with Integrity and Fiduciary Focus
Disciplined Advisory,
Regulatory Alignment
At Trailhead Digital Advisors, our leadership team reflects a diverse blend of fiduciary expertise, disciplined investing, and innovation-driven thinking. Each member brings deep experience from traditional wealth management, regulatory compliance, and digital asset allocation. Together, we form a multi-disciplinary advisory group with a shared commitment to clarity, discipline, and investor protection.
Team Member Profiles
Evan Whitaker (USA)
Chief Analyst, Trailhead Digital Advisors (US) | Chief Analyst (Joint Position), NovumX
Evan Whitaker is currently the Chief Analyst at Trailhead Digital Advisors (TDA), where he leads the Whitaker Advisory Team, where he has a long-standing commitment to the intersection of macro and digital assets, connecting research directly to asset allocation and execution processes. He has established a research and education collaboration relationship with NovumX, serving as the platform’s chief analyst, focusing on cycle observation, market microstructure, and user education, and participating in the rule-making and post-competition review of trading competitions for teaching purposes.
Current Responsibilities
TDA | Principal Analyst (Full-time):
Build and implement a three-layer framework of Trail Map – Waypoints – Guardrails; leading asset allocation, risk budgeting and rebalancing rules; Provide research-driven advice to clients while being compliant and auditable.
NovumX | Chief Analyst (Joint Position):
Research on the release cycle and microstructure of platform users, improve risk control and educational content specifications; Maintain a clear “research-disclosure-education” boundary with the product/compliance team.
Public Events:
Participate in the NovumX trading competition with a regular account and use post-mortem to review and preserve best practices. All displays are accompanied by risk control parameters and limitations, which do not constitute a return commitment or personalized advice.
Research Areas and Methods
Macro and on-chain: liquidity cycle, net flow of stablecoins, activity and network health indicators, and linkage analysis with traditional macro variables (growth, inflation, policy, US dollar cycle).
Market microstructure: order book depth, spreads and slippage, transaction quality assessment; Price protection and self-transaction protection mechanism.
Risk and behavior: Risk budgeting, batch entry (DCA), volatility targets and scenario analysis as the core; Emphasize “reviewable, quantifiable, and implementable”.
Representative Practice
Standardize the “three-tier framework” into a team operation process to achieve research-execution-review full-link traces and audit-friendly.
Launched a column on cycle observation and microstructure on NovumX, using a “one-page diagram” to reduce complexity and improve user understanding and execution.
Construct an “Asset Scorecard” methodology to observe key assets (for educational purposes) in layers by technical/fundamental/compliance dimensions.
Dr. Cassandra Thorne (USA)
Chief Compliance Officer (CCO)
Dr. Thorne is a leading expert in regulatory affairs for digital assets and wealth management. As CCO, she oversees the firm’s adherence to all federal and state Registered Investment Advisor (RIA) regulations. She focuses on risk mitigation, document retention, and conflict disclosure, ensuring Trailhead’s fee-only model and fiduciary standards are embedded in every client interaction and operational process.
Marcus Chen (USA)
Chief Technology Officer (CTO)
Marcus leads the secure, efficient execution of all client services. As CTO, he is responsible for the firm’s cybersecurity, client data privacy standards, and integration with qualified, third-party custodians. He ensures the technology stack supports a minimal-custody, maximum-security approach, aligning IT infrastructure directly with regulatory requirements.
Avery Collins (USA)
Research & Client Operations Associate
Avery supports the Chief Analyst and the Whitaker Advisory Team, focusing on research synthesis, data visualization, and the operational compliance of client materials. Her core role is ensuring the firm’s “Trail Map—Waypoints—Guardrails” method is translated into clear, auditable client onboarding, review, and quarterly communication packages. She prioritizes clear documentation and risk-first communication.
Sarah J. Davies (USA)
Head of Client Strategy & Education
Sarah is responsible for the overall client journey and the firm’s educational initiatives. She translates complex advisory strategies into plain-English resources, overseeing the Basecamp Education Hub. She works directly with clients to ensure their personal goals and risk profiles are accurately mapped into a disciplined, long-term Trail Map strategy.
David H. Thompson (USA)
Director of Portfolio Allocation & Research
David focuses on the quantitative aspects of digital asset management. He specializes in optimizing the core/satellite allocation, developing disciplined rebalancing targets, and analyzing the impact of on-chain metrics on systemic market risk. He plays a key role in developing the Asset Scorecard and the firm’s Cycle Watch reports for internal use and client guidance.
Liam O’Connell (USA)
Chief Fiduciary Officer (CFO) / Head of Advisory
Liam oversees all client-facing advisory functions, ensuring every strategy adheres strictly to the firm’s fiduciary standard. With a background in traditional wealth management and RIA compliance, he is responsible for training the advisory team, auditing client suitability processes, and translating complex regulatory requirements into practical, client-first advice.
Dr. Kenji Sato (USA)
Director of Quantitative Risk
Dr. Sato is responsible for the statistical modeling and backtesting of the Trail Map framework. He develops and monitors the quantitative Guardrails (e.g., maximum drawdown limits, volatility targets, correlation analysis), ensuring the firm’s risk-budgeting philosophy is mathematically sound and consistently applied across all client allocations.
Maya Sharma (USA)
Head of Investor Education & Outreach
Maya leads the creation and delivery of the Basecamp Guide and all client education materials. She is focused on improving financial literacy in the digital asset space, designing accessible courses, webinars, and content that empower clients to understand why they are investing, not just what they are investing in.
Ben Carter (USA)
Senior Research Analyst (Macro & On-Chain)
Ben focuses on translating macro-economic trends and on-chain metrics into actionable insights for the Chief Analyst’s team. His work informs the firm’s strategic positioning within the Trail Map (core vs. satellite allocation) and provides the fundamental data used to define Waypoints for cycle adjustments and rebalancing opportunities.
Charles "Chuck" Davis (USA)
Director of Client Onboarding & Technology
Chuck manages the seamless and secure client lifecycle, from initial digital identity verification (KYC/AML) to setting up client portal access. He ensures the technology stack used for data collection and reporting is both compliant with data privacy regulations and exceptionally user-friendly, minimizing friction while maximizing security.
Dr. Elena Rodriguez (USA)
Director of Fiduciary Documentation & Client Experience
Dr. Rodriguez specializes in the crucial intersection of client communication, compliance documentation, and user experience (UX). Her role ensures that every document, from the initial Form ADV disclosure to quarterly performance reviews, is presented clearly, is legally sufficient, and aligns with the client’s understanding. She manages client feedback and process improvement to make the disciplined approach feel intuitive and transparent.