alphastrat.ai

Fractional CTO & CISO · Investment management

Senior technology and security leadership, sized for your firm.

Alpha Strategy works with RIAs, family offices, and alternative investment managers that need a seasoned technology executive in the room without adding one to the payroll. We set the strategy, run the security program, and get you ready for the questions regulators and LPs ask.

Former Global CTO, Bregal Investments Microsoft & Google stack depth AI governance for regulated firms

Services

Three seats at the leadership table.

Engage one role or combine them. Either way you get one accountable advisor who knows your environment, your vendors, and your regulators.

Fractional CTO

Technology strategy & operations

A roadmap tied to how your firm invests, reports, and grows, and the follow-through to deliver it.

  • Technology roadmap and budget
  • Platform selection: portfolio reporting, CRM, data
  • Microsoft 365, Azure, and Google Workspace architecture
  • MSP and vendor management
  • Office moves, integrations, and transitions
Fractional CISO

Cybersecurity program

A security program that stands up to an SEC exam, an LP due diligence questionnaire, and a real incident.

  • Written policies and annual program review
  • Identity, device, and email hardening
  • Incident response and disaster recovery plans
  • Tabletop exercises for leadership
  • DDQ and exam response support
AI Governance & Enablement

Put AI to work, safely

Clear rules for how your team uses AI, and practical deployments that save real hours.

  • AI acceptable use policy mapped to SEC expectations
  • Approved tool inventory and data controls
  • Enterprise AI rollout: Claude, Copilot, ChatGPT
  • Workflow automation for research and reporting
  • Staff training and adoption

Who we work with

Built for lean investment firms.

Our clients run sophisticated strategies with small teams. They need institutional-grade technology without institutional overhead.

Registered investment advisers

Exam readiness, client data protection, and a security program sized to an RIA's headcount and budget.

Family offices

Consolidated reporting, privacy for principals and their families, and a single point of accountability across vendors.

Alternative investment managers

Private equity, credit, and real estate managers facing LP due diligence, fund launches, and operational build-outs.

Approach

How an engagement runs.

Every engagement starts with an honest look at where you are today, then moves to a plan your partners can approve and a cadence that keeps it on track.

  1. Assess

    Review your environment, vendors, policies, and recent exam or DDQ findings.

    Weeks 1–3
  2. Roadmap

    A prioritized plan with owners, costs, and dates, written for the investment committee.

    Weeks 3–5
  3. Execute

    Lead the projects, manage the MSP and vendors, and close the gaps that matter most.

    Ongoing
  4. Govern

    Monthly reporting, annual program review, and evidence ready for regulators and LPs.

    Monthly · Annual

About

Rob De Gracia, Principal

Rob has spent his career leading technology and security inside financial services firms. As Global CTO at Bregal Investments, he ran technology across a multi-strategy private investment platform, from infrastructure and security to the systems investment teams relied on every day.

He founded Alpha Strategy to give smaller firms that same level of leadership. Clients get an executive who can brief the partners in the morning and configure conditional access in the afternoon.

Microsoft 365AzureEntra IDIntuneSharePointGoogle WorkspaceClaude EnterpriseMicrosoft Fabric

Engagement models

Pay for the leadership you need.

No long implementation contracts. Scope is agreed up front and reviewed with you regularly.

Monthly retainer

Ongoing fractional role

A set block of hours each month as your CTO, CISO, or both, with a standing meeting and monthly report.

Fixed-scope project

Defined deliverable

A platform selection, security assessment, policy set, or AI rollout, delivered on a fixed timeline.

Half-day session

Tabletop exercise

A facilitated cyber incident scenario for your leadership team, with a written after-action report.

Start with a 30-minute conversation.

Tell us what's on your plate: an upcoming exam, a DDQ, a platform decision, or a team asking how to use AI. You'll leave the call with a clear next step, whether or not we work together.

info@alphastrat.ai
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