Tim Sinclair
Member of Technical Staff and Founder, TrueRock.AI
Tim Sinclair spent 34 years at Microsoft in product development, IT, data science and AI engineering — across the web, security and small business: General Manager roles in security products (the Defender antimalware engine), System Center/Intune best practices, Microsoft IT in the USA, India and China; team incubation of Microsoft.com to a global presence and the front door of Microsoft; the key data science point person for Microsoft 365’s SMB engineering team, whose insights helped lead to products for Managed Service Providers; and, most recently, data science and AI engineering for internal Copilot usage insights and narratives. Today he brings those roles together, building TrueRock.AI hands on as its architect and AI engineer: a governed, evidence-backed way for MSPs to deliver AI to the small and medium businesses they serve.
Tim Sinclair in brief.
- Role
- Member of Technical Staff and Founder, TrueRock.AI (since July 2026)
- Company
- TrueRock AI LLC, Redmond, Washington
- Most recently
- Data scientist and full-stack engineer: LLM-first knowledge retrieval for Microsoft 365 Copilot metrics, for internal use at Microsoft (through June 2026).
- Earlier at Microsoft
- General Manager roles: security products (Defender antimalware engine), System Center/Intune best practices, Microsoft IT (USA, India, China)
- Teams built and led
- 600-FTE worldwide team for Microsoft.com; distributed engineering teams of 300+ FTEs — USA, Israel, India, China
- Before Microsoft
- Silicon and hardware design at Texas Instruments (electrical engineer); built secure hardware and a distributed operating system and applications for the National Emergency Airborne Command Post, the President’s and Joint Chiefs of Staff’s national-emergency aircraft; technology leadership at two startups
- Domains
- Internet, security, systems management, small business and Managed Service Providers, AI — including AI observability, grounding and corrections that reduce hallucinations
From designing silicon and hardware to 34 years of product development, IT, data science and AI engineering at Microsoft.
Before Microsoft, Tim did silicon and hardware design at Texas Instruments as an electrical engineer and led technology at two startups. Also before Microsoft, he built secure hardware and a distributed operating system and applications for the National Emergency Airborne Command Post — the national-emergency aircraft for the President and the Joint Chiefs of Staff.
Most recently: Copilot usage insights
Data scientist and full-stack engineer — LLM-first knowledge retrieval for Microsoft 365 Copilot metrics, for internal use at Microsoft (through June 2026).
General Manager roles
- Engineering General Manager, security products: led engineering for the Defender antimalware engine; Threat Management Gateway, Phishing Filtering and Anti-Malware.
- General Manager, System Center/Intune best practices team (including virtualization).
- General Manager at Microsoft IT with engineering teams in India and China — IT data projects, and led to a digital marketing role in China that needed deep engineering knowledge to build data sets and digital marketing solutions.
Microsoft.com
Built a 600-FTE team worldwide that led technology innovations to create Microsoft.com — full stack, from the UI and databases to operations teams, multiple data centers and languages. Microsoft’s front door on the web, and one of the most scalable and trafficked sites on the internet.
Enterprise and SMB. Engineering and go-to-market.
Across his career Tim has worked at both ends of the market — enterprise and small business — and on both sides of the business: engineering and go-to-market.
With the advent of AI, that combination is the setup for the next generation of AI-led solutions. It takes domain judgment to know what an AI product for MSPs must get right, engineering depth to make it trustworthy, and market sense to bring it to the people who need it.
Security & systems management
Led engineering for the Defender antimalware engine and the System Center/Intune best practices team as GM; led technology innovation on phishing filtering and Threat Management Gateway; contributed to virtualization and to multi-tenant management for MSPs as the Lighthouse product.
Small business & MSPs
The key data science point person for Microsoft 365’s SMB engineering team, whose insights helped lead to products for the Managed Service Providers who serve small and medium businesses.
Distributed engineering at scale
Shipped commercial products leading distributed engineering teams of 300+ FTEs across the USA, Israel, India and China.
Strategy & go-to-market
As a General Manager, worked closely on strategy with Microsoft vice presidents, CIO- and CEO-level leaders in the internet, systems management and security domains. Brings business development and marketing experience as well.
A General Manager returns to roots as hands-on builder.
The return is to building: at TrueRock, Tim combines the many roles of his career — engineering, product, IT, data science, management and go-to-market — to build an AI-forward product, as its architect and AI engineer. That combination is why he chose the title Member of Technical Staff — a title many frontier AI companies use, and one that in today’s world means combining many roles to produce product. He has built the platform hands on, working with colleagues, his own coding and architecture knowledge and AI coding agents under a written set of engineering standards, many of them enforced by the build itself. Those standards are the product’s own promise — evidence over assertion — applied to the way the product is made.
Evidence, not assertion
Findings are held to the evidence observed in the tenant — and when the product could not read something, it says so rather than reporting that nothing is there.
A second reader
Code changes go through an independent review before they ship.
Guards, not good intentions
Automated checks in the build look for silent failures and for fallbacks that would hide an outage.
People stay in the loop
TrueRock recommends and shows the fix; a technician decides whether to apply it.
AI is reaching small businesses faster than anyone approves it.
People connect AI tools to their work accounts long before anyone reviews what those tools can read, and paste company data into consumer AI because there is no sanctioned alternative. The Microsoft 365 business plans small businesses buy leave gaps here — Business Basic and Standard ship without sensitivity labeling, data loss prevention or Conditional Access, and even Business Premium does not classify data automatically. Many of these businesses rely on a Managed Service Provider to run their technology, which puts the question of governing AI on the MSP’s desk, client by client.
Tim founded TrueRock.AI to meet that need where it lands: with the MSP. TrueRock.AI is an AI governance and Microsoft 365 security platform built for MSPs. It finds the AI apps connected to each client’s tenant and what they can reach, brings data-protection intelligence to every Microsoft 365 tier, and gives staff a governed AI assistant — secrets redacted before a prompt reaches a model, every conversation metered per client — with findings that carry their evidence and curated runbooks to fix them. It complements Microsoft: it helps every client get the most out of the Microsoft 365 they own, and amplifies E5, Copilot and Agent 365 where a client has them. The MSP turns AI from a risk its clients carry into a governed service it delivers.
The platform today — open a card to watch its demo.
And the rest of the platform — 18 more capabilities
- A read-only First Look assessment of a client tenant, under the access the client grants — naming every surface it read and every surface it could not, with the reason
- Sensitive-data discovery — AI surfaces the PHI and PII nobody labeled, with the fix
- Real sensitivity labels applied on Business Premium
- Per-client AI chargeback — token spend, cost and margin
- Security posture scoring, drillable to evidence
- Vulnerability & threat intelligence — CVEs ranked by real exploitability
- AI readiness — scored across six dimensions before you deploy
- Device compliance across every endpoint (Defender + Intune)
- Conditional Access coverage gaps
- Email authentication (SPF · DMARC · DKIM)
- External-sharing exposure, ranked by sensitivity
- Blast radius — who (and what) can reach the exposed data
- Scheduled per-tenant security reports (DOCX + PDF)
- Cross-client portfolio, every tenant ranked by risk
- Build your own grounded report generators — run, fork and edit as templates
- Drive it from your team’s own AI client — governed, redacted and metered per client
- Findings routed to PSA tickets by your own rules — ConnectWise, Autotask and HaloPSA adapters, connected with your credentials
- Connect your first tenant in minutes
Education
Master’s in Computer Science
University of Colorado at Boulder
Bachelor’s in Electrical Engineering
Texas Tech University
Talk to Tim.
For interviews, analyst briefings and product walkthroughs, email hello@truerock.ai or connect on LinkedIn.