25 years of building enterprise revenue.
Operator-turned-fractional CRO. $100M+ personally closed. $1B+ delivered by teams I've built and led. Based in Atherton, California — working with founders across the Bay Area and remote.
My career has been a single long thread: building B2B SaaS revenue engines for enterprise software companies, starting as an individual contributor closing the first deals and growing into Chief Revenue Officer roles where I owned the full motion from ICP definition through 20+ rep teams.
The arc has covered most of the categories that matter in enterprise: AI and agentic GTM tooling (Aisera, FluidCloud), FinTech and WealthTech (Investor Services, with Acorns, Charles Schwab, LendingClub, and Wealthfront on the customer list), cloud infrastructure and Infrastructure-as-Code across all major hyperscalers, cybersecurity, dev tools, and the broader ISV/OEM partnership ecosystem at SAP, IBM, Oracle (via Instantis), and Micro Focus.
What I've learned across these companies is that the patterns are remarkably consistent. The transition from founder-led selling to a repeatable revenue engine is almost identical whether the product is a security platform, an AI agent, or a FinTech custody service. The buyers are different. The motion is the same.
Founder, A8 Core™ and B5 Secure™ · Corporate Advisor & CRO, TrustModel AI.
I am the founder of A8 Core™ — financial-account infrastructure: an API-driven account operating system for fintech, wealthtech, retirement, private markets, custody, and trust — and B5 Secure™ — continuous, per-data-element Zero-Trust authorization for .NET applications, APIs, services, and AI agents, enforced inside the application with verifiable evidence. I also authored the ocsf-authority proposal, an open OCSF extension for authorization decisions at the data element.
At TrustModel AI I serve as Corporate Advisor and Chief Revenue Officer, defining the enterprise revenue strategy for an AI safety and governance platform serving regulated, high-consequence use cases.
Alongside these roles, I take 1–2 selective fractional CRO engagements at a time with technical founders at Seed–Series B where the work fits my background and schedule, and I invest as an angel in early-stage B2B software.
Selected milestones.
- Founder, A8 Core™ — API-driven account operating system for regulated financial services; 45 account types across five account natures and 10 asset classes.
- Founder, B5 Secure™ — in-process, fail-closed Zero-Trust authorization for .NET; author of the ocsf-authority OCSF extension for authorization decisions at the data element.
- VP Global Alliances & Partners, Aisera — led the partnership that earned Microsoft Partner of the Year — Business Transformation. Built the Alliances and Channel Ecosystem (ACE) program.
- Founder & CRO, Investor Services — scaled platform from concept to 2M+ accounts and $15B+ in assets under custody. Tier 1 FinTech customers including Acorns, Charles Schwab, LendingClub, Wealthfront.
- VP Strategic Sales (ISVs & OEMs), SAP — led global ISV and OEM partnerships with HP, Oracle, Trizetto.
- Strategic Sales (ISVs & OEMs), IBM — achieved #1 business unit worldwide at 555% of plan.
- SVP Worldwide Sales, Instantis (acquired by Oracle) — built global enterprise sales org, delivered 100+ net-new customers and $42M+ revenue.
- VP Sales, Versata — grew revenue from $379K to $20M+; top global revenue rankings 1999–2001.
Background.
- Massachusetts Institute of Technology (MIT) — Finance, Executive Program (2016–2017)
- Stanford University — Business, Executive Program (2008–2009)
- Southern California College — Bachelor of Science in Business and Communication
Writing worth your time.
The thinking behind the work — frameworks and field notes from 25+ years building enterprise revenue.
Framework
The Seven C’s of Selling
A deal-dynamics model for enterprise sales — the seven forces that decide whether a complex deal closes, and when. Read →
Essay
Founders Don’t Fail on Product
Why most Seed–Series B startups stall on the chasm between founder-led selling and a repeatable revenue motion. Read →
Let's talk.
If your stage and sector fit and you're ready to graduate from founder-led selling, I'd be glad to spend thirty minutes.
Book a 30-min call → todd@yancey.com • +1 (650) 572-5000 • linkedin.com/in/toddyancey