Structural viability is determined by operators who have built under scale, capital pressure, and institutional constraint.
2ndSys combines executive-scale engineering leadership with enterprise-grade architectural rigor under capital pressure. Founded by operators who have built, stabilized, and recovered enterprise-scale systems under real capital exposure.
Founder & Structural Viability Lead
Brett leads structural viability determinations for AI-native systems operating under projected growth load. He previously served as Head of Engineering at EquipmentShare (Nasdaq: EQPT), where he scaled the engineering organization more than 300% during rapid national expansion, hiring and onboarding 70+ engineers and technical leaders while establishing the delivery systems, decision rights, and operating structures required for sustained scale.
Earlier in his career, Brett led enterprise architecture at H&R Block, overseeing modernization within a regulated, institutionally governed environment — experience that informs his focus on structural clarity under capital, compliance, and operational pressure.
Across 20+ years in executive engineering leadership, Brett has built and stabilized organizations responsible for mission-critical systems operating under real capital exposure and uptime risk. His work centers on structural survivability: decision authority boundaries, operational coherence, delivery predictability, and leadership systems capable of scaling without centralized control.
At 2ndSys, he leads engagement delivery and ensures determinations reflect both technical architecture and organizational structure required to sustain growth.
Relevant Experience:
Head of Engineering, EquipmentShare (Nasdaq: EQPT) — scaled org 300%+ during hypergrowth
Enterprise Architecture Leadership, H&R Block — modernization in regulated enterprise environment
Senior Director of Engineering, FireMon — delivery modernization
Engineering leader at DST Systems (now SS&C Technologies) — supported mission-critical financial platforms
Co-Founder & Technical Architecture Lead
Ken leads structural assessment methodology and technical determinations during viability engagements at 2ndSys. With over 20 years architecting enterprise platforms across financial services, defense, and legal technology, he specializes in systems where correctness, compliance, and deterministic behavior are non-negotiable.
His work focuses on eliminating ambiguity between intended system behavior and actual execution — particularly at the boundary between probabilistic AI inference and deterministic business logic. Ken developed the 2ndSys structural taxonomy, scorecard, and classification framework from direct experience diagnosing and recovering complex AI-native systems operating under scale and regulatory pressure.
He oversees repository analysis, architectural evaluation, and application of the structural framework during viability determinations.
Relevant Experience:
20+ years architecting enterprise systems across regulated industries
Built Roslyn-based code generation systems compiling business rules into deterministic, testable logic
Deep expertise in rules engines, compliance automation, and structural boundary design
Creator of the 2ndSys structural taxonomy and classification scorecard

Structural viability for AI-native systems
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