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Christopher DiPesa

Executive DevOps & Platform Engineering Leader specializing in cloud, SRE, and DevSecOps

RemoteHead of DevOps12 years experienceExecutiveCloud ComputingDevOpsEnergy
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About

Fintech startup veteran (8+ years) building TrustRelay, a control-plane product between ERPs and banks to verify vendors, enforce pre-flight payout policies, automate reconciliation, and produce deterministic audit evidence. Currently at MVP stage and planning to pursue Founders Institute Boston Sprint 2026 while lining up design partners and raising pre-seed/seed.

Experience

Head of DevOpsPriority Technology Holdings
Fractional CTOShipmint
Director, Technology and Data OperationsStord
CTO/AdvisorGiv
Vice President, InfrastructurePriority Technology Holdings
Director, DevOps & SREPlastiq
Manager, Cloud DevOpsHomesite Insurance
Senior Cloud Operations EngineerEnel X (EnerNOC)
Manager, Cloud EngineeringEnel X (EnerNOC)

Education

Northeastern Universitymaster, High Tech Management & Innovation Entrepreneurship (MBA) (2016)
Northeastern Universitybachelor, Management Information Systems & Marketing (2003)

Key Strengths

  • 8+ years fintech experience identifying repeatable AP/vendor payment risk patterns
  • Structured PMF and idea-evaluation framework (YC, Sequoia Arc, CB Insights, Steve Blank, Paul Graham, First Round)
  • Ability to define and build a wedge MVP ("30-day Safety Pilot") targeting a specific buyer pain
  • Strong understanding of finance-team workflows: vendor onboarding, first-payment/bank-change risk, brittle manual reconciliation, audit evidence gaps
  • Lean execution approach: pre-sell pilots, build thinnest end-to-end golden path, prove value fast then scale
  • Startup leadership experience including taking companies through acquisitions

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Languages

English

Skills

Agile MethodologiesAmazon BigQueryAmazon EKSAmazon Web Services (AWS)API Performance OptimizationArgo CDAudit ReadinessAWS Network FirewallAWS WAFCI/CDClickHouseCloud ArchitectureCloud Cost OptimizationCloud EngineeringCloud Migration