Rocky Warren

Senior Staff Engineer leading AI strategy at Clipboard, a $1B+ GSV healthcare marketplace. I led the re-architecture of marketplace pricing into a real-time rules engine worth 8 digits in additional yearly net revenue, and I build autonomous agents that write, verify, and fix production code across a 3M+-line codebase. I lead teams as a Founding Principal Engineer, Architect, Product Manager, and Startup Co-founder shipping distributed systems that move billions of dollars each year. CISSP and AWS Certified Solutions Architect and Security Specialty.

github.com/therockstorm linkedin.com/in/rockywarren rocky.dev

Skills

TypeScriptPythonJavaScriptLLM AgentsAgent OrchestrationEvalsMCPContext EngineeringDynamic PricingPricing StrategyDistributed SystemsPostgreSQLKafkaRedisAWSDockerReactNextJSREST APIsContinuous DeliveryDevSecOpsCybersecurityCloud Security

Recommendations

Chief Product Officer: "I've been impressed with your leadership of the Curated Shifts project. You've been able to organize a wide range of people and drive important, challenging decision-making without getting stalled out in trying to create consensus. Now that we're in execution phase, you've managed the work of a number of engineers seamlessly and have made critical decisions about design choices to manage project risk successfully, oftentimes showing your technical judgment in these areas to be far superior to my own."
Chief of Staff: "Curated Shifts is an incredible piece of technology. You are decisive, think from first principles, and produce such a high volume of output it is astounding."
CEO describing a Fortune 100 company's reaction to a demo I created: "Slam dunk with [Company]! Thank you for all your efforts on this! [Company VP] was visibly and vocally excited. I think his voice cracked a little when he exclaimed, 'how did you do that!'."
CTO: "Rocky embodies a Principal Software Engineer. He can identify the most important problems, work out different solutions, and choose the most appropriate way of moving forward. He'll then own that solution and see it through to the end. He's also never content with his current skill set and always wants to continue growing. Whether it's books, classes, or certifications, he's willing to put in the work to better himself and the team."
VP of Product: "If no one is telling you, it's appreciated how intentional you are with growing our collective knowledge and being a champion for training. Thanks for doing this stuff, Rocky. I've also been hearing great things about your contributions and speed-of-delivery. The leadership team is impressed."
Technical Lead and Manager: "He's a one-man wrecking crew, one of the most productive engineers I've worked with."

Experience

Clipboard

Healthcare staffing marketplace with $1B+ annual GSV.

Senior Staff Software EngineerMar 2024 - Present(2 yrs 4 mos)

Remote

Marketplace pricing (Curated Shifts): Led six engineers re-architecting pricing for our $1B+ GSV marketplace into a real-time, per-worker rules engine, driving challenging cross-functional decisions across product, ops, and engineering. Increased margins by multiple percentage points—8 digits of additional yearly net revenue. The engine now powers our next-generation dynamic pricing, and its rules library is adopted across multiple products.
Defining and leading Clipboard's AI strategy: Condensed our best practices into AGENTS.md rules with learning feedback loops and shipped them to 30+ microservices across a 3M+-line codebase, raising the share of AI-written code to 95%, doubling merged pull requests, and tripling production deploys per engineer.
Agentic CI reliability: Built autonomous agents that triage, diagnose, and fix flaky tests via multi-agent consensus, reducing CI flakiness by 85% in six weeks. Added fast agent guardrails across the organization.
Notification platform migration: Led company-wide migration from Braze to Knock across thousands of notifications and 10+ teams, built migration tooling and AI prompts so teams could self-serve the migration. Negotiated vendor contracts and contributed to vendor open-source repos to unblock teams.
Platform modernization: Cut linting time 100x by switching from ESLint to Oxlint and introduced the strictest TypeScript configuration.
Engineering culture and leadership: Defined Staff Engineering at Clipboard and introduced a formal mentorship program pairing senior and staff engineers. Established ADRs and a technical design review process through a senior engineer committee. Founded the Security and Staff+ teams.

Staff Software and Security EngineerMar 2023 - Mar 2024(1 yr)

Remote

Platform modernization: Transitioned the company from weekly releases to continuous delivery and trunk-based development across (at the time) 50 microservices.

Warren Park

Advise engineering organizations on agentic delivery to ship customer value faster while raising the verification and quality bars.

Founding AdvisorDec 2025 - Present(7 mos)

Remote

Publish playbooks on agentic delivery, including multi-agent consensus for eliminating flaky tests.

Brale

Stablecoin issuance platform.

Principal Software and Security EngineerAug 2022 - Mar 2023(7 mos)

Remote

Encrypted sensitive data using 256-bit AES-GCM envelope encryption backed by AWS KMS, random initialization vectors, and tagged ciphertexts for quarterly rotation. Searchable fields use HMAC SHA-512 hashes.
Built SIEM on Datadog ingesting application, CloudTrail, GuardDuty, VPC flow, Route53, and load balancer logs. Achieved 95%+ cloud security posture management (CSPM) rule findings passing for PCI, SOC 2, and GDPR, with alerting on new findings and anomalous activity.

Founding Principal EngineerJan 2022 - Aug 2022(7 mos)

Remote

Architected cost-efficient, secure cloud infrastructure across multi-account, multi-region, multi-subnet VPCs protected by WAFs, with automated IAM and resource provisioning via AWS Organizations and CDK IaC.
Proposed and implemented multi-party computation (MPC) asset custody enabling multi-blockchain custodial wallets. Authored ERC-20 compatible Solidity smart contracts, coordinated external audits, and built automated multi-blockchain deployment infrastructure.

Vertex Software

Cloud-native 3D digital twin platform.

Principal Technical Lead and Product Manager, APIs & SDKsAug 2020 - Jan 2022(1 yr 5 mos)

Remote

Managed and mentored the API team, driving product discovery and prioritization. Focused on customer satisfaction via interviews, step-by-step guides, interactive demos, a CLI, and always up-to-date API code samples. Implemented "No Meeting Wednesday" and asynchronous stand-ups to increase focus time.
Created uptime and availability tests with automatic rollback and alerting, enabling continuous delivery.

Principal Software ArchitectSep 2019 - Aug 2020(11 mos)

Remote

Built public REST APIs from scratch to OpenAPI, JSON:API, and CloudEvents specifications. Inter-service communication via Kafka and gRPC. Code coverage >90%.
Architected distributed, streaming, event-driven systems delivering sub-second bill of materials (BOM) and scene updates on CAD models with hundreds of thousands of BOM lines. Search over hundreds of millions of pieces of CAD metadata via Elasticsearch and Postgres full-text.
Created core libraries and build plugins to reduce duplication, improve security, and multiply the engineering team's productivity.

Dwolla

Payments API moving billions of dollars a year over ACH and RTP.

Principal Software EngineerJun 2016 - Sep 2019(3 yrs 3 mos)

San Francisco, CA

Transitioned most business-critical database table from mutable to immutable, enabling point-in-time user balance queries, robust statements, and snapshots. Snapshots led to 200x faster database queries and 75% reduction in overall database deadlocks.
Migrated webhooks to serverless Lambda functions, scaled to millions of daily messages, reduced peak delays from hours to minutes, cut costs by 50%, and launched with zero downtime.

Lead DeveloperJul 2014 - Jun 2016(1 yr 11 mos)

San Francisco, CA

Led development of API responsible for moving billions of dollars per year while decreasing partner "time to first API call" from hours to minutes with step-by-step guides and SDKs.
Led Instant Bank Verification, cutting account verification times from three days to a few seconds via 3rd party integration. Built as containerized, auto-scaling microservice.

Senior Software EngineerJul 2012 - Jul 2014(2 yrs)

Des Moines, IA

Led company's foray into microservices with Dwolla Credit, integrating credit provider to inject millions in buying power into network. Mitigated partner downtime with caching and fault-tolerant background processes.
Won internal hackathons by reducing ACH clearing times and allowing account creation via API. Each influenced what are now best-selling products.

Crucible Commodities

Real-time commodities trading startup.

Co-founderJul 2014 - Dec 2016(2 yrs 5 mos)

San Francisco, CA

John Deere

Technical LeadJan 2008 - Jul 2012(4 yrs 6 mos)

Des Moines, IA

Led CommandCenter, a 2M+-line in-cab self-driving GPS guidance display now factory-installed in all large-scale John Deere vehicles worldwide. Released on schedule with all known defects closed. Coordinated fortnightly meetings of 25 tech leads across 150+ developers.
Organized and won the company's first two hackathons, judged by 200+ employee votes; demoed results to the CEO and staff.

Software Engineer InternMay 2006 - Jan 2008(1 yr 8 mos)

Des Moines, IA