# **RJ Lindelof** 815-354-4531 [rj@rjl.dev](mailto:rj@rjl.dev) Lake in the Hills, IL LinkedIn: [/in/rjlindelof](https://www.linkedin.com/in/rjlindelof) | About Me: [RJL.bio](https://rjl.bio) | Resources: [RJL.link](https://RJL.link) **VP of Engineering | Head of Engineering | CTO** **AI-Native SDLC | Agentic AI in Production | Regulated B2B SaaS | Player-Coach Engineering Leader** 20+ years leading engineering organizations at PE-backed, venture-backed, bootstrapped, and mid-market SaaS companies across regulated B2B: GovTech, HealthTech, EdTech, and FinTech. Drives technology strategy, platform scalability, and AI adoption in close partnership with product and the C-suite, with a track record of scaling multi-tenant SaaS platforms, putting agentic AI into production, and modernizing cloud infrastructure on AWS and Azure. Currently Senior Director of Engineering, AI & Automation at SteadyIQ, leading the platform rewrite onto a TypeScript/Node/Python stack and running Claude Code, Copilot, and GPT-5.6 as production SDLC infrastructure, not demos. Player-coach who still reviews code and architecture, hires and retains high-performing technical teams, and has run hybrid teams since 2006 and fully distributed global teams since 2012 as one engineering organization, not a vendor at the far end of a ticket queue. Prefers engineering teams sized for direct impact, where every hire and architectural decision matters. # **Leadership Scope** * **Company stages:** PE-backed, venture-backed, bootstrapped, and mid-market enterprise * **Org scale:** 10 to 175+ engineers; 15+ senior managers and directors reporting in * **Global teams:** hybrid since 2006, fully distributed since 2012; onshore, nearshore, and offshore engineers across the United States, Ukraine and wider Eastern Europe, Germany, India, China, and the Philippines * **Cloud and compliance:** AWS, Azure; HIPAA, SOC 2, ISO 27001; HL7/FHIR and Epic EMR integration * **AI in production:** Claude Code, GitHub Copilot, GPT-5.6, AWS Kiro, Vertex AI Gemini, self-hosted vLLM (Qwen); multi-model by design, no single-vendor dependency * **Delivery outcomes across roles:** LLM inference cost down 90%, 5x deploy frequency, 23% PR throughput gain, code-to-release cycle time down 40%, PR merge time down 90%, 99.95% SLA at sub-second response for 10k concurrent users # **Professional Experience** ### **Senior Director of Engineering, AI & Automation**, **SteadyIQ**, Atlanta, GA (remote) **06/2026 \- Present** *Venture-backed, AI-driven cloud income verification platform sold to US state agencies. Ingests bank transaction (Plaid) and payroll (Argyle) data, resolves real recurring income from noisy raw transactions, and produces verification reports government benefit programs can rely on.* * **Lead engineering execution and AI/automation strategy** across the existing application and the new platform being built to feature parity on a modern stack. Focus: delivery, quality, and moving the team's AI workflows from individual experimentation to standardized agentic team practice. * **Own the platform rewrite** onto a TypeScript/Node/Python monorepo: Next.js, React, and Tailwind 4 on the frontend; tRPC, better-auth, Prisma, and Supabase on the backend; Google Vertex AI Gemini for production AI with custom failover and circuit breaker. * **Integrations:** Plaid and Argyle for financial and employment data verification; PostHog for A/B testing, feature flags, and error observability; Resend for mail; Twilio for SMS. * **Member of the executive leadership team**, partnering with the CPO on FY27 product strategy and turning strategy and customer needs into clear engineering plans. * **Cut LLM inference cost 90%** by partnering with Data Science to profile the workload, which was using under 2% of the frontier capability it paid for, and moving it to low-cost and no-cost models. Designed and architected in-house document OCR with a self-hosted vLLM (Qwen) fallback. * **Built a sprint dashboard** tracking story-to-prod cycle time, escaped defects, release frequency, percent of stories with AI-assisted tests, and engineering cost per shipped feature. * **Moved the team to 1-week sprints** to align with customer needs and rolled out a lightweight process to raise delivery visibility and sharpen velocity. * **Hold the Eastern Europe offshore contracting team to the same quality and delivery standards as staff**, run as one engineering organization. ### **Senior Director of Software Engineering**, **hc1**, Indianapolis, IN (remote) **11/2025 \- 06/2026** *Venture-backed healthcare analytics platform converting clinical and operational data from labs, health systems, and payer networks into real-time intelligence.* * **Led the full SaaS engineering organization** across a multi-language platform portfolio (Java, C\#, Python), ingestion pipelines, data lake, core platform services, M\&A and post-merger integration, and two flagship FY26 initiatives anchored in agentic AI. * **Operationalized an AI-native SDLC as production infrastructure**, not sandbox tooling. GitHub Actions, Claude Code, Copilot, and AWS Kiro drove code generation, test synthesis, cloud architecture scaffolding, and documentation as first-class pipeline stages. * **Drove an org-wide shift from "AI-curious" to "AI-proficient"** in deliberate waves \- engineering and data first, then DevOps, Integrations, Professional Services, Product, and HR. Built a multi-model strategy (Kiro, Claude, Copilot, Gemini, Snowflake Cortex) so teams developed fluency across platforms with no single-vendor dependency, tracked prompt throughput as a leading indicator alongside delivery and quality metrics, and ran hc1's first AI Hackathon with rolling Show & Tell sessions to turn individual experiments into shared playbooks. * **Built the foundation for AI governance in a regulated environment** \- multi-model policies, prompt use frameworks, and code-assist tool boundaries across the SDLC while preserving HIPAA and SOC 2 posture. * **Built a quality-ownership culture with no dedicated QA team.** Cross-trained Product on Playwright for smoke and release-regression tests; AI-assisted test generation lifted code coverage from under 10% to 40%, with Engineering, Product, and Services jointly accountable for release quality. SonarQube enforced project standards as part of CI/CD. * **Cut new-engineer onboarding time 70%** through an AI-assisted documentation refresh and a lead-mentor program \- measurable DevEx and time-to-first-commit improvement. * **Partnered with the CPO on FY26 product strategy** including a Source IQ gap analysis driving a three-phase roadmap. Both flagship SaaS initiatives have AI at the core: * **Source IQ** \- greenfield agentic supply chain intelligence platform combining contract performance with utilization analytics across client networks. Python FastAPI on vLLM (Qwen3.6-27B), consolidated late-stage from hybrid Java \+ Python to remove a service hop. Production AI contract extraction and compliance scoring. * **Clinical IQ** \- led the FY26 build of a .NET/C\# clinical intelligence SaaS with direct Epic EMR integration via HL7/FHIR on HIPAA-compliant AWS. Surfaces AI-detected patterns and lab/test recommendations to close care gaps and support earlier intervention. * **Led the AWS partnership** for the Epic integration build (AWS contractor team) and served as an early-adopter design partner for AWS Kiro (Amazon Q replacement), bringing external partner muscle and pre-GA tooling into the platform roadmap. * **Drove post-merger integration** \- portfolio rationalization and organizational alignment to scale the combined platform. * **Shifted the org from reactive firefighting to proactive observability.** CloudWatch Canaries, PagerDuty, and custom Grafana dashboards delivered executive-level visibility into uptime and platform health for the first time. ### **Senior Director of Software Engineering**, **GlobalMed**, Scottsdale, AZ (remote) **06/2024 \- 10/2025** *Founder-owned, privately held telehealth technology provider powering the VA and White House Medical Unit.* * **Owned engineering for the SaaS portfolio**, including roadmap, budget, and delivery. 4 Senior Managers and 30 engineers across onshore and offshore teams. * **Led the company-wide AI Taskforce** spanning Engineering, Product, QA, Operations, HR, and Finance. Identified high-ROI use cases and standardized the enterprise AI stack across business units. * **Built an enterprise AI literacy program** with hands-on training in prompt engineering, AI capabilities, and limitations \- making every employee "AI-capable" as a baseline competency. * **Established a Confluence AI Knowledge Hub and cross-functional Innovation Sprints**, capturing a shared Prompt Library and reusable workflows across departments and surfacing production-ready workflows from frontline staff. * **Owned end-to-end AI product strategy** from build/buy/partner evaluation through vendor selection and responsible-AI launch of triage, symptom analysis, and ambient listening features for critical care workflows. * **Pioneered Claude Code adoption (May 2025\)** \- authored guardrails, usage policies, and decision frameworks for AI coding assistants in regulated delivery. Added OpenAI Codex (June 2025\) as a complementary tool and ran Tuesday Technical Talks codifying when to use which. Cut time-to-productive for new developers 35%. * **Drove a .NET 8 platform rebuild and Azure cloud modernization** under an Agile hybrid delivery model that retired 65% of technical debt and lifted deployment frequency 25%. * **Partnered with Sales, Marketing, and Product on technical pre-sales**, presenting roadmap and architecture to enterprise customers and federal stakeholders. * **Closed 95% of critical vulnerabilities** with the vCISO; held HIPAA, SOC 2, and ISO 27001 posture and secured HL7/FHIR data exchange across the platform. ### **Senior Director of Software Engineering,** **Successware**, Columbia, MD (remote) **03/2021 \- 06/2024** *PE-backed B2B home-services SaaS providing the full back-office platform for home-services operators.* * **Owned the full SaaS engineering org through a PE growth phase**, replatforming a legacy monolith to a multi-tenant, AWS-native architecture. Scaled the team from 30 to 175+ engineers across onshore, nearshore, and offshore (15+ Senior Managers/Directors reporting in) when the business needed that scale. * **Delivered 99.95% SLA at sub-second response for 10k concurrent users** by re-architecting service orchestration and application routing. * **Grew engineering 80% in a single 9-month window** through a deliberate global talent strategy and a culture of autonomy with accountability that materially improved retention. * **Presented architecture and investment cases directly to PE advisors, investors, and the C-suite;** secured approval and offshore investment for a React Native mobile platform, delivered on schedule and within budget. * **Built the platform's CI/CD foundation and Internal Developer Platform** \- code-to-release cycle time down 40%, manual QA effort down 30%, regression coverage up 45%. * **Drove FinTech revenue expansion** via GraphQL and AI-enabled APIs that accelerated merchant onboarding and unlocked new integration partnerships. * **Pushed offshore partners to adopt generative AI** for DevOps automation, performance test generation, MVP scaffolding, and synthetic user creation \- a measurable productivity multiplier across vendors. * **Established Datadog and Splunk observability standards,** cutting MTTR 30% and unifying mobile, data, and backend telemetry. * **Unified mobile, data, and backend teams** under a single delivery model to strengthen feature interoperability and reduce hand-off friction. ### **Head of Software Engineering,** **Ruffalo Noel Levitz**, Cedar Rapids, IA (remote) **01/2019 \- 03/2021** *HigherEd fundraising SaaS powering engagement and donor outreach for universities and nonprofits.* * **Owned the engineering org** for the company's mission-critical fundraising SaaS \- 5 Senior Managers, 25+ engineers across distributed locations. * **Lifted system throughput 25% and team velocity 30%** through outcome-driven roadmaps and disciplined backlog prioritization tied to customer value. * **Cut incident frequency 40%** by investing in observability, environment parity, and release confidence \- fewer fires, faster cycles. * **Modernized the main platform** (Java backend, Bootstrap frontend) for responsiveness and broader browser support; UI support tickets dropped 85% and defect escape rate dropped 40%. * **Replaced legacy telephony with a WebRTC infrastructure**, cutting communications cost 30% and broadening platform reach via integrated payments, messaging, and video. ### **Head of Software Engineering,** **DebtPayPro**, Schaumburg, IL (hybrid) **01/2018 \- 01/2019** *Bootstrapped FinTech startup providing debt settlement and financial services software.* * **Joined as employee \#38** to own engineering across the platform; 10+ direct reports. * **Led a zero-downtime data center to AWS migration** (EC2, MariaDB) coordinating 30+ vendor, payment gateway, and finance integrations \- no business disruption. * **Unified product, support, implementation, and sales** around a product-focused operating model, replacing siloed delivery with end-to-end accountability. * **Cut pull-request merge time 90%** and materially increased throughput by introducing modern branching, CI, and review practices. ### **Head of Accelerated Solutions Group (R\&D), Follett School Solutions**, McHenry, IL (hybrid) **06/2012 \- 01/2018** *Education technology leader providing innovative solutions for K-12 schools and libraries.* * **Founded and ran an internal R\&D startup** chartered to accelerate K-12 product innovation; 10+ direct reports across engineering, UX, and QA, overseeing 25+ staff. * **Led a fully distributed, global engineering team from 2012**, spanning US sites (McHenry, IL; Greenville, SC; Minneapolis, MN; Hingham, MA) and offshore engineers in India, before distributed work was the default. * **Partnered directly with product teams and customers** to ship MVP solutions on compressed cycles, creating market-differentiating features that fed the broader portfolio. * **Stood up the company's first true CI/CD practice** and ran multi-framework Agile execution (Scrum, Kanban, Lean, SAFe, Scrumban) tuned to team and product context. ### **Senior Software Engineering Manager,** **Follett Learning**, McHenry, IL (hybrid) **04/2006 \- 06/2012** * **Provided technical leadership across 6 independent SaaS products** with a team of 25+ senior developers; grew the org 38% while establishing KPIs that drove alignment across platforms. * **Led hybrid onsite and remote teams from 2006**, establishing the operating cadence later scaled to fully distributed global delivery. * **Led technical due diligence and post-close integration on multiple acquisitions** \- strategy through execution \- onboarding acquired teams and harmonizing engineering standards. # **Education & Selected Engagements** Columbia College Chicago \- Bachelor of Science, Computer Science McHenry County College \- Associate in Applied Science in Computer Information Systems **Industry Writing:** AI-native engineering leadership, operationalizing AI across the engineering org, scaling engineering teams, and platform modernization, drawn from production practice at [RJL.ai](https://RJL.ai), [RJL.dev](https://RJL.dev), and [RJL.guru](https://rjl.guru) **Certifications:** DataCamp (AI Governance, Understanding AI); Anthropic (Claude Agent Skills, Claude Subagents, Advanced Model Context Protocol, and Claude Integrations)