Technology
Technology modernization
Led the digital transformation of multiple traditional companies, resulting in a 35% increase in operational efficiency and the development of new data-driven revenue streams.
RJ Lindelof
RJ Lindelof's Career Timeline and Track Record
7 min read
RJ Lindelof's Career at a Glance
Thirteen years as an engineer, then two decades leading engineering organizations in regulated B2B SaaS, with RJL Software, Inc. running alongside since 1994. Team sizes from 10 to 175+. Ownership models from bootstrapped to private equity.
| Years | Role | Company | Industry and stage |
|---|---|---|---|
| 2026 - now | Senior Director of Engineering, AI & Automation | GovTech SaaS company | GovTech, venture-backed |
| 2025 - 2026 | Senior Director of Software Engineering | hc1 | HealthTech analytics SaaS, venture-backed |
| 2024 - 2025 | Senior Director of Software Engineering | GlobalMed | Telehealth technology, founder-owned |
| 2021 - 2024 | Senior Director of Software Engineering | Successware | Home-services B2B SaaS, PE-backed |
| 2019 - 2021 | Head of Software Engineering | Ruffalo Noel Levitz | Higher-ed fundraising SaaS |
| 2018 - 2019 | Head of Software Engineering | DebtPayPro | FinTech, bootstrapped |
| 2012 - 2018 | Head of Accelerated Solutions Group, R&D | Follett School Solutions | K-12 EdTech |
| 2006 - 2012 | Senior Software Engineering Manager | Follett Learning | EdTech |
| 1994 - 2006 | Software engineer (individual contributor) | Various | 13 years of writing code |
| 1994 - now | CEO | RJL Software, Inc. | Independent software business |
This is the evidence page. The opinions are on the leadership page.
Newest first
Career Timeline: Results by Role
June 2026 - Present
Senior Director of Engineering, AI & Automation
Venture-backed GovTech SaaS company
- Cut LLM inference cost 90% by profiling the workload first. It was using under 2% of the frontier capability it was paying for, so it moved to low-cost and no-cost models.
- Built a delivery and AI-impact dashboard: story-to-production cycle time, escaped defects, release frequency, share of stories with AI-assisted tests, and engineering cost per shipped feature.
- Own a platform rewrite from legacy .NET to a TypeScript, Node, and Python monorepo, to feature parity, on one-week sprints.
- Hold an Eastern Europe contracting team to the same standards as staff, run as one engineering organization. Member of the executive leadership team.
November 2025 - May 2026
Senior Director of Software Engineering
hc1 - HealthTech analytics SaaS
- Operationalized an AI-native SDLC as production infrastructure, with GitHub Actions, Claude Code, Copilot, and AWS Kiro as pipeline stages: 5x deploy frequency and a 23% gain in pull-request throughput.
- Raised code coverage from under 10% to 40% with no dedicated QA team, by cross-training Product on Playwright and putting SonarQube in CI/CD.
- Cut new-engineer onboarding time 70%.
- Moved the organization from AI-curious to AI-proficient in waves, starting with engineering and data, and ran the company's first AI Hackathon.
- Built multi-model AI governance in a HIPAA and SOC 2 environment, and led the AWS partnership for Epic EMR integration.
June 2024 - October 2025
Senior Director of Software Engineering
GlobalMed - telehealth technology
- Led 4 Senior Managers and 30 engineers, onshore and offshore, at a telehealth company whose customers include the VA and the White House Medical Unit.
- Retired 65% of technical debt through a .NET 8 platform rebuild and Azure modernization, and raised deployment frequency 25%.
- Introduced Claude Code in May 2025 with guardrails and usage policies, then OpenAI Codex a month later. Time-to-productive for new developers dropped 35%.
- Led the company-wide AI Taskforce across Engineering, Product, QA, Operations, HR, and Finance, and closed 95% of critical vulnerabilities with the vCISO.
March 2021 - June 2024
Senior Director of Software Engineering
Successware - PE-backed home-services SaaS
- Grew engineering from 30 to 175+ across onshore, nearshore, and offshore teams, with 80% of that growth in a single nine-month window and 15+ Senior Managers and Directors reporting in.
- Delivered a 99.95% SLA at sub-second response for 10k+ concurrent users on a replatformed multi-tenant, AWS-native architecture.
- Built the CI/CD foundation and an Internal Developer Platform: code-to-release cycle time down 40%, manual QA effort down 30%, regression coverage up 45%.
- Set Datadog and Splunk observability standards that cut mean time to recovery 30%.
- Presented architecture and investment cases to PE advisors, investors, and the C-suite, and secured approval for a React Native mobile platform delivered on schedule and within budget.
January 2019 - March 2021
Head of Software Engineering
Ruffalo Noel Levitz - higher-ed fundraising SaaS
- Led 5 Senior Managers and 25+ engineers.
- System throughput up 25%, team velocity up 30%, incident frequency down 40%, defect escape rate down 40%.
- UI support tickets down 85%.
- Replaced legacy telephony with WebRTC and cut communications cost 30%.
January 2018 - January 2019
Head of Software Engineering
DebtPayPro - bootstrapped FinTech
- Joined as employee number 38.
- Ran a zero-downtime migration from a data center to AWS, coordinating 30+ vendor, gateway, and finance integrations.
- Cut pull-request merge time 90% and raised PR throughput 23%.
April 2006 - January 2018
Senior Software Engineering Manager, then Head of Accelerated Solutions Group, R&D
Follett Learning and Follett School Solutions - EdTech
- 2006 to 2012 at Follett Learning: technical leadership across 6 independent SaaS products and 25+ senior developers. The organization grew 38%. Hybrid onsite and remote teams from 2006.
- Ran technical due diligence and post-close integration on multiple acquisitions.
- 2012 to 2018 at Follett School Solutions: founded and ran an internal R&D startup with a fail-fast model that turned experimentation into product advantage.
- Fully distributed from 2012, across several US states plus offshore engineers in India, and stood up the company's first true CI/CD practice.
1994 - 2006
Software engineer
Individual contributor; RJL Software, Inc. founded 1994
- Thirteen years of writing code for a living: Java, Delphi, ASP.NET, and C++, among others.
- RJL Software, Inc. dates from the same year, 1994.
- The reason I can still tell when an estimate is fiction. More on that in the outtakes.
Key achievements
Results That Held Up
Across 20+ years of executive leadership: 4 companies scaled by 50% or more, 15% average month-over-month revenue growth, and 4 global markets entered. Three results worth spelling out.
Growth
Market expansion
Expanded business operations into 4 new global markets, growing international revenue from 3% to 28% of total company revenue within three years.
People
Organizational leadership
Built and led cross-functional teams that delivered three consecutive successful product launches, each exceeding revenue targets by more than 30% and capturing significant market share.
Regulated industries
HealthTech, EdTech, GovTech, and FinTech
Most of this career happened where an auditor eventually asks who approved the change. HIPAA and SOC 2 environments in HealthTech. Student and institutional data in EdTech. Payment gateways in FinTech. State agencies in GovTech.
What changes in a regulated shop is not the speed limit. It is the evidence requirement. The teams I run ship quickly because the audit trail, the review tiers, and the tool boundaries are built into the pipeline, so nobody has to reconstruct them the week before an audit. More on that under regulated B2B SaaS expertise.
Investors and boards
PE-Backed and Venture-Backed Context
At Successware, a PE-backed company, I presented architecture and investment cases directly to PE advisors, investors, and the C-suite. At Follett I ran technical due diligence and post-close integration on multiple acquisitions, and at hc1 I led post-merger integration work.
The lesson from all three: investors do not need a tour of the architecture. They need to know what it costs, what it risks, and when it pays back. If that sounds like the conversation you need, see how I work with private equity and venture investors.
Testimonials
What Colleagues Say About RJ Lindelof
RJ's strategic vision transformed our company from a regional player to a global leader. His ability to anticipate market shifts while building a strong organizational culture was instrumental to our success.
As a board member, I've seen many executives come and go. RJ stands out for his combination of strategic thinking and operational excellence. He delivers results while building sustainable organizations.
Working with RJ was transformative for my career. His mentorship and leadership approach creates an environment where people are empowered to do their best work while driving remarkable business outcomes.
From LinkedIn recommendations
RJ is a standout technology leader who balances high-level strategy with a true "roll up your sleeves" work ethic. As Director of Engineering, he was a driving force behind our most critical technical transitions, most notably the shift toward an AI-native SDLC. Rather than just overseeing the change, RJ spearheaded the effort by first mastering the AI development tools himself.
If you are looking for someone to come into your organization and help drive AI adoption then I would definitely recommend RJ for that. He helped us go from a low AI use company to one that embraces AI across the business, acting as the driving force to rally people to change their mindset about using AI to both get more done, and to provide more value for our products
It's an old adage, but it's what separates a boss from a leader. In short, a leader will inspire their team. I can't recommend RJ enough. In the short time he was at hc1, I saw a boost in performance across the entire division.
I consider my own familiarity and growing expertise in AI to come in two phases: Pre-RJ and Post-RJ.
The Parts That Did Not Go to Plan
A timeline like this one is edited. The lessons that did not fit in a bullet point, and a few facts that keep me humble, are on the outtakes page. For what all of this adds up to, see the expertise areas and the roles RJ considers.
Want the next entry on this timeline to be yours?
I am open to the right VP of Engineering, CTO, or CEO conversation. Tell me about the company and the problem.