Platform Re-Architecture
Designed and implemented a multimillion-dollar re-platform from VMWare to OpenStack.
- 2-3x real-world performance increase
- 2x customer density improvement
- 30% decrease in COGS
- Eliminated single points of failure
Build the right product. Ship it on bulletproof infrastructure.
Automate everything in between.
We provide fractional CTO, CPO, CISO, and COO leadership to growth-stage companies, with deep expertise spanning product strategy, cloud infrastructure, data, DevOps, and information security, powered by dark factory AI automation.
Full Stack
Product to production
50%+
Cloud cost reduction
2-3x
Performance gains
AI-Native
Dark factory operations
Meet Jon Roemer
Founded by Jon Roemer, Cygnus Strategy provides fractional executive leadership to companies navigating complex product, technical, and organizational challenges. Our team has spent the last decade building and leading at companies like Cytracom, Drizly (acquired by Uber), Datto (acquired by Kaseya), and Incredible Health, spanning product management, infrastructure, data, DevOps, and information security.
We've designed and shipped products used by thousands of businesses, led multimillion-dollar platform migrations, and written and enforced SOC2 and HIPAA compliance programs. Today, we build and deploy AI automation at a level most software organizations haven't reached: agent orchestration platforms, AI-native development workflows, and full dark factory operations where non-technical stakeholders ship features without engineering involvement.
Our team brings strategic leadership across the full product and technology stack. Whether you need senior guidance without the full-time commitment or hands-on implementation that moves fast, we go deep.
Real Results, Not Buzzwords
Every engagement is measured by outcomes that matter to your business.
Cloud Migration & Modernization
Zero-downtime migration of a telecommunications platform from on-prem VMWare to Kubernetes on AWS via EKS.
- Decreased COGS and customer churn
- Improved call quality and signaling
- Enhanced reliability and observability
- Better developer experience
Cost Optimization
Systematic cloud cost analysis and remediation across multiple client engagements.
- 50%+ reduction in AWS bills
- Improved availability alongside savings
- Better performance, not just lower costs
Career Transformation
Mentorship and career guidance for technical professionals.
- Mentees moved from factory floor to six-figure tech jobs
- $0 education or certification investment required
- Focus on practical skills and positioning
How We Can Help
We operate as fractional executives across the full product and technology stack, from product strategy through infrastructure and security. When the situation calls for it, we roll up our sleeves and go deep on implementation, powered by dark factory AI automation.
Product & Technology
Product Strategy & vCPO
End-to-end product leadership from discovery through delivery. We've designed and shipped platforms used by thousands of businesses, including product marketplaces, CRM systems, and identity management. Deep experience in stakeholder management, roadmap prioritization, and aligning technical execution with business outcomes.
Outcome: Products that ship on time, solve real customer problems, and drive measurable business results.
AI Strategy & Dark Factory Automation
We don't just advise on AI. We build and operate it. Our own workflows use agent orchestration platforms that convert product specs into production-ready code with live preview environments. Non-technical stakeholders can trigger, iterate, and ship features without engineering involvement. We bring this same capability to your organization.
Outcome: AI integrations that actually work in production, dramatically reduced cycle times, and operations that scale without headcount.
Systems Architecture & vCTO
Expert guidance on systems design, architecture decisions, and technical strategy. From multimillion-dollar platform re-architectures to zero-downtime cloud migrations, we build scalable, resilient infrastructure that performs.
Outcome: A clear technical roadmap aligned with business goals, reduced technical debt, and infrastructure that scales.
Data Strategy & Engineering
Strategic guidance on data architecture, pipelines, analytics infrastructure, and data team operations. Experience leading data engineering teams and building the systems that turn raw data into business intelligence.
Outcome: Data infrastructure that scales with your business and actually informs decisions.
Infrastructure & Security
DevOps, SRE & Platform Engineering
Concrete, actionable strategies to improve your operational efficiency, deployment velocity, and system reliability. From Kubernetes migrations to CI/CD modernization, we've led these teams at scale across multiple organizations.
Outcome: Faster deployments, fewer incidents, happier engineers.
Cybersecurity & vCISO
Comprehensive cybersecurity and compliance solutions. SOC2, HIPAA, and security program development. We've written and enforced these policies at multiple organizations, not just checked boxes on an audit.
Outcome: Pass your audits, protect your assets, move your business forward with confidence.
Cost Optimization
Identify and eliminate inefficiencies in your cloud spend. Not just cost-cutting, but right-sizing for performance and reliability. We've reduced AWS bills by over 50% while simultaneously improving availability.
Outcome: 25-50%+ reduction in cloud costs while maintaining or improving performance.
Technical Due Diligence & Advisory
Looking to acquire or be acquired? Want to know where your next P0 incident might come from? Thorough technical assessments, post-acquisition audits, and leadership coaching that inform critical business decisions.
Outcome: Clear-eyed risk assessment, actionable remediation roadmap, and leaders who drive technical excellence.
What People Say
"Jonathan is a rare technical leader with a warm, empathetic leadership style. He's able to accurately assess the security and operational efficiency of your team, product, and company, then lay down his assessment accompanied by a pragmatic set of recommendations. Even when his recommendations are going to be hard to achieve, his engaging leadership style will win over the stakeholders needed to get the work done."
"I've had the privilege to work with a Security leader who demonstrates exceptional leadership style, partnership, emotional intelligence and influencing capabilities. What sets Jonathan apart is not just his technical prowess but also his exceptional interpersonal skills. He fosters an environment of trust and open communication. One of his most impressive qualities is his knack for gaining buy-in and influence. He has a natural ability to articulate the importance of security measures to both technical and non-technical stakeholders."
"Jonathan brings a vibrant energy to the IT world, as well as an exceptional skillset. His suggestions and insights into our processes and internal products helped pave the way to not only reduce risks in Security but also streamline execution for some of the company's most critical structural components. Jonathan brings bright ideas to the table and is ready to waste no time implementing them."
"Sarah was a critical team member within our CDP team. Her organization and communication skills kept the team moving forward when we went remote. Everyone knew they could lean on her to work through any difficulty. She worked directly with architects and data analysts to ensure data brought into the tool was what our business users needed. The team was one of the most productive in IT and she was a major reason for that."
"Sarah consistently demonstrated strong skills in managing expectations, continuous product discovery, and stakeholder management. Her ability to balance technical and business aspects made her a reliable product manager. Her commitment to gathering user feedback and market insights led to several product improvements."
Confidentiality & Security
We take information security, confidentiality, and compliance seriously. Having written and enforced SOC2 and HIPAA policies at multiple organizations, we practice what we preach.
- Strict data protection aligned with NIST recommendations
- NDAs executed before any sensitive discussions
- Full information security policy available by request
Ready to Talk?
Schedule a free consultation to discuss your technical challenges. No sales pitch, just a conversation about what you're facing and whether we can help.
Schedule Your Free Consultation