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
Cut your cloud costs in half.
Double your infrastructure performance.
We provide fractional CTO, CISO, and COO leadership to growth-stage companies, delivering strategic clarity alongside measurable results.
50%+
AWS cost reduction
2-3x
Performance gains
30%
COGS decrease
I'm Jon Roemer
As founder of Cygnus Strategy, I provide fractional executive leadership to companies navigating complex technical and organizational challenges. I've spent the last decade at companies like Cytracom, Drizly (acquired by Uber), Datto (acquired by Kaseya), and Incredible Health.
I've led multimillion-dollar platform migrations from VMware to OpenStack and on-prem to AWS. I've written and enforced SOC2 and HIPAA compliance programs. I've built products that serve thousands of MSPs.
Our team brings strategic leadership to companies who need senior guidance without the full-time commitment, and we can go deep on implementation when needed.
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 for companies who need senior leadership without the full-time commitment. When the situation calls for it, we roll up our sleeves and go deep on implementation.
Technical Leadership
Systems Architecture & vCTO
Expert guidance on systems design, architecture decisions, and technical strategy to build scalable, resilient infrastructure.
Outcome: A clear technical roadmap aligned with business goals, reduced technical debt, and infrastructure that scales.
DevOps, SRE & Platform Engineering
Concrete, actionable strategies to improve your operational efficiency, deployment velocity, and system reliability.
Outcome: Faster deployments, fewer incidents, happier engineers.
Cybersecurity & vCISO
Comprehensive cybersecurity and compliance solutions. SOC2, HIPAA, and security program development from someone who's written and enforced these policies.
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.
Outcome: 25-50%+ reduction in cloud costs while maintaining or improving performance.
Strategic Advisory
Technical Due Diligence
Looking to acquire or be acquired? Want to know where your next P0 incident might come from? Thorough technical assessments that inform critical decisions.
Outcome: Clear-eyed risk assessment and actionable remediation roadmap.
Leadership Development & Executive Coaching
Develop strong technical leaders through personalized coaching and strategic guidance. I've managed engineering teams at scale and mentored engineers into leadership roles.
Outcome: Leaders who inspire, retain talent, and drive technical excellence.
Process Optimization & vCOO
Streamline operations through modern engineering practices, AI, automation, and process refinement.
Outcome: Reduced operational overhead, faster time-to-value, less firefighting.
Product Vision & Strategy
Strategic planning to guide your product vision and align technical execution with business outcomes.
Outcome: Products that ship on time and solve real customer problems.
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