About me

Oleg Simonov

As a value creation CTO with 17+ years of driving enterprise value, I founded Engineering Outcomes on a fundamental principle: margin is engineered. The technology a company builds, buys, and operates represents one of its most potent P&L levers, yet it is rarely governed with that level of financial discipline.

What I do

I focus on growth startups and lower-mid-market B2B SaaS and B2C companies where technology can materially increase revenue, growth and enterprise value. I partner with leadership teams and investors on product and customer impact, technology-led value creation, building and repairing engineering organizations, and modernization across the transaction lifecycle. I combine hands-on expertise in mission-critical SaaS, high-volume data-intensive B2C platforms and regulated environments with a Columbia MBA. My leadership experience includes scaling engineering teams from 20 to 60, rightsizing organizations from 150 to 90, and integrating teams after acquisitions.

How I think about technology and the P&L

Built on the principle that margin is engineered, my framework connects tech investment to financial return through a clear chain of causality:


  • Technology Lever: What capability are we deploying?

  • Operating Mechanism: What process or behavior does it change?

  • Performance Metric: What operational indicator shifts?

  • Financial Outcome: How does it impact the P&L?


It is a simple discipline, and it separates technology activity from technology results.

Work with me

CTO advisory and execution for growth startups and lower-mid-market PE-backed companies.

Engineering assessment

An independent view of technology, delivery, and organizational health.

Engineering assessment

An independent view of technology, delivery, and organizational health.

Ongoing CTO advisory

A trusted thinking partner for executive decisions, investment priorities, and organizational change.

Ongoing CTO advisory

A trusted thinking partner for executive decisions, investment priorities, and organizational change.

Fractional CTO leadership

Embedded technology leadership when your business needs hands-on direction and accountability.

Fractional CTO leadership

Embedded technology leadership when your business needs hands-on direction and accountability.

If something here matches what you’re working on, tell me about it.

Engineering Outcomes is the CTO advisory practice of Oleg Simonov: technology, teams and AI capabilities that drive profitable growth and enterprise value.

Insights

Elsewhere

© 2026 Engineering Outcomes, LLC. All writing by Oleg Simonov.

The content of this site may not be used to train AI models without written permission.

Engineering Outcomes is the CTO advisory practice of Oleg Simonov: technology, teams and AI capabilities that drive profitable growth and enterprise value.

© 2026 Engineering Outcomes, LLC. All writing by Oleg Simonov.

The content of this site may not be used to train AI models without written permission.

Engineering Outcomes is the CTO advisory practice of Oleg Simonov: technology, teams and AI capabilities that drive profitable growth and enterprise value.

© 2026 Engineering Outcomes, LLC. All writing by Oleg Simonov.

The content of this site may not be used to train AI models without written permission.