-min.webp)
Mechanical Orchard is a GenAI-native technology company that modernizes critical legacy applications without disrupting what they’re doing.
We replicate what’s working today into a modern form that is ready for anything you need it to do in the future—or anything you wished it could do in the past.
We use an iterative, Al-enhanced, reverse-engineering and replication approach that helps companies adapt quickly to competitive threats and market opportunities with the least possible risk.
We observe data flows of the legacy system and gain a deep understanding on how it interacts with other systems and users. Together with the client IT team, we then isolate and pick apart one component at a time to fully comprehend how it behaves, operates and relates to the rest of the current system. Throughout each step of the process, we continuously identify and prioritize the biggest risks of the modernization effort.
Based on our learnings, we build a perfect replica of this component in a secure cloud environment where it’s subject to rigorous performance and functional criteria before it goes live. Now this component is modern, tested, instrumented and well understood. Most importantly, it’s ready for innovation—while running smoothly with the rest of the legacy system.
The process iterates with the next component until the entire system has deployed into the cloud environment. Each subsequent component could take progressively less time through applying our AI tools and organizational learnings.
Because we only work with a single component at a time, each one has a proven fallback method. This profoundly limits the risk to your living, breathing system at any given time.
Generative AI promises to make legacy modernization faster and easier; however, it is still fundamentally a tool that needs to be used with skill, intention, and purpose. We’re exploring large language models to:
At the helm of Mechanical Orchard is a roster of disciplined, driven and curious individuals. We’re a mix of former founding members of Pivotal Labs, Dev-Ops specialists, Software pioneers, visionary Directors and industry shaping innovators.
A software engineer by trade, I began my career writing natural language translation systems in Lisp at an artificial intelligence laboratory in Tokyo. I later launched Pivotal Labs, which was acquired in 2019, and has been credited for shaping the software development cultures of some of Silicon Valley’s most influential and valuable companies. Today, I’m tackling what I envision as the last major problem of software; modernizing and future-proofing the critical systems that support the corporations that run our global economies.
I’ve spent my career shaping markets before they were markets: SaaS before it was SaaS, Big Data when it was just data, ML when search was still clunky, and EV before it was popular. While I’m typically responsible for scaling revenue and go-to-market strategies, I’ve also been CSO, COO, CFO, CRO and CEO, taking companies from garage to four exits (Amazon.com via Alexa Internet, Alta Motors, Cognizant, Discovery Mining) and one IPO (Dice.com).
Before becoming Chief Scientist at Mechanical Orchard I was Fellow at Gusto, Staff Engineer at Facebook, signed the Agile Manifesto, invented Extreme Programming, rediscovered Test-Driven Development, co-authored JUnit, & wrote 10 books, the latest of which, “Tidy First?” which appeared in 2023. The unique engineering & cultural challenges of legacy modernization fascinate me. Exacting work with high costs if done poorly is the opposite tradeoff to new product development.
I’m responsible for all things marketing—brand, positioning, product, content, demand gen— at Mechanical Orchard. I began programming on a Commodore 64 and have held product management and senior marketing positions at Cisco Systems and Cognizant Technology Solutions, where I was on the Executive Leadership Team. After nearly two decades in the corporate world building high-performing teams, I’ve returned to startups: Mechanical Orchard is my seventh.
Mechanical Orchard is my fifth startup, where I lead sales. I began my career as a paratrooper for the U.S. Army, shifting to tech when I joined Accenture as a consultant developing software for clients. Over the past 25 years, I’ve introduced technologies like e-commerce, SaaS, e-signatures, APIs, and now, AI, to enterprises. For fun, I adventure travel.
A software engineer by trade, I began my career writing natural language translation systems in Lisp at an artificial intelligence laboratory in Tokyo. I later launched Pivotal Labs, which was acquired in 2019, and has been credited for shaping the software development cultures of some of Silicon Valley’s most influential and valuable companies. Today, I’m tackling what I envision as the last major problem of software; modernizing and future-proofing the critical systems that support the corporations that run our global economies.
I am driven by curiosity and a passion for creation. For two decades, I have focused on developing scalable and fault-tolerant software architectures, drawing from a diverse background spanning engineering, finance, and the arts. I’m fond of agile practices focused on test-driven development, pair programming, short development cycles and continuous verification and integration of code (essentially, Extreme Programming). Mechanical Orchard is my sixth startup.
My first programming job was in Smalltalk, which spoiled me forever, and eventually led me to Extreme Programming and the founding crew of Pivotal Labs. I launched and grew Pivotal Tracker to millions of users, and helped lead the company through two acquisitions and an IPO. Two startups later, I’m now VP Product at Mechanical Orchard, and leading the R&D team focused on accelerating delivery efforts with AI.
I'm a passionate organizer with a keen eye for identifying problems and solving them pragmatically and creatively. I've rolled three decades of experience in marketing, operations, and administration into Human Resources, where I foster a positive workplace culture, create an inclusive and supportive work environment, and partner with my colleagues to build high-performing teams. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
I have worked across a variety of roles: software engineer, co-founder of a successful SaaS product, management consultant, product manager and sales leader. I’ve also contributed to the industry as a speaker and an advisor to venture leaders at a F150 accelerator. But mostly, I find creative joy in turning ideas into new ventures and scaling them into high-functioning organizations that customers and employees love.
Sed ut perspiciatis unde omnis iste natus error sit voluptatem accusantium doloremque laudantium, totam rem aperiam, eaque ipsa quae ab illo inventore veritatis et quasi architecto beatae vitae dicta sunt explicabo.
At the helm of Mechanical Orchard is a roster of disciplined, driven and curious individuals. We’re a mix of former members of Pivotal Labs, Dev-Ops specialists, software and AI pioneers, and industry shaping innovators.
A software engineer by trade, I began my career writing natural language translation systems in Lisp at an artificial intelligence laboratory in Tokyo. I later launched Pivotal Labs which was acquired in 2019, and has been credited for shaping the software development cultures of some of Silicon Valley’s most influential and valuable companies. Today, I’m tackling what I envision as the last major problem of software; modernizing and future-proofing the critical systems that support the corporations that run our global economies.
I’ve spent my career shaping markets before they were markets: SaaS before it was SaaS, Big Data when it was just data, ML when search was still clunky, and EV before it was popular. While I’m typically responsible for scaling revenue and go-to-market strategies, I’ve also been CSO, COO, CFO, CRO and CEO, taking companies from garage to four exits (Amazon.com via Alexa Internet, Alta Motors, Cognizant, Discovery Mining) and one IPO (Dice.com).
.webp)
I love helping companies improve their business by becoming great at software development. After my experience with startups, I was drawn to consulting, helping to grow Pivotal Labs from a handful of like-minded engineers into a respected business. As Pivotal formed and grew its developer platform product, I oversaw the rapid expansion of the Customer Success organization to thousands of technical staff globally while pioneering techniques with the subscription business model. I oversaw the integration and four subsequent years of operation as VMware Tanzu, following Pivotal’s IPO and acquisition.
I’m responsible for all things marketing—brand, positioning, product, content, demand gen— at Mechanical Orchard. I began programming on a Commodore 64 and have held product management and senior marketing positions at Cisco Systems and Cognizant Technology Solutions, where I was on the Executive Leadership Team. After nearly two decades in the corporate world building high-performing teams, I’ve returned to startups: Mechanical Orchard is my seventh.
Before becoming Chief Scientist at Mechanical Orchard I was Fellow at Gusto, Staff Engineer at Facebook, signed the Agile Manifesto, invented Extreme Programming, rediscovered Test-Driven Development, co-authored JUnit, & wrote 10 books, the latest of which, “Tidy First?” appeared in 2023. The unique engineering & cultural challenges of legacy modernization fascinate me. Exacting work with high costs if done poorly is the opposite tradeoff to new product development.
Mechanical Orchard is my fifth startup, where I lead sales. I began my career as a paratrooper for the U.S. Army, shifting to tech when I joined Accenture as a consultant developing software for clients. Over the past 25 years, I’ve introduced technologies like e-commerce, SaaS, e-signatures, APIs, and now, AI, to enterprises. For fun, I adventure travel.
I lead the team that builds and operates software for our customers. Previously at Pivotal Labs, I was in charge of directing some of the largest and most successful modernizations in the company's history. I believe that tight customer collaboration and delivering software to production early and often are the keys to long-term modernization success. Beyond my work, I am a multi-instrumentalist musician, language learner, and avid traveler.
I am driven by curiosity and a passion for creation. For two decades, I have focused on developing scalable and fault-tolerant software architectures, drawing from a diverse background spanning engineering, finance, and the arts. I’m fond of agile practices focused on test-driven development, pair programming, short development cycles and continuous verification and integration of code (essentially, Extreme Programming). Mechanical Orchard is my sixth startup.
My first programming job was in Smalltalk, which spoiled me forever, and eventually led me to Extreme Programming and the founding crew of Pivotal Labs. I launched and grew Pivotal Tracker to millions of users, and helped lead the company through two acquisitions and an IPO. Two startups later, I’m now VP Product at Mechanical Orchard, and leading the R&D team focused on accelerating delivery efforts with AI.
I'm a passionate organizer with a keen eye for identifying problems and solving them pragmatically and creatively. I've rolled three decades of experience in marketing, operations, and administration into Human Resources, where I foster a positive workplace culture, create an inclusive and supportive work environment, and partner with my colleagues to build high-performing teams. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
I have worked across a variety of roles: software engineer, co-founder of a successful SaaS product, management consultant, product manager and sales leader. I’ve also contributed to the industry as a speaker and an advisor to venture leaders at a F150 accelerator. But mostly, I find creative joy in turning ideas into new ventures and scaling them into high-functioning organizations that customers and employees love.
A software engineer by trade, I began my career writing natural language translation systems in Lisp at an artificial intelligence laboratory in Tokyo. I later launched Pivotal Labs, which was acquired in 2019, and has been credited for shaping the software development cultures of some of Silicon Valley’s most influential and valuable companies. Today, I’m tackling what I envision as the last major problem of software; modernizing and future-proofing the critical systems that support the corporations that run our global economies.
I’ve spent my career shaping markets before they were markets: SaaS before it was SaaS, Big Data when it was just data, ML when search was still clunky, and EV before it was popular. While I’m typically responsible for scaling revenue and go-to-market strategies, I’ve also been CSO, COO, CFO, CRO and CEO, taking companies from garage to four exits (Amazon.com via Alexa Internet, Alta Motors, Cognizant, Discovery Mining) and one IPO (Dice.com).
I love helping companies improve their business by becoming great at software development. After my experience with startups, I was drawn to consulting, helping to grow Pivotal Labs from a handful of like-minded engineers into a respected business. As Pivotal formed and grew its developer platform product, I oversaw the rapid expansion of the Customer Success organization to thousands of technical staff globally while pioneering techniques with the subscription business model. I oversaw the integration and four subsequent years of operation as VMware Tanzu, following Pivotal’s IPO and acquisition.
I’m responsible for all things marketing—brand, positioning, product, content, demand gen— at Mechanical Orchard. I began programming on a Commodore 64 and have held product management and senior marketing positions at Cisco Systems and Cognizant Technology Solutions, where I was on the Executive Leadership Team. After nearly two decades in the corporate world building high-performing teams, I’ve returned to startups: Mechanical Orchard is my seventh.
Before becoming Chief Scientist at Mechanical Orchard I was Fellow at Gusto, Staff Engineer at Facebook, signed the Agile Manifesto, invented Extreme Programming, rediscovered Test-Driven Development, co-authored JUnit, & wrote 10 books, the latest of which, “Tidy First?” which appeared in 2023. The unique engineering & cultural challenges of legacy modernization fascinate me. Exacting work with high costs if done poorly is the opposite tradeoff to new product development.
Mechanical Orchard is my fifth startup, where I lead sales. I began my career as a paratrooper for the U.S. Army, shifting to tech when I joined Accenture as a consultant developing software for clients. Over the past 25 years, I’ve introduced technologies like e-commerce, SaaS, e-signatures, APIs, and now, AI, to enterprises. For fun, I adventure travel.
I lead the team that builds and operates software for our customers. Previously at Pivotal Labs, I was in charge of directing some of the largest and most successful modernizations in the company's history. I believe that tight customer collaboration and delivering software to production early and often are the keys to long-term modernization success. Beyond my work, I am a multi-instrumentalist musician, language learner, and avid traveler.
I am driven by curiosity and a passion for creation. For two decades, I have focused on developing scalable and fault-tolerant software architectures, drawing from a diverse background spanning engineering, finance, and the arts. I’m fond of agile practices focused on test-driven development, pair programming, short development cycles and continuous verification and integration of code (essentially, Extreme Programming). Mechanical Orchard is my sixth startup.
My first programming job was in Smalltalk, which spoiled me forever, and eventually led me to Extreme Programming and the founding crew of Pivotal Labs. I launched and grew Pivotal Tracker to millions of users, and helped lead the company through two acquisitions and an IPO. Two startups later, I’m now VP Product at Mechanical Orchard, and leading the R&D team focused on accelerating delivery efforts with AI.
I'm a passionate organizer with a keen eye for identifying problems and solving them pragmatically and creatively. I've rolled three decades of experience in marketing, operations, and administration into Human Resources, where I foster a positive workplace culture, create an inclusive and supportive work environment, and partner with my colleagues to build high-performing teams. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
I have worked across a variety of roles: software engineer, co-founder of a successful SaaS product, management consultant, product manager and sales leader. I’ve also contributed to the industry as a speaker and an advisor to venture leaders at a F150 accelerator. But mostly, I find creative joy in turning ideas into new ventures and scaling them into high-functioning organizations that customers and employees love.
We believe that every company deserves to realize their vision, free of constraints from the past. Our team's approach, learning aptitude and experience can help them move into this evolving version safely, reliably, fearlessly.
Mechanical Orchard is a legacy modernization technology company headquartered in San Francisco, CA. We apply AI-enhanced tools and disciplined methods to continuously modernize, operate, and innovate on critical business applications, especially those on mainframes, allowing our customers to regain their ability to innovate and win in their markets again with the least risk possible.
Not exactly. Take mainframes, for example: 71 percent of Fortune 500 companies rely on mainframes as their systems of record. This means mainframes support roughly US$13 trillion of revenue each year, half of the entire US GDP of US$25 trillion (2022). Every time you bank, purchase an item online for delivery, or book travel, you’re likely interacting with a mainframe.
Many of the world’s most successful corporations run on older systems that, though they work, constrain their ability to respond and adapt. Mechanical Orchard sets companies up to be able to genuinely innovate in the cloud through a different approach. Common approaches today have several drawbacks:
Migrating the mainframe code “as-is” to the cloud postpones the problem: the code is still old, the constraints still exist, and the skill set keeping it going is still fading because the people who understand it are leaving the workforce.
Converting the mainframe code to a “modern” language using automated tooling simply rewrites code that few human beings understand, into machine-generated code that now nearly no one does. Ignoring the context surrounding the code—the people who use it and the other systems that interact with it—creates further constraints and delays usability.
Overhauling the entire mainframe code and reimagining it from scratch may sound compelling but imposes serious risks: it involves interfering with multiple dimensions of your critical system simultaneously, without knowing if everything will work until the very end. This could mean massive delays, offline systems, unanticipated costs, extended timelines, even changes of management potentially.
Mechanical Orchard understands the behaviors of a system and its interdependencies with other systems, dissects each component to clearly define its purpose and how it works, and delivers modern code incrementally into the cloud. The result is a critical system that is now on a malleable and modern foundation, one that keeps all the essential functions you need, and none of the layers of old workarounds and outdated adaptations that you don’t.
As our Chief Scientist, Kent Beck, puts it: “First make the change easy, then make the easy change.” It might sound counterintuitive, but we believe the fastest and safest way to get to where you want to go is by rewriting what’s already working. And since we deliver incrementally, you can start innovating on each slice as soon as it’s modernized.
Companies that are looking to the cloud for a competitive edge are ideal. This is less about running away from mainframes and their constraints, and more about running toward the boundless opportunities available once existing constraints disappear. Our iterative approach, grounded in always-working software, means that even critical workflows can begin migrating onto the cloud in weeks, not years, and without ever having to go offline. Organizations can capture market shifts and opportunities quickly and elegantly, and accelerate or decelerate as timing, executive support, and market cycles allow.
The beauty of our approach is that it creates a replica in the cloud of a particular workload based on its data flows across component interfaces. Because we can capture sufficiently representative data flows into and out of a given component, we can treat the component itself as a black box and reproduce its behavior in any language. Language choice, either source or target, doesn’t matter.
Continuous modernization means continuous delivery: that’s how we reduce risk and get workflows in production faster. That means we need to run the system while we incrementally modernize it until the entire system is migrated. During that time, customers benefit from a finely-tuned, test-driven, automated cloud environment that is doing everything the mainframe did, with the same performance and functionality—except more and more components are running on modern code. When the modernization of the system is complete, customers can pair in with us and learn and/or take over anytime — the company retains the intellectual property and maintains control.
