Modernize with Confidence—without disruption or risk
Modernize with Confidence
—without disruption or risk
Mechanical Orchard is an AI-native technology company reinventing the software that runs the world—safely, reliably, fearlessly.
Modernize with
Confidence—without disruption or risk
Modernize with Confidence
—without disruption or risk
Mechanical Orchard is an AI-native technology company reinventing the software that runs the world—safely, reliably, fearlessly.
Modernize to
Innovate—without Disruption
Mechanical Orchard
Explainer Video
Mechanical Orchard's low-risk legacy modernization approach is unorthodox but highly effective.
We recreate 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.
Our approach
Modernizing legacy systems is crucial for competitiveness, security and innovation, yet it often fails due to complexity and risk, leading to operational downtime, cost overruns, and incomplete efforts.
Mechanical Orchard provides a better way to overcome legacy system constraints, especially for the most challenging applications. Our holistic approach focuses on three core principles for safely rewriting, and moving applications to the cloud:
The system in action is the specification
Recreate its behavior exactly in a modern language
Roll increments into production
Meet the team
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.
Rob Mee,
CEO and Founder
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.
Matthew Work,
COO and Co-Founder
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).
Edward Hieatt,
Chief Customer Officer
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.
Irene Sandler,
CMO
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.
Roberto Ostinelli,
CTO
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.
Joe Militello,
CPO
I’m the Chief People Officer at Mechanical Orchard, where I lead the global People organization. Over a 25 year career, I’ve been the Chief People Officer for two publicly traded companies—PagerDuty and Pivotal—helping scale organizations, build high-performing teams, and achieve major milestones, including Pivotal’s IPO. Earlier, I was a VP at EMC and served as a Captain in the U.S. Marine Corps. I’m deeply passionate about building mission-drive organizations that deliver real value to customers, while fostering a culture where employees are excited about their work and feel a strong connection to their team.
Mikey McCormack,
SVP Engineering
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.
Dan Podsedly,
VP Research & Development
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.
Martine Boyer,
VP of Engagement
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 fostering a positive community culture that’s inclusive and supportive of doing what’s right, what works, and what makes good change happen. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
Rachit Awasthi,
VP Strategy & Operations
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.
Want to connect?
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Meet the team
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.
Rob Mee,
CEO and Founder
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.
Matthew Work,
COO and Co-Founder
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).
Edward Hieatt,
Chief Customer Officer
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.
Irene Sandler,
CMO
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.
Roberto Ostinelli,
CTO
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.
Joe Militello,
CPO
I’m the Chief People Officer at Mechanical Orchard, where I lead the global People organization. Over a 25 year career, I’ve been the Chief People Officer for two publicly traded companies—PagerDuty and Pivotal—helping scale organizations, build high-performing teams, and achieve major milestones, including Pivotal’s IPO. Earlier, I was a VP at EMC and served as a Captain in the U.S. Marine Corps. I’m deeply passionate about building mission-drive organizations that deliver real value to customers, while fostering a culture where employees are excited about their work and feel a strong connection to their team.
Mikey McCormack,
SVP Engineering
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.
Dan Podsedly,
VP Research & Development
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.
Martine Boyer,
VP of Engagement
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 fostering a positive community culture that’s inclusive and supportive of doing what’s right, what works, and what makes good change happen. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
Rachit Awasthi,
VP Strategy & Operations
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.
Rob Mee,
CEO and Founder
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.
Matthew Work,
COO and Co-Founder
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).
Edward Hieatt,
Chief Customer Officer
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.
Irene Sandler,
CMO
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.
Roberto Ostinelli,
CTO
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.
Joe Militello,
CPO
I’m the Chief People Officer at Mechanical Orchard, where I lead the global People organization. Over a 25 year career, I’ve been the Chief People Officer for two publicly traded companies—PagerDuty and Pivotal—helping scale organizations, build high-performing teams, and achieve major milestones, including Pivotal’s IPO. Earlier, I was a VP at EMC and served as a Captain in the U.S. Marine Corps. I’m deeply passionate about building mission-drive organizations that deliver real value to customers, while fostering a culture where employees are excited about their work and feel a strong connection to their team.
Mikey McCormack,
SVP Engineering,
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.
Dan Podsedly,
VP Research & Development
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.
Rachit Awasthi,
VP Strategy & Operations
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.
Martine Boyer,
VP of Engagement
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 fostering a positive community culture that’s inclusive and supportive of doing what’s right, what works, and what makes good change happen. My superpower? An ability to win any thumb war challenge. My current obsession is growing sugar cane so I can make my own rum.
Want to connect?
Our insights
Your New Legacy
Starts Here.
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.
30 years of pioneering
the best practices in software development.
Still disciplined,
opinionated, and
innovative.
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 legacy 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 legacy 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 legacy 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 former 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 legacy system 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.
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