👾Phil Calçado

CEO

Brooklyn, New York, United States22 yrs 7 mos experience
Most Likely To SwitchAI Enabled

Key Highlights

  • 20 years of experience in engineering leadership.
  • Expert in AI, microservices, and distributed systems.
  • Successfully led teams to build scalable platforms.
Stackforce AI infers this person is a SaaS and Cloud Infrastructure expert with a strong focus on microservices and AI technologies.

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Skills

Core Skills

Cloud-native ApplicationsDevopsLeadership

Other Skills

Amazon Web Services (AWS)Back-End Web DevelopmentAgile MethodologiesArtificial Intelligence (AI)ManagementScalabilityArchitectureJava.NETSystem ArchitectureAgile Project ManagementCloud ComputingWeb ServicesSpringJavaScript

About

I’m a hands-on engineering executive with 20 years of experience and a recognized expert in AI, microservices, and distributed systems. I’ve built and led high-performing teams while architecting complex platforms at scale. I specialize in creating lean organizations and resilient systems that punch above their weight—consistently delivering products and infrastructure that succeed against much larger competitors. From SoundCloud to DigitalOcean and SeatGeek, I’ve helped underdog teams grow into market leaders. I’m known for bridging executive vision and technical execution—equally effective in the boardroom and at the command line.

Experience

New york cto club

Member

Jan 2024 – Present · 2 yrs 3 mos · New York, New York, United States · Hybrid

PontifĂ­cia universidade catĂłlica do rio de janeiro

Guest Lecturer

Jan 2023 – Present · 3 yrs 3 mos · New York, United States · Remote

  • At PUC Rio, one of the top 10 universities in Latin America, I serve as a guest lecturer for graduate-level courses, sharing my expertise in microservices architecture and distributed systems with the next generation of technology professionals.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Outropy

Founder & CEO

Nov 2022 – May 2025 · 2 yrs 6 mos · New York City Metropolitan Area · Remote

  • We are the Heroku of AI development.
  • Outropy is the AI developer platform that makes sense to software engineers.
  • No fluff, no jargon, no buzzwords.

Picpay

Global Chief Technology Officer (CTO)

Jan 2022 – Oct 2022 · 9 mos · New York City Metropolitan Area · Remote

  • Hired as CTO to prepare the company for growth and an eventual IPO, I led global engineering teams across multiple domains, including platform, data/AI/ML, security, and product lines. After 10 months, the CEO decided to centralize the leadership team in SĂŁo Paulo. I opted not to relocate and amicably parted ways.
  • Key contributions during my tenure:
  • Reduced infrastructure costs by 50%, saving over $10 million annually and accelerating profitability.
  • Launched Open Finance products and marketplace integrations with partners like Xbox, Shopee, Roblox, and Uber.
  • Introduced a crypto exchange and stablecoin to over one million users.
  • Established job levels, salary bands, and improved hiring/onboarding processes, boosting team satisfaction and retention.
LeadershipDevOpsAmazon Web Services (AWS)Agile MethodologiesBack-End Web Development

Seatgeek

Senior Director of Engineering

Aug 2019 – Dec 2021 · 2 yrs 4 mos · New York City Metropolitan Area · Hybrid

  • SeatGeek started as a two-sided marketplace where ticket brokers and consumers could buy and sell tickets. In 2017, the company made a big bet on becoming a "full-stack" ticketing provider. Since then, we have signed many NFL, NBA, Premier League, Broadway theaters, MLS teams, and various live events venues as clients.
  • As the leader of SeatGeek's Platform organization, I directed several small teams in the design, construction, and management of critical applications, APIs, shared services, infrastructure, processes, and developer tools for our engineers and third-party integrators. Our work, which facilitated high-scalability components to manage seasonal usage peaks in ticket sales and venue admissions, was often showcased by Amazon, Datadog, InfoQ, and other industry leaders as best practices. My primary achievements include the following:
  • Migrating on-premise systems to AWS initially through lift-and shift, followed by the gradual replacement of legacy components with cloud-native counterparts without disrupting service quality and availability.
  • Updating our consumer systems from unsupported versions of Python and MySQL to the latest versions.
  • Transitioning our MySQL databases to RDS and initiating the SQL Server migration to RDS, which was completed in 2023.
  • Renegotiating all infrastructure vendor contracts and downsizing our systems during the pandemic, achieving over 20% infrastructure cost reduction.
  • Creating an in-house virtual queuing system to replace a legacy third-party solution, designed to handle high demand.
  • Consolidating tools from multiple vendors into Gitlab, Docker, and Datadog
  • Our complex architecture blended cloud-native systems in Go, Python, and .Net Core with traditional Windows-based .Net workloads.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Meetup

Director, Platform Engineering

Jun 2018 – Aug 2019 · 1 yr 2 mos · New York City Metropolitan Area · On-site

  • (Meetup was a wholly-owned subsidiary of WeWork, which was my employer)
  • WeWork acquired Meetup.com as part of its expansion strategy. The new leadership hired me to build the architecture and platform that would allow for the projected hyper-growth.
  • I headed three teams focused on the web, cloud, and microservices architecture and infrastructure. Our main goal was to make it productive for engineers to build product features and other business software outside Meetup's 12 years old legacy monolith.
  • We built an architecture based on cloud-native microservices, AWS Lambda, and DynamoDB. This allowed feature teams to work with more modern languages and tools, which immediately resulted in the company being able to deploy multiple different features and experiments. However, with the issues around their IPO, WeWork decided to reduce investment in Meetup and ultimately sell the company.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Wework

Director, Platform Engineering

Jun 2018 – Aug 2019 · 1 yr 2 mos · New York, United States

  • (Meetup was a wholly-owned subsidiary of WeWork, which was my employer)
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Buoyant, inc

Principal Software Architect

Aug 2017 – May 2018 · 9 mos · San Francisco Bay Area · Remote

  • Buoyant was founded to productize technology originally developed at SoundCloud and Twitter. I joined at an early stage, when the company was about five people and building a Service Mesh from scratch.
  • In about six months, I designed and built the control plane for Linkerd, along with its CLI, establishing the foundation for what became the company’s flagship product and remains in use today. The system manages and coordinates network proxies and integrates deeply with Kubernetes primitives and container networking, at a time when these systems were still emerging.
  • To make this feasible within that timeframe, I created a property-based testing framework using Minikube that could procedurally generate and validate complex microservice topologies on demand, allowing us to test a wide range of configurations and failure scenarios in a repeatable way.
  • In parallel, I led the integration of Linkerd with Istio, making it the first alternative data plane for Istio (later followed by NGINX and HAProxy). This positioned Linkerd within the emerging service mesh ecosystem and validated its interoperability with early standards.
  • Left following a company shift to an in-office model in San Francisco.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Digitalocean

Director, Product Engineering

Nov 2015 – Nov 2017 · 2 yrs · Greater New York City Area · On-site

  • DigitalOcean hired me to build their Product Engineering organization. The company had been very successful with its original offering, the Droplet, but struggled to deliver new products and keep itself competitive.
  • I've developed and implemented a technology and delivery strategy focused on shortening our time-to-market, from years to months. Changes included:
  • Build a world-class software engineering team, increasing team from ~25 to ~150 over 24 months
  • Introduce feature teams and Continuous Delivery as the default way to build products
  • Reduce the investment in internal tools by automating and outsourcing non-critical business functions
  • Migrate all of our legacy and new systems to a 100% Container-based environment running on stock Kubernetes clusters
  • Coach Product Managers and Engineering Managers in agile and lean product management
  • Refactoring our legacy code base and moving towards a microservices architecture
  • These changes had a massive positive impact in product development. In my time there, we built and delivered several products, including block storage, load balancers, high-memory servers, the community platform, new data centers in India and Germany, the telemetry product, and team management tools for our users.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Soundcloud

Director, Product Engineering

Sep 2011 – Nov 2015 · 4 yrs 2 mos · Berlin Area, Germany · On-site

  • At SoundCloud, I built and managed the Product Engineering organization, growing from 10 to about 250 people over a few years. My organization was responsible for all mobile, web, API, and back-end services and was spread across Berlin, Bulgaria, and NYC.
  • SoundCloud grew from 10 to 250 million active users during this time, and I headed the effort to refactor our systems and applications to cope with this demand. I was the technical leader in developing one of the industry's first and more successful microservices architectures.
  • I was initially very hands-on in our architecture reimagining efforts. As we sourced senior technical staff, I was able to delegate the heavy technical work and focus on strategy and portfolio management. We changed our engineering organization and culture from a throw-over-the-wall-and-wait start to cross-functional teams focused on delivering features end-to-end to all platforms.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Bank of america merrill lynch

Consultant

May 2011 – Sep 2011 · 4 mos · London Area, United Kingdom

DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

The guardian

Consultant

May 2011 – Jun 2011 · 1 mo · London Area, United Kingdom

  • https://soulmates.guardian.co.uk/
Back-End Web Development

Technology one

Consultant

Feb 2011 – Mar 2011 · 1 mo · Greater Brisbane Area

  • Software architecture coaching for the Cloud Computing team.
Back-End Web Development

Aapt

2 roles

Consultant

Jun 2010 – Jan 2011 · 7 mos

  • Working on the core platform technology refresh.
Back-End Web Development

Tech Lead/Iteration Manager

Feb 2010 – May 2010 · 3 mos

  • New customer portal project.
Back-End Web Development

Power.com

Consultant

Jan 2010 – Feb 2010 · 1 mo · Salvador, Brazil

  • Coaching on agile and technical practices.
Back-End Web Development

The walt disney company

Consultant

Nov 2009 – Jan 2010 · 2 mos · Greater Sydney Area

  • I was the Technical Director for the inception for the 'Coinland'​ project. The project delivered a massive multiplayer online game for the Commonwealth Bank with artistic direction by Disney.
  • I've worked with the creative team to develop the game concept and slice it in a backlog suitable for Agile software development. I was also responsible for the systems architecture and a project plan that would let the client accelerate delivery by contracting freelance Flash designers on-demand without much impact to the software development process and quality. The game uses Adobe Flash (with all client logic written in ActionScript) and Java for the back-end.
Back-End Web Development

Macquarie group

Consultant

Jul 2009 – Dec 2009 · 5 mos · Sydney Area, Australia

  • Project management for the Market Risk Online platform.
Back-End Web Development

Ticketek

Tech Lead

May 2009 – Aug 2009 · 3 mos · Greater Sydney Area

  • For the core systems re-platform.
Back-End Web Development

Lonely planet

Tech Lead

Feb 2009 – Apr 2009 · 2 mos · Greater Melbourne Area

  • Developing the main website, http://www.lonelyplanet.com
Back-End Web Development

Bt financial group

Consultant

Nov 2008 – Dec 2008 · 1 mo · Greater Sydney Area

  • Working together with BT teams in developing new offerings.
Back-End Web Development

Sensis

Lead Developer

Dec 2007 – Oct 2008 · 10 mos · Melbourne Area, Australia

  • In the team developing http://www.whitepages.com.au
Back-End Web Development

Thoughtworks

Lead Consultant

Nov 2007 – Oct 2011 · 3 yrs 11 mos · Australia and UK · Hybrid

  • ThoughtWorks is the industry leader in agile software development, continuous delivery, and DevOps.
  • Over my tenure there, I have engaged with clients in Australia and the UK, focusing on bridging the gap between business and technology. At times I've taken a more hands-on role, writing code and defining architecture and standards, but often I was playing a project manager role. As a project manager, I was usually brought in to either take part in a project's ideation/inception phase or to lead the team focused on recovering a project that had gone off the rails.
DevOpsCloud-Native ApplicationsAmazon Web Services (AWS)Back-End Web Development

Globo.com

Head of Software Development, Digital Media

Oct 2006 – Oct 2007 · 1 yr · Rio de Janeiro Area, Brazil

  • The Globo Group is the largest mass media group in Latin America, and owns the second-largest commercial TV station in the world.
  • At Globo.com, its Internet arm, I was the architect and engineering manager of the teams responsible for delivering video and audio over the Internet, both live and on-demand. I was responsible for Brazil's main Internet video (http://video.globo.com) and radio (http://globoradio.globo.com) portals.
  • We moved from a monolithic J2EE code base, centered around direct database integration, to a huge set of webservices. These services take care of ingestion, encoding, and streaming of media, and also make metadata from this content available to other systems, websites, and services across the whole group.
  • We also used what's now known as isomorphic JavaScript, using the Mozilla Rhino engine, to deliver a vast range of widgets that could be easily embedded in the organisation and their partners'​ websites with minimal development effort. This was responsible for a massive growth in audience as Social Networks became common in Brazil.
  • In order to rescue several projects I had inherited, I've my introduced agile practices to my team, the first team to do so in the whole group. We followed XP and Scrum practices, and the reduction in time-to-market and improvements in quality of the product made it such that today Globo.com is globally recognised as a case study in agile adoption.
Back-End Web Development

Cpm s/a

Systems Architect

Apr 2006 – Sep 2006 · 5 mos

  • Phillip was the lead architect of all Java and Microsoft .Net systems developed in the Rio de Janeiro Software factory, focused on logistics (CVRD) and retail (Dell Brazil/USA).
  • Worked directly with client's technology teams to build up distributed and integrated solutions using SOA and ESBs for railway management systems and passenger control and transport optimization, updating, extending and enhancing their old reference architecture models to modern standards and technologies of he Java platform.
  • Designed the architecture behind systems on HR training programs and budget management.
  • He also acted as a consultant for several off-shore projects in architecture, development methodologies and standards.
Back-End Web Development

Sakonnet technology

Software Engineer

Sep 2005 – Mar 2006 · 6 mos · Rio de Janeiro Area, Brazil

  • Philip was member of the System Infrastructure and Optimization Group, department responsible for the development of internal frameworks and the architecture of a highly distributed trading and risk management solutions based in the Java EE platform, including rich Swing clients.
  • His job included maintenance, performance tuning and extension of a real-time commodity trading system, heavily based on asynchronous operations and Message-Oriented Middleware, deployed in a Software as a Service (SaaS) environment using HTTP/RMI/JMS over SSL.
Back-End Web Development

Orga systems

Software Engineer

Jun 2004 – Aug 2005 · 1 yr 2 mos

  • Phillip was the responsible for the specification, development and maintenance of mobile phones / GSM networks applications for billing & costumer management based on C and Java platforms.
  • He designed, implemented and deployed systems using Java EE platform, including the creation of custom JCA adaptors, JDBC drivers and clustered solutions for massive reporting tools and integration between Internet and GSM protocols and services such as HTML, HTTP, IP, USSD and SMS. Acted as an architect and developer on a bonus management solution integrated to the GSM network through SMS and USSD gateways.
  • He was also responsible for the maintenance and evolution of a real-time hybrid (post and pre-paid) corporative mobile PABX system (OVPN).
Back-End Web Development

Fragmental tecnologia da informação ltda

Independent Consultant

Jan 2004 – Dec 2006 · 2 yrs 11 mos

  • Designed software architecture for special needs. Acted as an independent advisor and reviewer of software architectures. Conducted training sessions on software development, design and methodologies.
Back-End Web Development

E4w

Tech Lead

May 2003 – Jun 2004 · 1 yr 1 mo

  • Phillip acted as the team leader of about 10 developers, from junior to senior professionals. Managed multiple simultaneous development projects in different technologies from CGI to Java EE.
  • He was an architect and lead developer for the first release of the Brazilian federal bank’s pension fund web portal, specifying the communication policies and platforms between mainframe and VB/SQL Server local deployments to the Internet (Java) for financial and healthcare transactions (HR, savings, retirement, etc.). Hired later as a third-party consultant for new phases of this project.
  • Also acted as the architect and lead developer of a CMS solution sold to several huge oil companies, such as ChevronTexaco and PETROBRAS.
Back-End Web Development

Education

Estácio

Information technology

Jan 2001 – Jan 2003

Escola Técnica Estadual Henrique Lage

Jan 1998 – Jan 2000

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