Marcos Toledo

Full Stack Engineer


Ruby & Rails, System Administration & Automation
Full Stack experience - From UI to Systems
12 years of professional programming experience


Web Applications & API Endpoints

From serving browsers to machines, through HTTPS, TLS or UDP, from the database to the javascript.

Systems Integrations

Payment systems, partner backends, 3rd party platforms. With me, they're all connected.

System Administration & Automation

Alerts monitoring, server stats, automation through configuration management, scripting.


  • Ruby, Rails, EventMachine
  • Javascript, CSS, HTML 5
  • AMQP, Sidekiq
  • Networking, Firewalls, TCP/UDP
  • Automation, Ansible
  • Linux & OSX
  • Java, C, Go
  • Unicode, Concurrency, Regex, Git
  • Other Tricky Things ™



01/2015 - 12/2016

Director of Engineering (San Francisco, CA) - 11/2015

Strategy and Vision

Engineering Culture

Recruiting and Retention

Senior Software Engineer (San Francisco, CA)

Frontend Engineer: React, Coffeescript

Backend Engineer: Rails, MySQL

DevOps: AWS, Chef

Private Internet Access

Chief Technology Officer (Los Angeles, CA)

01/2013 - 12/2014

Current acting CTO after being employee #1

Growth & Challenges

Responsible for deploying / managing 1700+ baremetal servers on 16 different dcs

From ~10k paying subscribers to orders of magnitude bigger


Website redesign & website/mobile payment processing

Client API serving tens of thousands of active concurrent users

Stripe, Paypal, Amazon, Google Play, Gift Card payment processing


Automated bare metal server deployments in order of hundreds per month using ruby then ansible

Customizing open source software, including adding bcrypt support to freeradius (in C)

Networking: OpenVPN, l2tp/ipsec, iptables, NAT, etc


Lead programmer (Remote, London, UK)

11/2008 - 12/2012

Worked as a senior programmer and then team lead, on three different projects:

Replay Poker
A playmoney poker website, rewritten from scratch in rails as well as a custom built, multi threaded tcp/ip ruby poker server which serves a stateful flash client
Rewrite in rails and redesign legacy sections, including full text search and single sign on with legacy application, and integration with ForexDesk
A social trading website where forex traders can watch other traders' stats and choose to do the same trades on their forex broker's accounts as other traders, literally 'following' their trades. Backend uses EventMachine, RabbitMQ and JRuby for integrating with a forex broker's Java API


Senior Java Developer (Sao Paulo, Brazil)

08/2005 - 11/2008

The biggest health insurance company in Brazil, with massive scale from beneficiaries, clinics and labs

Architected and worked on the implementation of the mission critical web service used by all hospitals and clinics in the country to request beneficiary information, schedule procedures and billing

Clustered web application and database servers infrastructure


R&D Java Developer (Sao Paulo, Brazil)

04/2003 - 08/2005

Work on tools used by network engineers to provision CDMA antennas and equipment on carriers

Both Java server side and client side development

Led team of 5 people locally plus 4 to 7 developers in India, working with teams on US, Canada and China


Pontificia Universidade Catolica - Campinas/SP - Brazil

BA in Computer Science (2000 - 2003)


Valid H1B Visa