Kostas Vassilakis

Experience

• PartsTech

  Chief Technology Officer

  Nov 2023 - Present

  A private equity-owned free online platform that helps 30+ K auto repair shops order parts and tires from suppliers. Acquired by OEConnection/Genstar Capital in January 2025.

  • Developed & implemented the organization’s technology strategy and roadmap, ensuring alignment with business objectives. Led a global team of 45 across US, UA, and Europe, including an SVP of Engineering, 1 Director, 3 Engineering Managers, and 1 IT lead
  • Led modernization efforts, transitioning architecture from monolith to microservices and updating the technology stack to foster innovation and accelerate growth.
  • Scaled and expanded operations across North America, driving rapid organizational growth.
  • Improved system availability from 91.5% to 99.9%, by reducing Mean Time to Detect (MTTD) to <10 minutes, and automating incident detection to 90%.
  • Prepared the technology organization for the acquisition by OEConnection/Genstar Capital.

• Multiply Force

  Founder & Managing Partner

  Jul 2020 - Present

  Provides technology strategy and organizational expansion consulting for small to medium-sized companies.

  • Serves as a fractional CTO on a contract basis.
  • Providing strategic technology guidance, contributing to business strategy, and supporting Bliss Market - https://blisfarms.com/ by securing funding to advance its mission of transforming food production.
  • Designed a multi-cloud platform for a Managed Service Provider (MSP).
  • Led the integration of transportation and shipping systems within an e-commerce platform and ERP for an online footwear retailer.
  • Established and scaled the technology organization for a direct-to-consumer (D2C) men’s cosmetic brand retailer.

• Roofstock

  Vice President of IT, Cloud Engineering, and PMO

  May 2022 - Jul 2023

  A privately held real estate investment platform for investors to buy, sell, and manage single-family rental properties.

  • Recruited to develop and execute a scalable IT and Cloud strategy. Led a team of 20 - supporting Cloud, IT, PMO, and Applications.
  • Developed and executed a scalable IT and Cloud strategy, optimizing infrastructure and reducing costs by 25%.
  • Partnered with executives to implement companywide objectives and key results, balancing ROI, strategic initiatives, and Keep the Lights On (KTLO) initiatives.
  • Led adoption of Agile and DevSecOps practices, accelerating delivery and enhancing security posture.
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  CHEWY.COM

  Senior Director of Cloud Engineering and Operations

  Apr 2021 - Jun 2022

  CHWY (NYSE): A $15.17B online retailer of pet food and related products.

  • Promoted to scale Platform org 5x (to 100+ engs). Managed 1 Eng Dir, 1 Assoc Dir, & 2 Eng Mgrs across Tech Prod Mgmt, Scrum Masters, Infra Arch, Cloud/SRE/Perf Eng, DevX/Tools, Ops, & Incident/Problem/Change Mgmt.
  • Contributed to the growth of revenue from $340MM to $4B via technology solutions.
  • Enhanced system resilience, implementing multi-region Active/Active in the public cloud and achieving 100% uptime during peak operations.
  • Reduced Cloud costs by ~35% and SaaS spending by ~20% respectively via FinOps-driven optimizations.
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  CHEWY.COM

  Head of Cloud & Platform Engineering

  Sep 2019 - Apr 2021

  CHWY (NYSE): A $15.17B online retailer of pet food and related products.

  • Established a scalable organization across Cloud, Release, Performance, Automation, and Site Reliability Engineering functions within nine months. Continued responsibility for the Transportation technology team.
  • Innovated a rapid technology growth strategy based on an internal development platform (Nebula) to move to the cloud.
  • Onboarded 30+ applications to AWS in six months and contributed to Chewy's successful IPO.
  • Spearheaded "Peak Season" operations, achieving 100% uptime during the peak sales periods (e.g., Black Friday, Cyber Monday) and setting the framework for future peak preparations.
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  CHEWY.COM

  Director of Software Engineering - Transportation Technology

  Mar 2018 - Dec 2018

  CHWY (NYSE): A $15.17B online retailer of pet food and related products.

  • Recruited to build the Transportation technology team responsible for outbound delivery of B2C orders. Recruited and trained a team of 6 – a manager and 5 Software Engineers
  • Launched applications for Address Validation, Enhanced Tracking, and WIZMO (Where Is My Order) delivering $8MM of annual savings while enhancing the customer experience.
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  STAPLES

  Director of Software Engineering, Ecommerce Operations Platform

  Feb 2017 - Apr 2018

  A $22.5B private equity-owned office supply retailer.

  • Managed global eCommerce operations for a $15B platform w/ 5MM+ SKUs. Supervised 4 Eng Mgrs & 90 indirects, incl. SWE, Infrastructure Automation, SRE, QA, Deploy Eng, & Tech Ops.
  • Improved operational efficiency by 80% by reducing MTTD and mean time to recover (MTTR) by applying best practices around people, processes, and technology.
  • Achieved 30% cost reduction while increasing productivity by 50% within 9 months.
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  Pitney Bowes

  Director of Product Management, Global Ecommerce and Shipping Solutions

  Mar 2015 - Mar 2017

  PBI (NYSE): A $3+B provider of SaaS shipping solutions, mailing innovation, and financial services.

  • Challenged to increase US and global market share for SendSuite (SaaS shipping solutions). Managed 2 Product Managers and 2 Product Analysts.
  • Launched SaaS solutions and USPS payment APIs, driving revenue from $1MM to $15MM in under 2 years.
  • Expanded adoption of shipping software across key European markets (UK, Germany).
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  Pitney Bowes

  Director of Program Management, Global Ecommerce Solutions

  Jun 2011 - Apr 2015

  PBI (NYSE): A $3+B provider of SaaS shipping solutions, mailing innovation, and financial services.

  • Developed Pitney’s $15MM digital platform & global logistics network for major retailers/marketplaces (e.g., eBay, Walmart) offering intl. B2B logistics/distribution. Supervised 5 SWE Mgrs (65 engs) & 5 PMs, managing 150 indirects incl. CS & Operations.
  • Increased sales revenue from $8MM to $170MM, driven by transaction fees as a percentage of Gross Merchandise Value (GMV), and shipping rates.
  • Co-founded Pitney Bowes' Global eCommerce division, scaling teams to 150+ across four countries.
  • Re-architected APIs, refactored monolithic systems to services, and implemented advanced caching strategies to efficiently handle 22B+ API transactions, driving $2B in GMV.
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  Pitney Bowes

  Director of Operations, Global Ecommerce Solutions

  May 2010 - Dec 2011

  PBI (NYSE): A $3+B provider of SaaS shipping solutions, mailing innovation, and financial services.

  • Built a pro-active “best in class” Partner Support Organization that can support strict SLAs for top tier eCommerce service providers and market places. Managed multiple partnerships simultaneously, including eBay, PayPal, US Postal Service, Royal Mail Group (UK), Canadian Postal Corporation at multiple levels. Successfully managed all partner SLAs.
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  Pitney Bowes

  Senior Engineering Manager

  Jan 2009 - Jun 2010

  Pitney Bowes (NYSE: PBI) is a technology-driven company that provides SaaS shipping solutions, mailing innovation, and financial services to clients around the world – including more than 90 percent of the Fortune 500. Small businesses to large enterprises, and government entities rely on Pitney Bowes to reduce the complexity of sending mail and parcels. For additional information, visit Pitney Bowes at www.pitneybowes.com.

  • Accountable for a portfolio of eCommerce products, Cross border Shipping Systems & On-line Payment Evidencing Solutions. Primary point of accountability to Business partners. Accountable for annual project portfolio Capex plan, technology direction, release planning, risk management, and resource planning.
  • Accountable for annual project portfolio Capex budget (release planning, cost estimation, and resource planning).
  • Delivered all annual releases on time, meeting performance metrics and quality criteria while staying within budget guidelines.
  • Managed multiple work streams (US, India, Engineering, IT, contractors).
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  Pitney Bowes

  Engineering Manager & Program Manager, Engineering PMO

  Feb 2000 - Jan 2009

  PBI (NYSE): A $3+B provider of SaaS shipping solutions, mailing innovation, and financial services.

  • Accountable for developing and delivering an On-line Payment Evidencing/Financial solution (Partner Shipping APIs) for the biggest shipper in the world (eBay/PayPal). Solution has become the flagship of PB’s eCommerce Solutions portfolio.
  • Delivered the first Shipping APIs to the market.
  • Extensive experience with annual budgeting process and other strategic plans (outsourcing, adapting to new software methodologies and processes, etc.)
  • Participated in technical Project Management Office (PMO) as a core team lead for a portfolio of major projects. Extensive experience with annual budgeting process and other strategic plans (outsourcing, adapting to new software methodologies and PM processes, moving to IaaS/Cloud solutions).

• Dataviz

  Senior Software Engineer & Project Lead

  Jan 1993 - Dec 1999

  Founded in 1984, DataViz, Inc. is an industry leader in developing productivity solutions for iOS, Android™, BlackBerry, Windows® and Macintosh®. DataViz partners include Microsoft®, Motorola®, BlackBerry, Samsung, Sharp®, and other industry leaders. DataViz began its business developing file conversion software and has since expanded its expertise to providing solutions that meet the increasing demands of mobile markets. With enterprise-grade solutions that include its award-winning and #1 selling mobile Office suite, Documents To Go, and password manager, Passwords Plus, DataViz is committed to providing premium solutions that mobilize ‘Microsoft Office’ without compromise and provide customers with instant access to critical files, business data and data security.

  • Accountable for designing, creating, developing, testing, and launching company’s first Internet cross platform product (Windows & Macintosh).
  • Designed and implemented connectivity and data conversion software for Macintosh and PC applications
  • Responsible for the development of Personal Information Manager Import technology licensed by Microsoft for the Office suite.
  • Provided hands on project management for multiple large scale projects.