← The journey

Sean Sackowitz

Summary

Software engineering leader with nine years across enterprise consulting and product engineering. Currently direct a five-person team at Snap! Mobile, a fundraising and ecommerce platform for schools and youth sports programs, owning nine products; Raise and Store alone process roughly $250M in annual GMV and generate 99% of company revenue. Grew GMV 35% and halved infrastructure spend while absorbing a company-wide reduction that cut the team in half. Co-founder of a self-funded software business bootstrapped since 2012.

Experience

Director of Engineering

– Present
  • Lead five engineers, including a principal engineer as team lead, owning nine products; Raise and Store alone process roughly $250M in annual GMV and generate 99% of company revenue.
  • Sustained delivery across all nine products through a company-wide reduction that halved the team, without dropping scope or retiring a product.
  • Grew annual GMV 35% while cutting portfolio infrastructure spend roughly 50%, migrating products off legacy VMs onto a shared Kubernetes platform.
  • Built an AI-assisted engineering practice, agentic coding tools plus automated CI/CD and operations, that lets five engineers cover nine products; ship AI-developed products behind rigorous testing and security auditing.
  • Own product roadmap jointly with Product and Design; report strategy, risk, and results to the executive team and board.
  • Shipped customer-facing AI in Raise and Store plus internal automation across sales, raising release frequency and cutting production incidents.

Senior Engineering Manager

  • Took over Raise and Store after a Director's departure, assuming the company's two highest-revenue products; promoted to Director six months later.
  • Replatformed Store from legacy PHP and Magento onto React and MedusaJS on Kubernetes, cutting over with minimal planned downtime.
  • Cut platform cost roughly $5,000 per month through that migration, moving the second-to-last product onto shared Kubernetes.

Engineering Manager

  • Owned a portfolio of legacy applications spanning .NET, end-of-life PHP, and AWS Lambda with MongoDB.
  • Authored the rewrite and migration strategy for each and led their move onto Kubernetes, retiring technical debt without taking products out of production.
  • Moved from individual contributor to people leader, establishing delivery cadence and engineering practices.

Principal Engineer

  • Hired as a senior IC to assess and set technical direction for Snap!'s legacy portfolio.
  • Defined the architecture and migration strategy later executed as Engineering Manager and Director; moved into leadership within five months.

Ansible Automation Architect

  • Led 4 to 8 consultants across 2 to 4 concurrent enterprise engagements, owning delivery from discovery through production.
  • Drove pre-sales and discovery for network automation at a Fortune 50 retailer, then led BGP and datacenter automation through to production.
  • Brought estates exceeding 10,000 network devices under automated management, replacing manual configuration with repeatable pipelines.
  • Mentored consultants through onboarding and certification; helped build the regional practice through talks and community events.

Senior Network Automation Consultant

  • Built Ansible automation letting a global industrial manufacturer stand up full Windows Server environments remotely, reaching isolated plants and offshore rigs.
  • Standardized deployments across sites and datacenters, collapsing provisioning from days to minutes and eliminating configuration drift.

Consultant

  • Delivered greenfield Ansible Automation Platform deployments for more than a dozen enterprise clients across telecom, retail, manufacturing, and healthcare.
  • Designed zero touch provisioning for a national wireless carrier's 4G network.

Associate Consultant

  • Led a small team improving performance of international freight transportation software in C and C++, increasing message throughput 46%.

Skills

Leadership
Engineering management, org design, hiring and mentoring, roadmap ownership, executive and board reporting, budget and vendor management, Agile and Scrum
Cloud and Infrastructure
Kubernetes, Docker, OpenShift, Google Cloud, AWS (EKS, RDS, S3, Lambda), Ansible, CI/CD, Jenkins, Git and GitLab, VMware vSphere
Application and Data
TypeScript, Node.js, React, MedusaJS, Ruby on Rails, .NET, PostgreSQL, MongoDB, AI-assisted development and agentic tooling
Languages
TypeScript, JavaScript, Python, C#, Java, Ruby, Go, SQL, C and C++, Rust, Lua

Education

UNC Charlotte

B.S., Computer Science

  • Focus in Artificial Intelligence
  • Certificate in Game Design and Development