Ryan Ferretti

CTO

Chicago, Illinois, United States21 yrs 3 mos experience
AI EnabledAI ML Practitioner

Key Highlights

  • Led a global organization of 200+ engineers.
  • Achieved 90% reduction in call center workload.
  • Scaled teams 10x while preserving revenue.
Stackforce AI infers this person is a technology executive specializing in AI-driven platforms and cloud-native solutions across FinTech and E-Commerce.

Contact

Skills

Core Skills

Artificial Intelligence (ai)Ai EngineeringE-commercePlatform EngineeringEngineering LeadershipCloud-native ArchitectureLarge Language Models (llm)Business-to-business (b2b)Enterprise ArchitectureConsultingTeam LeadershipMicroservicesData SecuritySolution Architecture

Other Skills

AI AgentsDistributed SystemsObservabilityIncident ResponseApache KafkaFinTechSEOKubernetesSupply Chain EngineeringLegacy ModernizationTypeScriptEvent‑Driven ArchitectureGraphQLSearch Engine Optimization (SEO)Windows Azure

About

I’m a hands‑on technology executive (CTO/Head of Engineering) who builds AI‑driven, cloud‑native platforms and scales high‑performing teams. Today I lead a 200+ global organization across Engineering, Product, AI/ML, Data, and Infrastructure, shifting the company to a product‑led EPAD model, building an FDE AI team, and delivering predictive models for demand and supply‑chain optimization. We modernize safely and fast: agent‑style automation cut upgrade timelines from months to days, and an internal developer platform plus Cursor and Claude Code with standard agent playbooks lifted delivery speed and developer experience. Previously at Angi, I directed the post‑acquisition integration of CraftJack into a modern Kubernetes and microservices stack, preserving $400M+ ARR, launching an SEO growth platform, navigating consumer‑choice compliance, and keeping 100% team retention through the change. At CraftJack, I grew the team 10×, moved from monolith to event‑driven microservices, and shipped LLM/RAG‑based personalization with MLOps and daily releases. Alongside operating roles, I’ve led consulting engagements as a practice lead, advising startups on architecture and process scaling and directing teams that delivered cloud migrations and legacy modernizations for major consulting and financial firms. My playbook blends strategy and execution: set clear technical vision and operating cadence, invest in platform and data foundations, apply AI where it compounds business value, and coach Directors/Staff to raise the bar on reliability, security, and speed. If your mandate is modernize, automate, and grow, I’m ready to lead the work and build the team to sustain it.

Experience

21 yrs 3 mos
Total Experience
3 yrs 1 mo
Average Tenure
1 yr 6 mos
Current Experience

Sears home services

2 roles

Head of Engineering

Promoted

Feb 2025Present · 1 yr 3 mos · Remote

  • Leading a global organization of 200+ across Engineering, Platform, AI/ML, Data Engineering, InfoSec, and Product, with teams spanning 5 continents (established South American group to diversify from NA/India). Direct reports include Directors, Engineering Managers, and Staff Engineers.
  • Created and led the Applied AI team that built multi-agent chatbots and voice assistants, achieving 90% reduction in call center associate workload while automating intake, routing, quality, and CX workflows.
  • Rolled out Cursor and Claude Code as the standard agentic IDEs and shipped a companion DX toolkit (internal SDK, code snippets, and CI/CD templates) that reduced median PR cycle time by 58% and achieved 93% weekly active engineer adoption.
  • Partnered with Shop Your Way (SHS' fintech arm) on platform features serving 80M+ users. Led architecture for credit card issuance integrations with Citibank, payment orchestration, and migration from in-house card vaulting to Stripe to reduce PCI scope and risk.
  • Modernized parts ordering with new APIs and event-driven architecture (Java/Spring/Kafka), cutting cycle time from 8.5 days to 3 days; raised same-day shipments from under 10% to 70% and 1-business-day delivery from 40% to 80%; reduced payroll costs by $930K; part-related delays for service orders were reduced by 30%.
  • Scaled ML and Data Engineering with standardized pipelines, MLOps, and AI observability (token usage, latency, drift detection). Built an evals platform with A/B testing and release gating for production model deployments.
  • Owned SearsPartsDirect.com ecommerce platform, leading modernization and adding A/B testing that lifted SEO conversions 18% and overall conversions 28%.
  • Rebuilt legacy systems post-mainframe migration by building specialized AI agents that incrementally orchestrate upgrades and improvements with minimal developer guidance, cutting upgrade timelines from months to days and lowering risk to the business.
Artificial Intelligence (AI)AI AgentsAI EngineeringDistributed SystemsObservabilityIncident Response+3

VP of Engineering

Nov 2024Feb 2025 · 3 mos · Remote

  • Led platform engineering to deliver a secure paved path for CI/CD and observability, with identity and secrets by default and golden service templates that embed InfoSec best practices, enabling teams to ship quickly and safely.
  • Implemented production guardrails for AI systems, including content filtering, prompt injection defense, and hallucination mitigation. Built an NLP-based evaluation system using intent classification and entity extraction for call center agent quality scoring.
  • Stood up an incident response program on a new observability platform: on-call rotations, escalation paths, postmortems, and automated stakeholder updates during incidents.
  • Owned a $73M cross-functional budget spanning technology and operations. Reduced spend by 12% in year one while maintaining reliability and investment in growth.
  • Delivered an org-wide agent authentication middleware with shared memory to persist and retrieve context across tasks and sessions, with short-lived access tokens, role-based permissions, and a unified audit history across environments.
  • Migrated the org to a product-led EPAD model (Engineering-Product-Analytics-Design), creating accountable domain squads with clear roadmaps, faster decision cycles, and tighter business alignment.
  • Automated evidence collection for PCI and SOC2 audits, cutting prep time from weeks to days and enabling continuous compliance tracking.
  • Enabled 70+ citizen engineers building on Replit by creating a platform ensuring data governance and security.
AI EngineeringArtificial Intelligence (AI)KubernetesSupply Chain EngineeringAI AgentsObservability+5

Angi

Director of Engineering

Jan 2024Nov 2024 · 10 mos · Remote

  • I drove the post-acquisition integration of CraftJack and led high-visibility growth, compliance, and infrastructure programs that impacted nearly every revenue line at Angi. Managed five cross‑functional engineering teams spanning the Growth and Pro Experiences pillars, partnered with multiple VP‑level stakeholders, and delivered every initiative ahead of schedule with 100 % team retention.
  • Integrated a $400 M+ business unit: Orchestrated the end‑to‑end migration of all CraftJack engineers and revenue‑producing applications to Angi's modern stack (Kubernetes, microservices, Next‑gen CI/CD). Completed cut‑over ahead of plan with zero production incidents, preserving >$400 M ARR.
  • Scaled SEO‑driven growth: Led Growth teams in building a new SEO platform that generates high‑performance landing, geo, and funnel pages for Angi Brands, improving page‑load times, boosting organic traffic, and strengthening brand distinction across marquee properties.
  • Protected a quarter of the company's revenue: Directed the seamless migration of Angi's partner‑leads platform (~25 % of total revenue) to the new architecture with zero downtime or data loss, ensuring uninterrupted lead delivery to thousands of service pros.
  • Navigated industry‑wide regulation: Spearheaded design and rollout of a consumer‑choice compliance framework that re‑architected user flows to satisfy emerging federal regulations, safeguarding the majority of Angi's $1 B+ revenue while enhancing transparency for millions of consumers.
  • Modernized cloud infrastructure: Drove company‑wide initiative to consolidate AWS workloads onto Angi's Kubernetes platform, hardening security, standardizing observability, and accelerating deploy frequency.
  • Multi‑pillar leadership & culture: Reported through multiple VPs, aligned roadmaps across Product, Growth, Compliance, and Infrastructure, and cultivated a psychologically safe, high‑ownership culture, achieving 100 % retention during significant organizational change.
Large Language Models (LLM)Engineering LeadershipCloud-Native ArchitectureSearch Engine Optimization (SEO)TypeScriptEvent‑Driven Architecture+1

Fiy.ai

Head of Engineering and AI

Jan 2023Jan 2024 · 1 yr

  • Led a team of ML Engineers to spearhead the designing and implementation of a state-of-the-art RAG system to enhance user queries when searching extensive technical manuals, incorporating NLP for context-aware retrieval.
  • Constructed robust data pipelines for aggregating and preprocessing from manuals, ensuring efficient data ingestion, normalization, and indexing to support scalable real-time query processing and retrieval operations.
  • Developed and integrated a multi-modal approach to process and analyze data from text, images, and diagrams in technical manuals.
  • Led quality assurance initiatives by establishing benchmarks and employing automated testing to validate the system's semantic search capabilities, achieving over 90% accuracy in context relevance.
RAGLarge Language Models (LLM)Artificial Intelligence (AI)Semantic SearchEarly-Stage Startups

Craftjack

2 roles

Chief Technology Officer

Promoted

Feb 2022Jan 2024 · 1 yr 11 mos

  • I joined CraftJack as a hands-on head of technology in charge of all decisions surrounding internal and external facing systems. Under my leadership, our team grew 5x in size while supporting a business whose revenue grew more than 10x during my tenure.
  • Collaborated with executive leadership to establish a clear connection between strategic objectives, process enhancements, and project implementation across the company.
  • Responsible for owning the development of the technology budget and roadmap, ensuring that projects adhered to defined timelines and scopes.
  • Designed and implemented a fully automated mission critical system for in-house and fast growing affiliate lead generation, boosting the amount of revenue ($30M to $450M) and profit ($5M to $115M) CraftJack takes in through its systems.
  • Led an AI/MLOps initiative to build a cutting-edge LLM and RAG model focused on improving the personalization of user profiles by providing recommendations based on successful cohorts. The RAG we built took in data from multiple sources and cleansed it to the required specifications so we could use that data in our models.
  • Guided the transformation of CraftJack's monolithic app to an event-driven microservices architecture, significantly enhancing application reliability and performance.
  • Streamlined the development process and release cycle from one month to immediate deployment post-testing, achieving rapid delivery of business value without compromising reliability.
  • Designed and implemented a comprehensive recruiting pipeline, including initial contact, assessment, and final face-to-face interview. During my tenure at CraftJack, I successfully hired Junior and Senior Engineers across Software, QA, and DevOps roles expanding the team by 5x over 5 years.
  • Fostered a collaborative environment that encouraged idea sharing, leading to increased employee retention and engagement. Our diverse team at CraftJack is thriving with a median tenure of over 5 years
Large Language Models (LLM)Business-to-Business (B2B)Windows AzureTest Driven DevelopmentDisaster RecoveryPassionate about Work+36

VP of Technology

Feb 2016Jan 2022 · 5 yrs 11 mos

  • Designed and developed a unified application, integrating 30+ targeted SEM sites, and created an intuitive CMS, empowering marketing team members with content editing capabilities, ultimately reducing release time by 20x.
  • Entrusted to oversee a team of external engineers, successfully delivering our native mobile apps 15% under budget, while ensuring alignment with our internal goals and user expectations.
  • Worked hand in hand with our Product team to identify features that drive impact and innovation focused on key business metrics and KPIs.
  • Transformed the QA team by pivoting to an automation-centric approach, dramatically enhancing system stability and reducing regression testing durations from several days to mere hours, thereby accelerating release cycles and bolstering product reliability.
  • Established a lean efficient DevOps team with a focus on automation and right-sizing of infrastructure processes. This resulted in cost savings of over $200k annually over a period of 2 years.
  • Served as a mentor for engineers aspiring to management roles, coaching them through pivotal aspects of their career transition. My mentees, now managers, supervise junior and mid-level engineers, while I oversee them in tandem with the senior engineering team, fortifying leadership and ensuring cohesive team management.
  • Spearheaded complex initiatives including migration to AWS, transition to PostgreSQL, and upgrading all applications to .NET Core.
  • Led a strategic shift to a new Payment Processor for web and mobile platforms, securing uninterrupted revenue streams for the company within a tight deadline of 60 days.
  • Championed a seamless integration of design and UX teams into engineering's Agile development process.
  • Founded CraftJack's machine learning team to build systems that accurately predicted profitable SEM spending and a robust recommendation engine for upsells, resulting in a 10% increase in SEM efficiency and a 50% boost in upsell revenue.

Accenture

Team Lead

Jan 2015Jan 2016 · 1 yr

  • Spearheaded a global team of engineers across Chicago, Spain, and India, dedicated to developing the company's comprehensive employee review process.
  • Introduced Agile methodologies to enhance team understanding of project scope and ensure timely progress toward established deadlines.
  • Provided leadership to engineering teams in crafting and implementing tailored solutions that catered to clients' distinct needs and objectives.
  • Designed a sophisticated React front-end and .NET API backend, seamlessly integrating with new and existing microservices for efficient data retrieval and updates.
  • Collaborated with various internal teams to streamline a global rollout strategy, ensuring a seamless release on a global scale.
Team LeadershipEnterprise ArchitectureC#Distributed SystemsMicroservicesCross-functional Team Leadership+2

Rally health

Team Lead

Jan 2015Jan 2015 · 0 mo

Team LeadershipTest Driven DevelopmentC#Agile MethodologiesMicroservicesTest Automation+3

Gcm grosvenor

Team Lead

Jan 2011Jan 2015 · 4 yrs

Windows AzureDisaster RecoveryEnterprise ArchitectureData SecurityNoSQLM&A Due Diligence+9

Springcm, a docusign company

Software Architect / Agile Coach

Jan 2011Jan 2011 · 0 mo

Rsm

Software Architect

Jan 2010Jan 2011 · 1 yr

Lynxit solutions

Senior iOS Engineer

Jan 2010Jan 2010 · 0 mo

Team LeadershipBusiness-to-Business (B2B)Remote Team ManagementJavaScriptSolution ArchitectureRuby on Rails

Accenture

Senior Software Engineer

Jan 2008Jan 2010 · 2 yrs

NoSQLC#Product DevelopmentiOS

Chicago tribune media group

Software Engineer

Jan 2007Jan 2008 · 1 yr

Spr

Senior Software Architect / Practice Lead

Jun 2005Feb 2016 · 10 yrs 8 mos

  • Experienced Practice Lead and Sr. Software Architect with over 10 years of expertise in application design and development. Possesses a comprehensive skill set in Java/J2EE, .NET, iOS (iPhone/iPad), Ruby on Rails, PHP and more. Demonstrated expertise in browser-side technologies such as CSS, HTML, and JavaScript, with a proven track record of developing AJAX-enabled web applications in various technology stacks.
  • Expert in delivering projects based on layered technologies and industry standard patterns, including ORM’s (NHibernate, ActiveRecord), MVC frameworks, and IoC containers like Spring, Spring.NET, and Autofac. Adept in utilizing Agile methodologies for over 10 years and well-versed in XP practices including Test Driven / Behavior Driven Development, and Continuous Integration. Completed numerous projects of national and global scale.
  • Actively led employee and client teams in developing custom enterprise applications.
  • Managed a .NET practice comprising 40+ consultants and managers, overseeing budgeting, sales, strategic planning, and training consultants in technical and company goals.
  • Gave strategic guidance to startups on effectively scaling architecture and processes for crucial growth milestones.
  • Directed teams assisting prominent consulting and financial firms in cloud migration and legacy system modernization and fostering a transformative engineering culture.
Windows AzurePassionate about WorkJavaEnterprise ArchitectureData SecurityAmazon Web Services (AWS)+19

Us foods

Software Engineer

Jan 2005Jan 2007 · 2 yrs

JavaAgile MethodologiesJavaScript

Education

DePaul University

Master's degree — Computer Science

Jan 2004Jan 2005

DePaul University

Bachelor's degree — Computer Science

Jan 2000Jan 2004

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