Ross Overstreet
About
Ross Overstreet is from Pensacola, Florida, United States. Ross is currently CTO & Founder at Overstreet & Co, located in Pensacola, FL. Ross also works as CTO & Co-Founder at Talent Pronto, a job Ross has held since Jul 2025. Another title Ross currently holds is Board Member at Rev.io. In Ross's previous role as a Founder, CTO, Executive Team at Rev.io, Ross worked in Atlanta, GA until Dec 2020. Prior to joining Rev.io, Ross was a Telecom Billing SaaS CEO & Founder at Telecom H2O and held the position of Telecom Billing SaaS CEO & Founder at Pensacola, Florida, United States. Prior to that, Ross was a Startup Weekend Project at InstantLoop, based in Greater Atlanta Area from Jan 2009 to Dec 2010. Ross started working as Founder - Internet Security Consulting at Overgroup Consulting in Pensacola, Florida, United States in Aug 2002. From Aug 2000 to Aug 2002, Ross was Software Engineer - Back Office Software at Plugit.com, based in Pensacola, Florida, United States.
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Ross Overstreet's current jobs
Systems I architected calculated & moved more than $17 billion in payments + invoices. Now I lead a small team of US-based engineers on up to three projects at a time: billing + payments systems, AI agents on a company's own data, stuck projects we take over and get to launch, data migrations and integrations, and new builds. Every project starts with a 30-minute call at overstreet.me.
Building conversational AI that conducts structured interviews, evaluates candidates against job requirements, and schedules top performers automatically. Weeks of screening in minutes. I'm the primary engineer. It runs on a custom behavior-tree runtime and has completed tens of thousands of interviews.
• Successful majority sale to private equity sponsor • Member of Board of Directors • Largest non-institutional owner • Completed 3x add-on acquisitions • Recruited Chief Executive Officer to lead growth
Ross Overstreet's past jobs
• B2B SaaS Billing Platform • Maintained a controlling ownership interest through growth • Member of Executive Team & Board of Directors • Lead approximately 50 team members in Product, Roadmap, Infrastructure, Engineering, & Platform teams • Created roadmap board for strategic platform product direction • Established customer advisory board & annual conference • Led & launched multiple products & large projects - REST API, Internationalization, Tokenization, Rev.io Payments, Enterprise Customer Portal, BillCenter.net, AgentClick.com, Enterprise Inventory, Cloud Migration, & more • Selected & managed all key technology systems & vendors company-wide • Established KPIs, goals, metrics for product, roadmap, infrastructure, & platform teams • Established application performance metrics, monitoring, and incident response & management. • Assisted & led key enterprise evaluations, pilots, proof-of-concepts, & presentations. • Executive-level escalation support for key relationships in client success & onboarding organizations • Chief infrastructure architect - dev, prod, QA, corporate w/mix of on-prem, cloud, & colo • Chief software architect - lead architecture review board, established best policies & practices
• Bootstrapped successfully • Developed integrations with AT&T, BellSouth, Verizon, Frontier, MCI, Global Crossing, & more • Telecom SaaS platform • Successfully implemented & supported 50 clients nationwide • Very hands-on with all aspects of the business
• Founder of an automated survey SaaS targeting SMBs • Won laptops for our team from Twilio's Startup Weekend Challenge. • Lead idea & development • Met & joined up with great team members • Had to be one of the best startup weekend demos ever!
• Started at the age of 20, bootstrapped • Consulted with network of 400 banks on Internet Security • Performed penetration testing, developer training, code audits, and demonstrated proof of concept exploits & bypasses • Internet security consulting company focused on banking, payments, & e-commerce. • Consulted with Fortune 500, global e-commerce brands, healthcare & banking SaaS providers • Developed scanning & audit tools • Developed prototype of application firewall • Returned all capital + dividends & closed to start Telecom H2O
• Lead engineer of nationwide SaaS platform for cable advertising • Lead engineer of healthcare SaaS platform that spun out into standalone company • Worked with startups to Fortune 500 • Worked on approximately 40 different web applications • Back office software development