Dmytro S.
Fractional CTO | Software Architecture | Engineering Leadership
I help founders and product teams make the right technical decisions, reduce delivery risk, and build software that holds up in production. I bring a mix of hands-on engineering depth, architecture judgment, and engineering leadership. Over the past 14 years, I’ve grown from builder to multi-team engineering leader inside a large-scale global marketplace environment, working across trust and safety, customer support, reputation, workflow, and platform systems. I can step in as a Fractional CTO, software architect, or player-coach engineering leader depending on what your business needs most. I am a strong fit when you need to: - define or reset architecture for a growing product - turn an unclear roadmap into an executable technical plan - modernize legacy services without freezing delivery - stabilize a delayed or high-risk initiative - improve engineering quality, system boundaries, and technical decision-making - mentor senior engineers or leads while staying close to the work What I typically help clients with: - software and system architecture - backend and platform design - API strategy, integrations, and service decomposition - microservices and distributed systems - technical due diligence - modernization and migration planning - delivery structure for cross-functional engineering work - architecture reviews, design reviews, and technical leadership - selective hands-on implementation where it meaningfully accelerates delivery I am comfortable both leading and building. I still enjoy going deep into architecture, reviewing designs and code, clarifying domain boundaries, and unblocking hard technical decisions. I do not add process for its own sake. My goal is to simplify, align, and help teams ship with confidence. Core areas of depth: Java, Spring, Dropwizard, PostgreSQL, Redis, Kafka, SQS, REST APIs, microservices, CI/CD, T&S systems (detections, enforcement and permissions, appeals and disputes), customer support tooling, reputation and risk systems, platform modernization, and AI-assisted engineering workflows. I work best in environments with real complexity: scaling products, messy handoffs, unclear ownership, legacy systems, competing priorities, and teams that need stronger technical direction without becoming slower or more process-heavy. If you need someone who can quickly understand a complicated system, make pragmatic technical decisions, and help your team execute with less chaos and better judgment, I’m a strong fit.
Earnings and projects
Last 6 months ÷ 6
Last 6 months: $59k
$29k in the last 6 months
Across 55 contracts
Earnings, last 30 days
Skill rankings: #1 in 1 skill of 11
Rarest: top 0.16% in Team Management, of 3,136. Ranked by MRR among everyone on Upwork with the skill.
- Decision Making475 freelancers · 🇺🇦 #1Top 0.21%🇺🇦#1 of 9
- Engineering Management174 freelancers · 🇺🇦 #1Top 1%🇺🇦#1 of 6
- #5Team Management3,136 freelancers · 🇺🇦 #1Top 0.16%🇺🇦#1 of 45
- #12Performance Optimization1,100 freelancers · 🇺🇦 #3Top 1%🇺🇦#3 of 103
- #22Microservice2,217 freelancers · 🇺🇦 #3Top 0.99%🇺🇦#3 of 99
- #23CI/CD3,691 freelancers · 🇺🇦 #1Top 0.62%🇺🇦#1 of 259
- #28Software Architecture & Design1,465 freelancers · 🇺🇦 #5Top 2%🇺🇦#5 of 131
- #43Java8,313 freelancers · 🇺🇦 #6Top 0.52%🇺🇦#6 of 441