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Andrew R.

Andrew R.

Fractional CTO | Solution Architect | Engineering & AI Transformation

I help companies make better technology decisions, design scalable solutions, and lead complex engineering initiatives without requiring a full-time CTO. I bring 17+ years of experience across software engineering, solution architecture, engineering leadership, cybersecurity, cloud, AI/data, and technology operations. My career has included CTO, COO, Senior Director, engineering leadership, and solution architecture responsibilities in both high-growth and enterprise environments. My background started deeply technical and evolved into architecture and executive technology leadership. Today, my primary value is helping organizations determine what should be built, how it should be architected, how teams should execute it, and how technology should support the business. I work especially well with companies facing situations such as: • A product or platform has become difficult to scale or maintain • Engineering delivery is slow, unpredictable, or lacking technical direction • Leadership needs a technology roadmap but does not need a full-time CTO • An AI initiative needs to move from experimentation to a practical architecture • A company needs an independent review of its architecture, engineering organization, vendor, or development plan • A growing team needs stronger SDLC, governance, security, or delivery practices • Business leadership needs someone who can translate between executives and technical teams • A complex initiative needs senior technical oversight without adding another permanent executive Fractional CTO & Technology Advisory I can serve as a fractional technology executive or senior advisor to help with: • Technology strategy and roadmaps • Architecture and platform decisions • Engineering organizational design • Build-vs-buy and vendor decisions • Technical due diligence • Product and engineering prioritization • Delivery and operating-model improvement • Executive and board-level technology communication • Interim technical leadership during transitions Solution & Enterprise Architecture I help turn business requirements into architectures that teams can actually build and operate. Areas include: • Cloud and application architecture • Distributed systems and API architecture • Microservices and event-driven systems • Integration architecture • Identity and access management • Data and AI architecture • Security architecture • Modernization and legacy-platform strategy • Architecture reviews and technical remediation plans I have worked across AWS, Azure, and GCP environments and with modern application stacks including React, Next.js, Node.js, TypeScript, .NET, Python, PostgreSQL, MongoDB, REST, GraphQL, Kubernetes, Docker, Terraform, queues/event-driven architectures, and enterprise platforms such as Salesforce and ServiceNow. AI, Data & Automation Strategy I help companies identify where AI can create real operational or product value rather than simply adding AI features for their own sake. My experience includes: • Generative AI strategy • RAG and enterprise knowledge systems • AI-enabled internal tools and agents • Grounding models in company documentation and proprietary knowledge • AI platform and vendor evaluation • Data and software engineering strategy • AI implementation roadmaps • Governance and security considerations for enterprise AI Engineering & Delivery Consulting I can also assess an existing technology organization and identify where execution is breaking down. Typical engagements include: • Architecture and codebase assessments • SDLC and engineering-process reviews • Technical debt prioritization • Team structure and leadership assessment • Delivery velocity and bottleneck analysis • Engineering metrics and operating cadence • Vendor/offshore team assessment • Security and application-risk review • Technical project recovery How I work I’m most effective in engagements where technology, architecture, delivery, and business decisions intersect. Depending on the need, I can help define the strategy, design the architecture, lead delivery, evaluate existing systems, coordinate technical teams, or bring in additional specialists where appropriate. I’m comfortable working with founders, executives, product leaders, engineering teams, vendors, and external development partners, and I can move between high-level decision-making and detailed technical problem-solving as needed. My goal is to create clarity quickly, reduce technical and delivery risk, and help organizations move from uncertainty to an executable plan.

🇺🇸Nashville, United States$150/hr40% JSS5.00 (4)Since Apr 2017

Earnings and projects

MRR (estimate)
≈$1.5k

An estimate from an earlier read

World#33,036 / 412k
🇺🇸Country#6,316 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $8.8k

Total earnings
$28k

Billed in all: $28k

World#114,813 / 412k
🇺🇸Country#19,651 / 62.1k
Per project
$4k

$8.8k in the last 6 months

World#42,667 / 412k
🇺🇸Country#7,119 / 62.1k
Projects, last 6 months
1
100% fixed0% hourly
World#128,092 / 412k
🇺🇸Country#16,472 / 62.1k
Projects in all
7

Across 8 contracts

63% fixed37% hourly
World#236,188 / 412k
🇺🇸Country#33,699 / 62.1k

Earnings, last 30 days

$27.9kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$27.0k$27.5k$28.0k$28.5kOct 8Oct 23Nov 7

No data since Nov 5, 2026.

Skill rankings: Top 8% in Data Analysis

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