About Tim Newsom &
Dioscuri Executive Services

Tim Newsom - Founder & Fractional CTO
28 years building software. 15+ years in leadership helping teams scale. 6+ years at executive levels as Director and CTO.
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I bring comprehensive software engineering expertise to growing companies navigating technical scaling challenges. My career spans leadership roles across fintech, retail analytics, and government systems, where I've guided organizations through critical technology decisions and complex transformations.
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Throughout my career, I've navigated the challenges that growing companies face when scaling their technology infrastructure and teams. This hard-earned experience enables me to anticipate potential pitfalls and guide clients toward proven solutions that drive sustainable growth.
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Current Focus
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I'm building a fractional CTO practice focused specifically on three client types:
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VCs and Investors who need technical support for portfolio companies at critical inflection points - post-seed through pre-Series B credibility building, technical crisis management, and leadership transitions.
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Founders and CEOs of growth stage companies who need CTO-level leadership but aren't ready for a permanent $400K+ executive hire.
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Partner Organizations - consultancies, investment firms, and advisory practices that need technical assessment and execution capabilities for their clients.
Currently pursuing MS in Artificial Intelligence to stay at the forefront of emerging technologies that will shape the next decade of software engineering.
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Career Highlights
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Prevented Loss of $24M Multi-Year Contract
Led team through emergency system stabilization and critical rewrites when major customer was ready to leave due to technical issues. Direct leadership of the technical response saved the relationship and preserved the contract.
Efficiency Through Architectural Innovation
Reduced development time 70% on critical feature - from 6 months with 5 engineers to 2 months with 1 engineer through architectural redesign and smart technology choices.
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From Losses to Profitability
Helped turn company losing $4-5M annually on $20M revenue into profitable operation on $24-26M revenue through technical stabilization, system improvements, and customer retention efforts.
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Team Scaling Excellence
Scaled engineering teams from 4 to 20+ members while maintaining delivery excellence and team morale. Built hiring pipelines, interview processes, and leadership development programs that attracted and retained senior talent in competitive markets.
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Algorithm Design & Cost Optimization
Created optimization algorithms saving clients $10M+ annually. Focused on high-impact technical decisions that directly affect bottom line.
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Industry Breadth
Led technical transformations across fintech, retail analytics, transportation and government.
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Technical Due Diligence Experience
Participated in technical due diligence as senior engineer when company was being acquired, providing detailed assessment of systems, architecture, and technical risks to potential buyers.
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Leadership Philosophy
Servant leadership is at the core of how I work. I don't build dependencies - I build capabilities. Success isn't measured by how much clients need me, but by what their teams can accomplish after I leave.
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I focus on building high-trust, high-performance teams through mentorship, career development, and fostering growth-oriented cultures. The best technical leaders make themselves progressively less necessary as they develop the people around them.
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Technical excellence matters, but people matter more. The best technical solutions come from teams that trust each other, understand the mission, and have the autonomy to execute. My job is to create that environment, not just fix systems and processes.
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Technical Background
Deep expertise in distributed systems, microservices architecture, cloud-native solutions (AWS primarily), CI/CD implementation, automated testing strategies, and system reliability engineering.
I can have technical conversations with your best engineers and strategic conversations with your board. I bridge the gap between technical reality and business requirements - translating technical constraints into business language and business objectives into technical strategy.
Current technical focus areas:
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Distributed systems and microservices architecture
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Cloud-native design patterns and infrastructure (AWS, some Azure/GCP)
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AI/ML integration and practical applications in software engineering
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Engineering team scaling and leadership development
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Security and compliance (SOC 2, GDPR, HIPAA)
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System reliability and operational excellence
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Capital-efficient technology choices and right-sizing infrastructure
Why Fractional
After 28 years, I've seen the same technical problems destroy companies repeatedly. The solution isn't always a permanent CTO. Often it's 3-6 months of focused technical leadership that establishes scalable foundations and prepares companies to hire permanent leadership from a position of strength.
Many companies need CTO-level thinking but aren't ready for the commitment and cost of a full-time executive. Fractional engagement provides the strategic guidance and hands-on execution needed to navigate critical inflection points - then transitions cleanly when objectives are achieved.
Common situations where fractional makes more sense than permanent:
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Post-Seed to Series A scaling when systems need redesign but company isn't ready for C-level overhead
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Pre-Series B when technical credibility is needed but permanent hire can wait until after raise
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Technical crisis requiring immediate expert intervention - can't wait 6 months for CTO search
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Bridge period during CTO search or leadership transition
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Technical co-founder augmentation - help them scale rather than replace them
After fractional engagement, companies typically:
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Technical co-founder successfully scaled to lead larger organization
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Ready to hire permanent CTO from position of strength (systems stable, team functional, company attractive to top talent)
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Extended engagement for next phase if additional scaling challenges require continued support
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Approach to Client Engagements
Every engagement starts with clear objectives and exit criteria. I succeed when clients no longer need me.
This means:
Building internal technical leadership capability - developing team members who can carry the vision forward, not hoarding knowledge or creating dependencies.
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Establishing processes and documentation that outlast my engagement - automated testing, code review practices, deployment pipelines, and documentation that actually gets maintained.
Creating architecture that scales without requiring constant expert intervention - systems designed for maintainability and growth, not just current needs.
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Transferring knowledge systematically - recorded walkthroughs, comprehensive documentation, training sessions that ensure continuity.
Right-sizing technology for stage - Not every company needs expensive cloud infrastructure and large teams. Sometimes the best decision is leveraging existing platforms and lean architecture that preserves runway while proving the model.
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Paul Graham Startup Principles
My approach to fractional CTO work is informed by Paul Graham's essays on startups and growth.
Key principles I follow:
Do Things That Don't Scale - Manual, high-touch service initially. Exceptional results over process automation. Free technical assessments to build trust. Coffee meetings to understand networks.
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Startup = Growth - Use growth as decision compass. Measure everything. Compound improvement beats linear thinking. Focus on 20% of technical problems causing 80% of growth friction.
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Founder Mode - Stay hands-on technically. Don't default to traditional management consulting approaches. Code reviews, architecture decisions, team mentorship - not just PowerPoint strategy.
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Be Good - Client success as primary metric drives sustainable growth and referrals. Do right by every engagement. Build reputation through delivered outcomes, not marketing.
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Live in the Future - Focus on real problems. Build what's actually missing, not what's trendy. Apply 28 years of experience to anticipate challenges before they become crises.
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Personal
Based in Indianapolis, Indiana. When not helping companies scale their technical operations, I'm pursuing my MS in AI, building my own ventures focused on AI applications, and exploring investment opportunities that generate reliable passive income streams.
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I'm actively building my network in the Indianapolis startup and VC ecosystem. New to the area and the startup scene here, focused on establishing relationships and building trust.
Our Story: Why Dioscuri
In ancient Greek mythology, the Dioscuri—Castor and Pollux—were twin brothers known as the protectors of sailors and guardians of those navigating treacherous waters. When storms threatened to destroy ships, these divine twins would appear as guiding lights, leading vessels safely to harbor. They were called upon not just in moments of crisis, but as trusted companions for any perilous journey across uncharted seas.
At Dioscuri Executive Services, we embody this same spirit of guidance and protection for modern enterprises navigating the turbulent waters of technology transformation.


Your Technology Guardian
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Just as the mythological twins provided safe passage through storms, we serve as your fractional CTO partner, illuminating the path through complex technical challenges. Whether you're a startup charting your first course or an established company venturing into new technological territories, we provide the strategic leadership and technical expertise to guide you safely to your destination.
Twin Pillars of Success
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Our approach rests on two fundamental strengths, like the divine twins themselves:
Strategic Vision – We chart the course, identifying opportunities and navigating around technological pitfalls before they become costly mistakes. Our fractional CTO services provide the high-level strategic thinking that transforms your technology from a cost center into a competitive advantage.
Practical Execution – Vision without action is merely dreaming. We will guide your team, ensuring that strategic initiatives translate into real results. From architecture decisions to team building, we're partners in your success.


When the Storms Come
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Every business faces technological storms - system failures, scaling challenges, security threats, or the need for rapid digital transformation. Like the Dioscuri appearing as beacons in the darkness, we're there when you need us most. Our fractional model means you get CTO-level expertise precisely when and how you need it, without the overhead of a full-time executive.
Guiding You Home
The ancient mariners knew they could count on the Dioscuri to bring them safely home. Today's business leaders can count on Dioscuri Executive Services to navigate them through their technology challenges and deliver them safely to their goals - whether that's successful product launches, seamless digital transformations, or building world-class engineering teams.
Your journey through the digital landscape doesn't have to be perilous. Let us be your guiding lights.

How We Work
Discovery Phase (Week 1)
Comprehensive assessment of your systems, team, and challenges. We align on specific problems to solve, success metrics, timeline, and engagement model.
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Execution Phase (Weeks 2-24)
Hands-on fractional CTO work structured in 40-hour monthly blocks (10 hours per week).
Engagements can scale from 1 block (strategic guidance) to 3 blocks (full-time equivalent) based on needs.
Mix of strategic planning, hands-on technical work, team mentorship, and process establishment. Some phases require intensive presence, others need lighter strategic guidance.
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Transition Phase (Final Month)
Knowledge transfer, documentation, internal leader development, and clean exit. You're positioned for permanent CTO hire, scaled technical co-founder, or self-sufficient operation.
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Throughout:
Regular progress reporting using DORA metrics and business outcomes. Clear metrics, honest assessment of what's working and what needs adjustment. Weekly reviews and approach adjustments based on results.
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Connect
Tim Newsom
Founder & Fractional CTO
Phone: 463-328-2524
Email: tim.newsom@dioscuri-es.com
LinkedIn: Connect with Tim
