How We Work
Our philosophy centers on understanding your business first, then building technology solutions that serve it. No cookie-cutter approaches—just honest assessment and practical guidance.
Listen & Learn
We invest time understanding your business context, goals, and constraints. Expect straightforward questions and visual diagrams to confirm we’re aligned.
Define Success
Before proposing solutions, we establish clear metrics for success. How will we know this worked? What does better look like?
Start Lean, Learn Fast
We favor minimum viable solutions over extensive planning. Real-world use teaches lessons no amount of preparation can provide.
Smart Resourcing
We handle what makes sense directly and partner with specialists for defined work outside our expertise. Our goal is delivering value at the lowest reasonable cost.
Services
Startup & Scale-Up Advisory
Strategic guidance for early-stage companies navigating technical decisions. We help you build foundations that support growth without over-engineering or under-investing.
M&A Technical Due Diligence
Expert assessment of technology assets during acquisitions. We identify technical risks, integration challenges, and opportunities to inform deal decisions and post-merger planning.
Technical Rescue & Remediation
When projects go sideways, we diagnose root causes and create practical paths forward. Our experience rescuing troubled initiatives informs proactive problem prevention.
Fractional CTO Services
Part-time technical leadership for organizations that need strategic oversight without a full-time executive. We provide direction, mentorship, and accountability.
About
Founded on the principle that good technology decisions come from understanding the business problem first, Systems Sense Advisory serves founders, executives, and technical teams navigating complex technology landscapes.
We bring experience from rescuing troubled projects, architecting enterprise systems, and advising startups through critical growth phases. Our mission is to make technology an enabler rather than a constraint—helping organizations build, scale, and integrate systems that actually work.
Contact
Contact us to discuss your enterprise architecture and due diligence needs. We’re here to assist decision-makers in initiating discussions.
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From the blog
- The Self-Funded Searcher’s Guide: When a Fractional CTO Beats a Full-Time Hire
Self-funded searchers face specific constraints that change the decision framework—you’re capital-constrained (every dollar counts), operationally hands-on (you wear multiple hats), holding long-term (7-15+ years), and have technical knowledge gaps (most have business backgrounds). Your needs change dramatically across three phases: survival and stabilization (months 1-6, highest vulnerability), foundation building (months 7-12, strategic planning), and strategic growth (months 13-24+, optimization). The optimal path for most self-funded searchers: start fractional for first 12-18 months, scale intensity down as you build capabilities (20-30 hours/month initially, reducing to 10-15 hours/month), then reassess based on business growth. Choose fractional when EBITDA is under $5M and full-time would be 6%+ of EBITDA, you’re in first 12 months post-acquisition, you have 0-5 technical staff needing strategic direction, technology enables but isn’t the core product, and you’re capital-constrained. The hybrid approach saves $200,000-$400,000 over 18 months while maintaining flexibility and reducing hiring risk. - Why Fractional CTOs Are the Secret Weapon for Post-Acquisition Technology Transitions
Fractional CTO engagement delivers executive-level strategic technical leadership at one-third the cost of full-time hiring, with dramatically lower risk and greater flexibility. For $36,000-$120,000 in year one versus $320,000-$520,000 for full-time CTO (including recruiting, onboarding, and risk buffer), you get strategic technical assessment and prioritized roadmap, team leadership and capability development, vendor optimization, technical due diligence validation, and business-technology translation. The critical 6-12 month transition window requires different intensity: months 1-3 need 20-30 hours/month for assessment and stabilization, months 4-6 need 15-25 hours/month for prioritization and execution planning, months 7-12 need 10-20 hours/month for strategic leadership. Conservative first-year ROI: 1.5-3x through optimized vendor contracts, avoided bad decisions, retained technical talent, and enabled growth opportunities. - Bridging the Gap: Translating Technical Findings for Non-Technical Searchers
Technical reports rarely answer the questions searchers need: Is this bad? Should I buy? Can I run it? Effective assessment separates technical evaluation from operational readiness. Five questions matter most: What technical tasks must I perform weekly? Who fixes problems? What knowledge leaves with the owner? Translation converts technical findings into actionable decisions and budgeted remediation plans. - How Technical Dependencies Impact Post-Acquisition Transition Plans
Technical knowledge transfer is the #1 cause of ETA acquisition failures, driving 36% of negative returns. Standard 30-60 day transitions fail because critical operational knowledge remains undocumented. Realistic technical transition requires 12 months: pre-close documentation, supervised operations, independent operation with a safety net, and an emergency backstop. Proper planning costs $20,000-$50,000 but prevents $100,000-$400,000 failures. - Why Traditional IT Due Diligence Fails Lower Middle Market Acquisitions
Traditional technical due diligence was built for PE firms acquiring $100M+ companies—it assumes professional IT departments, significant technology budgets, and 3-5 year hold periods. Applied to lower middle market deals, it creates expensive noise instead of actionable insight. LMM technical assessment should start with operational questions (Can I operate this business post-acquisition?), distinguish “different from enterprise” from “actually problematic,” quantify findings in business terms, map knowledge transfer requirements explicitly, and focus on a 12-month operating plan. Effective LMM assessment costs $15,000-$30,000 versus $50,000-$150,000 for traditional enterprise-style TDD—the difference isn’t cutting corners, it’s asking the right questions for your context. - What Self-Funded Searchers Need to Know About Legacy System Risk
Legacy technology creates hidden acquisition risks. Five questions reveal whether old systems are stable-and-manageable or dangerous-and-fragile: When were systems last changed? What’s the downtime history? Who holds critical knowledge? Is platform support ending? What’s maintenance spending? Technical debt should influence valuation—estimate remediation costs and negotiate appropriate price reductions. - How AI Automation Changes Technical Due Diligence for Service-Based Businesses
AI and automation tools are democratizing technical due diligence for lower middle market deals. Automated analysis now handles 60-70% of traditional consultant work—security scanning, code quality, dependency checks—at a fraction of the cost. Five key metrics reveal 80% of technical risk, enabling self-funded searchers to conduct thorough assessments within tight budgets. - The AI Dependency Risk Your Searcher Clients Need to Understand
When acquisition targets depend heavily on AI tools for operations, searchers face unique risks. AI providers change pricing, capabilities, and policies with minimal notice. Five red flags signal danger: single-provider lock-in, undocumented workflows, revenue-critical AI dependencies, no usage monitoring, and untested alternatives. Proper AI integration requires guardrails, documentation, and contingency planning.
Systems Sense Advisory 