Technical Strategy and Roadmapping Questions

Covers defining, communicating, and operationalizing multi quarter to multi year technical and engineering strategy that aligns engineering investments with product and business objectives. Candidates should be able to describe planning horizons, trade offs between near term delivery and long term investment, and how strategic direction maps to architecture and platform decisions. Topic coverage includes migration and modernization planning, assessing current state and technical debt, sequencing initiatives and milestones, prioritization frameworks and cost of delay thinking, capacity and resource planning including hiring and team structure, vendor evaluation and integration, compliance and data considerations, governance and operating model, and execution planning with timelines and review cadences. It also includes balancing feature delivery, reliability, platform evolution, developer experience, and maintenance; making the business case for infrastructure and platform investments; defining success metrics and objectives and key results and measuring outcomes; risk identification, mitigation and contingency planning; and communicating roadmaps and trade offs to engineers, product leaders, business stakeholders, and executives. Domain specific concerns such as cloud adoption, business intelligence roadmaps, and marketing technology integration are included as examples of how technical strategy varies by context.

HardTechnical

0 practiced

A platform refactor would delay a revenue-generating feature by three months but is expected to double feature velocity after six months, increasing ARR by an estimated 20% over two years. The immediate feature would generate $2M ARR if shipped now. Calculate the cost-of-delay and recommend whether to proceed with the refactor or ship the feature now. State assumptions and show your calculation logic (no need for formal discounting but include sensitivity considerations).

MediumTechnical

0 practiced

You need to justify a $2M platform investment intended to reduce time-to-market by 30% over two years. Outline the business case you would prepare: stakeholders to involve, quantifiable benefits, all cost categories (one-time and recurring), risk-adjusted ROI, sensitivity analysis, and how you would present this to finance and the executive committee.

MediumTechnical

0 practiced

Developer onboarding currently takes four weeks and the product goal is to reduce it to two weeks within six months. As a Solutions Architect, propose a concrete roadmap of tooling, documentation, platform, and process changes to cut onboarding time in half. Include prioritization of initiatives, measurable success metrics, and how you'd run pilot(s) to validate improvements.

EasyTechnical

0 practiced

You must evaluate a SaaS identity-management vendor for a customer. Provide a vendor evaluation checklist covering technical fit, security and compliance posture, integration effort, licensing and cost model, vendor viability and roadmap, migration risk, and operational support SLAs. Explain how you'd score vendors and present a recommendation to procurement and engineering.

HardTechnical

0 practiced

You must align three business-unit roadmaps (consumer, enterprise, partner integrations) that have conflicting priorities and constrained budgets. Propose a structured process to create a unified multi-year roadmap: workshops, scoring models, allocation of shared platform investment, governance for conflicts, and a mechanism to re-evaluate priorities when market signals change.

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