Robots and Pencils

Analyze and modernize a multi-service .NET ecosystem, implement DevOps practices, and integrate AI systems within a large enterprise platform. | Deep expertise in .NET, Azure, enterprise integrations, DevOps, and AI system support, with strong documentation and client-facing skills. | Robots & Pencils is seeking a senior-level Solutions Architect to embed directly with a client’s engineering organization and modernize a mobile-first workforce management platform operating in production today. This is a hands-on architectural leadership role. You will analyze and document a multi- service .NET ecosystem, introduce modern DevOps and cloud practices, and define a clear technical vision ahead of a new VP of Engineering hire. You will actively shape backend architecture, integration strategy, CI/CD maturity, and AI- powered capabilities within a live enterprise system. This is not an advisory from a distance. This is embedded in delivery, influence, and execution. You will partner closely with the client’s Technical Lead to establish architectural clarity, reduce systemic risk and position the platform for scalable growth. Key Responsibilities Architecture Analysis & Road mapping Analyze and document 4 domain-specific .NET 8 / ASP.NET Core APIs and supporting SQL Server databases Map and rationalize 8+ enterprise integrations and system dependencies Produce clear architectural diagrams, integration flow documentation, and system boundary definitions Identify technical debt, scalability constraints, and modernization opportunities Develop phased architectural roadmaps aligned to business priorities Prepare cost-benefit analyses and evidence-based proposals for platform evolution DevOps & Engineering Maturity Design and implement CI/CD pipelines aligned with Azure-native practices Introduce sustainable branching strategies and release management standards Improve observability and monitoring using Azure Application Insights and related tooling Establish architectural standards for reliability, maintainability, and performance Promote automation and infrastructure best practices across environments AI & Intelligent Systems Integration Support architecture and integration of an Azure-hosted LLM / RAG-powered Q&A system Define retrieval workflows, integration points, and security boundaries Evaluate operational cost, performance, and scalability implications of AI workloads Ensure AI components align with enterprise authentication standards (Okta OAuth2 / OIDC) Integration & Platform Engineering Architect solutions across Azure services including Service Bus, Functions, and Notification Hubs Design event-driven and service-oriented patterns appropriate for enterprise scale Interface with SQL Server and distributed data architectures Maintain awareness of AWS ecosystems where cross-cloud considerations apply Provide architectural guidance across mobile clients (Swift/Kotlin) at a systems level Client Leadership & Consulting Act as a trusted technical advisor within the client organization Introduce change diplomatically through data-driven recommendations Translate technical trade-offs into business-relevant impact Facilitate architectural decision-making conversations with multiple stakeholders Partner with the client’s Technical Lead to define a forward-looking engineering vision Required Skills & Qualifications 8+ years of backend engineering experience with deep expertise in .NET and distributed systems Strong proficiency in .NET 8, ASP.NET Core, C#, and SQL Server Experience architecting systems in Microsoft Azure environments Hands-on experience implementing CI/CD pipelines and DevOps best practices Experience designing enterprise integrations and event-driven systems Familiarity with OAuth2 / OIDC authentication patterns (Okta or similar providers) Experience supporting or integrating LLM-based systems (RAG, embeddings, retrieval patterns) Strong architectural documentation skills (diagrams, decision records, system mapping) Proven experience operating in client-facing or consulting environments Strong written and verbal English communication skills Nice to Have AWS architectural awareness Mobile architecture exposure (Swift, Kotlin at system design level) Experience preparing technical proposals and cost analyses Experience guiding organizations through engineering maturity transitions Familiarity with Azure-hosted AI infrastructure and governance considerations Personal Competencies Trusted Advisor Mindset – Builds credibility quickly and introduces change through influence rather than prescription. Strategic Systems Thinking – Understands how APIs, databases, integrations, DevOps, AI systems, and organizational structures interact. Consultative Communication – Frames recommendations in terms of business impact, risk, and ROI. Execution Ownership – Drives initiatives from architectural analysis through implemented improvements. Collaborative Leadership – Leans on subject matter experts (mobile, domain) and strengthens the broader team rather than centralizing authority. Continuous Learner – Uses unstructured time for growth and skill development; stays ahead of platform and AI trends. Why This Role Matters At Robots & Pencils, we build smart systems for a human world. This role directly shapes the stability and evolution of a workforce platform relied upon daily by real users. By clarifying architecture, modernizing engineering practices, and introducing intelligent capabilities responsibly, you enable faster feature development, stronger system reliability, and long-term scalability. The architectural patterns established here will influence how this organization builds, integrates, and governs technology for years to come. This is embedded transformation with measurable business impact. Why Join Robots & Pencils? We don’t deliver slide decks. We deliver working systems and sustainable architectural Foundations. You’ll operate as a senior technical leader inside a live enterprise environment, influence long-term platform strategy, and shape how AI and backend systems coexist at scale. You'll grow through ownership, trust, and meaningful delivery outcomes.

Leading complex, enterprise-grade digital projects involving AI, cloud-native platforms, and cross-disciplinary teams, ensuring delivery aligns with client expectations and regulatory constraints. | Extensive experience in software delivery, technical program management, or engineering leadership, with strong understanding of cloud-native architectures, AI workflows, enterprise integrations, and managing distributed teams. | At Robots & Pencils, we drive digital innovation by building meaningful, scalable software products for forward-thinking clients. We are seeking an experienced and strategic Senior Delivery Manager to lead complex, enterprise-grade programs involving AI-enabled automation, cloud-native platforms, and mobile-first experiences. This role will lead distributed teams across North America and Eastern Europe and is responsible for aligning delivery execution with client expectations, regulatory constraints, and long-term business outcomes. You will play a critical role in high-impact engagements within highly regulated environments, including utilities and government-adjacent organizations. This position includes monthly travel to client sites in the U.S. to support relationship building, delivery alignment, and strategic planning. Key Responsibilities Team Leadership & Coordination Lead high-performing, distributed delivery teams across backend, mobile, web, data, and AI disciplines, fostering accountability, collaboration, and delivery excellence. Act as the operational bridge between onshore stakeholders and offshore development teams, ensuring clarity, alignment, and cohesive execution. Partner closely with client-side project managers and technical leads, operating as a trusted extension of the client team. Provide mentorship and delivery leadership across technologies including iOS (Swift), Android (Kotlin), React, Node.js, .NET, Python, and cloud-native services. Encourage cross-disciplinary collaboration and continuous learning across evolving technical stacks. Project & Program Delivery Own end-to-end delivery of complex, multi-phase programs, ensuring scope, budget, timelines, quality, and operational readiness are consistently met. Lead delivery for systems involving: AI-powered automation (e.g., voice AI, workflow automation) Event-driven architectures Mobile and web portals Enterprise data integrations (e.g., SAP) Manage phased releases, production readiness, and transition into operations and maintenance (O&M) models. Define, track, and report delivery KPIs, leveraging data-driven insights to guide decision-making and continuous improvement. Apply proactive risk management, especially in environments with compliance, security, and operational reliability requirements. Client Engagement & Stakeholder Management Serve as the primary delivery contact for clients, building trusted, long-term relationships through transparency, consistency, and strategic insight. Navigate complex stakeholder landscapes, including unionized workforces and operational teams that may be skeptical of automation. Lead executive-level status updates, roadmap discussions, and escalation management. Translate complex technical initiatives—such as AI-driven call automation and cloud modernization—into clear business value. Travel monthly to client sites to support relationship-building, alignment, and strategic planning. Technical Oversight & Strategic Enablement Partner with architects and technical leads to align delivery execution with AWS-first, cloud-native architectures. Oversee delivery of systems leveraging: AWS Lambda, API Gateway, DynamoDB (single-table design), Amazon Connect Voice AI technologies (e.g., Amazon Nova 2 Sonic) WebSocket APIs, AWS Cognito, and event-driven services React-based web portals and mobile applications (React Native or native iOS) Ensure seamless integration with enterprise systems such as SAP and third-party services (e.g., Twilio). Support observability and monitoring strategies using tools such as Langfuse, logging, and metrics frameworks. Balance innovation with reliability, security, and compliance requirements. Process Optimization & Delivery Excellence Continuously evolve agile delivery practices (Scrum, SAFe, Kanban) to support distributed teams and enterprise clients. Identify and remove delivery bottlenecks using tools such as Jira, Confluence, GitHub, and Azure DevOps. Champion automation, CI/CD pipelines, and quality-first engineering practices. Foster a culture of transparency, accountability, and continuous improvement across Pods. Required Skills & Experience 12+ years in software delivery, technical program management, or engineering leadership. 5+ years managing distributed teams across onshore and offshore locations (Eastern Europe experience preferred). Proven success delivering complex, regulated, multi-platform systems in agile environments. Strong understanding of: Cloud-native architectures (AWS preferred) AI-enabled workflows and automation Enterprise integrations and data systems Hands-on familiarity with delivery tooling including Jira, GitHub, Azure DevOps, CI/CD pipelines, and cloud observability tools. Exceptional client-facing communication skills with experience working in high-stakes, compliance-oriented environments. Ability to operate consultatively thinking beyond immediate deliverables to long-term client outcomes. PMP, Scrum Master, SAFe, or equivalent certifications are strongly preferred. Personal Attributes Client-Centric & Strategic: Builds trust and aligns delivery to real business and operational outcomes. Calm Under Pressure: Comfortable leading through ambiguity, scrutiny, and high-impact decision-making. Collaborative & Empathetic: Effective working across cultures, time zones, and diverse stakeholder groups. Outcome-Oriented: Holds teams accountable while enabling sustainable delivery. Consultative Leader: Thinks beyond “what to build” to “why it matters” and “how it lands.” Adaptable & Proactive: Anticipates risk, navigates resistance, and leads to change thoughtfully. Why Join Robots & Pencils? We blend strategy, design, and engineering to craft technology that transforms businesses and improves human experiences. As a Senior Delivery Manager, you’ll lead high-impact AI and cloud transformation programs, work alongside world-class technologists, and help clients modernize critical systems with confidence, clarity, and care.