Robert Crossland
Senior Software Engineer & Technical Leader | AI-Enhanced, Cloud-Native, and Scalable Solutions
Professional Summary
Highly accomplished Senior Software Engineer and Technical Leader with over 20 years of experience designing, developing, and modernizing complex, scalable software solutions. Proven expertise in AI-enhanced systems, cloud-native architectures (AWS, Azure), and full-stack development. Adept at driving significant improvements in system performance, data integrity, and team efficiency through technical innovation and leadership.
Experience
Prism Creative
Oklahoma City, OK
Senior Software Engineer
January 2025 – Present
- Led the modernization of a legacy VB6 system (“Intake”) into a robust, web-based legal operations platform (“Hub”) using Next.js, Tailwind CSS, Shadcn UI, and TypeScript, significantly enhancing usability and long-term maintainability.
- Developed comprehensive backend services with NestJS and TypeScript, featuring C#-based authentication and seamless cloud integrations (AWS S3, cron jobs) for critical operational workflows.
- Designed and implemented a nightly statistical pipeline leveraging government APIs and demographic data to intelligently rank counties by risk based on speeding violation rates, providing crucial insights for trucking route planning and policy decisions.
- Engineered an intelligent document migration tool capable of moving millions of records from Laserfiche to AWS S3, storing metadata in MSSQL, drastically improving data retrieval efficiency and scalability for essential legal documents.
- Developed an AI-powered classification system to auto-categorize previously unusable free-text violation tickets (e.g., mapping “sp 35/20” to “speeding”), enabling valuable actionable analytics and streamlined data processing.
- Created robust tools within Hub for securely uploading and attaching Motor Vehicle Records, court documents, and traffic tickets to cases, incorporating intuitive drag-and-drop support and secure storage via Shadcn components and AWS S3.
Heartland Pay Systems
Oklahoma City, OK
Senior Software Engineer
November 2021 – January 2025
- Served as a core contributor to “Serverless,” a mission-critical backend platform built primarily with TypeScript and deployed through AWS Lambda, integrating RESTful services and select PHP components to support scalable payment infrastructure.
- Maintained and significantly expanded a complex React + Redux enterprise application (“Admin Portal”), empowering restaurant operators with robust configuration tools for menus, schedules, and tax rules.
- Introduced and successfully evangelized the adoption of Zod across the TypeScript ecosystem to enforce runtime schema validation, establishing it as a company-wide standard for ensuring critical data integrity.
- Championed the migration from raw SQL strings to Drizzle ORM, substantially improving readability, maintainability, and type safety across critical backend operations.
- Engineered and deployed advanced billing logic using fp-ts, including a high-performance Lambda for handling simultaneous transaction splits in complex financial workflows.
- Led third-party integration efforts for major platforms like DoorDash, Como, and Opera, coordinating frontend enhancements and orchestrating communication via Lambda-based APIs for seamless interoperability.
- Enhanced mobile authentication experiences by implementing OAuth 2.0 in React Native applications, improving user security and convenience.
- Modernized development practices by successfully shifting the team from a fragile, homegrown Git flow to trunk-based development with LaunchDarkly feature flags, significantly boosting deployment confidence and fostering greater collaboration.
- Actively contributed to Agile ceremonies and team retrospectives, consistently helping improve sprint planning, estimation accuracy, and overall delivery cadence across multiple teams.
Pearson OBL/Connections
Columbia, MD
Senior Software Engineer
May 2020 – November 2021
- Applied deep technical expertise to architect and develop enterprise software solutions within Azure Cloud, leveraging ASP.NET MVC/Web Forms, Angular, AngularJS, TypeScript, Node.js, C#, SQL Server, Entity Framework, and Dapper.
- Led the development of the Identity Enablement System (IES) for centralized login and session management, streamlining secure access across multiple platforms and incorporating SAML authentication protocols.
- Designed and launched a scalable, real-time customer support chat system using Angular, Ejabberd, and custom Erlang/XMPP infrastructure, integrating RabbitMQ-based queuing to efficiently manage user flow based on dynamic questionnaires and agent availability.
- Engineered a collaborative whiteboard tool supporting live drawing (shapes, images, annotations) with metadata, enabling rich, real-time interaction among chat participants.
- Contributed significantly to the company's LMS platform by building intuitive portal applications that improved usability and operational efficiency for students, staff, and administrators.
Manager of Software Engineering
January 2014 – May 2020
- Directed up to four concurrent teams—including both onshore and offshore units—delivering mission-critical software initiatives aligned with enterprise goals.
- Owned full-cycle engineering management operations: encompassing staffing, budgeting, mentorship, code reviews, performance evaluations, compensation planning, and contractor oversight.
- Played a key leadership role in the company's transition from SCRUM to the SAFe Agile framework, facilitating multi-team planning sessions, roadmap alignment, and executive sign-off meetings.
- Acted as a vital voice for engineering in strategic forums, partnering with product owners and business leaders to accurately represent team capacity, shape initiatives, and prioritize deliverables.
- Championed privacy, accessibility, and compliance at scale, leading development efforts to implement GDPR-style data controls and full accessibility support across multiple complex platforms.
- Collaborated cross-functionally with security, architecture, and legal teams to design POCs for penetration testing and technical strategy, ensuring robust quality and compliance from ideation through delivery.
- Launched successful developer enablement programs, including team-led and self-led training sessions, workshops, and talks on emerging technologies, fostering a strong learning-oriented engineering culture.
Advanced Academics
Oklahoma City, OK
Lead Developer & Engineering Manager
August 2010 – January 2014
- Led comprehensive development and engineering efforts for ROADs, a proprietary education management system later acquired by Connections and Pearson OBL.
- Oversaw the platform's significant evolution from .NET 2.0 WebForms to .NET 3.5 MVC, and eventually to a modern Node.js + Express + Socket.IO architecture, substantially improving scalability and maintainability.
- Designed and optimized high-performance MSSQL stored procedures, including extensive index tuning and table flattening, to enhance reporting workloads.
- Built core modules crucial for course delivery, content authoring, assessment, and student-teacher communication, directly supporting online learning at scale.
- Developed an innovative mobile chat application using C# and PhoneGap, enabling teachers to efficiently fulfill mandatory student engagement requirements across various devices.
- Integrated SQL Server Reporting Services (SSRS) into the platform to support dynamic, role-based reporting for administrators and educators.
- Played a dual role as technical lead and manager, mentoring developers, coordinating complex cross-functional initiatives, and ensuring the delivery of high-impact features in a fast-paced edtech environment.
21st Century Technologies / Sumeria Systems
Tinker AFB Contract
Lead Developer & Site Manager
2006 – 2010
- Promoted through the ranks from developer to lead developer, and ultimately to site lead, overseeing all contract personnel—including developers, DBAs, QAs, business analysts, and system administrators—supporting the Programmed Depot Maintenance Scheduling System (PDMSS) at Tinker Air Force Base.
- Managed the full lifecycle of staffing operations: including interviewing, hiring, onboarding, performance management, and offboarding, while serving as the on-site liaison for the contracting company.
- Developed and maintained mission-critical applications within the PDMSS suite, directly supporting complex aircraft maintenance scheduling, parts ordering, cannibalization tracking, and depot workflow coordination.
- Navigated a diverse tech stack including Classic ASP, VBScript, JavaScript, and C# with .NET 2.0 Web Forms, effectively modernizing legacy systems and ensuring critical operational continuity.
- Administered team systems and infrastructure, maintaining Security+ certification to meet stringent Air Force compliance requirements for administrative access.
- Coordinated seamlessly with base personnel and federal stakeholders to ensure the secure and timely delivery of software solutions in a high-stakes defense environment.
Early Career Summary
Various Roles at FSSE, Sirius Systems, Halliburton, and Docsoft | 1998 – 2006
- Held formative software engineering roles across government, corporate, and tech startups, contributing to systems ranging from transcription platforms to military logistics tools.
- Developed interactive media software to accompany Element A/V, including a sophisticated transcript-to-video synchronization system using C#, XML, and XSLT, enabling dynamic highlighting and real-time editing of low-confidence utterances.
- Completed impactful back-to-back internships at Halliburton, where I piloted an automated testing framework for C++/Win32 desktop software (Opticem) using WinRunner, laying crucial groundwork for QA automation within enterprise environments.
- Contributed to diverse projects leveraging HTML, JavaScript, SQL, XML, SGML, XSLT, C++, WinRunner, MFC, and OpenGL, demonstrating early adaptability across evolving platforms and technology stacks.
Skills
Front-End Development
- TypeScript, JavaScript
- React (Next.js, Shadcn UI), React Native
- Angular, AngularJS, HTML, CSS, Tailwind CSS
Back-End Development
- Node.js
- .NET Framework & Core (C#, VB.NET)
- NestJS
Cloud & DevOps
- AWS (Lambda, S3, extensive cloud services experience)
- Azure Cloud
Databases
- MSSQL, MySQL, Oracle, MongoDB, PostgreSQL
Additional Technologies
- C, C++, Rust (earlier exposure)
- Elixir, Erlang, Elm
- TCL/TK, Bash
- WinRunner, Win32 API, MS MFC
Key Proficiencies
- Software Architecture & Design
- Requirements Gathering & System Analysis
- Automated Testing & Performance Optimization
- Agile & SAFe Methodologies
- Team Leadership & Mentorship
- Cross-functional Collaboration
- Adaptability Across Diverse Technologies
Education
Cameron University
Lawton, Oklahoma
Bachelor of Science in Computer Science | 2001 – 2004