Edtech.com's Summary

Frontline Education is hiring a Principal Software Engineer, Back-End .NET. The role involves leading the design and development of scalable back-end enterprise systems using C#, .NET, and AWS, while integrating AI-enabled workflows into regulated, compliance-driven products. The engineer will provide technical leadership, establish architectural standards, mentor senior engineers, and ensure secure, compliant, and high-quality AI integrations within enterprise applications.

Highlights

Lead design and modernization of back-end systems using C#, .NET, ASP.NET Core, Microsoft SQL Server, microservices, and cloud-native patterns.
Integrate AI workflows for intelligent document processing, anomaly detection, recommendation systems, and workflow automation.
Ensure system compliance with regulatory, security, and audit requirements in risk-sensitive industries.
Work with cross-functional teams including product, compliance, security, and data science to align technical solutions with business needs.
Mentor senior engineers and influence multi-team engineering practices and architecture.
Experience with AWS and cloud-based production environments preferred.
Strong skills in secure software development, distributed systems, event-driven architecture, and API design.
Compensation ranges from $160,000 to $180,000 annually, with bonus eligibility and benefits including 401(k), health coverage, stock purchase, and tuition reimbursement.
Preferred knowledge includes AI platforms such as AWS Bedrock, OpenAI APIs, vector databases, and DevOps tools like Docker, Kubernetes, and Terraform.
Background in regulated industries such as education technology, healthcare, finance, or compliance software is valuable.

Principal Software Engineer, Back-End .NET Full Description

Principal Software Engineer, Back-End .NET

Location: United States

Description

Location: Remote, USA

Enterprise AI Workflow Integration | Regulatory / Compliance-Driven Products

About the Role

We are seeking a Principal .NET Software Engineer to help lead the evolution of our enterprise platform in a highly regulated, compliance-driven industry. This role is ideal for a senior technical leader who has deep expertise in building scalable back-end systems with the Microsoft technology stack and AWS, with hands-on experience integrating AI-enabled workflows into real-world enterprise workstreams.

As a Principal Engineer, you will operate at the intersection of architecture, product delivery, engineering excellence, and applied AI. You will be expected to design and deliver resilient back-end services, guide technical strategy, mentor senior engineers, and help establish practical patterns for safely incorporating AI capabilities into production systems where accuracy, auditability, security, and compliance are critical.

This is not a purely research-focused AI role. We are looking for someone who understands how to apply AI pragmatically inside enterprise software: automating workflows, enhancing decision support, improving data extraction, enabling intelligent recommendations, streamlining compliance operations, and embedding human-in-the-loop controls where needed.

Key Responsibilities

Technical Leadership & Architecture

Lead the design, development, and modernization of enterprise-grade back-end systems using C#, .NET, ASP.NET Core, Microsoft SQL Server, APIs, microservices, event-driven architecture, and cloud-native patterns.

Define and influence architectural direction for critical capabilities, ensuring solutions are scalable, secure, observable, maintainable, and aligned with long-term product strategy.

Serve as a technical authority across engineering teams, helping evaluate tradeoffs related to performance, resiliency, data integrity, compliance, integration complexity, and operational supportability.

Partner with engineering leadership, product management, architecture, security, compliance, platform teams and data teams to translate complex business and regulatory requirements into durable technical solutions.

Establish reusable engineering patterns, reference architectures, and implementation standards for back-end services, API design, data access, integrations, and AI-enabled workflow components.

AI Workflow Integration

Design and implement back-end services that integrate AI capabilities into enterprise workstreams, including use cases such as intelligent document processing, classification, summarization, anomaly detection, recommendation workflows, knowledge retrieval, workflow automation, and decision support.

Work with product, compliance, legal, and security stakeholders to ensure AI-enabled features are implemented with appropriate controls, explainability, audit trails, data protection, and human review mechanisms.

Collaborate with data science, platform, and vendor teams to integrate LLMs, AI services, model APIs, vector search, retrieval-augmented generation patterns, prompt orchestration, and workflow automation tools into production software.

Help define engineering standards for responsible AI usage, including model interaction logging, prompt/version management, evaluation strategies, fallback handling, access controls, and monitoring for quality, latency, cost, and risk.

Identify opportunities to use AI to improve internal engineering and operational workstreams, including developer productivity, testing, support triage, compliance reviews, and operational analysis.

Regulatory, Security & Compliance Alignment

Build systems that meet the expectations of regulated environments, including strong controls around data privacy, auditability, traceability, identity, authorization, retention, and change management.

Ensure software designs account for compliance obligations, risk management practices, secure SDLC standards, and enterprise governance requirements.

Partner with security and compliance teams to support threat modeling, secure architecture reviews, audit readiness, incident response planning, and evidence generation.

Design AI-enabled workflows with appropriate safeguards, including data minimization, role-based access, explainable outputs, human approval gates, and defensible records of system behavior.

Engineering Excellence

Set a high bar for code quality, automated testing, reliability, observability, CI/CD practices, and production readiness.

Drive improvements in system performance, scalability, reliability, and maintainability across core back-end services.

Review complex designs and code changes, providing constructive technical guidance to engineers at all levels.

Lead efforts to reduce technical debt, modernize legacy components, improve integration patterns, and simplify system complexity.

Promote strong operational practices, including structured logging, distributed tracing, metrics, alerting, runbooks, and post-incident learning.

Mentorship & Cross-Functional Influence

Mentor senior and staff-level engineers, helping them grow in architecture, technical decision-making, system design, and leadership.

Influence engineering direction across multiple teams without relying solely on formal authority.

Communicate clearly with technical and non-technical stakeholders, especially when explaining complex architecture, compliance implications, AI limitations, and delivery tradeoffs.

Act as a trusted advisor to product and engineering leadership on how to safely and effectively incorporate AI capabilities into enterprise product experiences.

Required Qualifications

10+ years of professional software engineering experience, with significant experience designing and building enterprise back-end systems.

Deep expertise with C#, .NET, ASP.NET Core, RESTful APIs, background services, dependency injection, asynchronous programming, and modern back-end engineering practices.

Strong experience with enterprise application architecture, including microservices, modular monoliths, distributed systems, event-driven patterns, messaging, API gateways, and service-to-service communication.

Experience designing and operating production systems in cloud environments such as AWS, Azure, or Google Cloud, with a preference for AWS-based enterprise platforms.

Hands-on experience integrating AI, machine learning, or LLM-enabled capabilities into business workflows, enterprise applications, or operational systems.

Experience with data-intensive applications, including relational databases, SQL performance tuning, data modeling, caching, indexing, and integration with analytics or search platforms.

Strong understanding of secure software development practices, including authentication, authorization, encryption, secrets management, secure APIs, and vulnerability management.

Experience working in or supporting regulated, compliance-driven, or risk-sensitive industries such as financial services, healthcare, insurance, legal technology, government, life sciences, audit, risk, or compliance software.

Demonstrated ability to lead complex technical initiatives across teams, influence architecture, and deliver high-impact engineering outcomes.

Excellent communication skills with the ability to explain technical decisions, risks, and tradeoffs to engineering, product, security, compliance, and executive stakeholders.

Preferred Qualifications

Experience with AWS Bedrock, OpenAI APIs, Microsoft Agent Framework, SpecKit, vector databases, embeddings, retrieval-augmented generation, prompt orchestration, and AI workflow automation platforms.

Experience designing human-in-the-loop workflows, approval flows, audit trails, or exception management systems for AI-assisted business processes.

Familiarity with responsible AI practices, model evaluation, AI governance, prompt/version control, AI observability, and risk management frameworks.

Experience with enterprise workflow platforms, rules engines, BPM tools, case management systems, document management systems, or compliance operations platforms.

Experience with messaging and event streaming technologies such as Kafka, RabbitMQ, or Event Grid.

Experience with containerization and orchestration technologies such as Docker and Kubernetes.

Experience with DevOps and infrastructure-as-code practices using tools such as GitHub Actions and Terraform.

Experience with domain-driven design, clean architecture, CQRS, event sourcing, distributed tracing, and high-scale API platforms.

Ideal Candidate Profile

The ideal candidate is a hands-on principal-level engineer who can move comfortably between code, architecture, strategy, and cross-functional leadership. You have built complex enterprise systems, understand the realities of regulated environments, and know how to introduce emerging technologies without creating unnecessary risk.

You are pragmatic about AI. You understand its potential, but you also recognize the importance of accuracy, governance, auditability, security, cost management, and human oversight. You can help teams separate hype from durable product value and turn ambiguous opportunities into well-designed, production-ready capabilities.

You are equally comfortable mentoring engineers, reviewing architecture, writing critical code, facilitating technical discussions, and partnering with senior leaders to shape product and platform direction.

Leadership Expectations

As a Principal Engineer, you will be expected to lead by influence, not just by implementation. You will help teams make better technical decisions, improve engineering discipline, and develop systems that can scale with the business.

You should bring strong judgment, intellectual humility, technical depth, and a bias toward practical delivery. We value engineers who can simplify complexity, communicate clearly, and build trust across functions.

Position Requirements Summary

The successful candidate will bring:

Deep back-end engineering expertise in C# and .NET
Enterprise architecture experience across complex distributed systems
Practical experience integrating AI workflows into production applications
Strong judgment in regulated, compliance-sensitive environments
A security-first and audit-ready engineering mindset
Proven ability to influence across teams and mentor senior engineers
A track record of delivering high-quality, scalable enterprise software

About Frontline Education

Frontline Education is a pioneer of school administration software purpose-built for K–12 districts. We provide innovative, connected solutions for student and special programs, business operations, and human capital management with powerful data and analytics to empower educators and administrators. We earn the trust of K–12 leaders across the U.S. by serving as a consistently high-performing, forthright partner of school districts through every dimension of the company.

We’re a group of unique and talented individuals who love what we do. We believe in servant leadership, collaboration, continuous improvement, and balancing great work with a healthy life outside of it.

Frontline embraces diversity, equity, and inclusivity and is an equal opportunity employer.

Our Mission, Our People, Our Purpose

At Frontline Education, we’re reimagining what’s possible by becoming an AI-first organization, transforming how we think, work, and serve the educators who shape our schools every day. By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most, their students.

As part of our team, you’ll be expected and empowered to build and apply AI skillsets that grow with you, because at Frontline Education, technology amplifies what matters most: the human drive to learn, improve, and make a difference.

Compensation & Benefits

$160,000-$180,000 a year salary

• Bonus eligibility and long-term incentive opportunities
• 401(k) with company match
• Comprehensive health, dental, and vision coverage
• Employee stock purchase plan
• Generous paid time off and tuition reimbursement

Inclusion, Belonging & Equal Opportunity

Frontline Education is an equal opportunity/affirmative action employer. We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.

Interview Process & Data Privacy

As part of our interview process, Frontline uses video conferencing tools that include photo capture and may include automated transcription features. A screenshot or photo will be taken at the start of the interview for internal identification and record-keeping purposes only, and transcription may be used to support notetaking and evaluation consistency. These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside the hiring process. Candidates may opt out of the transcription at any time by notifying their recruiter in advance. Frontline processes this information in accordance with applicable data privacy laws and only for legitimate business purposes related to recruitment and hiring.

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Original Job Description