SkillUp Coalition Head of Engineering Remote · Full time Company website

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Founded in July 2020, SkillUp Coalition is an innovative nonprofit connecting more than 5 million individuals skilled through alternative routes (STARs) with the right tools, resources, and support to make confident career shifts, find quality living-wage jobs, and achieve promising career growth without the need of a college degree. Through its cutting-edge technology platform and step-by-step career guidance options, SkillUp has connected STARs with career, training, and job support nationwide. The coalition brings together more than 170 leading organizations, including training and education providers, technology developers, policymakers, employers, and philanthropies. SkillUp is a remote-first organization rooted deeply in our values to Champion Worker-First, Empower Impact, Embrace Collaboration, Exemplify Curiosity, and Embody Accountability. By 2030, we plan to serve 10 million users and help more than 1 million workers and learners attain quality employment.

Key Responsibilities

Architecture & Technical Leadership

• Own platform architecture decisions across the full stack (MongoDB, APIs, Azure/GCP), establishing technical standards and guiding long-term platform evolution to support SkillUp's growth objectives.
• Partner with the Head of Product to assess technical feasibility, identify trade-offs, and inform product roadmap decisions.

Hands-On Software Development

• Maintain sufficient technical depth to provide architectural guidance, support critical initiatives, review complex implementations, and contribute directly to the codebase when organizational needs require. 

Engineering Operations & DevOps

• Lead CI/CD pipelines, infrastructure-as-code, monitoring, and incident response. Build and manage on-call rotation schedules ensuring platform reliability. Own cloud infrastructure management across Azure and GCP.
• Establish engineering processes that improve delivery predictability, operational excellence, and team effectiveness.
• Establish engineering practices for AI observability, model monitoring, evaluation pipelines, and operational response to model degradation or hallucination risks.
• Optimize infrastructure for performance and cost across cloud compute, vector databases, inference services, reporting systems, and AI workloads.
• Develop CI/CD processes that support both traditional software deployments and AI model/prompt iteration.

Security & Compliance

• Ensure security best practices across the platform, including data protection, access controls, vulnerability management, and responsible stewardship of sensitive user information.

People & Vendor Leadership

• Lead, manage, and develop internal engineering staff and a near shore engineering team (engineers, QA, DevOps), fostering growth, accountability, and a culture of collaboration, continuous learning, and inclusivity. Develop engineering practices that support effective cross-functional partnership and sustainable team performance.
• Manage Senior AI technical talent and external technical partners responsible  for delivering secure, scalable AI product vision and capabilities in alignment with SkillUp’s product strategy.

Product Partnership & Delivery Leadership

• Partner closely with the Head of Product to translate user and business needs into actionable engineering plans and delivery roadmaps.
• Provide engineering perspectives to the CEO and leadership team on technical feasibility, scalability, sequencing, and resource requirements during roadmap planning.
• Drive execution against agreed-upon priorities, balancing delivery speed with quality, maintainability, and platform sustainability.
• Foster strong collaboration between engineering, product, design, analytics, and AI stakeholders to maximize user impact.

AI Platform & Engineering Leadership

• Partner with the Head of Product and the engineering teams to build and scale SkillUp's AI-native career navigation platform, ensuring AI capabilities are reliable, secure, observable, and production-ready.
• Establish engineering patterns for integrating large language models (LLMs), AI agents, retrieval systems, orchestration frameworks, and structured data services into production applications.
• Build the technical infrastructure necessary to evaluate, monitor, and continuously improve AI system performance, including latency, cost, quality, safety, and user outcomes.
• Ensure AI services are architected with appropriate guardrails, testing strategies, human oversight, and responsible AI practices.
• Develop engineering standards for prompt management, model versioning, experimentation, observability, and deployment across AI-powered services.

Qualifications

• 8+ years of professional software engineering experience, with 4+ years leading engineering teams and technical initiatives.
• Experience managing nearshore and/or contract engineering teams, including vendor relationships, SOWs, delivery oversight, and performance management.
• Experience partnering effectively with product leaders to deliver customer-facing technology solutions.
• Demonstrated ability to balance strategic technical thinking with hands-on execution in lean environments.
• Experience delivering AI-enabled or machine learning products into production, ideally leveraging LLMs, generative AI, agentic workflows, or intelligent automation.
• Familiarity with modern AI engineering patterns, including retrieval-augmented generation (RAG), vector databases, orchestration frameworks, prompt management, evaluation frameworks, and AI observability.
• Demonstrated ability to partner with AI engineers, data scientists, and product leaders to translate emerging AI capabilities into scalable customer experiences
• Entrepreneurial mindset — comfortable navigating ambiguity, balancing competing priorities, and driving progress in resource-constrained environments.

And while all of the above qualifications are important, there are three demonstrated capabilities most important for this job, and they are (blatantly borrowed from Jeff Weiner of LinkedIn):

• Dream Big
• Get Sh*t Done
• Know How to Have Fun

Compensation & Benefits 

Target salary for this position is $175,000–$200,000, depending on experience, geography, and internal equity.

SkillUp offers a generous compensation package which includes employer-sponsored healthcare, vision and dental, 401K employer match, 25 days of office closure, PTO, education stipend, and annual salary increases based on performance.

Our Commitment to Diversity 

At SkillUp, our mission is to help workers get hired for in-demand jobs in high-growth industries. Success in this mission requires that we don’t just accept differences, but that we celebrate and embrace the diverse community and backgrounds individuals come from. We stay true to our mission by ensuring that our place can be anyone’s place, and we embrace diversity and equal opportunity in a serious way. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better our work will be. 

As a proud equal opportunity employer, SkillUp does not discriminate on the basis of race, color, ancestry, national origin, religion or religious creed, mental or physical disability, medical condition, genetic information, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity, gender expression, age, marital status, military or veteran status, citizenship, or other characteristics protected by state or federal law or local ordinance.