Vice President of Engineering

atSundaySkyRemoteUS flagUnited StatesFull-timeVice PresidentLead$260k – $280k/year

Posted 5 days ago

This is a fully remote position, open to applicants in United States.

📋 Description

• Build, lead, and expand a high-performing Engineering organization across U.S.-based, nearshore, and offshore teams.

• Define the Engineering operational model, organizational structure, ownership boundaries, technical leadership framework, and delivery expectations.

• Recruit, develop, and retain Engineering leaders, architects, full-stack engineers, QA professionals, DevOps resources, and technical leads.

• Establish performance expectations, career paths, Engineering standards, team health metrics, and leadership development initiatives.

• Design scalable team structures and create an effective mix of employees and delivery partners.

• Implement onboarding, documentation, knowledge-sharing, code ownership, architecture review, and technical readiness practices.

• Develop repeatable processes for planning, delivery, support, technical decisions, and cross-functional coordination.

• Collaborate with Product, Customer Success, Sales, Operations, Finance, HR, and executive leadership to align resources with company priorities.

• Design and execute an AI-enabled software development lifecycle.

• Operationalize AI-assisted tools for coding, testing, documentation, code review, refactoring, debugging, requirements interpretation, release readiness, and production support.

• Establish responsible AI development standards addressing security, intellectual property, privacy, code review, test coverage, architectural consistency, and human accountability.

• Develop internal Engineering agents, accelerators, automation, and workflows.

• Provide technical leadership for AI-powered product capabilities, platform services, internal tools, and customer experiences.

• Evaluate opportunities involving AI, automation, agents, LLM integrations, personalization, recommendations, content generation, and intelligent workflows.

• Guide architecture for model integrations, prompt orchestration, data pipelines, APIs, permissions, observability, auditability, and human-in-the-loop workflows.

• Ensure AI features comply with quality, security, privacy, compliance, monitoring, explainability, and governance standards.

• Drive consistent, predictable, high-quality delivery across teams and initiatives.

• Establish planning, estimation, dependency management, technical review, release readiness, and executive reporting rhythms.

• Implement automation-first CI/CD, testing, QA, observability, security scanning, infrastructure provisioning, deployment, and release management practices.

• Define and track cycle time, deployment frequency, lead time, defect escape rate, test coverage, incidents, reliability, capacity, and release predictability metrics.

• Establish definitions of ready and done, automated quality gates, disciplined releases, and measurable success criteria.

• Translate company and product strategy into a scalable technical strategy and execution roadmap.

• Lead architecture, platform scalability, reliability, security, performance, data, APIs, integrations, DevOps, AI enablement, and technical debt management.

• Align Engineering investments with business outcomes, revenue priorities, customer commitments, enterprise readiness, and platform health.

• Manage budgets, hiring plans, contractor expenditure, vendors, software tools, infrastructure costs, and resource allocation.

• Identify and mitigate operational, security, scalability, architectural, delivery, personnel, compliance, and platform risks.

• Establish incident management, production support, monitoring, alerting, reliability, and postmortem practices.

• Contribute directly to architecture, technical design, prototyping, troubleshooting, and implementation when necessary.

• Serve as an escalation point for complex platform, scalability, reliability, performance, integration, data, and security challenges.

• Work directly with engineers to facilitate delivery and model exemplary Engineering practices.


⛳️ Requirements

• Over 10 years of Engineering leadership experience, including managing teams of managers, architects, technical leads, and distributed teams.

• Proven experience as a VP of Engineering, Head of Engineering, Senior Director of Engineering, or a comparable leadership role within a SaaS, enterprise software, platform, or technology company.

• Demonstrated success in building, restructuring, scaling, and leading high-performing Engineering organizations.

• Strong full-stack expertise covering frontend, backend, APIs, data, cloud infrastructure, and integrations.

• Hands-on software development experience with the ability to contribute to architecture, prototypes, technical design, coding, and critical problem-solving.

• Excellent architectural judgment related to scalable systems, cloud-native platforms, data models, security, observability, reliability, and performance.

• Experience in managing onshore, nearshore, and/or offshore teams and partners.

• Proven ability to improve Engineering operating models, delivery practices, technical ownership, velocity, and predictability.

• Experience in implementing automation across CI/CD, testing, infrastructure, observability, security, quality gates, and release management.

• Familiarity with adopting and operationalizing AI-assisted Engineering tools and workflows.

• Experience in building AI-powered features, internal accelerators, workflow automation, LLM-enabled capabilities, or intelligent developer tools.

• Ability to effectively collaborate with Product, UX, GTM, Customer Success, Finance, HR, and executive leadership.

• Excellent communication skills, including the capacity to articulate technical strategy, risks, architecture, capacity, and trade-offs to executive and board audiences.

• Strong judgment, urgency, accountability, and the ability to lead amidst ambiguity, growth, and change.

• Preferred: experience in B2B SaaS, enterprise software, marketing technology, fintech, financial services, insurance, or other regulated industries.

• Preferred: experience with GitHub Copilot, Claude Code, Cursor, ChatGPT, or similar AI-assisted development platforms.

• Preferred: experience in delivering LLM, agent, prompt orchestration, personalization, recommendation, content generation, workflow automation, or intelligent analytics capabilities.

• Preferred: experience with nearshore, offshore, contractor, or global delivery models.

• Preferred: experience with cloud-native, API-first, data-driven, multi-tenant, configurable, or enterprise-grade platforms.

• Preferred: experience enhancing roadmap visibility, backlog discipline, technical ownership, delivery accountability, or release predictability.

• Preferred: experience implementing automated regression and performance testing, security scanning, observability, and production-readiness practices at scale.

• Preferred: experience in a growth-stage company managing customer commitments, platform modernization, technical debt, team scaling, and product innovation.


🏝️ Benefits

• Annual bonus

• Equity

• 401(k)

• Medical insurance

• Dental insurance

• Vision insurance

• Short-term disability coverage

• Paid parental leave

• Inclusive work environment

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