Vice President of Engineering

Company Overview

SundaySky is a category-defining SaaS platform that enables enterprises and upper mid-market organizations to deliver highly personalized video experiences at scale across the entire customer lifecycle. Built for modern, data-driven teams, the platform empowers marketers, CX leaders and field organizations to transform complex data into dynamic, relevant video communications that deepen engagement, improve the customer experience, increase conversion, and strengthen long-term relationships. Founded in Tel Aviv in 2007, SundaySky serves some of the world’s most recognized banking, financial services, and insurance firms. As the pioneer of AI-powered video personalization, SundaySky reimagines how enterprises communicate. Moving beyond static, one-size-fits-all content to intelligent, adaptive video experiences. The platform combines generative AI, real-time rendering, and an intuitive creation workflow to make personalized video fast, scalable, and measurable. By unifying creation, personalization, distribution, and optimization in a single system, SundaySky enables teams to deliver emotionally resonant experiences that drive outcomes, turning video into a core growth and engagement engine rather than a costly, slow-moving production exercise.

Investment History

In July 2022, SundaySky completed a $100 million investment from the private equity firm Clearhaven Partners, providing capital for growth and innovation. This investment completes the transition of the business from a managed services company to a SaaS company, enabling the next stage of growth. Clearhaven is a Boston-based private equity firm focused exclusively on software and technology investments. Founded in 2019 by an investor-operator team with over 50 years of combined experience, Clearhaven was purpose-built to partner with differentiated, growth-stage software companies. The firm invests thematically in high-quality B2B software businesses, supporting management teams seeking an operationally focused partner to drive transformational growth.

The Opportunity

SundaySky is positioned in an incredible market for personalized, enterprise video. The company represents an extremely attractive opportunity in a fast-growing market:

●       Compelling financial profile

○       $25M+ revenue

○       20%+ SaaS bookings growth 2025 vs 2024

○       EBITDA positive

○       80 FTE globally

●       Significant market opportunity

○       TAM for Enterprise Video Content Management

○       $48B+ TAM with a growing CAGR of 13% by 2030

○       65% of businesses use videos for customer service, 61% of companies use videos for employee communications

○       Opportunity to activate moments that matter during the customer lifecycle through personalized video to drive real business outcomes

●       Strong Customer Base

○       Blue chip customer base in banking, financial services and insurance

○       Leading banks and financial service firms such as Bank of America, Schwab, Morgan Stanley, T. Rowe Price, Ascensus, Broadview and Bread Financial

○       Health, commercial and property insurance firms including Chubb, Zurich America, Progressive, Liberty, Aetna, UnitedHealth Care, Anthem, Emblem, Kaiser Permanente , and Floriday Blue

About the Role

SundaySky is seeking a deeply technical, AI-native engineering leader to define our architecture, transform how software is built, and lead a focused team of highly experienced engineers. This is not a traditional, management-first Vice President of Engineering role. We are not looking for an executive who has moved away from software development or whose primary strength is managing managers. We are looking for an exceptional architect, distinguished engineer, or hands-on Engineering Director who is ready to assume broader ownership for an Engineering organization while remaining directly involved in architecture and implementation. Our Engineering model is intentionally different. We believe a smaller team of accomplished senior engineers—equipped with well-designed AI agents, automation, and disciplined technical oversight—can outperform a much larger traditional development organization. In this model, AI performs much of the implementation work typically assigned to junior developers, while experienced engineers provide architecture, context, judgment, review, and accountability. The successful candidate will personally help build this model. They will work in the codebase, develop reference implementations, establish architectural patterns, create AI-enabled engineering workflows, and guide engineers through complex technical decisions. They will also lead the Engineering team, establish delivery discipline, and ensure that speed does not come at the expense of security, maintainability, reliability, or product quality. This is an opportunity for a technically exceptional and ambitious leader to take the next step in their career, shape SundaySky’s technical future, and demonstrate what an AI-native software organization can accomplish.

Responsibilities

Technical Architecture and Implementation

• Own SundaySky’s application, platform, data, integration, cloud, and AI architecture.
• Work directly in the codebase through prototyping, implementation, code review, debugging, refactoring, and complex problem-solving.
• Translate product strategy into pragmatic technical designs and executable implementation plans.
• Create reference architectures, reusable components, engineering patterns, and technical standards that accelerate development.
• Make sound tradeoffs between immediate delivery, architectural quality, platform scalability, and technical debt.
• Lead the modernization of legacy components while preserving platform stability and customer commitments.
• Serve as the principal technical escalation point for difficult architecture, performance, security, reliability, integration, and production issues.

AI-Native Software Development

• Design and personally implement an AI-native development model in which AI agents perform a meaningful portion of coding, testing, documentation, analysis, and maintenance.
• Build the context, instructions, tools, guardrails, evaluation methods, and human-review practices required for agents to produce production-quality software.
• Use AI coding tools actively and regularly—not simply as productivity add-ons, but as core components of the development lifecycle.
• Develop internal agents and automated workflows for implementation, testing, code review, debugging, documentation, migration, release readiness, and production support.
• Determine which work can be safely delegated to AI and where experienced engineering judgment must remain directly involved.
• Establish measurable standards for the quality, security, maintainability, and productivity of AI-produced code.
• Continuously evaluate emerging models, tools, frameworks, and agentic development techniques.

Hands-On Technical Leadership

• Lead from within the work by pairing with engineers, reviewing implementations, solving difficult problems, and modeling strong engineering practices.
• Provide clear technical direction to a small, senior, highly leveraged Engineering team.
• Break ambiguous product requirements into well-defined architectures, technical plans, and AI-executable units of work.
• Raise the technical capabilities of the team through coaching, direct collaboration, architectural guidance, and rigorous review.
• Remain close enough to the code and platform to make informed technical decisions without relying entirely on secondhand reporting.
• Create an environment in which engineers have high autonomy, clear ownership, strong standards, and accountability for outcomes.

Delivery and Engineering Operations

• Establish a lightweight, automation-first development lifecycle optimized for speed, quality, and predictability.
• Improve CI/CD, automated testing, observability, security scanning, infrastructure automation, and release management.
• Define clear standards for technical readiness, code review, test coverage, release readiness, and production quality.
• Use metrics such as cycle time, deployment frequency, defect escape rate, reliability, and AI-generated contribution quality to improve execution.
• Partner closely with Product and Design to convert strategy and requirements into executable technical work.
• Provide clear visibility into delivery status, capacity, dependencies, technical risks, and tradeoffs.

Team Leadership

• Build and lead a deliberately small team of highly experienced U.S. and nearshore engineers.
• Recruit engineers who combine strong technical judgment with effective use of AI-assisted development.
• Create clear ownership across applications, services, platform components, and production operations.
• Manage performance directly and candidly while minimizing unnecessary organizational layers and process.
• Scale the organization thoughtfully, using automation and AI leverage before defaulting to additional headcount.
• Foster a culture of urgency, experimentation, craftsmanship, accountability, and continuous learning.

Requirements

• Significant hands-on software engineering experience, including recent and substantive involvement in architecture, implementation, code review, and production problem-solving.
• Deep architectural expertise across modern frontend and backend systems, APIs, data, cloud infrastructure, integrations, security, observability, performance, and reliability.
• Demonstrated use of AI coding agents to build, test, refactor, debug, or maintain production software.
• Ability to design development workflows in which AI performs implementation work under experienced human direction, review, and accountability.
• Experience creating technical specifications, architectural context, coding standards, guardrails, and validation methods that enable reliable agentic development.
• Evidence of personally building prototypes, production capabilities, internal developer tools, agents, or engineering automation.
• Experience providing technical leadership across multiple engineers, teams, or complex initiatives, whether as an architect, distinguished engineer, technical lead, Director, or Engineering executive.
• Ability to lead and develop senior engineers without becoming disconnected from implementation.
• Strong judgment regarding architecture, technical debt, security, scalability, platform reliability, and build-versus-buy decisions.
• Experience modernizing development practices, CI/CD, automated testing, observability, infrastructure, and release processes.
• Ability to operate effectively in a growth-stage environment with ambiguity, legacy constraints, limited resources, and demanding customer commitments.
• Clear, direct communication with technical and nontechnical stakeholders.
• A builder’s mindset, high personal ownership, intellectual curiosity, urgency, and the desire to create something meaningfully different.
• Revised preferred qualifications
• Experience as a principal engineer, distinguished engineer, chief architect, hands-on Engineering Director, startup CTO, or similarly technical leader.
• Experience building AI agents, LLM-enabled applications, agent orchestration systems, evaluation frameworks, or intelligent automation.
• Advanced use of tools such as Claude Code, Codex, Cursor, GitHub Copilot, or comparable agentic development platforms.
• Experience designing systems that combine deterministic software, generative AI, human review, and automated evaluation.
• Experience with cloud-native, API-first, multi-tenant, data-driven enterprise SaaS platforms.
• Experience with media generation, browser-based rendering, personalization, content technology, marketing technology, fintech, or regulated industries.
• Experience leading a blended team of U.S.-based and nearshore engineers.
• Experience taking broader organizational ownership after succeeding in a senior technical or architectural role.

This Role Is Not

• A management-only position.
• A role for someone who wants to delegate architecture and implementation entirely to others.
• A traditional executive position centered on board communication, organizational layers, or managing managers.
• An opportunity to scale Engineering primarily by adding headcount.
• A fit for someone whose AI experience is limited to sponsoring adoption or purchasing developer tools.
• A CTO-in-waiting role designed around corporate strategy, fundraising, or external visibility.

Location: remote

Compensation & Benefits

Base salary: $260,000-$280,000 annually

Additional compensation and benefits include an annual bonus, equity, 401(k), medical, dental, and vision insurance, short-term disability coverage, and paid parental leave.

SundaySky is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. Different makes us better.