Vice President, Head of Technology

Chief•New York, NY

1d•$285,000

About The Position

We are seeking a Vice President, Head of Technology to lead our engineering and product organizations and steward a mature but evolving platform at a critical stage of growth. As a 7-year-old startup, we are past “greenfield” but not finished. We need a leader that has strong technical and strategic thinking skills to help lead the organization to build for today with an eye for the future. This leader will own our technical and product vision, oversee a team of full-stack engineers and product team, and partner closely with leadership to deliver scalable, intelligent, and member-centric experiences. The ideal candidate is comfortable operating in ambiguity, balancing long-term architecture with near-term execution, and leveraging existing systems (including Salesforce and Braze) rather than defaulting to rebuilds.

Requirements

Engineering Leadership: You bring 10+ years of software engineering experience, with at least 5+ years in senior leadership roles, having built and scaled high-performing teams that turn technical vision into high-trust execution.
Technical Strategy & Architectural Stewardship: Developed and executed comprehensive strategies—owning the roadmap and leading hands-on execution of microservices, APIs, and distributed systems to deliver stable, resilient platforms that evolve without unnecessary or costly rewrites.
Legacy Modernization & Pragmatism: Thrived in dynamic environments, finding creative ways to simplify and modernize legacy systems and navigate technical debt while making the difficult trade-offs and prioritization calls required under constraints.
GTM Stack & Cloud Optimization: Operated with deep fluency in Salesforce, Braze, and cloud environments (AWS/GCP/Azure)—leveraging your expertise in data models and pipelines to transform our tech stack into a powerful enabler for the member journey rather than a constraint.
AI/ML Integration: Architected and deployed AI/ML features within production consumer products—leveraging intelligence and data experimentation to deliver features that materially improve member engagement and business outcomes.
Cross-Functional Partnership: Partnered effectively across the C-Suite and GTM, Marketing, and Operations teams—thriving in a hybrid environment where you translate complex technical trade-offs into clear alignment and actionable plans based on a shared understanding of member experience and business goals.
Team Leadership & Mission: Coached and inspired multidisciplinary teams to stretch toward ambitious goals—maintaining a people-first, mission-driven culture while making difficult prioritization calls under constraints. You are deeply passionate about driving technical excellence and find fulfillment in building an enduring organization where systems, teams, and member experiences reflect a shared purpose.

Responsibilities

Own the technical strategy and roadmap, balancing scalability, reliability, and delivery velocity.
Lead and mentor a team of full-stack engineers (frontend, backend and mobile), fostering a culture of accountability and thoughtful decision-making
Evaluate existing systems with a pragmatic lens—clearly identifying what is worth fixing, refactoring, or rebuilding vs. what should be maintained.
Architect and maintain a microservices-based platform, ensuring services are well-scoped, resilient, and observable.
Establish best practices for engineering quality, CI/CD, testing, documentation, and incident response without introducing unnecessary processes.
Provide executive oversight of internal IT infrastructure and operations, including employee laptops, email systems, identity and access management, security tooling, and core SaaS applications.
Manage and support the individual responsible for day-to-day IT operations, ensuring clear priorities, strong service levels, and appropriate security and compliance standards.
Establish lightweight, scalable processes for onboarding/offboarding, device management, access controls, and vendor management.
Establish clear privacy and security protocols throughout the organization and ensuring products and new features meet latest security guidelines.
Lead the application of AI and machine learning to meaningfully improve our social/network experience (e.g., personalization, recommendations, matchmaking, insights, moderation).
Drive responsible experimentation with AI tools to improve both member experience and internal efficiency.
Translate emerging AI capabilities into practical, high-impact product features.
Own the product and design organization and function, ensuring tight alignment between product strategy, engineering execution, and business goals.
Partner with stakeholders to define priorities, tradeoffs, and success metrics.
Lead product discovery and delivery with a bias toward learning, iteration, and measurable outcomes.
Ensure product decisions reflect both member needs and technical realities.
Own the technical relationship with Salesforce, including architecture, integrations, data flows, and system reliability.
Ensure Salesforce supports business needs without becoming a bottleneck or source of excessive complexity.
Oversee integration with Braze, enabling effective lifecycle messaging, personalization, and engagement.
Partner with GTM, marketing, and operations teams to ensure systems are well-integrated and purpose-built.
Design and oversee data pipelines and integrations across product, Salesforce, Braze, and other systems.
Establish clear data governance standards for data quality, privacy, security, and access.
Enable trusted data for personalization, analytics, and decision-making without over-engineering.
Own and optimize use of Sanity (or similar headless CMS) as part of the experience layer.
Ensure content systems integrate cleanly with product and support flexibility and scale.
Serve as a strategic partner to executive leadership on technology, product, and platform decisions.
Clearly communicate tradeoffs and recommendations to technical and non-technical audiences.
Lead hiring, team structure, and long-term capability development across engineering and product.

Benefits

Competitive salary and equity
Flexible vacation policy
20 weeks of paid gender neutral parental leave
Full medical, dental, and vision packages, 401(k)
Opportunity to work for a startup focused on driving real change for women in business
Opportunity to create and attend inspiring experiences and events with leaders of the industry
Access to our ongoing virtual Chief member exclusive content, including workshops, thought leadership, and iconic speakers

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