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Role Description

We are seeking a highly strategic and experienced Vice President of Engineering for B2B innovation and infrastructure services. You will lead a dynamic team responsible for driving technological advancements and maintaining robust infrastructure that supports our B2B clients. This executive-level role reports directly to the Chief AI, Product & Engineering Officer and involves strategic oversight of engineering initiatives that enhance product innovation, ensure seamless service delivery, and scale operations to meet evolving market demands.

You will bridge the gap between engineering, product, sales, and customer success teams, fostering a culture of innovation while prioritizing reliability, security, and efficiency in our infrastructure services. You’ll lead a team of experienced engineering managers and their teams, providing guidance and setting strategic direction for our technology efforts across the organization. This leader will oversee the development and deployment of innovative B2B solutions, such as API integrations, cloud-based platforms, and AI-driven tools. You will manage infrastructure services, including cloud architecture, DevOps practices, and system reliability engineering.

This opportunity has a large impact by collaborating on company-wide strategies to align engineering efforts with business objectives in a fast-paced Health tech landscape.

What you will do:

• Develop and execute an engineering roadmap that accelerates B2B innovation, including the launch of new features and services that address client pain points and drive revenue growth.
• Build, mentor, and lead high-performing engineering teams (e.g., 50+ members across development, ops, and QA), promoting best practices in agile methodologies, CI/CD pipelines, and cross-functional collaboration.
• Ensure the scalability, security, and resilience of our infrastructure, achieving 99.99% uptime for critical services and optimizing costs through efficient resource management.
• Spearhead R&D efforts to integrate emerging technologies (e.g., machine learning, or edge computing) into our B2B ecosystem, resulting in at least 2-3 major product enhancements per year.
• Deliver on key KPIs such as reduced time-to-market for new features, improved system performance benchmarks, and enhanced client satisfaction scores through proactive infrastructure improvements.
• Partner with sales and product teams to translate client feedback into engineering priorities, contributing to a 20-30% year-over-year increase in B2B client retention and expansion.

Qualifications

• 10+ years of progressive engineering experience, including 5+ years in a senior leadership role (e.g., Director or VP level), with a history of scaling teams and delivering complex projects on time and within budget.
• Deep knowledge of software engineering principles, cloud infrastructure (e.g., AWS, Azure, GCP), microservices architecture, and DevOps tools (e.g., Kubernetes, Terraform, Jenkins). Experience with B2B platforms, APIs, and data-intensive systems is essential.
• Demonstrated ability to foster innovation, such as leading hackathons, adopting new tech stacks, or patenting solutions in B2B contexts.
• Strong understanding of B2B market dynamics, with experience in aligning engineering strategies to business goals, including ROI analysis and client-facing technical discussions.
• Excellent communication and interpersonal abilities to influence stakeholders at all levels; a collaborative approach to problem-solving; and resilience in managing high-stakes, fast-changing priorities.
• Bachelor’s or Master’s degree in Computer Science, Engineering, or a related field. Relevant certifications (e.g., AWS Certified Solutions Architect, PMP) are a plus.

Requirements

• Prior work in SaaS, Healthtech, or enterprise software companies; familiarity with compliance standards (e.g., SOC 2, GDPR); and a passion for mentoring diverse teams in a healthy, inclusive workplace.
• Location: We are currently hiring this role in San Francisco (hybrid), Los Angeles (remote), New York City (remote), and Seattle (remote). Candidates must permanently reside in the US full-time and be based in these cities.
• For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in-office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week.

Benefits

• A mission that matters—with impact you can see and feel.
• A culture that’s collaborative, inclusive, and grounded in our values.
• The chance to shape what mental health care looks like next.
• Competitive pay and benefits that support your whole self.

Company Description

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily:

• Make the Mission Matter
• Iterate to Great
• Own the Outcome
• Connect with Courage

These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.