VP of Engineering, B2B Platforms

Overview

VP of Engineering, B2B Platforms at Headspace:
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 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 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, Dev Ops practices, and site reliability engineering, with the opportunity to impact company-wide strategies in a fast-paced Health tech landscape.

• Develop and execute an engineering roadmap that accelerates B2B innovation, including the launch of new features and services addressing client pain points and driving 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, aiming for high uptime and cost-efficient resource management.
• Innovation initiatives: spearhead R&D efforts to integrate emerging technologies (e.g., machine learning, edge computing) into our B2B ecosystem, delivering major product enhancements annually.
• Deliver on key KPIs such as time-to-market, system performance benchmarks, and client satisfaction through proactive infrastructure improvements.
• Partner with sales and product teams to translate client feedback into engineering priorities, contributing to YoY increases in B2B client retention and expansion.

Required Skills:

• 10+ years of progressive engineering experience, including 5+ years in a senior leadership role, with a track record of scaling teams and delivering complex projects on time and within budget.
• Deep knowledge of software engineering principles, cloud infrastructure (AWS, Azure, GCP), microservices, and Dev Ops tools (Kubernetes, Terraform, Jenkins). Experience with B2B platforms, APIs, and data-intensive systems is essential.
• Demonstrated ability to foster innovation through initiatives like leading hackathons, adopting new tech stacks, or patenting solutions in B2B contexts.
• Strong understanding of B2B market dynamics, alignment of engineering strategies to business goals, ROI analysis, and client-facing technical discussions.
• Excellent communication and interpersonal abilities to influence stakeholders at all levels; collaborative problem-solving; resilience in 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.

Preferred

Skills:

• Experience in SaaS, Healthtech, or enterprise software; familiarity with compliance standards (SOC 2, GDPR); and a passion for mentoring diverse teams in an inclusive workplace.

Locations:
San Francisco (hybrid), Los Angeles (remote), New York City (remote), and Seattle (remote). Candidates must reside in the US and be based in one of these areas. For candidates with a primary residence in the greater SF area, a hybrid model is available: 3 days per week in the office with remote work for the rest of the week.

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.

We value collaboration, inclusion, and impact, and strive to build a human-centered team that redefines mental health care for today and the future.

• A mission with measurable impact
• A collaborative, inclusive culture grounded in our values
• The opportunity to shape the future of mental health care
• Competitive pay and comprehensive benefits

Headspace is an equal opportunity employer. We prohibit discrimination based on protected status and are committed to fostering a diverse, inclusive environment where everyone can thrive. Reasonable accommodations are available on request.

For more information about applying, visit our applicant notice.