VP of Engineering, B2B Platforms

About the 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 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 be overseeing the development and deployment of innovative B2B solutions, such as API integrations, cloud-based platforms, and AI-driven tools. You will be managing 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.
• Innovation Initiatives: 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.

What you will bring:

Required Skills:

• 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.

Preferred Skills:

• 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. Your recruiter will share more details about our hybrid model.

About Headspace

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, and 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.

Why You’ll Love Working Here:

• 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

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

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Privacy Statement

All member records are protected according to ourPrivacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice