Head of Product and Engineering

About Supportiv

Supportiv is a peer-to-peer mental/emotional wellbeing and resource navigation platform providing on-demand human connection and support for everyday life struggles, 24/7/365.

Our multi-patented technology matches users in seconds to dynamically formed, real-time professionally moderated small peer group live chats based on the similarity of their natural language-expressed needs. As the peer support conversations unfold, we use proprietary AI and NLP to contextually understand those needs and link users with relevant resources and services using retrieval systems and adaptive agentic flows.

We serve large employers and health plans, including two Fortune 10 companies, and deliver widely-published clinical-grade outcomes unmatched in the industry at pennies on the dollar compared to other mental health services.

The Role

As Head of Product & Engineering, you will determine the product roadmap and execution for a technology platform where the quality of the product shapes whether someone gets the emotional support they need. You’ll own how client needs get translated into product, what gets built and why, how the user experiences it, how we measure and iterate for improved user experience, and the engineering organization responsible for delivering it.

This role is highly customer-facing. You will represent Supportiv’s technical capabilities directly to enterprise customers, health plans, and partners, and interface on technical reviews, and security and compliance conversations throughout the sales and renewal cycles.

You’ll partner closely with our Founder as well as Clinical, Customer Success, Business Intelligence, Design, and Engineering team members to scale Supportiv into its next chapter of large-scale enterprise and health plan deployments, plus direct to consumer marketplaces. To begin, you’ll lead a team of 8+ engineers across our core platform, AI/ML systems, and security/compliance. As Supportiv grows, you will help recruit future Director-level engineering leadership and thoughtfully transition deeper engineering management and technical responsibilities.

Your Skillset

Deep experience at a digital health, behavioral health, mental health, or other healthcare technology company strongly preferred.

Strong experience in software and product development lifecycles and pipeline, cost benefit analysis, multidisciplinary team coordination across time zones, consensus building, and execution of long-term strategy.

Security-first mindset that treats HIPAA, SOC 2, and FedRAMP not as checkboxes but as core elements of product development and compliance.

Strong experience translating opportunities into PRDs, user flows, user stories, acceptance criteria, technical requirements, success metrics, and executable engineering initiatives.

Fluency required in: Python, Angular, TypeScript, NgRx, Firestore, GCP, and AWS. Go and Rust experience also helpful.

An eye for UX, always noticing friction, unnecessary complexity, confusing user flows, gaps and opportunities that others miss.

Demonstrated experience using product analytics, funnels, cohort analysis, A/B testing, experimentation, user research, and usability testing to improve end-user products.

Eagerness to lead and develop our engineering team, establish priorities, remove roadblocks, and hold the team accountable for strong execution.

Enjoy working with senior engineers to evaluate feasibility, architecture, dependencies, effort, risk, reliability, and scalability without needing to personally architect or implement every solution.

Strong working understanding of software development, APIs, integrations, cloud applications, architecture, reliability, and scalability.

Prior experience or strong understanding of bringing AI/ML capabilities into production and understanding their ongoing lifecycle, including evaluation, monitoring, maintenance, and retraining.

Deep enough understanding to challenge assumptions and evaluate technical tradeoffs without needing to be the strongest technical expert in every room.

Able to make thoughtful tradeoffs among user value, customer needs, development effort, technical debt, security, scalability, and speed.

Highly hypothesis- and data-driven and enjoy testing assumptions.

Exceptional communicator, comfortable in the room with Fortune 10 customers, health plan security teams, clinicians, and engineers.

Strong manager and communicator who creates clarity, accountability, and momentum.

Strong recruiter, mentor, and coach who elevates everyone around you.

Compensation & Benefits

Fully remote, location-agnostic within US time zones

Target base salary range: $225,000-$250,000/yr.

Meaningful equity in a VC-backed, revenue-generating, self-sustaining startup

Comprehensive health benefits including vision and dental

401k with vested match for full-time, US-based employees

Generous PTO and company-wide breaks

In-person team gatherings focused on collaboration and team building

Interview Process

[30 min] Initial interview with Founder/CEO

[Up to 2 hours] Timed exercise

[60 min] Technical leadership interview

[45 min] Cross-functional partners interview

[60 min] In-person meeting with Founder/CEO

References, background check, and offer

How To Apply

To beat the bots, we’re going old school. Email us your resume and a non-AI-generated message about why Supportiv is a fit for you to careers@supportiv.com. AI-generated messages will be disqualified.