Head of Product

Location: Remote

About This Opportunity

Purple Squirrel Enterprises has been supporting startups and global firms through growth, change, and expansion for 19+ years. We provide flexible HR and recruiting solutions that allow leaders to focus on strategy while we handle people operations — and this search is no exception.

We are exclusively engaged by a high-growth health technology company to help them identify and hire exceptional product leadership talent for this role. We are embedded directly with their leadership team, have deep knowledge of the company, the culture, and what it takes to succeed here — and we will be your dedicated recruiting partner from first conversation through offer.

This is not a blind submission. When you apply, you are working with a team that knows this opportunity inside and out and will advocate for you every step of the way.

💜 If this opportunity resonates with you, we encourage you to apply. We will be in touch promptly. Applications submitted directly to our client will be redirected back to Purple Squirrel Enterprises. To be considered for this role, all candidates must apply through this posting.

About Our Client

Our client builds software and connected hardware that makes medication management safer for vulnerable populations in group homes, supported living, assisted living, behavioral health, and long-term care. In these settings, a large share of medication administration is handled by non-clinical staff working from paper, spreadsheets, and memory.

Their platform combines eMAR+ software, Smart Medboxes, emergency kits, and gamified self-medication tools into one connected system that prevents errors before they happen rather than documenting them after. They support providers, state agencies, and pharmacy partners across 20+ states, and recently won the first statewide medication management contract of its kind in the United States.

Their results so far:

• 48% reduction in medication errors
• 39% increase in compliance
• 69% improvement in audit-ready documentation

💜 This company was built around a cause that is both personal and urgent. That authenticity shows in how they operate, who they hire, and what they build. If you are looking for work that matters — this is it.

A Note on Title, Reporting Line & Scope

Our client is posting this role as Head of Product, but the final title, reporting structure, and scope will be shaped by the experience and leadership level of the person they hire. Depending on your background, this could ultimately be structured as VP of Product or other. Reporting line will most likely be directly to the CEO, though for a more foundational-level hire it could sit under Engineering leadership instead. These specifics — along with compensation — will be part of the conversation as we get to know your experience and how it maps to what they need.

This is intentional flexibility, not indecision: our client is committed to bringing in the right level of leadership for where they are today and where they're headed.

About the Role

Our client is looking for a Head of Product to own product strategy and execution and to build the Product function from the ground up. You will lead a team of two today — a Product Lead and a Product Specialist — with real influence over the type, number, and pace of hires as the team grows.

This is a startup, and this function is being built rather than maintained. You will have real ownership, very little inherited process, and a direct line to executive leadership. Product has been driven by the leadership team to date, and they are committed to a deliberate, unhurried handoff of that ownership to you — including knowledge transfer, context on customers and commitments, and hands-on support while you take the reins. You will not be handed a backlog and left to guess.

They are building toward empowered product teams, where leadership sets priorities and outcomes and teams have real autonomy to discover how to achieve them. You and engineering leadership will define how Product and Engineering work together — engineers here are product-minded and deeply involved in how the product takes shape, and the handoff model is intentionally not prescriptive.

Their product operates in a regulated, high-stakes environment. A missed dose is a patient safety event, not a support ticket, and their customers are audited by state agencies whose requirements differ state by state. Product judgment here means understanding what actually happens in a group home at 7am during a shift change, not what looks good in a spec.

As with all leaders at this company, you'll need to be both hands-on and strategic — that combination is core to their culture. Priorities, travel, and schedules shift with the pace of a growing company and its leadership team, so you'll need to bring your own ideas, act autonomously when needed, and stay a strong team player at the same time. Communication — proactive, reactive, and yes, sometimes over-communication — is essential in an environment like this.

What You'll Do

Own the Roadmap

• Own product strategy and the roadmap across the full surface area: software, connected hardware, and pharmacy/EHR integrations. Publish it so the company can see what is coming and why
• Bring a point of view on where the platform should go over the next 12–24 months, and make the case for it
• Weigh patient safety, HIPAA, and state-by-state regulatory requirements from the start rather than retrofitting them
• Treat reporting, audit trails, and business intelligence as first-class product — audit-ready documentation is a primary reason customers choose this platform

Lead Discovery

• Spend real time with caregivers, house managers, administrators, nurses, and state agency stakeholders — observing workflows rather than consuming feedback secondhand
• Distinguish recurring needs from individual feature requests, and explain the difference to Sales and Customer Success
• Design for three very different users: administrators (oversight/audit), caregivers (speed/clarity mid-shift), and the individuals receiving care
• Design into existing routines rather than around them — usability is a safety requirement here, not a preference
• Set the bar for product definition: clear problem statements, acceptance criteria, and edge-case thinking Engineering can build from without guesswork

Build the Function

• Establish how product gets practiced: how problems get framed, how discovery happens, how decisions get made, how outcomes get measured
• Lead, coach, and develop the Product team, and shape the hiring plan — including roles that don't exist yet — as scope expands
• Keep Engineering, Customer Success, Sales, and Operations aligned on priorities and support strategic accounts and state-level opportunities where product credibility matters

Work With AI

• Set the standard on AI rather than delegate it — use tools like Claude Code, Codex, or equivalent agentic environments to explore the codebase, work with data, and build functional prototypes
• Establish these practices across the Product team and coach your people into them
• The goal is better-informed decisions about scope and value — not handing engineering a flashy prototype to productionize

You do not need to be a software engineer, and you will have strong engineering partnership. You do need to be willing and able to build.

What This Role Is Not

This is not a purely strategic or advisory position, and it is not a roadmap-maintenance or backlog-management role. You will be the most senior product person in the company, with no layer between you and the problem. If you're looking to set direction and hand execution to a team of PMs, this isn't the right fit today. If being close to customers, requirements, and shipped software is what you've been missing, it likely is.

What Success Looks Like

• Ownership Established: You've taken clear, visible ownership of the roadmap and the leadership team trusts your judgment on what's next and why
• Discovery in Motion: You are spending real time with caregivers, administrators, and state stakeholders — and using what you learn to shape decisions, not just validate them
• Function Taking Shape: Product process, definition standards, and team rhythms exist where little or none did before
• Team Growing With Intention: You have a clear point of view on team structure and hiring, and the team feels coached, not just managed
• Trusted Cross-Functionally: Engineering, Sales, and Customer Success see you as the person who keeps priorities clear and aligned across the company

What We're Looking For

Required

• 6 - 8+ years in product management, including end-to-end ownership of a roadmap covering discovery, definition, and delivery — not solely execution of a roadmap someone else set
• Experience leading product people, including hiring and onboarding rather than only managing an inherited team
• A track record of shipping B2B SaaS in close partnership with Engineering
• Experience building product process where little or none existed
• Strong discovery skills: customer interviewing, problem validation, prototyping, and experimentation
• Experience with products where the buyer and the user are different people
• Practical, frequent use of LLMs in day-to-day work
• Comfort working with data directly, strong written communication, and judgment to decide with incomplete information
• Willingness to travel occasionally, up to roughly 15%, for customer/facility visits, team meetings, and industry events

Nice to Have

• Experience in healthcare technology, IDD services, assisted living, behavioral health, long-term care, or medication management, or another regulated environment
• Experience with enterprise, government, or state agency customers, including procurement and reporting requirements
• Experience shipping products that combine software and connected hardware
• Experience with integration-dependent products (HL7, JSON, REST APIs, pharmacy management systems, EHRs)
• Experience scaling a Product function from a small team, or shipping products/internal tools personally prototyped using AI-assisted development

Personal Attributes

• A builder — your instinct when you have an idea is to make something and test it
• Low ego, strong point of view — you advocate hard and change your mind when the evidence changes
• Comfortable with ambiguity
• Intellectually curious about why, not just what was requested
• Energized by the mission — many affected by this product cannot advocate for themselves

Compensation & Benefits

Base salary: $183,000 – $225,000, depending on experience, skill set, and the ultimate scope/level of the role (Head of Product, VP of Product, or other) — final title and comp will be calibrated to the candidate

• Potential Equity participation
• 100% company-paid medical coverage (base plan)
• Dental & vision available
• 401(k) retirement plan
• Company-paid life, AD&D, STD & LTD insurance
• Lifestyle Spending Account (wellness, personal use, and company swag)
• Flexible PTO + company holidays
• Flexible, remote-friendly work environment

💜 Mission-driven work with real impact on vulnerable populations

Why This Role — And Why Now

Real problems, real stakes — your work directly affects patient safety for a population that often cannot advocate for itself

True ownership — you'll build the Product function, not inherit one

Direct access to leadership — a real seat at the table, with influence over team structure and roadmap

High-growth trajectory — recent statewide contract win signals significant expansion ahead

Authentic mission — 💜 this company was built around a cause that matters

Working With Purple Squirrel Enterprises

We are exclusively engaged by this client — meaning we are not one of many agencies submitting resumes. We are their dedicated recruiting partner, embedded in their process, and we know this role inside and out.

Here's what that means for you as a candidate:

• A dedicated PSE point of contact throughout the entire process
• Advocacy with the hiring team to make sure the role is mutually beneficial
• Preparation for each interview stage so you can put your best foot forward
• Honest, timely feedback at every step
• Support through offer negotiation to ensure the outcome is right for you and the company
• Deep experience navigating complex hiring processes to get great candidates across the finish line

Our client is an equal opportunity employer committed to building a diverse and inclusive team. They welcome applicants of all backgrounds, experiences, and perspectives.