Head of Product

Purple Squirrel Enterprises • Baltimore, MD

7d • Remote

About The Position

Purple Squirrel Enterprises is exclusively engaged by a high-growth health technology company to identify and hire exceptional product leadership talent for the role of Head of Product. This company 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. Their platform combines eMAR+ software, Smart Medboxes, emergency kits, and gamified self-medication tools into one connected system that prevents errors before they happen. They support providers, state agencies, and pharmacy partners across 20+ states and have achieved significant reductions in medication errors and increases in compliance. This role is for someone looking for work that matters, with a company built around a personal and urgent cause. The final title, reporting structure, and scope will be shaped by the experience and leadership level of the hired individual, potentially being structured as VP of Product or other, and will likely report directly to the CEO. The company is committed to bringing in the right level of leadership for its current stage and future direction.

Requirements

• 6 - 8+ years in product management, including end-to-end ownership of a roadmap covering discovery, definition, and delivery.
• Experience leading product people, including hiring and onboarding.
• 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 skills.
• Judgment to decide with incomplete information.
• Willingness to travel occasionally, up to roughly 15%, for customer/facility visits, team meetings, and industry events.
• Must be willing and able to build, not just set direction and hand off execution.

Nice To Haves

• 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.

Responsibilities

• Own the roadmap, product strategy, and execution across software, connected hardware, and pharmacy/EHR integrations.
• Publish the roadmap 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.
• Treat reporting, audit trails, and business intelligence as first-class product.
• Lead discovery by spending time with caregivers, house managers, administrators, nurses, and state agency stakeholders to observe workflows.
• Distinguish recurring needs from individual feature requests and explain the difference to Sales and Customer Success.
• Design for three different user types: administrators, caregivers, and individuals receiving care.
• Design into existing routines rather than around them, prioritizing usability as a safety requirement.
• Set the bar for product definition with clear problem statements, acceptance criteria, and edge-case thinking.
• Build the Product function by establishing how product gets practiced, including problem framing, discovery, decision-making, and outcome measurement.
• Lead, coach, and develop the Product team, and shape the hiring plan as scope expands.
• Keep Engineering, Customer Success, Sales, and Operations aligned on priorities and support strategic accounts and state-level opportunities.
• Set the standard on AI by using tools like Claude Code, Codex, or equivalent agentic environments to explore the codebase, work with data, and build functional prototypes.
• Establish AI practices across the Product team and coach team members.

Benefits

• Base salary: $183,000 – $225,000, depending on experience, skill set, and the ultimate scope/level of the role.
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed