Head of Product

Purple Squirrel Enterprises • Baltimore, MD

1d • $183,000 - $225,000 • Remote

About The Position

Purple Squirrel Enterprises is partnering with a high-growth health technology company to find an exceptional Head of Product. This role involves owning product strategy and execution, building the Product function from the ground up, and leading a small team with the potential to grow. The company develops software and connected hardware for medication management in group homes, supported living, assisted living, behavioral health, and long-term care settings. Their platform aims to prevent medication errors by combining eMAR+ software, Smart Medboxes, and other tools. The company has demonstrated significant improvements in medication error reduction, compliance, and audit-ready documentation. This is a startup environment where the Head of Product will have significant ownership, minimal inherited process, and direct access to executive leadership. The role requires a hands-on and strategic approach, with a strong emphasis on customer understanding, product judgment in a regulated environment, and cross-functional collaboration. The company is committed to building empowered product teams and fostering a culture of autonomy and product-minded engineers. The final title, reporting structure, and scope will be determined based on the candidate's experience and leadership level, with potential for VP of Product or similar, likely reporting to the CEO.

Requirements

• 6 - 8+ years in product management.
• 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 make decisions with incomplete information.
• Willingness to travel occasionally, up to roughly 15%, for customer/facility visits, team meetings, and industry events.

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.
• Experience shipping products/internal tools personally prototyped using AI-assisted development.

Responsibilities

• Own product strategy and the roadmap across software, connected hardware, and pharmacy/EHR integrations.
• Publish the roadmap to ensure company-wide visibility and understanding of upcoming developments and rationale.
• Develop and articulate a vision for the platform's future over the next 12-24 months.
• Integrate patient safety, HIPAA, and state-specific regulatory requirements into the product development process from the outset.
• Treat reporting, audit trails, and business intelligence as core product features, recognizing their importance for customer choice.
• Conduct in-depth discovery by engaging directly with caregivers, house managers, administrators, nurses, and state agency stakeholders to observe workflows.
• Differentiate between recurring needs and individual feature requests, and communicate these distinctions to Sales and Customer Success teams.
• Design solutions for three distinct user groups: administrators, caregivers, and individuals receiving care.
• Ensure product designs integrate with existing routines, recognizing usability as a critical safety requirement.
• Establish high standards for product definition, including clear problem statements, acceptance criteria, and thorough edge-case analysis.
• Define and implement the product development process, including problem framing, discovery methodologies, decision-making frameworks, and outcome measurement.
• Lead, coach, and develop the existing Product team (Product Lead and Product Specialist).
• Shape the hiring plan for the Product team, identifying future roles as scope expands.
• Ensure alignment across Product, Engineering, Customer Success, Sales, and Operations on priorities.
• Support strategic accounts and state-level opportunities where product credibility is crucial.
• Utilize AI tools (e.g., Claude Code, Codex) to explore codebases, work with data, and build functional prototypes.
• Establish and coach the Product team on AI-assisted development practices.
• Collaborate with engineering leadership to define the interaction model between Product and Engineering.
• Act as the most senior product person, directly engaging with customers and requirements.

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