Director of User Experience

Second Nature helped define resident experience as a category in property management. 2,500+ property management companies run on our platform, we've delivered over 2 million resident experiences, and we've been named NARPM Affiliate of the Year seven times. Holding that position depends on whether the experience is genuinely better at every touchpoint. Our experience surfaces touch Resident Onboarding, the Resident Benefits Package and the services inside it; Maestro™, our experience orchestrator; and the internal tooling our operations teams run on. Every decision has to account for the property manager, resident and the people who support them.

AI is now part of how we build: product managers explore concepts, engineers can produce interfaces and content, and our design system lets either of them ship. We want a design leader who uses that speed and still defends a high bar of what great design, content and interaction looks like.

You will lead content and user experience, reporting to the VP of Product, managing a team of 4-6 across product domains and strategic initiatives. We work in the "Product Trio" model, and your team embeds into the leadership structure of each team it works with, operating as a strategic counterpart to product and engineering leadership across multiple product areas rather than a single stream. You'll also partner directly with Customer Success, Implementation, and Data leaders, who depend on these experiences as much as our customers do.

This role is a strategic player-coach position (roughly 80% leadership & team development, 20% hands-on strategic design direction). Your hands-on contribution focuses on high-level framing, experience architecture, and driving design sprints for ambiguous, high-stakes new product surfaces.

The Experience Vision. A cohesive UX strategy and North Star for the Resident Experience Platform, aligned to company and product strategy.

Design Culture. Critique that improves the work, cross-functional collaboration, and knowledge sharing. You raise the UX bar across the whole company through coaching, workshops, and design share-outs, not just inside your team.

The team's growth & development. Hiring, Growth plans, leveling, compensation conversations, and feedback delivered early enough to be useful.

A design portfolio of your own. Named strategic projects, carried end to end.

The Design System. Tokens, patterns, accessibility standards, governance, and an adoption number you report on.

The Research Practice. Who we talk to to drive the most leverage, how often, and how evidence reaches a decision. Including what we learn that contradicts our thinking.

Content Design. Supporting the practice alongside interaction and visual craft.

The AI UX/Content operating model. Tooling, risk tiering, guardrails, and demonstrable examples that show whether it's meeting outcomes.

Within 90 days. Know each designer's strengths and blind spots, with growth plans established. Publish a design coverage map: where support is real, where it's thin, what you'd trade off. Finish a design system audit with a component inventory, adoption baseline per surface, and the biggest sources of drift ranked by cost.

By six months. Design system adoption up on net-new UI across resident and property-manager surfaces, with a refined contribution model engineers/pm use without needing to route everything through your team. A research cadence with residents and property managers that produces evidence teams cite in decisions. Published risk-tiering criteria, with a measured split of async versus full review and a rework rate you watch. Your first strategic project delivered.

By twelve months. Measurable movement on resident onboarding completion, move-in satisfaction, and support deflection, along with a fourth metric you and the domain product leads agree on. Lower time-on-task across our highest-volume internal operations workflows. A shorter path from problem framing to testable prototype, with rework flat or down.

8+ years in digital product UX, with 3+ years managing designers directly.

Current craft. You still design, and you can show recent work you made yourself.

Evidence you grow people. We'll ask you to name someone you leveled up, what you did, and where they are now.

Design systems at the architecture level. How tokens and patterns compose, how contribution works when it's distributed, how you hold drift down without becoming a gate.

The ability to look at a body of UX or content work and say what's strong, what's derivative, and what level it maps to.

Measurement. You define the metric before the work starts, instrument it, and change course when it moves the wrong way.

Executive communication. You can put UX strategy, tradeoffs, and outcomes in front of the exec team and explain what design decisions do to business metrics and the Triple Win.

Research leadership. You can build a practice: a repeatable cadence of talking to residents and property managers, usability testing before launch, behavioral data used to decide.

A position on AI and design , covering both the product surface and your team's own practice.

Hands-on with AI tooling. Prototyping, content, research synthesis, or design-system compliance on real shipped work.

You don't hold your biases too closely, and you know when to compromise.

Range across consumer and operator design. Residents and property managers want different things, and a leader fluent in one register risks underserving the other.

We get it. Requirements can sometimes hold people back from applying to a job, but don't let that be the case here. If you believe you have the skills it takes to elevate this role, team, and company, we encourage you to apply for this role.

This position is a remote-first, work from home position. Second Nature is committed to creating a culture and workplace where remote work fosters collaboration and connections and is a key part of our company story and success. To be successful in a remote work role at Second Nature you must:

Be available during your scheduled working hours and give your full attention to the completion of your Second Nature job duties

Have a quiet, professional, distraction-free environment in which to complete your work

Have access to your own reliable high-speed internet connection

Attend our bi-annual in-person company meetings (Second Nature will reimburse the cost of your business travel per company guidelines)

🏴‍☠️ Pirate Ship; not a cruise ship. Bias towards action. 💪 Massive Growth takes massive growth. We embrace challenges to increase our impact. 🥧 Grow the Pie. We focus on results so our customers & their customers win. Triple Win! 💜 Purple Heart. We put the team before ourselves. 🤝 Extreme Ownership. See something? Say something; right the ship to get us back on course. 🙌 Be a moment maker. We aim to shatter the status quo.

🩺 Health First: Medical, Dental, Vision, & Life Insurance; 401K Plan

📍 Location: Work Remotely from anywhere in the US

📆 Flexibility: Open PTO and sick days

🤩 Culture: Diverse, inclusive, supportive, and growth-focused

🚀 Growth: Be part of a fast-growing team building a new category and making a real difference

💻 The Product: Award-winning, customer-loved platform that truly delivers on our mission

Second Nature is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. We take action to ensure equal employment opportunities for all candidates and employees and to provide employees with a workplace free of discrimination and harassment. Our hiring decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, family or parental status, or any other status protected by federal and/or state law.