Head of Digital Client Experience

Today, we live in a world where everything has become convenient. Now you can get a ride anywhere, buy anything, answer any question with just a couple clicks on your phone. Convenience isn’t a luxury, it’s an expectation.

So why not renting? It’s still a chore to get utilities set up, buy renters insurance, get air filters changed, handle pest control, and more.
That’s why we’ve built the world’s first Resident Experience Platform that makes resident onboarding, resident services, and ancillary revenue effortless for property managers.

We’re passionate about turning friction into triple win experiences for residents, property managers, and investors. That way renting can be easy and rewarding for everyone.
And now you can join us. Apply today to join 220+ passionate, creative people who strive to make a difference each day so residents, property managers, and investors all win; creating the ultimate Triple Win.

About the Role

As the Head of Digital Client Success, you will build and lead digital strategies ensuring clients achieve outcomes that drive retention, expansion, and long-term loyalty. You will define and scale the post-sales digital client strategy — from onboarding and activation to ongoing value delivery — for clients leveraging Second Nature’s platform to power resident experiences.

Key Responsibilities

Leadership & Strategy

• Own the full digital client success strategy and roadmap, aligning with company goals for adoption, retention, and growth.

• Partner with the Client Experience leadership team to define success metrics, client segmentation, and growth objectives.

Client Journey & Experience

• Design and optimize scalable success frameworks for onboarding, adoption, and ongoing value delivery across all customers.

• Develop digital first client experiences that connect ROI to segmented stakeholders.

• Create outreach campaigns which drive clients to educational resources and deeper engagement with their Client Success Managers.

• Implement repeatable playbooks to improve product adoption, usage, and measurable ROI for clients.

• Champion the voice of the customer — translating insights into strategic actions across cross-functional teams.

Operational Excellence

• Establish success KPIs (e.g., activation rates, retention, expansion, NPS) and implement dashboards/reports to monitor performance trends.

• Build automated triggers for CSMs based on the client journey leveraging our client success platform.

• Drive predictive health scoring and early-warning systems to proactively mitigate churn.

• Create measurable outcomes from digital strategies to reduce labor costs associated with account management and drive revenue growth.

• Lead continuous process improvement initiatives to enhance efficiency and customer outcomes.

Cross-Functional Collaboration

• Collaborate closely with the CX Operations team to properly scope and deploy tooling that overlaps with human led activities.

• Influence product development with qualitative and quantitative customer insights.

• Work closely with Product, Marketing and Sales teams to ensure consistency with message and intended client outcomes.

About You

Experience & Skills

• 8+ years of experience in Customer Success, Client Services, or related roles with at least 3 years in a leadership position.

• Proven track record of scaling customer success teams and driving measurable impact in adoption, retention, and revenue growth.

• Demonstrated ability to build and execute strategic playbooks in a SaaS or digital platform environment.

• Strong experience using customer success platforms (e.g., Totango, HubSpot, Salesforce) and analytics tools to inform decision-making. Client success platform ownership experience required.

• Strong communicator and relationship builder with experience engaging with C-level stakeholders.

Leadership & Mindset

• Inspires teams with a customer-first mentality and fosters a culture of accountability, curiosity, and continuous improvement.

• Data-driven, metrics obsessed, and comfortable setting priorities in a fast-paced startup environment.

• Collaborative leader who thrives on cross-functional partnership and solving complex business problems.

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.

Our Core Values

• 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.

Remote Work Statement
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 vital 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

• 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)

Why Second Nature?

🩺 Health First: Medical, Dental, Vision, & Life Insurance, 401K Plan
📍Location: Work remotely from anywhere in the US
📆Flexibility: Open PTO and sick days
🤩 The Product: Beyond the 7 awards and 5-star reviews, our clients and customers love what they can do with a fully managed RBP
🤗 Diverse, inclusive culture: We embrace employees from all backgrounds with openness and respect
💻 Training: A supportive team to help you grow and unlock your full potential
🚀 Growth: The opportunity to get in on the ground floor of a fast-growing startup

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.