Head of Digital Client Experience

Second Nature

9d • Remote

About The Position

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.

Requirements

• 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.
• 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.
• 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)

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• Medical, Dental, Vision, & Life Insurance, 401K Plan
• Work remotely from anywhere in the US
• 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
• A supportive team to help you grow and unlock your full potential
• The opportunity to get in on the ground floor of a fast-growing startup

What This Job Offers

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