Customer Success Lead - Remote Eligible

Customer Success Lead

Wander is expanding into a new business unit — Wander Sites — and we're hiring a Customer Success Lead to help customers onboard, adopt, and thrive with the platform.

You'll work directly with our customers to ensure they achieve measurable outcomes, design scalable onboarding and engagement playbooks, and partner with cross-functional teams to improve the overall customer experience. This is a strategic and hands-on role — ideal for someone who enjoys both building systems and managing relationships.

What You'll Do

1. Manage onboarding, adoption, and retention for Wander Sites customers.
2. Design scalable Customer Success playbooks, lifecycle touchpoints, and health metrics.
3. Act as a trusted advisor to customers, helping them achieve their goals with Wander Sites.
4. Partner with Sales on renewals and expansion opportunities.
5. Analyze customer usage data and feedback to surface insights for the Product and Engineering teams.
6. Define and report key success metrics to help guide strategic decision-making.

What You Bring

• 4–7+ years of experience in Customer Success or Account Management at a B2B SaaS company.
• Track record of managing customer portfolios and driving measurable outcomes.
• Excellent communication, consultative, and relationship-building skills.
• Experience implementing or using Customer Success tools (Gainsight, Vitally, HubSpot, etc.).
• A proactive, analytical mindset — you anticipate issues and seek continuous improvement.

Bonus Points For

• Experience in Property Management, Vacation Rentals, or PropTech SaaS.
• Background in fast-scaling startups or new business units.
• Familiarity with customer lifecycle automation tools or data-driven retention strategies.
• Experience collaborating with Product and Sales teams to shape customer outcomes.
• Interest in the intersection of real estate, technology, and hospitality.

You'll be building the Customer Success function for Wander Sites — a new business within Wander — with the tools, autonomy, and cross-functional support to make a measurable impact. You'll shape how we deliver value to our customers and set the tone for the team that grows around you.