Pebble is the all-in-one operating system for real estate investors. We help real estate investors streamline their operations, close more deals, and grow their businesses—all from one beautifully simple platform.
We’re a lean, fast-moving team with a big vision: to become the command center for investors buying and selling property at scale.
🎯 The Mission
As our Customer Success Lead, your mission is simple:
Turn every new user into a confident, thriving operator using Pebble.
You’ll be the force behind onboarding, retention, proactive outreach, and customer education. You’ll build processes, host live trainings, and get hands-on with users to help them win and love it.
🧩 What You’ll Do
Run 1:1 and group onboarding sessions that get users moving fast
Lead live trainings, workshops, and webinars to drive deeper adoption
Build relationships through calls and conversations, not just tickets
Spot at-risk users before they churn—and turn them around
Promote and manage our white glove migration services
Collaborate with sales, support, and product to improve customer outcomes
Track user success metrics and help us improve our playbooks
Build lightweight automations using tools like Zapier, HubSpot, and AI
Keep docs and training materials updated and actually useful
🚀 What Success Looks Like
90% of new users onboarded within 14 days
80%+ using core features within 30 days
Increased retention and reduced voluntary churn
50%+ of eligible users enrolled in paid migration services
Engaged users showing up to live sessions, and asking for more
A growing knowledge base that users actually rely on
💡 You Might Be a Fit If…
You’ve led customer success or onboarding in a SaaS company before
You don’t wait—you chase clarity and make things happen
You love hopping on calls and talking to customers
You’re comfortable running group sessions and leading with confidence
You’re tech-savvy—you can build a basic Zapier workflow with your eyes closed
You’re a builder at heart—always improving systems, docs, and processes
You take full ownership of results, not just tasks
You want to grow in your role and shape the direction of customer success
🛠 Tools We Use
Stripe, Helpscout, HubSpot, Zapier, Notion, Slack, Zoom, and a few clever AI tools. If you’ve used some of these—or want to learn them fast—you’ll fit right in.
❤️ Why You’ll Love Working at Pebble
Small team, big impact - you’ll help shape the future of the product and the company
Fully remote with flexibility in hours and async communication
You’ll work directly with the founders and leadership team
Real autonomy and ownership
A mission that matters: helping real estate entrepreneurs scale their dreams
✨ How to Apply
Send us a short video message and tell us:
Why this role at Pebble excites you
A time you turned a struggling customer into a success
We can’t wait to meet the right person. If you’re reading this and feeling the itch—let’s talk. 💬