Customer Success Manager

Wayline is the voice AI operator & telephony system powering real estate managers. We operate nationally with customers managing thousands of rental units. We're seasoned entrepreneurs with repeat exits, venture backing, and deep industry experience (i.e. WeWork, WeLive). We need someone to keep those customers thriving while building the processes to take us to the next level.

What you'll actually do

You'll split your time between supporting existing customers and building the infrastructure we need to scale. That means owning customer relationships end-to-end, running onboarding and implementation, and creating the playbooks and documentation that don't exist yet.

A meaningful part of the role is telephony implementation. You'll help customers configure their phone systems, provision and port phone numbers, set up routing and forwarding, troubleshoot call flows, and coordinate migrations from existing providers into Wayline.

You'll work closely with our founders and engineers, translating customer feedback into product requirements and helping diagnose technical issues across telephony, integrations, and AI workflows.

You should have

• 2–4 years in a customer success, implementation, or technical customer-facing role at prop tech companies serving single-family, multi-family, or commercial real estate customers
• Hands-on experience with business telephony systems such as Quo (formerly OpenPhone), Dialpad, Twilio, RingCentral, or similar platforms
• Experience provisioning and porting phone numbers between carriers or telephony platforms, including coordinating port requests, understanding required documentation, and troubleshooting migrations
• Comfort working with call routing, forwarding, IVRs, extensions, business hours, voicemail, and other common telephony configurations
• Hands-on experience guiding customers through onboarding, setup, and implementation
• Real fluency with AI tools: you regularly use Claude, ChatGPT, Cursor, or similar and understand how to prompt effectively
• Some exposure to voice AI or conversational AI, either professionally or as a power user
• Property management, real estate, or prop tech background strongly preferred. You know what a maintenance coordinator's day looks like
• Enough technical ability to read API docs, understand webhook payloads, troubleshoot integrations, and explain technical requirements to customers
• The builder mentality: you see gaps and fill them without being asked
• Bonus: You've built hobby projects or demos with AI tools you can show us

Location

We're based in San Francisco and work out of the office several days per week. You should be located in the Bay Area or willing to relocate, and able to be in the office regularly.

You'll succeed here if you

• Thrive in ambiguity and enjoy building processes from scratch
• Are comfortable getting into the weeds of customer implementations, including debugging phone routing, number ports, integrations, and call-quality issues
• Are willing to do whatever it takes, including unglamorous work like data entry or call QA
• Take ownership of problems without waiting to be asked
• Get energy from building new systems rather than maintaining existing ones
• Can flex your schedule when customers need you

Why this might be interesting

You'll have real influence on our product roadmap and go-to-market strategy. The systems you build in year one will scale with the company. You'll work at the intersection of customer success, telephony, AI, and real estate—and become deeply familiar with how modern voice AI systems operate in production.

If you're good at this, you'll likely grow into leading a CS team or owning a customer segment entirely.

We're a small team of founders and engineers, growing quickly. Compensation includes competitive salary, meaningful equity, and standard benefits including health and dental.

If you've been at a larger company and want to experience zero-to-one, or you're at another early startup and specifically excited about AI, telephony, and real estate, let's talk.