Sidekick is seeking an experienced Customer Success Manager to join its core operations team.

The $100 billion residential real estate industry is powered by real estate agents and brokerages who are radically underserved by the existing, legacy software ecosystem. Sidekick, the leading generative AI assistant purpose built to help agents and brokerage drive efficiency and business growth, is creating a new category of transformative technology for real estate.

Sidekick is backed by some of the world's leading investors including Cox Enterprises/Socium Ventures, Craft Ventures, Threshold Ventures, Zigg Capital, Good Friends, and 75 & Sunny.

If you’re passionate about AI and real estate — and want to help build something from the ground up — read on.

In this role, you’ll be the go-to partner for agents and brokerages using Sidekick, helping them onboard, succeed, and stay excited about what we’re building. You won’t just be supporting users — you’ll help create a community of engaged, enthusiastic advocates who love the product and want to get the most out of it.

Responsibilities

Be the expert on how agents can use Sidekick to save time and grow their business
Deliver onboarding, product training, and ongoing day-to-day support
Build community through webinars, email campaigns, and other engagement initiatives
Gather and synthesize user feedback to help shape the product — working closely with our product, engineering, and executive teams
Set up scalable systems to track and implement feedback effectively

Required Qualifications

Has direct experience working with real estate agents and/or at a brokerage
Is passionate about the latest AI tools (ChatGPT, Claude, Gemini, etc) and can show how they’ve used them
Is a self-starter who thrives in fast-paced, 0-to-1 environments
Is a phenomenal communicator — both in writing and on calls
Loves helping people and can explain ideas clearly and enthusiastically
Is excited about joining a startup early and growing with the team

Select Benefits

Ground-floor equity in a fast-growing, high-potential startup
Medical, Dental, and Vision
Unlimited vacation days
Flexible work environment

Location

This is primarily a remote position. Sidekick is optimizing for hiring in the Northern and Southern California areas, prioritizing Los Angeles, Orange, and San Diego counties. Travel may be required on an ad-hoc basis for team planning + events in the area.

Sidekick

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