Customer Success Manager

United States·Chicagofull-timemid

Customer Success ManagerCustomer

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Requirements Summary

3+ years of experience in customer success, account management,

Technical Tools

Customer Success ManagerCustomer

About Letter AI

Letter AI is the world’s first revenue enablement platform powered natively by AI. We’re reimagining the end-to-end revenue journey by turning real customer conversations and account data into actionable insights, personalized coaching, meeting prep, and next steps.

Revenue teams aren’t asking for more content or tools. They’re asking for better outcomes. Letter does just that, empowering them to learn faster, sell smarter, and win more.

We recently raised a $40M Series B and are already helping leading companies like Adobe, Lenovo, and Figma transform how their teams work. We 10xed our revenue last year and are looking for the best of the best in Chicago to help us build on that momentum.

The Role

We are looking for a Customer Success Manager to join our expanding team. You will play a meaningful role in helping define how we support and engage our customers as we scale. In this role, you will own key aspects of the customer success journey and ensure both existing and new customers derive maximum value from our platform.

Own day-to-day customer relationships, serving as the primary point of contact and trusted partner for our clients
Deliver a high-touch, highly responsive customer experience, with frequent touchpoints and fast turnaround on customer needs
Onboard new customers and guide pilot customers through successful conversion and long-term adoption
Proactively monitor customer health and engagement, quickly identifying risks and taking action to ensure retention and success
Actively gather customer feedback and partner with the product team to continuously improve the customer experience
Build deep relationships with customers by understanding their goals, challenges, and definition of success
Collaborate closely with Sales and Marketing to support renewals, expansions, and upsell opportunities

Qualifications for the role include:

3+ years of experience in customer success, account management, or a related field (we are hiring across different levels of experience)
Proven track record of managing customer relationships and driving customer success
Strong problem-solving skills and ability to think strategically about customer needs
Excellent communication and interpersonal skills
Ability to work in a fast-paced startup environment and manage multiple priorities
Experience with customer success tools and platforms is a plus

As a part of the team at this early stage, you will not only receive a competitive salary and benefits, but also a meaningful equity stake in the company.

How We Operate

At Letter AI, we want you to be unapologetically you while operating with our core principles in mind:

Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
Driven yet humble: Push for excellence and deliver fast, but keep your humility

What’s In It For You?

Compensation: $100k–$160k base salary, depending on experience, expertise, and expected impact
Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
Build with us: Join a fast-growing startup where you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter