The Customer Success Manager will manage customer relationships, ensure successful onboarding, monitor customer engagement, gather feedback, and collaborate with Sales and Marketing to drive renewals and upsell opportunities.
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
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