Weekend Cs Core Engineer Jobs in Chicago, IL (NOW HIRING)

Fin is the AI Customer Agent company on a mission to help businesses provide perfect customer experiences.
Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey - from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk for one single system that is designed to meet the needs of modern day support teams.
Founded in 2011, Fin became one of the fastest growing companies and remains one of the largest private software companies in the world with nearly 30,000 global businesses using our products to transform their customer support. Driven by our core values, we push boundaries, build with speed and intensity, and relentlessly deliver incredible value to our customers.
What's the opportunity?
We're building Fin's Scaled Customer Success team to reach more customers, provide consistent high-impact outcomes, and lean even harder into what makes us unique: our AI-powered products (especially Fin) and deep domain expertise. As a Scaled Customer Success Manager, you'll be the customer's trusted guide-helping them adopt and embed Fin's suite at scale, extracting real value, and scaling processes so more businesses succeed, more reliably.
If you're excited by working at the intersection of AI, product adoption, and operational excellence-and you want to help define how scaled CS works in practice-this is your role.
What will I be doing?

• Drive broad product adoption, with special focus on Fin and AI-powered features: helping customers understand how Fin can automate support, enhance service, and deliver self-serve experiences, alongside human support.
• Design, implement, and iterate on engagement strategies and playbooks that can scale across customer segments-leveraging technology, automation, digital content, and smart touchpoints.
• Own implementation and onboarding conversations for your customers, ensuring they are being set up for success from Day 1.
• Monitor usage & health signals proactively-identifying risks, opportunities, and expansion paths; drive intervention where needed.
• Collaborate closely with Sales, Solution Engineering, Education, and Product to ensure a seamless customer journey from purchase through expansion.
• Act as the Voice of the Customer: feed insights from scaled engagements back into the product roadmap, feature improvements, messaging, and internal training.
• Help define what "Scaled CS" means here: you'll be a builder-defining processes, tools, metrics, and models for what high volume, high value looks like.

What skills do I need?

• 3-5 years of experience in a customer-facing role in SaaS / technology / product success or similar, with a track record of managing many customers or high-volume engagement.
• Strong interest in / experience with AI & automation support tools; ability to explain AI/Fin features and use cases to customers, and help them build workflows around them.
• Comfortable discussing technical topics such as APIs, integrations, and workflows-not an expert, but confident engaging with customers on technical questions and guiding them to resources.
• Excellent communication skills: can break down complex product and technical topics clearly for different audiences (executives, operations, support leaders).
• Data-driven mindset: able to monitor usage metrics, define success metrics, analyse what is / isn't working, and adapt strategy based on results.
• Self-starter, entrepreneurial, comfortable in ambiguity; able to build processes from scratch and consistently improve them.
• Strong relationship builder: you can maintain trust even with many customers, manage expectations, and partner with internal stakeholders.

Bonus skills & attributes

• Interest in consumption or usage-based SaaS models.
• Exposure to Generative AI, chatbots, virtual agents, or AI-assisted support tools.
• Experience in operations, scaling CS / onboarding / customer education / digital engagement programs.

Benefits
We are a well-treated bunch with awesome benefits! If there's something important to you that's not on this list, talk to us!

• Competitive salary and meaningful equity
• Comprehensive medical, dental, and vision coverage
• Regular compensation reviews - great work is rewarded!
• Unlimited access to Claude Code and best-in-class AI tools; experimentation & building is encouraged & celebrated.
• Flexible paid time off policy
• Paid Parental Leave Program
• 401k plan & match
• In-office bicycle storage
• Fun events for employees, friends, and family!

*Proof of eligibility to work in the United States is required.
The OTE range for candidates within the Greater Chicago Area is $135,300 - $161,550. Actual base pay will depend on a variety of factors such as education, skills, experience, location, etc. The base pay range is subject to change and may be modified in the future. All regular employees may also be eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).
Policies
Fin has a hybrid working policy. We believe that working in person helps us stay connected, collaborate easier and create a great culture while still providing flexibility to work from home. We expect employees to be in the office at least three days per week.
We have a radically open and accepting culture at Fin. We avoid spending time on divisive subjects to foster a safe and cohesive work environment for everyone. As an organization, our policy is to not advocate on behalf of the company or our employees on any social or political topics out of our internal or external communications. We respect personal opinion and expression on these topics on personal social platforms on personal time, and do not challenge or confront anyone for their views on non-work related topics. Our goal is to focus on doing incredible work to achieve our goals and unite the company through our core values.
Fin values diversity and is committed to a policy of Equal Employment Opportunity. Fin will not discriminate against an applicant or employee on the basis of race, color, religion, creed, national origin, ancestry, sex, gender, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, gender identity, gender expression, marital status, or any other legally recognized protected basis under federal, state, or local law.