Founding Client Deployment & Success Lead

Location: Hybrid – Chicago, IL (3 days in office required)

Job Type: Full-time, 90 day contract-to-hire

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About the Role

This is not a traditional client success role.

It’s a hybrid of relationship management, product enablement, and light technical troubleshooting. To succeed here, you must have a demonstrated willingness to learn, adapt quickly, and take initiative.

At Aviary AI, we are building a new kind of post-sales experience, one where client success means configuring real-world voice AI workflows, solving technical issues, analyzing client data, and continuously improving how we deploy and support our product.

We are looking for someone early in their career, potentially even a recent graduate, who is curious, adaptable, and excited to learn. This role is ideal for someone who wants to grow into a hybrid skill set that includes project management, client engagement, light technical implementation, and AI tools. You do not need to know everything on day one, but you do need to be energized by solving problems and learning fast.

As our Founding Client Deployment and Success Lead, you will help shape how we onboard, support, and grow with clients. You will work closely with our product, engineering, and sales teams, and you will play a hands-on role in delivering real value to our clients.

What You Will Do

• Run client onboarding projects, including coordinating data handoffs, setting up integrations, managing go-live checklists, and tracking progress against timelines.
• Analyze client usage and surface insights to support quarterly success reviews with client executives.
• Troubleshoot first-line technical issues and open clear support tickets when needed.
• Create client-facing resources like FAQs, video guides, and webinar content to make onboarding and usage smoother.
• Work closely with sales on upsells and renewals, including forecasting client health and expansion opportunities.
• Share client feedback with our product team and contribute ideas to improve our tools and processes.
• Continuously improve onboarding and success playbooks so we scale efficiently

What We Are Looking For

Must-Haves:

• Strong organizational and communication skills.
• A self-starter attitude with a willingness to learn technical tools like Postman, Power BI, or ChatGPT.
• Comfort with ambiguity and a desire to work in a fast-paced startup environment.
• Ability to think critically and take ownership of problems.
• Bachelor’s degree or equivalent experience.

Nice-to-Haves (but not required):

• Internship or school experience in client success, operations, support, or technical roles.
• Familiarity with SaaS products, APIs, CRM tools, or light analytics.
• Experience using AI tools to streamline work or solve problems.

Why This Role is Unique

You will not just be managing accounts, you will help build the client success function from the ground up.

You will be working in a startup environment where your ideas and execution will shape how we support our clients as we grow.

If you are the kind of person who likes to figure things out, take initiative, and make things better each time you do them, you will thrive here.

This role is well-suited for early-career professionals or recent grads who are ready to grow into a broader operational or product-facing role over time.

Benefits

• Competitive salary and equity.
• Health, dental, and vision insurance.
• 401(k) plan.
• Unlimited PTO.
• Hybrid work model.
• Opportunity to work directly with the founding team and grow with the company.

About Aviary AI

Aviary AI is transforming how financial institutions engage their customers. Our AI-powered voice agents help credit unions, banks, and insurers connect with members in a scalable, compliant, and human-like way.

We are backed by Y Combinator and rapidly growing, with clients across financial services. Join us in building the future of AI-powered communication.

• Introductory Call (15–30 minutes): Meet our CEO and get to know each other.
• Hiring Manager Interview (30 minutes): Deep dive into the role and expectations.
• Practical Assessment Interview (60 minutes): You will complete a short project and present how you would improve an onboarding process and identify “at-risk” clients using simple tools and AI assistance.
• Final Interview (15–30 minutes): Meet with the leadership team (CEO, CTO, COO, and Head of Data).
• References and Offer.