About Us
CollectWise is a fast growing and well funded Y Combinator-backed startup. We’re using generative AI to automate debt collection, a $35B market in the US alone. Our AI agents are already outperforming human collectors by 2X, and we’re doing so at a fraction of the cost.
With a small team, we scaled to a $3M annualized revenue run rate in just over a year, and we’re now hiring a Founding Customer Success Engineer to help us reach $10M+ over the next year.
The Role
We’re looking for a Founding Customer Success Engineer to own customer relationships after launch and ensure customers are successful with CollectWise.
You’ll work at the intersection of customer success, engineering, and operations, managing customer communication, resolving technical issues, optimizing AI agents, supporting implementations, and identifying opportunities to expand accounts.
This is a highly hands-on role. You should be comfortable working directly with customers, troubleshooting technical problems, working with code when needed, and collaborating with engineering on more complex issues.
Your success will be measured by customer satisfaction, retention, product usage, account expansion, and customer performance.
Responsibilities

Own day-to-day customer relationships after customers have gone live
Troubleshoot and resolve technical customer issues by adjusting configurations, shipping code when appropriate, and escalating to engineering when necessary
Monitor customer usage, performance, and trends to identify opportunities to improve results and increase adoption
Continuously optimize customer AI agents and workflows through prompt engineering
Upsell customers on additional products, use cases, and increased usage to expand revenue
Proactively engage customers when usage declines to reduce churn
Support new implementations and product rollouts for existing customers

Desired Qualifications

3+ years of experience in technical customer success, solutions engineering, sales engineering, technical operations, product management, technical support, software engineering, or a similar role
Excellent written communication skills with a high level of responsiveness
Strong technical background with experience writing and debugging code and working with APIs, integrations, and data flows
Strong verbal communication and relationship-building skills
Strong attention to detail and ability to manage multiple customer issues and priorities simultaneously
Highly proactive with a strong sense of ownership
Commercial mindset with the ability to identify upsell and account expansion opportunities

Compensation

$150,000 to $180,000 OTE, including a $130,000 to $160,000 base salary plus variable compensation tied to customer expansion and retention
Equity: 0.03% to 0.10%

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Founded in 2023, Flint is an AI-powered platform built for schools. In three years, we’ve partnered with hundreds of schools across the U.S. and internationally, supporting 750,000+ students.
We’re now looking for a Customer Success Engineer who cares deeply about customer outcomes and is excited to use systems, automation, and AI to deliver them better at scale.
You’ll be the second member of Flint’s Customer Success team, owning real accounts, real renewals, and real outcomes while helping improve how the entire function operates. You’ll interface very regularly with the CEO and GTM Chief of Staff.
Our customers are schools: teachers and administrators navigating AI for the first time. They need someone who listens well, explains clearly, and shows up consistently.
This role is not a fit if you want a fully built-out org with fixed processes and a narrow lane. It is a fit if you like ownership, ambiguity, and building the plane while flying it.
The Big Picture
At Flint, we believe every role should be AI-native. That means using AI not just as a feature we sell, but as a core part of how we work: writing, analyzing, supporting customers, building workflows, and scaling impact.
As a Customer Success Engineer, you’ll do both sides of the job: directly own customer outcomes and continuously improve the systems that make those outcomes repeatable.
You’ll learn exactly what drives retention, adoption, expansion, and NRR—and then help turn those learnings into better processes, tooling, automation, and AI-assisted workflows.
This is a builder role inside Customer Success—not just support, and not just operations.
What You’ll Do

Own inbound customer communication
Manage a portfolio of school accounts, ensuring adoption and successful renewals
Create and improve customer-facing resources, including product updates, help center content, and teacher PD materials
Use AI tools and lightweight internal systems to improve the speed, quality, and consistency of customer work
Run virtual (and sometimes onsite) PD sessions to teachers at Flint partner schools

Who You Are

You have ~1–3 years of experience in Customer Success, Support, Ops, or a similar customer-facing, systems-adjacent role
You care about outcomes, not just activity—retention, adoption, and customer impact actually matter to you

Bonus Points For

Experience in education, including teaching, or EdTech
Startup experience

What We Offer

Meaningful early-stage equity
Health and dental insurance
The opportunity to shape how Flint supports schools as we scale