Customer Experience Engineer

Awardspring; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

401(k) match

Unlimited PTO

Paid parental leave

Job summary

AwardSpring, an AI-native SaaS platform for scholarships and donor management, is seeking a Customer Experience Engineer to shorten the path from problem to solution. You’ll run self-serve support, maintain docs, and drive onboarding data pipelines.

You’ll tackle escalations, build repeatable fixes, and create tools to automate repetitive tasks for CX teams. The role reports to the Chief AI Officer with a dotted line to the Director of Customer Experience, is hybrid in Chicago, and emphasizes

Qualifications

• You work with Claude Code, Codex or similar every day, and your agentic process is robust enough that you don't need to read the code you ship.
• You debug in steps. You reproduce it, read the logs, check the network tab, and find the cause before you reply.
• You write documentation people actually use, and you notice an out‑of‑date help article before a customer does.
• A customer's messy spreadsheet doesn't scare you. You can map someone else's data into our schema and prove it landed right.
• You can explain a technical problem to a stressed financial aid director without making them feel foolish.
• You fix things for good. When you see the same issue twice, you build what stops the third.
• Support, implementation, solutions or engineering backgrounds all work. We care about what you've built, not where you trained.

Responsibilities

• Run our support agents. Read the conversations they get wrong, fix the answer or the documentation behind it, and widen what they can resolve on their own.
• Keep the documentation current with every release.
• Take the technical escalations that get past the agents and our support team. Find the cause, fix it or hand engineering a bug report they can act on in one read, and walk the customer through it.
• When you see the same issue twice, build what stops the third.
• Own the data side of onboarding: map, clean, load and verify each new customer's data, and get their sign-off.
• Build the onboarding pipeline so each migration takes fewer human steps than the last.
• Build tools that remove the repetitive parts of the work for Support Reps and Onboarding Specialists.

Job description

Who we are

AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.

About this role

The Customer Experience Engineer is responsible for shortening the distance between a customer's problem and a solution, and between a signed contract and a live customer.

You own our automated support. Most customer questions should be answered without waiting for a person: by our documentation, by our AI support agents, or by the product itself. You keep the documentation current as the product changes, run the support agents, read the conversations they get wrong, and widen what they can resolve on their own.

When a problem gets past the agents and our support team, it comes to you. You find the cause, fix it or hand engineering a bug report they can act on in one read, walk the customer through it, and then build whatever stops it from happening again.

You also own the data side of onboarding. Getting a new school or foundation live means taking their spreadsheets, mapping years of scholarship, donor and award history into our schema, and verifying every record. Today that is a long, manual process with dozens of steps. Your job is to make it fast, repeatable and right.

This is a hands‑on building role reporting directly to the Chief AI Officer, with a dotted line to the Director of Customer Experience, who sets what the CX team needs next. You build for our Support Reps and Onboarding Specialists: agents and automation that take the manual steps out of their day. You'll find the next wins yourself in our support conversations, escalation reasons and onboarding timelines.

How we work

AwardSpring is an AI‑native company. Nearly 100% of the code in our product is AI‑generated, and every team here operates on the same principle: routine work gets delegated to AI so people spend their hours on the problems that actually need judgment.

We hire for three things:

• Intellectual curiosity. When you don't know something, you go learn it instead of waiting to be taught.
• Agency. You act without waiting for permission. You take ownership of the problems in front of you and move on them decisively.
• Ambition. You want your work to matter. You are here for real impact, and you are willing to push past your own limits to make it.

We are a small, focused team on a mature, multi-tenant platform. Nobody here has a narrow lane.

What you'll do

• Run our support agents. Read the conversations they get wrong, fix the answer or the documentation behind it, and widen what they can resolve on their own.
• Keep the documentation current with every release.
• Take the technical escalations that get past the agents and our support team. Find the cause, fix it or hand engineering a bug report they can act on in one read, and walk the customer through it.
• When you see the same issue twice, build what stops the third.
• Own the data side of onboarding: map, clean, load and verify each new customer's data, and get their sign-off.
• Build the onboarding pipeline so each migration takes fewer human steps than the last.
• Build tools that remove the repetitive parts of the work for Support Reps and Onboarding Specialists.

Who you are

• You work with Claude Code, Codex or similar every day, and your agentic process is robust enough that you don't need to read the code you ship.
• You debug in steps. You reproduce it, read the logs, check the network tab, and find the cause before you reply.
• You write documentation people actually use, and you notice an out‑of‑date help article before a customer does.
• A customer's messy spreadsheet doesn't scare you. You can map someone else's data into our schema and prove it landed right.
• You can explain a technical problem to a stressed financial aid director without making them feel foolish.
• You fix things for good. When you see the same issue twice, you build what stops the third.
• Support, implementation, solutions or engineering backgrounds all work. We care about what you've built, not where you trained.

What we're not looking for

• Someone who avoids the customer. Half of this job is getting on a call with someone who is stressed and making it solvable.
• Someone who closes tickets without fixing the cause.
• Someone who trusts the script. A migration isn't done because it ran without errors.

How we'll measure you

Also reviewed every week: contact rate, time to resolution, customer satisfaction, data migration turnaround, migration defects, and human hours per onboarding.

1. Escalation rate. The share of support conversations our AI agent or self‑serve can't resolve and hands to a person. A conversation the customer reopens within 7 days counts as escalated.
2. CX cost to serve. What it costs to run Customer Experience, against our subscription revenue. Prevention shows up here: the best ticket is the one that never gets opened.
3. Time to launch. Median days from contract start to a live customer. How fast a new customer starts getting value from AwardSpring.

On the AI part of this job

Unlike most roles here, we won't teach you to work AI‑native. You arrive fluent: directing agents is already how you build, every day. We check in at day 30 on how you're working, not only on what you've shipped.

How you advance

Growth here doesn't require a management ladder. Strong CX Engineers will slowly but steadily be given more autonomy, more scope, and ownership of higher‑level KPIs. If you're looking for career progression into a people management track, this likely isn't the role for you.

What we give you

• Top‑tier AI tooling with unlimited token budgets
• Day‑one access to the latest models as they ship
• A mature, multi‑tenant production codebase with real users and real stakes
• Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave

Our values

• Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.
• Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.
• Take pride in the process. Fast is the standard and thoughtfulness is non‑negotiable. Eyes on the work you control, not the scoreboard.
• Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.

Work location

Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week. In‑office presence is part of the job, with the specific schedule set with your manager.

How we hire

1. A conversation with our CEO.
2. A short take‑home: build something small with AI, then walk us through how you built it.
3. Interviews with the team you would work with.
4. A second, longer take‑home.
5. A final debrief and an offer.

AI in hiring

We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. Prefer a review without AI assistance? Email our hiring team at [e-mail] to request it. It will not disadvantage you.