System Support Specialist

Plymouth, MN (On-Site)
40 hrs/week | Start: Immediate


The Opportunity

The SaaSpocalypse is real. Salesforce, Workday, ServiceNow, and Epic are all feeling it. The per-seat, legacy-workflow model is being dismantled in real time, and the companies that built their moats around it are scrambling. We are not.


Think Harvey for legal, Sierra for customer service, Ramp for finance - vertical AI companies built from the ground up to displace the incumbents, not compete with them on features. We are that company for healthcare.


EWINGS, INC. is a 24-year-old firm with active Fortune 500 clients, battle-tested delivery workflows, and deep regulatory domain expertise that most software companies will never acquire. We are now converting that institutional knowledge into an AI-native operational platform purpose-built for enterprise health plans - one of the most complex, high-stakes segments in the entire enterprise software market ripe for disruption.


This is not a seat-license play. This is not a dashboard bolted onto a legacy workflow. This is vertical AI infrastructure, built AI-first from the ground up, with human-in-the-loop design at its core and agentic workflows surfacing as clear, actionable intelligence for enterprise operators. The incumbents in this space are slow, expensive, point solutions incapable of moving at AI speed. We are not.


We are well-capitalized, operationally stable, and already generating revenue. Live client pilots are underway. The platform is real, the clients are real, and the urgency is real.


You Don't Have to Move to San Francisco for This

For two decades, the most compelling platform opportunities - the ones where you build something that matters, with people who know what they are doing, with real clients and real stakes - have been concentrated on the coasts. The AI wave has made that worse, not better.


This one is in Plymouth, MN.


If you have been watching the AI wave build from the Midwest and waiting for something real to land close to home - a vertical AI platform with Fortune 500 clients, live pilots, domain depth that startups cannot fake, and a founding team that has been executing at the highest level for over two decades - this is it.


Who You'll Be Working With

Most AI startups are being built by first-time founders who are learning management, sales, domain expertise, and product strategy in real time - at your expense. The pressure is real, the learning curve is steep, and the failure rate reflects it.


This is not that.


The founder and CEO leading this platform brings 24 years of executive operational, sales, and market development experience inside Fortune 500 healthcare - including UnitedHealth Group, Optum, HealthNet, Ascension, and the VA Community Care Network. This is not someone learning healthcare. This is someone who built it.


The broader team matches the ambition. Our operational and delivery leadership includes people who have sat in the same seats as our clients - direct experience inside the nation's largest health plans. That team is complemented by engineers and builders with backgrounds at industry-defining companies like Google and Amazon. You will be working with people who have built at scale before and know what that requires.


The Culture

A lot of companies say they are "AI-forward." Most of them mean they added a ChatGPT integration and declared victory. The engineers who join those teams spend the next two years watching leadership catch up to where the market already was.


We are not debating anything.


At EWINGS, learning and leveraging AI every single day is the starting point, not an aspiration. Every person on this team is expected to use AI tools actively and fluently - not because we asked them to, but because that is the only way to move at the speed this market requires.


The window of pre-adoption in this market is open right now. Our competitors are still holding meetings about whether to adopt. We are already building. That gap closes fast and the engineers who are inside it when it closes are the ones who define what the platform becomes.


What you will find here is a fast-paced, highly collaborative environment with genuine enthusiasm for what we are building, clear ownership of meaningful work, and leadership that has been doing this long enough to know what good looks like.


If that is the kind of environment that energizes you, you will fit in immediately.


About the Role
You'll keep the platform reliable as it scales and be the person who turns real user friction into fixes that ship. This is a high-visibility seat close to both the customers and the build, ideal for someone who wants to understand the whole system and grow into more as the company does.

What you'll do:
- Monitor platform health and respond to issues quickly, ideally before users feel them.
- Be the bridge between users and the build team: capture real friction, reproduce it, and drive it to a fix.
- Triage and resolve support issues, escalating with clear, well-documented detail when engineering is needed.
- Build and maintain runbooks, internal tooling, and documentation that make support faster over time.
- Use observability and logging tools to investigate problems and spot patterns.
- Track recurring issues and feed them back into product and engineering priorities.
- Use AI tools to investigate, document, and resolve faster. This is how we work.

What you need:
- Strong troubleshooting instincts and the persistence to chase a problem to its root.
- Clear written communication. You can explain a technical issue to a developer and to a non-technical user with equal ease.
- Comfort reading logs, writing basic SQL queries, and using monitoring and observability tools.
- Organized, detail-oriented, and calm under pressure.
- Genuine curiosity about how the whole system fits together.

Nice to have:
- Experience in a technical support, QA, or platform reliability role for a software product.
- Familiarity with SaaS platforms, APIs, or cloud-native environments.
- Healthcare or regulated-environment experience.
- Some scripting ability.

Where it goes:
This seat sits close to both customers and the build, which makes it one of the best places in the company to learn the entire platform. For someone with drive, it's a launch point into engineering, product, or operations as the company grows.

Tech environment:
The same core platform as the rest of the team, with observability and logging tooling for investigating issues. Specific tooling is shared during the interview process.