Sincsports

SincSports builds the software behind youth sports tournaments: registration, scheduling, payments, communication, scoring, standings, mobile app access, and event-day operations.

We have been doing it for more than 20 years, and real events depend on our software every weekend of the season.

We are hiring our second full-time engineer. You would work directly with Jonathan, our CEO, who is still hands-on in the code every day.

We are profitable, revenue-funded, and have no outside investors. Our roadmap is driven by our customers and the business, not by a board or the next fundraising round.

This is a remote, full-time role within the United States.

What you should know up front

Most job postings save the awkward parts for the third interview. We would rather tell you now.

The legacy platform is VB.NET, not C#

The legacy platform is a large ASP.NET WebForms application on .NET Framework 4.8 - two decades of accumulated business logic, some of it in very large files.

It works, and it runs real tournaments every weekend.

New development is C# on .NET 10, and you would work in both. During your first year, a meaningful share of your time will still be spent understanding, supporting, and improving the legacy platform.

We are not looking for someone who loves VB.NET.

We are looking for someone who can read it without flinching, understand why a 20-year-old system is shaped the way it is, and improve it incrementally rather than campaign for a rewrite.

If that sounds like a nightmare, this is probably not the right role - and we would rather you know that now than in month three.

The modernization is not aspirational - it is already underway

“Help us modernize our legacy system” is a promise a lot of companies make and few keep.

Here is exactly where we are:

• A new platform on .NET 10 using Razor Pages, Blazor Server islands, and htmx runs alongside the monolith using the strangler-fig pattern.

• Our entire scheduling module - one of the most complex surfaces in the product, including the auto-scheduling engine - has already been migrated and is running in production.

• The new platform is built test-first, with a versioned public API, background job host, and structured logging.

• We have a documented, phased roadmap with per-module migration ledgers and a repeatable migration process already proven on the first major module.

• Our Azure migration is complete: App Service, Azure SQL, Blob Storage, Key Vault, Redis, Application Insights, and GitHub Actions deployments through staging slots.

You would be joining to help drive the next modules - not to wait for a rewrite that never gets funded.

What you will work on

• Building and improving features across the platform: registration, scheduling, team management, scoring, communication, reporting, and event operations.

• Migrating legacy modules into the new .NET 10 platform, one module at a time.

• Consolidating our payments stack - several gateways accumulated over the years - behind a single abstraction that is already partially built.

• Supporting production: troubleshooting real problems for real customers and making the system more reliable, observable, and easier to support.

• Improving deployment, database change management, monitoring, testing, and engineering documentation.

• Turning customer and business needs into practical product decisions while working directly with the CEO and operations team.

• Exploring and building practical AI-powered features that reduce work for tournament directors, simplify complicated workflows, surface useful information, and help our customers make better decisions.

• Owning systems end to end, with real authority over how they evolve.

This is not a role where the architecture has already been decided for the next five years and your job is simply to implement tickets.

You will have meaningful influence over how a mature SaaS platform is modernized, how we use AI internally and within the product, and what our engineering organization looks like as the company grows.

The honest shape of the week

We are a small team supporting live events, so this is not an all-greenfield job.

Youth sports is seasonal, and spring and fall are our heaviest periods. Our customers’ events run on weekends, so a scheduling bug on Friday evening can become a live-event problem on Saturday morning.

Concretely, a typical in-season weekend brings zero to three urgent issues, most of which are resolved in under 10 minutes. Weekend availability is a real part of this role - bounded, but real - and it is shared, not yours alone.

We also work heavily with AI-assisted development.

AI is a normal part of our engineering workflow for implementation, analysis, testing, documentation, modernization, debugging, and understanding a large codebase. Our codebase carries a documented architectural contract, purpose-built tooling, and written migration ledgers designed so both engineers and AI models can work effectively from them.

It is a major part of how a very small engineering team can maintain and modernize a system this size, and we expect the engineer joining us to be comfortable working that way too.

What we are looking for

You might be a great fit if you are a senior engineer who enjoys ownership, practical problem-solving, and working close to the product and the business.

• 7+ years of professional software engineering experience.

• Strong .NET and SQL Server background - fluent in C# and willing to work in VB.NET.

• Experience with modern .NET: ASP.NET Core, Razor, Blazor, or similar.

• Strong SQL skills, including schema design, query optimization, and performance troubleshooting.

• Experience with Azure or another major cloud platform.

• Experience building or integrating APIs.

• Comfort using AI-assisted development tools thoughtfully as part of a professional engineering workflow.

• Good judgment about when to improve something and when to leave it alone.

• Clear communication and comfort working independently as part of a very small engineering team.

• Genuine interest in the product, the customers, and the business - not just the ticket.

• A security-conscious approach to data, access control, payments, and privacy.

Bonus points for experience with:

• Modernizing legacy applications, especially incremental or strangler-fig migrations.

• SaaS platforms, payments, registration, events, scheduling, or sports technology.

• Scheduling, logistics, ticketing, events, or booking software - anywhere you had to solve constraints against messy real-world rules.

• Azure App Service, Azure SQL, Blob Storage, Key Vault, Redis, and Application Insights.

• CI/CD with GitHub Actions, staging environments, and structured release processes.

• Growing into a technical leadership role as a team expands.

And one that is not a requirement, but tell us if you have it:

If you have coached, refereed, run a tournament, managed a team, or spent your weekends at a soccer complex, you will understand our customers faster than most people can learn to.

A surprising amount of what looks arbitrary in this product makes immediate sense once you have stood on the other side of it.

How we build

These are settled decisions, and we would much rather hear you disagree with them in an interview than discover it in month two.

• Modular monolith. We enforce module boundaries and extract a separate service when something specific justifies it - our payments service is separate for compliance isolation - not because microservices are the default answer.

• The data-access tool matches the schema. We use hand-written async SQL against the legacy schema where query shape and round-trip count matter, and EF Core in newer services with schemas we own.

• Strangler fig, module by module. Never a big-bang rewrite.

• Test-first on new code. Coverage on the legacy side is thin, and improving it as we touch those areas is part of the job.

• AI-assisted development is expected. We use AI as leverage, not as a substitute for engineering judgment. The person writing or changing the code is still responsible for understanding it, reviewing it, and making sure it belongs in the system.

How we think about AI

AI is already changing how we build software at SincSports. We think it will also change what the product itself can do.

Tournament management involves an enormous number of decisions, repetitive tasks, exceptions, communications, schedules, and real-world constraints. Tournament directors often have to understand large amounts of information and make decisions quickly, particularly as events approach.

We believe there are meaningful opportunities to use AI to eliminate repetitive work, simplify complicated workflows, surface useful information, assist with decision-making, and make the platform easier for our customers to operate.

We are not interested in adding a chatbot simply so we can say SincSports has AI.

We want to find places where AI solves real problems.

The engineer joining us will have a meaningful role in identifying those opportunities, prototyping ideas, deciding what belongs in the product, and building the capabilities that work.

Why this role is different

You would be engineer #2 at an established, profitable software company — not employee #2 at a startup trying to find product-market fit.

There are real customers, real revenue, a mature product, and more than 20 years of domain knowledge already here.

At the same time, the engineering team is small enough that your decisions will matter.

You will work directly with the CEO and the people who support our customers every day. You will see the problems customers are actually having, help decide what we should build, and have the authority to carry those decisions all the way through production.

As the engineering team grows, we expect this role to have the opportunity to grow with it - technically, architecturally, and potentially into engineering leadership.

Compensation and benefits

• Salary: $130,000–$165,000, depending on experience and fit.

• 401(k): 3% employer contribution after one year of continuous employment.

• Paid time off: 20 days annually, plus 5 days of paid sick leave.

• Equity: This role is cash compensation and does not include equity.

• Health: We do not currently offer a group health insurance plan.

Location

Remote within the United States.

We are already set up for payroll and tax in Illinois, Colorado, and Ohio, so candidates in those states are simplest for us. For the right person, however, we are willing to work through establishing employment in another state.

Hiring process

• An intro conversation with Jonathan about the role, the company, and what you are looking for.

• A technical conversation working through a real problem from our codebase — no take-home project and no algorithm puzzles.

• A final conversation with the leadership team.

• Roughly two to three weeks from first conversation to decision.

Two things we would genuinely like to hear about:

• A large or messy system you inherited and made meaningfully better - ideally without rewriting it.

• What you want to be doing three years from now.

And if youth sports is already part of your life in some way, mention it.

It is not a requirement and it will not make up for the rest, but it is the kind of thing we notice.