Shilling was my own venture-backed startup. Like many startups, the path to product–market fit was not linear.

We pivoted several times before landing on something that customers truly needed.

We started with a consumer-facing COVID safety product called Gather Safe, which allowed individuals to prove their COVID-negative testing status to employers, airlines, restaurants, or universities. This was before vaccines were widely available and there was real demand for ways to verify health status safely.

From there we pivoted to a developer API for accessing pharmacy health data, after realizing the infrastructure we had built to ingest testing data could support broader patient data access for health-tech companies.

That space turned out to be extremely crowded with long enterprise sales cycles, so we pivoted again.

Eventually we found our footing by solving a very different problem: healthcare providers struggling to manage scheduling as they transitioned from purely in-person care to a hybrid model that included telehealth.

That final product, a scheduling orchestration layer for healthcare providers, is where we ultimately found product–market fit.

The Problem

COVID fundamentally changed how healthcare providers delivered care.

Practices that previously operated entirely in person suddenly had to support a mix of:

• in-person visits

• telehealth appointments

• remote patient monitoring

Most clinics were still running on scheduling systems designed for a world where every appointment happened in a physical room. The result was chaos.

Providers struggled to manage:

• room availability

• clinician schedules

• virtual vs physical appointments

• resource allocation

On top of that, provider burnout was becoming a major issue.

Clinicians were being pushed into extremely dense schedules with little flexibility or recovery time.

My Role

As founder, I led the product strategy, customer discovery, and development direction for the company.

The most important decision I had to make repeatedly was whether to continue investing in an existing direction or pivot toward a new opportunity based on customer feedback.

Every pivot required stepping back from work we had already invested heavily in and asking whether we were actually solving a real problem.

This meant having difficult conversations with the team, talking to customers constantly, and being willing to abandon months of work when the signal wasn’t strong enough.

The Product

The product we ultimately built sat on top of existing healthcare scheduling systems and added the flexibility that clinics suddenly needed.

Instead of forcing providers to replace their existing systems, we built a layer that could orchestrate scheduling across them.

Key capabilities included:

• hybrid scheduling across telehealth and in-person visits

• resource management for rooms, equipment, and clinicians

• configurable gaps between appointments to reduce provider burnout

• limits on appointment density across days or weeks

• patient intake workflows integrated directly into the scheduling process

The patient intake feature allowed clinics to collect structured information from patients before appointments, reducing administrative overhead and improving the quality of the visit.

The goal was not to replace the clinic’s existing systems, but to make them behave like modern software.

Results

After several pivots, the scheduling platform was the first product where we saw clear traction.

Healthcare providers were actively looking for ways to manage hybrid care and were willing to adopt new tooling if it could sit on top of their existing systems rather than replacing them entirely.

The product addressed two urgent problems simultaneously:

• operational complexity caused by hybrid care

• clinician burnout caused by overloaded schedules

Once we focused on that problem space, customer conversations became dramatically easier.

Lessons

The biggest lesson from Shilling was about avoiding the sunk cost fallacy.

It is incredibly easy to fall in love with the first idea you build, especially after investing months of effort into it.

But startups don’t succeed because the first idea is perfect. They succeed because the team is willing to keep searching until they find a problem that customers truly care about.

Each pivot we made came from talking to customers and paying attention to what they were actually struggling with.

In the end, the most important skill as a founder wasn’t building the product.

It was knowing when to change direction.