The Golden Age of the Small Business Owner

I started my first company as a recent college graduate at the start of the dot-com boom. It was an exciting time to be a disruptor. The rules were being rewritten in real time. Companies that seemed invincible lost relevance overnight. New startups changed entire industries. I believe this moment with AI is bigger than what happened then. Because more than anything that has come before, AI enables small teams to do big things.

We are entering a golden age of entrepreneurship and small businesses.

The basic math of starting a company is changing. With AI, a founder can research a market, build a prototype, create content, support early customers, and generate demand at a speed and scale that used to require a larger team. You see it in the headlines: more new business applications than ever before, more solopreneurs, and more small teams hitting big revenue milestones. And the wave of people ready to build has never been larger. Some are taking the leap after they were laid off by big companies. Some are career entrepreneurs who have new tools to make building that next start-up easier, faster, and more capital efficient. Some are first-generation business owners building something because the barriers that used to stop them are lower than they have ever been. This golden age of small business will make communities, industries, and the economy stronger. Small businesses bring new ideas into the world. They make markets more competitive. They create jobs that bring meaning to people’s lives. But the optimistic narrative glosses over a hard reality.

Starting a business may be easier than ever. Running one has never been more complicated.

The moment a founder hires their first employees, a whole layer of complexity arrives: payroll, benefits, taxes, state registrations, insurance, employment law, and potentially international hiring. As the business gets bigger, so does everything that pulls the founder's attention away from the reason they started their company in the first place. Now, as small businesses are able to do more with AI, they are encountering more complexity earlier in their lifecycles. Small teams have to manage expansive modes of employment (full-time employees, contractors, AI agents), the challenges of diverse geographies, and a growing lattice of local, state, and federal regulatory obligations. More payments to manage, more rules to stay compliant, and more coordination across systems. The “complexity-to-employee ratio” is going way up. As more small businesses form, this generation of small business owners needs great partners to help them carry this complexity. And historically, they have not had them Small businesses have always been underserved because they are hard to reach and because providers don’t make much money from any one small business. Upmarket gravity pulls providers toward enterprise customers and the allure of larger deals. At the same time, once a small business owner gets payroll, benefits, and compliance running, they are reluctant to go through the pain & suffering of switching providers, even when they receive bad service. This combination of limited options and high-switching costs has made it so that legacy players in this industry haven’t had to be all that customer-centric or innovative to build enormously profitable companies. That has been well and good for those legacy providers. But, it has been a real drag for the small business owners who, while already trying to overcome long odds, have been perpetually underserved. You see, small businesses never wanted software. They never wanted tools. What they always wanted was certainty. The certainty that payroll will run on time. That compliance will be handled. That when something complicated comes up, the kind of thing that can derail their business if it goes wrong, there is a real partner on the other side who owns the outcome through the last mile. There is a meaningful difference between tools that help you do the work and a partner that takes the work — and the risk — off your plate entirely. For Justworks, this was our core insight at our inception. And now with AI, we are taking that insight much further.

We are a company of about 1,500 people, serving 15,000 small businesses, on track to do more than $500 million in net revenue this fiscal year (ending May 31). For our customers, we handle payroll, taxes, benefits, compliance, and the back office work involved in managing a workforce. We have done that work for over a decade. And we have always done it by delivering service as software – owning outcomes end-to-end, enabled by technology. For most of the SaaS era, that model was ahead of its time. Pure software was the simpler, more rewarded business. But now the world is skating our way. Here is what we have learned from our years of owning outcomes and delivering certainty for small businesses.

Trust: Owning an outcome means owning the relationships and obligations.

For a small business to manage a workforce, they need to interact with government agencies, insurers, financial institutions, and many other providers. To provide small businesses with certainty that this complexity is fully handled, we manage relationships with thousands of tax authorities and jurisdictions across the United States. We own entities in 50 countries so our customers can confidently hire all around the world. We negotiate and administer health insurance risk pools covering hundreds of thousands of people with major carriers. We manage thousands of small businesses within a single high-functioning workers' compensation policy. We manage tight integrations with dozens of providers to automate workflows around things ranging from IT provisioning to business insurance. We move roughly $40 billion a year across major financial institutions on our customers' behalf. None of this is easily automated. Many of these entities and providers have complicated, inconsistent, and somewhat archaic ways of working – all of which make it hard for small businesses to navigate. Even still, we have automated much of what it takes to deliver these end-to-end outcomes. This has required us to build trusted relationships with these entities and providers. Over time, we built the scale to incentivize these partners to try new things that are beneficial to both sides. And now, with AI agents, we can go further and redesign every job that customers trust us to manage on their behalf. For example, AI enabled us to reimagine how we provide Certificates of Insurance. For years, this was a workflow constrained by the systems and processes of outside partners. Because we understood the relationships, the obligations, and the customer needs, we were able to redesign the work around the outcome instead of waiting for the outside system to change. As a result, our system processed more than 1,000 certificates in the last 30 days with no human touch, with a median turnaround time of two minutes. Customers get what they need 24/7 and our teams are freed up for higher-value work. We now look at every institutional relationship and every end-to-end outcome with a fresh set of eyes, asking how we would redesign it from scratch given everything we know and every tool now available to us. We are focused on the intersection of delivering a consistently improving customer experience while also doing things more efficiently. This is where some of the greatest opportunities with AI will come from.

Speed: Owning an outcome means owning the time it takes to get there.

For a small business, the worst thing is getting stuck. Stuck with a problem, stuck waiting, stuck carrying a risk they do not have the time or expertise to resolve themselves. Large companies can absorb delays. They have teams of people who can sit with problems until they are solved. Small businesses do not have this luxury. When they get stuck, the thing they are trying to build falls behind. AI lets us attack that drag differently for our customers, compressing the time between a problem arising and it being resolved. Insufficient funds to cover their payroll, taxes, and benefits is a good example. For small businesses, cash is often in motion. Money may sit across multiple accounts. A customer may need to transfer funds from one account to another before payroll can run. A financing event may land later than expected. We have invested heavily in the automation and technology required to manage these moments quickly and responsibly. The goal is simple: keep payroll moving so employees get paid on time. By taking on risk, intervening earlier, and helping customers resolve issues before the window closes, we turn potential hard stops in their business into managed paths forward. Our AI and automation investments have already reduced time to resolution of insufficient funds by 50% over the past four months.

Service: Owning an outcome means building around the human moments that define the relationship.

The most valuable job AI does in a relationship-driven business like ours is not to replace the customer interaction. It is to make sure our people are present for the interactions that truly matter. Our customers and their employees prefer to self-serve and get on with their days as quickly as possible. But from time to time they really want to talk with a human. When they are buying another company for the first time. When they are hiring internationally. When they get a scary letter from the state of California that they do not understand. When a customer’s employee is at the doctor with their new baby and they are uncertain that their new child is covered on the medical plan. These are moments, which may only be 1-2% of all interactions a customer has with Justworks, that define their experience. In those moments, our customers never have to wonder who is going to help them or how long it will take. They deserve and expect to have access to a human within 60 seconds, 24 hours a day, 7 days a week, who knows their situation, can answer their questions, and make their problems go away. That is the standard we hold ourselves to. And it is the standard that turns customers into advocates who tell every founder they know to use Justworks. The point of AI is not to replace that kind of human relationship. The point is to handle the vast majority of interactions – the pattern-based, transactional ones – so our people can be fully present for the unforgettable moments that matter most.

Trust. Speed. Service designed around the human moments. These are not new ideas for Justworks. What is new is that AI lets us deliver them to many more small businesses at a level that has never existed before. That is what makes this moment so important. AI is helping more people start businesses. But starting is only the first step. The real question is whether those businesses can keep moving when the complexity comes at them at record speed. This is where small businesses have always been let down. They were sold tools when they needed someone to own outcomes. They were sold software when they needed certainty. If this is going to be the golden age for small businesses, they will need real partners in their corner. Not providers that automate tasks. Partners that take full responsibility for results. Small businesses deserve better than what this industry has given them. We intend to be the company that delivers it.

Mike Seckler is the CEO of Justworks.