It’s time to start taking online booking seriously

Most painting companies lose money before a brush ever touches a wall - not from bad estimates, not even from underpricing, but from the gap between when a homeowner decides they want an estimate and when someone picks up the phone.

As industries from healthcare, to grocery delivery, to hospitality have fully embraced digital booking over the past decade - allowing a customer to actually schedule an appointment - the painting industry has largely held out. In 2026 - a year when we’re constructing data centers in space and building DNA robots - the “callback model” is still the standard.

The reasons make sense - painting is complex; coordinating people is really hard, and great companies often want to preserve the human touch. And frankly, there hasn’t been a great scheduling product. I know many companies have tried and backed off of online booking because of the internal cost, and for good reason.

But the delta between that practice and customer expectations is widening. And its going to cost companies who don’t keep up. A full 35-40% of online appointments are scheduled after-hours when no one’s in the office. That’s nearly half your potential demand guaranteed to hit a wall if your site’s best offer is “we’ll call you back”, before even counting the ones that don’t reach you during the business day.

The vast majority of customers prefer to book online, and it’s dictating what they buy

In 2007, a lanky tech entrepreneur known for his black turtlenecks named Steve Jobs launched the iPhone and put on-demand services and information right in people’s hands. Online booking had already been popularized a decade prior (credit to Expedia and Travelocity who pioneered it in 1996), but - as we all know - smartphones put it on steroids. Today it’s in every corner of our economy. Your customers likely use Calendly at work, Uber to get places, Airbnb to schedule vacations, and more, every day.

Whether or not you see online booking as essential, your customers do. Housecall Pro’s 2025 survey found that 80% of homeowners now factor in online booking availability when choosing a service provider. That’s huge. And this isn’t just a younger-customer phenomenon. Research shows upwards of 90% of Gen Z and of Millennials prefer online booking, but more than 75% of Boomers prefer it when available. Now 30 years in to our online booking experiment, we have all been trained, across industry after industry, to expect control over our own calendars.

AI is raising the stakes - from a matter of convenience, to whether your business is even visible to customers

But there’s more: Traditionally the conversation about online scheduling has been about convenience, but that’s no longer the full picture. AI is now making it about discoverability - whether your customers can even see you when they look for your services.

Imagine going to ChatGPT and saying: “I need to get my house painted. Can you book me estimates with the top three painting companies in my area?”. Sixty seconds later you get a response: “Done. I looked at 10 companies and booked estimates with the best three. I’ve added the invitations to your calendar. Do you have any questions about how to prepare for your estimate”? That’s “agentic AI” at work - AI tools that can go out and complete tasks for you based on goals and rules you give it.

‘Booking with agents’ is real and it’s already here. Google launched agentic booking in AI Mode in late 2025, so now when someone searches for a restaurant or beauty appointment, Google’s AI searches across platforms for real-time availability and links the user directly to a booking page. It’s live now with OpenTable, Booksy, Fresha, and others, with plans to expand to more service categories. OpenAI’s Operator, now in ChatGPT, does something similar: navigating booking flows and then actually completing reservations on the user’s behalf.

Now translate that to home services. When a homeowner asks an AI assistant to “find someone who can give me an estimate on painting my living room next Tuesday,” the agent looks for providers with real-time availability it can book into. A callback form is not just an inconvenience to muscle through, it’s a dead end - the agent can’t complete the task it was asked to do on your site. It moves on and you lose that lead.

Capgemini found that 25% of consumers are already using generative AI for shopping and service discovery. Among Gen Z, more than 70% say they’re willing to hand product research to an AI assistant entirely. If you don’t have a site that allows the agent to complete the task it’s sent to do, you’re going to become increasingly invisible to these customers.

You’ve already paid for the marketing - don’t throttle the business you’ve earned

Imagine taking $25,000 and handing it over to your closest competitor every few weeks.

If you’ve gotten to this point, you’ve probably already started to do the math for your business. The simple reality is that forcing a call to schedule is increasingly going to cause business to bounce and put pressure on margins. If you’re a business with a $5,000 average job size and 50% win rate, then every 10 estimates you let bounce is $25,000 left on the table. You’ve already paid to generate the demand. The question is how much of it you’re letting walk because your booking flow requires a human in the loop.

Complexity has been a barrier, but it’s being solved

Scheduling painting and home services is absolutely complex, particularly if you have multiple sales leads and crews spread across large territories. I’ve spent a ton of time working with companies through the logic behind how they schedule, and it gets deep. Sending an estimator to lead with needs that are out of scope, or sending them back and forth across town has a real cost. So for good reason, most businesses have stayed away.

AI is the major unlock, because for the first time software can apply the critical human-like judgement that turns self-service scheduling from a liability that sends your team all over the place to bad leads, to a super power - and do so affordably. If you’ve built your business on differentiated customer service and human touch, that no longer needs to be a trade-off.

Healthcare resisted online scheduling for years, with managers similarly arguing “too complex, too many variables”. Then patient demand won out. Today, 67% of patients prefer online booking, and over 50% of Millennials and Gen Xers report they would switch providers specifically to get it. Actually proactively change providers. Travel went through the same curve earlier. A hotel requiring a callback to book a room would be out of business tomorrow.

Home services is on the same path. The convergence of demographic shift and AI infrastructure means the gap between “book now” and “we’ll call you back” is going to widen fast, with the former becoming a leak that gets more expensive every year.

Companies that get started early have an opportunity to lock-in outsized returns

How you approach scheduling should ultimately reflect your business strategy. Some companies use the effort of a phone call or call-back as a mechanism to screen for intent - accepting a lower volume of leads, with a higher target conversion rate. That’s a valid strategy and can be effective depending on your market, strengths and goals for the business. The question is whether the change in customer behavior that pushes them further into digital channels makes this as sustainable, for as many businesses, as it once was. I think it’s a fair bet to say that window is already narrowing and will further.

You can adapt - without compromising

This all goes to say - we started building scheduling software for painting businesses because we believe giving customers an easy onramp to your business and efficient, high margin operations doesn’t need to be a trade-off. We also believe that this is route to a business that is actually more distinctly human, not less, and this is incredibly important in a world that is increasingly remote and digital. Imagine a world where your people are freed up to dedicate their full attention to customers when it matters, when they want to be talking to you, or when you really need something from them, versus spending their time on administrative calls and data entry. That’s the grounds for truly exceptional customer service.

Doing AI right is all about finding those points of leverage - using it not just to automate for automation’s sake, but to power high impact human experiences.

Not all scheduling solutions are alike. In our next newsletter, we’ll talk about the cost of depending on online scheduling tools that don’t fit your business, and what we believe the right solution needs to do. In the meantime, give us a shout if you have questions.

[Up Next: Online scheduling doesn’t have to be terrible - Why we’re building scheduling software Pt II]