Bryan Shankman's SaaS Journey: From Jobber Plugin to AI Lead Qualifier

Our CEO Bryan Shankman recently sat down with Jeremy Rivera, SEO author & Podcast host, to discuss our company's evolution from a Jobber plugin to our new AI-powered lead qualification tool. Here are the key insights from that conversation.

The Origin Story

When asked about how Tool Desk began, Bryan shared the unconventional start:

"We started with Tool Desk, the Jobber plug-in... The insight that led us to build there starting about a year ago was that we connected with a Pest Control owner. She owns a Pest Control up in Seattle. And she had posted on Reddit, believe it or not, asking about a ringless voicemail system."

That initial connection led to a custom solution that yielded impressive results:

"She got her accounts receivable down by about $50,000. And she was using Jobber. And so when we were building this custom thing for her, we hopped into the Jobber app store... We'd both worked previously on Shopify apps and realized that there was a very nascent marketplace with Jobber with maybe 40 apps at the time and said, if you could get in on the Shopify app store when it had 40 apps, that would be a home run."

The Pricing Strategy

On the business side, Bryan explained our approach to pricing the Jobber plugin:

"For Tool Desk, the Jobber plug-in... it's 149 a month. And that includes SMS and email marketing campaigns, flows, automations. Our biggest costs there are the SMS credits, so we kind of price around that."

He highlighted how our deep integration with Jobber creates value that justifies the price:

"What makes us compelling... is that we have a really deep integration with Jobber. We completely built a custom built integration where we essentially clone the Jobber data into our system so that you have it in real time to build filters on, filter your audiences on, and you don't have to worry about a CSV export the moment you add a new client to Jobber."

The Platform Risk Challenge

One of the most candid parts of the discussion centered around the challenges of building on another platform:

"When we started with them, had, you could not send an email campaign. You couldn't do it. This is a seven, eight year old company. You couldn't do a blast email through their system, let alone do an SMS blast... That was what inspired us like, man, we can fill in the gaps on all of these things that Jobber is missing."

However, this strategy came with significant risks:

"The following Monday, they do this like big event and they basically ship our entire product... If you're building something that's truly working, they probably will. Why wouldn't they? Just game theory. If you're making 20 grand a month on some thing they could ship in 30, 90 days and then absorb all of that. Why would they not do that? Really?"

The Pivot to AI Lead Qualification

This experience accelerated our move toward a standalone product:

"Aaron and I said, okay, what would we do that would be entirely separate from any existing system? What can we connect to all systems with Zapier? What has minimal onboarding lift? What doesn't what can't be like totally baked and taken away by a bigger CRM we're tied to. And that's where we landed with Tool Desk AI, the AI lead qualifier."

Bryan describes our new offering, now rebranded as LeadTruffle, in simple terms:

"The elevator pitch is Tool Desk AI's 24/7 sales rep that captures leads on your website and then qualifies them over SMS using AI."

The AI Approach

During the interview, Jeremy shared an anecdote about his friend Michael McDougald who installs toilet partitions and has "a very long, surprisingly long challenging process to get a proper quote built out in his system." This highlights the complexity that different home service businesses, like asphalt contractors face when trying to automate their processes.

When asked about potential concerns with AI hallucinations, Bryan explained our measured strategy:

"We started with just capturing the data from the lead and then allowing our users, our end, our business users to qualify manually, basically look at the data... Initially, almost like not even really using AI. Like it was AI, but it wasn't because it was so deterministic."

He elaborated on how we've expanded the AI capabilities:

"The AI is trained on each customer's website. So we scraped the website, and that's sort of the initial training data... We basically give open AI two prompts. One of them is like a system prompt, which is more general... If you ever get confused, don't make stuff up... And then the lower priority prompt is from our user, which is, hey, I need you to ask these five questions."

Onboarding Simplicity

For LeadTruffle's onboarding process, Bryan emphasized our focus on simplicity:

"We're ruthless about removing friction from the onboarding process. Right now the process what we do is when you first sign in, we ask for your website... We then scrape your website and that fills out two key sections of the agent instructions. One's your company description... And then the second section is your products and services."

This approach reflects our understanding of our customers:

"You and I sit behind our computer all day, as do probably a good amount of people listening to this. These folks don't. Home service owner operators really don't. They're out and about."

Advice for SaaS Entrepreneurs

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Bryan offered valuable advice for aspiring SaaS founders:

"Unless you have an absolute home run, no brainer, people, letter of intent, ready to pay you to use the thing you're about to build, I would not even think about starting a SaaS company unless you know how to code, you're willing to learn how to code, or you have a great partner that can code."

He stressed the importance of being able to iterate quickly:

"What we're realizing here with V2 is speed and iteration... We do that at like a ruthless pace... if I had had to spend $100 an hour to go back and forth with a dev agency offshore. That would have taken weeks, probably. It would have taken $500 to $1,000 or more, probably. But Aaron, who's a great developer on his own and thanks to things like AI, can ship super fast."

Connect With Us

Want to learn more about our journey or try our products? Visit:

• Tool Desk - email & SMS marketing for Jobber
• LeadTruffle - text-based AI sales rep for local business.

You can also connect with Bryan on Twitter @BryanShankman.

This article is based on Bryan's interview on the Unscripted Saas Podcast with Jeremy Rivera.