By: Emily Rumball

When Omer Gotlieb launched Salespeak, he wasn’t trying to create yet another tool in the already crowded AI space. Instead, he was addressing a challenge he had experienced for years: the way B2B companies sell isn’t always effective.

“I’ve worn all the hats: seller, buyer, founder, and executive. And each time, I kept hitting the same barrier. The process simply didn’t seem to work,” he recalls.

From Totango to Salespeak

Gotlieb is no stranger to creating new categories. He co-founded Totango, one of the early customer success platforms, and managed its go-to-market strategy for over a decade before selling to private equity. That journey gave him an understanding of the ups and downs of building an industry from the ground up and the patience it takes.

After Totango, he took some time off, invested in startups, and even earned a pilot’s license. But when ChatGPT came out, curiosity brought him back. “One of the first things I asked it was, ‘Tell me about Totango.’ The response was better than what most SDRs could have provided. That was when the idea sparked,” he says.

If AI could already explain companies better than humans, what did that mean for the future of buying and selling? That question became the foundation for Salespeak.

Redefining the Website

The company’s first product tackles what Gotlieb sees as a significant flaw in B2B sales: the website.

“CMOs spend millions driving traffic there, and what do buyers find? Static pages, forms, and a big red ‘Request a Demo’ button that leads to a multi-day wait and a junior rep who can’t address real questions. It’s an outdated system,” he says.

Salespeak replaces that with what he calls an AI Sales Brain, a conversational layer that can respond to questions in real time, whether they’re about pricing, security, or competitive comparisons. Just as importantly, it listens.

And that listening generates value in two ways:

For buyers, it means immediate, expert-level conversations rather than endless forms.

For companies, it provides insight into what visitors are actually asking, where messaging may be lacking, and which content gaps need attention.

“Our AI doesn’t just assist a buyer in moving forward. It also helps a company understand itself from the buyer’s perspective,” Gotlieb explains. “That balance is what makes a website truly intelligent.”

For Gotlieb, the aim isn’t about reducing costs or replacing salespeople. It’s about building trust. “Buyers don’t want to feel qualified. They want to feel understood. If we can foster that experience at scale, everyone benefits.”

Lessons in Leadership

Gotlieb describes his leadership style as visionary yet pragmatic. He encourages his team to think boldly about the future while emphasizing constant experimentation. “We don’t wait for perfection. We test, learn, and move forward,” he says.

Three values guide him: transparency, empathy, and perseverance. Transparency fosters trust with both customers and employees. Empathy, he says, is central to creating great products. And perseverance, something he learned during the long years of building Totango, helps him stay focused even when progress feels slow.

When asked about his greatest strength, he highlights his ability to identify friction. “Whether it’s in a product flow or a sales process, I can tell when something doesn’t feel right. And I’m relentless about addressing it.”

The area he’s currently working on is developing his public voice. “In customer success, everyone knew to go to Nick Mehta at Gainsight. I want to be that person for intelligent buyer experiences. Not just the founder of a company, but the person people turn to for insights on where the market is headed.”

Vision for the Future

Gotlieb believes we’re only at the start of a significant change in how companies and buyers interact. Right now, Salespeak operates on websites. But soon, he predicts, buyers won’t visit websites at all. Instead, their AI agents will do the browsing.

“Your buyer’s agent won’t wait for a callback. It will expect an immediate response, complete with context,” he says.

In that future, companies will need infrastructure that can communicate directly with those agents. Salespeak is preparing for that shift. But Gotlieb is quick to acknowledge that the timeline is unpredictable. “We tend to overestimate what happens in one year and underestimate what happens in ten. What I do know is that the change is already underway.”

Building Beyond Metrics

Salespeak customers have reported impressive numbers, with conversions increasing from 8% to 50% in some cases. However, Gotlieb is careful not to focus on success purely through metrics.

“The numbers are exciting, of course. But what excites me more is when a CMO tells me they finally understand what buyers are truly asking, or when a visitor says, ‘This felt like talking to your founder.’ That’s the real success.”

He also sees an opportunity to reshape company culture. “AI doesn’t have to lead to layoffs. It offers a chance to rethink roles. Sales Development Representatives (SDRs) were created for the company, not the customer. Now we can place people in positions where they can truly add value, rather than just moving leads along a process.”

Advice to Future Leaders

For aspiring CEOs, Gotlieb’s advice is simple: don’t just build products, create experiences. “The best technology fails if the experience is poor. The companies that eliminate friction and build trust will always have an edge.”

His influences range from mentors in the customer success space to pilots he’s trained with. “Flying sharpens your decision-making. At 10,000 feet, hesitation isn’t an option. That mindset influences how I lead companies, too.”

Adapting to the Future of B2B Sales in an AI-Driven Landscape

Gotlieb has a clear message for today’s leaders: if your website isn’t AI-ready, you risk becoming irrelevant.

“Buyers and their AI tools are already making decisions without you. The companies that adapt now will help define the next era of B2B sales. Those that don’t will likely miss the opportunity to even make their pitch.”

To see how your site measures up, Salespeak offers a free audit at isyourwebsiteready.ai.