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Omer Gotlieb
Redefining the B2B Buying Experience. Building, Mentoring, Investing.
Omer Gotlieb is the Co-Founder and CEO of Salespeak.ai, a company he established in May 2023.2 Salespeak.ai is an AI-driven sales enablement platform that aims to revolutionize the B2B buying experience for both sellers and buyers.1
Prior to founding Salespeak.ai, Gotlieb co-founded Totango, a customer success platform, where he served in various roles including Co-Founder, SVP Business Development, and Chief Customer Officer from 2010 to 2022.2 His professional experience also includes:
- Builder, Mentor & Investor at Gotlieb Ventures (April 2022 - Present)2
- VP, GM Service Providers Division and VP Products at MTS (2005 - 2010)2
- Senior Account Manager at Addwise (2002 - 2004)2
- Director of Client Services at AtHoc (2000 - 2001)2
Gotlieb is passionate about mentoring founders and sharing his experience in scaling companies and navigating entrepreneurship. He is on a mission to transform the B2B buying experience, driven by his firsthand frustrations as both a buyer and a seller.3 Based in Palo Alto, California, Gotlieb continues to lead Salespeak.ai in developing AI-powered solutions for inbound sales and customer engagement.12
Highlights
After 2 decades, why did I decide to jump into another startup, this time as CEO? The answer is simple, but the journey to get here wasn’t...
Over the years, I grew tired—tired of being sold to in ways that felt impersonal, time-wasting, and disconnected from my actual needs. We’ve all been there: the endless cold calls, the spammy emails that use our first names in the subject lines, but don’t speak to us; the sales scripts that make us feel like just another target.
I’ve been in the GTM trenches wearing different hats: seller, buyer, sales manager, etc. And what I’ve consistently felt is that people selling to me were wasting my time; making me feel like I was just a cog in a sales process designed for them—not for me. I’ve been involved in startups for over two decades, never as a CEO, but this time, I decided to jump into that role because I felt so excited about solving this problem.
Sales should be about delivering real value, not how many times you can “hack” your prospect into answering a call or responding to an email. The old B2B GTM playbook is outdated and focused on the seller. That’s why I started Salespeak—we're focused on helping customers deliver the experience buyers want. We’re here to redefine what it means to engage with customers, to create genuine interactions, and to ensure that value is at the heart of every conversation.
Am I alone? I want to hear: what frustrates you the most when it comes to today’s selling tactics?
One of the most challenging yet crucial lessons in sales is learning when to say "no" to customers...
It can be tempting to try and close every deal, but not every customer is the right fit for your product. And that's okay.
It’s far better to walk away from a deal that doesn’t align with your strengths than to force a sale that could lead to frustration, churn, and ultimately, damage to your company reputation.
By setting clear expectations from the start, thoroughly understanding the customer's needs, and being honest about what your product can—and cannot—deliver, you create a foundation of trust. In some cases, a well-timed "no" can be more valuable than a premature "yes."
What was one of the hardest lessons you've learned? I'm curious to learn from others.
