How Outreach’s CEO Went From Selling PCs to Building a $4.4B Sales AI Powerhouse

Manny Medina had $1 million in investment capital left and was selling office computers to pay outstanding bills. His first startup, GroupTalent, was two months away from shutting down. Today, he’s built Outreach along with Wes Hather, Gordon Hempton, and Andrew Kinzer into a $4.4 billion company that processes over 33 million sales interactions weekly and serves more than 6,000 customers including Zoom, Twilio, and McKesson.

Breaking Family Traditions

Born to engineer parents in Ecuador, Medina’s childhood blended hard work on his stepmother’s shrimp farm with mandatory summer reading. “My family was well-educated but we didn’t have a lot of money. I was sent to private schools and there wasn’t money left to buy a computer,” he shares.

Like many teenagers, he rebelled against his parents’ career plans. “I told them that I didn’t want to be an engineer. I told them that I wanted to be an economist,” Medina recalls. “Of course, my parents completely ignored me.”

His decision to study in America rather than Europe came from a similar spirit of defiance. “The original plan was to go to Germany. My parents put a higher value on the education you could get in Europe when it came to engineering. I think that I came to the US mostly because I was fighting with my dad.”

From Language Barrier to Harvard

Landing in the U.S. with limited English skills, Medina took an unconventional approach to mastering the language. He studied The Economist magazine extensively, learning to write and speak in its style. This dedication led him to complete his Master’s in Computer Science at Penn State, followed by an MBA at Harvard.

“I was blown away by the opportunity I found in the US, with the amount of available capital and freedom of ideas. The fact that you can be whatever you wanted,” says Medina.

The First Startup

After successful roles at Amazon and Microsoft, Medina and his partners launched GroupTalent, a recruiting solution. “My partners and I were looking for ideas that were broken and that software could fix. We were looking for things with very high friction, and very high price,” he explains.

The venture nearly ended in bankruptcy. “We were literally two months from going out of business,” Medina reveals. “We were inventorying computers and selling them for cash to pay for outstanding invoices. It was that close to the end.”

This near-failure proved transformative. “It made me fearless,” says Medina. “When you have a successful career where everything goes right – you go to all the right schools, you get all the right jobs – and then to have a company and run it to the ground and may need to shut it down. Once you stare down that situation, nothing else will break you.”

Birth of Outreach

The breakthrough came when Medina noticed something unexpected. Their recruiting software’s email feature was getting unprecedented response rates. “They were asking us things like, ‘How is it that your software is getting a 40% reply rate on email when we get 5%?'”

This insight led to Outreach’s creation in 2014. The company’s early days were marked by intense customer focus. “We took the ability to land something with a customer so incredibly seriously that to us was paramount to religion,” Medina emphasizes. “We would never dare to write a line of code without knowing that a customer was not only willing to use it but use it regularly and pay for it.”

Building Through Customer Obsession

Outreach developed what Medina calls “uncomfortably close customer success.” “We would call the customer nearly every week,” he recalls. “We were calling them and saying, ‘What’s going on?’ Where do you get stuck? It was literally like we were watching you from behind so we could jump in and identify the problem.”

Rootly saw a significant transformation after implementing Outreach, with a 41% increase in prospects contacted, a 130% surge in emails delivered, and a 69% rise in meetings scheduled. Reflecting on the change, JP Cheung, Rootly’s Business Development Leader, explained, “We were using a different sales software, but the manual steps involved were slowing our team down. Outreach offered far more advanced functionality, support, and integrations compared to our previous system. Sometimes, choosing the top brand truly pays off.”

Technical Innovation and AI Leadership

Over the past seven years, Outreach has made significant strides in AI, reshaping how sales teams operate. The platform processes over 33 million action-outcome pairings weekly and leverages more than 3 billion signals to train its machine learning models. With capabilities like predicting deal closures with 81% accuracy and forecasting revenue outcomes with 99% accuracy, Outreach delivers real-time AI-powered insights that drive decision-making. It offers features such as account summaries, sentiment analysis from meetings, calls, and emails, and auto-generated messages based on conversation context. Additionally, it provides call and meeting summaries with key topic timestamps, detects action items during live calls, and analyzes pipeline coverage and trends. As CEO Medina emphasizes, “AI needs to work in real time—if the direction of an outcome doesn’t change, it doesn’t matter.”

Outreach has been committed to advancing AI for over seven years, aiming to transform the way sales teams operate. CEO Medina explains, “We fundamentally believe AI will change the way we sell… our goal is to make all 30 million B2B reps incredibly successful.” The company’s AI initiatives focus on several key areas. Its AI-assisted selling streamlines the sales cycle by drafting emails, recommending next steps with prospects, evaluating pipeline health with over 81% accuracy, and predicting deal closures. Natural language processing (NLP) capabilities analyze sentiment and intent in communications, identifying appointments, deferrals, and objections while processing email content for deeper insights. Outreach also excels in data standardization, converting diverse inputs like voicemails, emails, and chat logs into machine-readable formats. Leveraging transfer learning, the platform incorporates advancements from Google, Microsoft, and Amazon to efficiently share insights across models, ensuring the latest AI technology powers its solutions.

Outreach recently introduced the Outreach Mobile App (BETA) redefines productivity for sellers on the move, putting the full power of Outreach directly in the palm of your hand. Designed to keep pace with the fast-moving world of field sales, this app streamlines task management, call logging, and account reviews, ensuring no opportunity slips through the cracks. With a user-friendly home screen to prioritize your day, call recording and seamless logging features to capture every detail, and comprehensive prospect and account views for instant preparation, the app keeps your deals moving forward effortlessly. And this is just the beginning—future updates like a Prospect Map, Kaia meeting summaries, and Assist will make meeting preparation and route planning even smarter. Whether you’re between meetings or on the road, the Outreach Mobile App ensures you’re always prepared, productive, and ready to close deals.

Kaia, Outreach’s AI-powered assistant, revolutionizes sales productivity by providing real-time support during calls and meetings. Seamlessly integrated with Outreach Voice, it automatically joins and enhances meetings on platforms like Zoom and Teams. Kaia offers features such as live transcription, automatic action item capture, and content cards that surface critical information like competitor insights or pricing details. It syncs notes, bookmarks, and action items directly to transcripts, enabling efficient follow-ups and reducing manual effort. Designed to streamline workflows, Kaia empowers sales teams with immediate insights and smarter decision-making during every interaction.

New Leadership for the Next Chapter

In 2024, Medina transitioned to executive chairman, appointing Abhijit Mitra as CEO. Under Mitra’s leadership, Outreach has already:

• Increased win rates by 26%
• Improved forecasting accuracy by 43%
• Shortened sales cycles by 19%

In 2024, Mitra took over as CEO, with Medina moving to executive chairman. “I am honored to become Outreach’s CEO,” said Mitra. “We are in a pivotal moment in sales, with AI delivering efficiency gains we’ve never seen before. Now is the time for Outreach to demonstrate our expertise in taking revenue technology to new heights – our current AI offering is just the beginning.”

At Outreach, a dynamic culture rooted in core values fuels the company’s success. The team embodies the spirit of hungry craftspeople, driven by an obsession with continuous improvement and the grit to tackle challenges head-on like true champions. They view their customers as partners, sharing in their triumphs and challenges with unwavering empathy. Honesty is the backbone of their relationships—with themselves, their colleagues, and their community. Outreach fosters a supportive, family-like environment, where everyone has each other’s backs and celebrates wins together. Embracing ownership of collective success, they encourage authentic self-expression and thrive on diverse perspectives, recognizing that inclusion is their greatest strength. Together, they craft not just solutions but a workplace where innovation and camaraderie go hand in hand.

The Road Ahead

With nearly $500 million in funding and backing from major investors like Sands Capital, Salesforce Ventures, and Lone Pine Capital, Outreach continues to grow. The company ranks No. 1 on the GeekWire 200 list of privately-held tech companies in the Pacific Northwest.

Medina remains focused on AI’s role in sales: “What I’m excited about is how much it’s going to elevate the sales profession… reps are now going to have way more time to really diagnose the problem for a customer, to really empathize with a buying committee.”

His grandfather, once head of Ecuador’s Communist Party, might seem an unlikely ancestor for a capitalist success story. But Medina sees alignment in their values: “His political conviction came from the fact that he really cared about people and wanted to help create a just society… With me starting a company and making sure that everybody here has great opportunities and the ability to participate — I think he would be fine with that.”

From near bankruptcy to building a $4.4 billion company, Medina’s journey shows that success often comes from recognizing opportunities in unexpected places. “I don’t have 10 great ideas,” he says. “I have one and this is my one shot.”