This Entrepreneur Raised $50 Million To Build A Conversion Platform and AI Sales Agents In Brazil

Matthew Kligerman’s path as a founder is a masterclass in vision, adaptability, and persistence. His entrepreneurial story is woven with bold moves, serendipitous moments, and relentless curiosity.

Matthew’s story offers rich insights from early ventures in South Florida and at Duke, bootstrapping ventures in Brazil, scaling a growth-stage business across telecom, health insurance, and banking sectors, and what it takes to build a company that thrives in challenging markets.

In this engrossing interview, Matthew talks about adapting his experiences as a climber into building, scaling, and financing his companies. He also reveals unique aspects of the adventure of building a company in Latin America.

Listen to the full podcast episode and review the transcript here.

The Seed of Entrepreneurship

Born in Florida, Matthew grew up in an entrepreneurial household where both parents operated small professional services businesses. The lessons began early—selling T-shirts door-to-door for fundraisers, selling muffins at flea markets, and even rolling a wagon full of toys to sell to neighborhood kids.

These ventures were childhood pastimes, but they laid the groundwork for a future marked by ingenuity and determination. Summers spent in North Carolina at Matthew’s grandfather’s summer camp, Blue Star, further shaped his outlook.

Matthew remembers working many jobs at Blue Star Camps, from counselor to coordinating counselors to running rock climbing programs.

Watching his grandfather’s creation thrive, touching thousands of lives annually, instilled in him the desire to build something that would create lasting memories and profound impact—not just profit.

Engineering a Path to Problem-Solving

Matthew’s fascination with engineering was sparked by his high school physics teacher, Mr. Arechabaleta, a Cuban nuclear physicist-turned-educator whose passion inspired a young Matthew to explore the mechanics of the universe and how things worked.

With his love for rock climbing and its ingenious devices and an affinity for math and sciences, Matthew pursued a degree in mechanical engineering at Duke University. Here, his knack for entrepreneurship surfaced in a rather unconventional way.

The Accidental Business: Legacy Links

While at Duke, Matthew served as the president and webmaster of the university’s Outdoors Club, updating HTML and other content. A seemingly innocuous email offering $10 monthly for a backlink on the club’s website piqued his interest.

One link turned into twenty, generating revenue worth $2400, which was big money then. He used the money to fund trips and equipment for the club. Curious about why companies were willing to pay for these links, Matthew delved into SEO (Search Engine Optimization).

Digging deeper, he found out about the link graph algorithm that Google had built. Matthew understood how other websites and the internet are linked to one another. And how websites receiving high-quality links ranked higher.

Matthew discovered a lucrative industry where backlinks were worth thousands of dollars. Seizing the opportunity, Matthew scaled the operation into the largest .edu backlink marketplace of its time, recruiting friends from universities nationwide.

Unknown to him initially, Matthew was engaging in “black hat” SEO practices, which were highly effective but not compliant with Google’s rules. Eventually, lead generation laid the foundation for a deeper understanding of digital marketing and business operations.

Matthew ended up building an agency and his own network of lead generation web properties, using his backlink network to drive the properties to the top of Google search pages quickly for valuable search items like “car insurance,” generating leads and then selling those leads to others in the market.

This side hustle taught Matthew invaluable lessons about digital marketing, scaling, managing teams, and evolving from short-term gains to sustainable, high-quality strategies.

Entering The Corporate World

Despite Legacy Links’ success, Matthew chose to enter corporate America post-graduation, joining Citi amidst the fallout of the 2008 financial crisis. He considers it a terrible time to be trying to enter the job market. He joined Citi but not on one of the typical investment banking or trading desks.

At Citi, Matthew worked on a product team building services and technology for fund managers, which they could use to manage their investment funds and firms better. He remembers it as an experience similar to building a business within a bank.

Matthew continued running Legacy Links while balancing corporate life. His exposure to venture-backed startups and private equity firms refined his business acumen, and learnings from both jobs complimented each other.

Working with the portfolio companies of a handful of VC and PE investors, Matthew learned the importance of data, preparation for pitching clients, and what true excellence looks like from seasoned A+ entrepreneurs.

A Brazilian Adventure Turned Decade-Long Journey

In a serendipitous twist, Citi offered Matthew an opportunity to work on a one-year project in Brazil. What began as a temporary assignment turned into a decade-long adventure redefining his career. Experiencing Brazil’s consumer market first-hand was a revelation for Matthew.

As he navigated everyday tasks like securing the internet, getting a mobile plan for his phone, opening a bank account, and getting health insurance, he encountered outdated processes and inefficient customer experiences.

The customer acquisition technology and methodologies used in the Brazilian market seemed several years behind those in the US.

Many companies’ conversion funnels weren’t even digital and operated out of brick-and-mortar stores or agents visiting customers’ homes to sell products, such as insurance agents visiting their homes with 100-page books of insurance plans that were difficult to understand.

This inefficiency in conversion funnels, juxtaposed with the billions spent on digital marketing by Brazilian brands, revealed a massive gap ripe for innovation.

Founding Escale: Revolutionizing Customer Acquisition

Fueled by this insight, Matthew left Citi to co-found Escale with Ken Diamond and Daniel Rosa. The company aimed to transform customer acquisition in Brazil by addressing inefficiencies in digital marketing funnels and creating seamless, impactful customer experiences.

Matthew’s decision to bring Ken to Brazil—with nothing more than a one-way ticket, a makeshift apartment, and a phone plan—epitomized his resourcefulness and belief in the venture and their partnership.

Matthew, Ken, and Daniel started by helping Brazilian telcos, insurance carriers, and banks to acquire incremental customers. Escale built and managed the end-to-end digital conversion funnels for brands.

Escale would not just generate the leads from proprietary channels such as lead gen properties and custom audiences but also convert those prospects into sales and activated customers for brands.

And in doing that, the trio perceived the most significant challenge that brands faced was specifically on the conversion side.

Building a Conversational Conversion Platform with AI Sales Agents

So, Matthew, Ken, and Daniel went all in toward building a conversational conversion platform that would help banks, telcos, insurance carriers, auto dealers, utilities, and others convert leads into customers with higher conversion rates and lower acquisition costs.

On average, Escale’s customers increase their conversion rate by 50%, with some success cases at a phenomenal lift of over 200% while also significantly reducing conversion costs.

The Escale conversion platform leverages AI and data from millions of customer interactions each month to create optimized sales journeys on a custom, one-on-one basis for each lead, with seven key modules:

1. Lead Qualification & Scoring – combining proprietary data sources, customer data, and customer business rules to determine product availability for that specific prospect and the likelihood of the lead converting.
2. Lead Channel Optimization & Routing – determining the ideal engagement channel (AI sales agent, human chat, phone agent, or eCommerce) to convert that specific lead and seamlessly routing the lead to the identified channel.
3. Lead Conversion with AI Sales Agents – a multi-channel lead conversion platform powered by AI Sales Agents that converts prospects into paying customers.
4. Customer Onboarding Automation – automating customer onboarding documentation and contract formalization.
5. Marketing Re-engagement – re-engaging leads that did not convert with custom, gen-AI messaging for each lead.
6. Data Attribution – sending the multi-channel conversion data back to the brands’ marketing platforms so marketing teams have granular marketing campaign ROI attribution.
7. Escale’s AI Sales Agents Perform 30% Better Than Humans in WhatsApp Sales A/B Tests
   The most recent aspect added to the conversion platform is Escale’s AI sales agents.

Formerly, Escale would direct leads requiring assistance to their customers’ call centers or their human chat teams. Now, Escale has added AI sales agents that convert prospects into leads autonomously and has reached more than human parity.

In A/B tests of WhatsApp sales channels, Escale’s AI Agents consistently deliver brands an additional 30%+ conversion lift vs their top-performing sales teams.

The AI Sales Agents are built on top of knowledge bases Escale builds with each customer, with information about their products and how to sell them, data from millions of sales conversations with prospects each month, and security and compliance guardrails.

Escale connects and integrates into its customers’ systems for credit checks, product availability, pricing, documentation, and contract finalization so AI sales agents can drive that conversion 100% autonomously.

In Brazil, Escale’s sales process is mainly conducted via WhatsApp, the primary chat platform consumers leverage day-to-day in the market.

However, Escale’s platform is agnostic and can run conversion through any chat channel, including native apps, third-party chat platforms, meta, or other channels.

Brands have adopted Escale’s platform extensively, given the value proposition of increasing conversion rates and reducing acquisition costs.

The Escale Business Model

Escale gets paid for incremental sales it generates for its clients. Escale implements its technology and measures transactions processed via the platform, earning a percentage of each transaction.

Most revenue is only generated when Escale delivers incremental sales for customers, strongly aligning incentives with its customers versus a traditional SaaS licensing model.

Bootstrapping to Institutional Funding

Matthew, Ken, and Daniel started off by bootstrapping Escale entirely and leveraging customer cash flows to fund it.

Matthew remembers trying to navigate the complexities of opening a bank account and, in the early days, traveling by metro to access the only ATM that accepted his US debit card for cash to pay his 15 employees.

Because of the limited withdrawals, Matthew would pay a little of each employee’s salary daily. Initially, Escale operated out of his apartment but eventually moved to a small office above a little pizza restaurant in São Paulo before moving to a larger space for several hundred employees.

However, their vision for building a conversion platform necessitated external capital. The breakthrough came with a deal to serve a major telecom company in Brazil. This milestone unlocked their first institutional round, raising $1.1M in seed funding.

One of the few Brazilian venture capital firms that invested in early-stage tech and software companies backed the company along with a few angel investors. This initial funding allowed the founders’ team to scale their platform and launch its first customer.

Escale significantly increased the telecom partner’s sales, becoming their largest sales channel. Building on this momentum, the team added a second telecom partner and secured additional investment from Global Founders Capital with a follow-on from Redpoint Ventures.

Sector Expansion and Strategic Partnerships

Escale builds customizations and integrations with market-specific systems and data sources in each market vertical the company enters. With a growing platform in the telco vertical, Escale expanded into health insurance and banking.

Partnering with Kasek Ventures, known for their expertise in scaling businesses like Mercado Livre, the team raised $7M in a Series A round. This funding helped them integrate their platform with major health insurers and branch into banking.

They worked with prominent Brazilian banks on auto finance loans, credit cards, collateralized loans, account opening, car equity, and more. To date, Matthew has successfully raised over $50M. The company’s following funding rounds, led by QED Investors and Invus, underscored a long-term vision.

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QED’s expertise in backing and building top fintech companies aligned with Escale’s expansion into banking. Invus, a top-tier evergreen family office, brought a private equity perspective, supporting the team’s goal to build a strong, long-term business.

Matthew explains that Ken’s and Daniel’s objectives have always been to build a long-term company without seeking a short-term sale. He and his co-founders wanted to double down at every milestone and take the business to the next level.

A Secondary Transaction and Mountain Climbing Insights

Matthew’s decision to step back into an executive chairman role coincided with his move back to North Carolina to be closer to his family. Matthew sold some shares via a secondary sale, allowing him to slightly diversify from 100% personal financial concentration in a single asset.

Matthew recalls how their funding rounds were oversubscribed beyond Escale’s mid-term cash requirements. This led to a dynamic where a modest secondary transaction as part of late-stage fundraising enabled funds to acquire their target allocation.

At the same time, the founders took some chips off the table while remaining deeply vested, with more than 95% of their net worth focused on Escale.

Though modest, this brought much-needed balance and peace of mind during the unpredictable rollercoaster of entrepreneurship and enabled the entrepreneurs to make decisions optimized toward long-term value creation.

Reflecting on this journey, Matthew highlighted the parallels between mountain climbing and business building. In both, he shared, you face uncertainty, develop trust with your team, and take one step at a time toward what initially seems like an impossible goal.

Lessons in risk mitigation, adaptability, and partnership from Matthew’s climbing adventures translated into his entrepreneurial ventures. Roping in his co-founders, he embarked on adventures, traveling and climbing mountains, including El Cap and a few routes in Yosemite and Patagonia.

Matthew remembers sleeping for four or five nights on El Cap’s vertical face and passing nights of heavy storms in Patagonia. The element of physical and emotional partnerships, complementary skills, and the ability to support and energize each other underscored their trips.

A New Venture on the Horizon

After a sabbatical, Matthew’s passion for building pulled him back into the entrepreneurial world. Drawing inspiration from Brazil’s advancements in customer engagement via WhatsApp, he aims to bring innovations to the U.S. market.

Matthew’s vision involves leveraging generative AI agents to transform how brands interact with customers—spanning beyond conversion to full client life-cycle management, including product usage, customer support, and customer fidelity and engagement, focusing on a particular vertical market of interest.

In Conclusion

Matthew Kligerman’s journey—from selling muffins at flea markets to revolutionizing AI-powered customer acquisition in Brazil—is an inspiring story in entrepreneurship.

His story reminds us that curiosity, adaptability, and a commitment to impact can turn even the most unexpected opportunities into thriving ventures.

Listen to the full podcast episode to know more, including:

• Matthew Kligerman’s journey began with childhood ventures that taught him ingenuity and determination.
• During his college years, he leveraged an accidental discovery about SEO to build Legacy Links, a highly profitable .edu backlink marketplace.
• Experiencing inefficiencies in Brazil’s customer acquisition processes inspired Matthew to co-found Escale, a company transforming conversion funnels.
• Escale’s AI sales agents outperform human counterparts by 30% on platforms like WhatsApp, revolutionizing sales conversions.
• Matthew and his co-founders started with limited resources but scaled Escale with strategic partnerships and funding rounds.
• Matthew applied insights from his mountain climbing experiences, such as trust, adaptability, and teamwork, to entrepreneurship.
• After stepping back from Escale, Matthew plans to bring generative AI-driven customer engagement innovations to the U.S. market.

 

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