He Raised $50M And Leveraged M&A Growth Strategies To Reimagine The Customer Support Experience And Disrupt A $500B Industry

For Matt Price, entrepreneurship was not a sudden leap but the culmination of decades working at the forefront of tech innovation. His journey progressed from his early days in the UK tech scene to executive leadership at Zendesk and to launching Crescendo.

What makes Matt’s story stand out isn’t just his transition from operator to founder in hyper-growth companies. It’s how he’s redefining customer service by building top-notch teams, combining AI and human support, and scaling through strategic acquisitions.

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

From Department Stores to Hypergrowth Tech

Matt was born and grew up in a small town in the UK. His fascination with technology began in a department store in a small English town. Too impatient to wait until Christmas for a computer, he taught himself to code in the store and ended up outselling the staff.

This was Matt’s first brush with problem-solving. He recalls that he wasn’t a great academic student or a book guy. But he managed to get through college just on his computing skills. These skills led him along a non-traditional educational path, leading to Borland International.

Borland was one of the fastest-growing PC software tools companies of the time, and quickly became Matt’s “hands-on MBA.” There, he worked with talents like Mark Randolph, who later co-founded Netflix.

Matt loved the exposure to an amazing caliber of people and the serendipity to fall into that dynamic environment. From those early operating roles, his mantra became simple: get into high-growth companies and learn everything about technology and business ideas.

That’s how Matt built a career as a cross-functional innovator inside corporations long before he launched his own venture. He dived into different roles and projects within that environment, which became a great foundation.

The Zendesk Era: A Front-Row Seat to SaaS Disruption

Zendesk brought Matt to the U.S., marking a pivotal shift in his journey. His motive for moving was to experience hypergrowth. Zendesk was a 50-person company with only a few million in ARR when he joined.

While he initially hesitated, Matt followed his instincts and Twitter feed into what would become one of the leading SaaS companies in the world. Over 12 years, he witnessed the birth of a new customer support paradigm, powered by real-time cloud tools and data transparency.

Looking back, Matt recalls how he had experienced many technology shifts, from basic PC, client-server, and web internet to SaaS. When large language models (LLMs) were launched, he knew this would reinvent the whole stack and domain.

Matt wanted to be part of this next wave, seeing an opportunity big enough to start from scratch. When his co-founders, Anand Chandrasekaran and Andy Lee, approached him with the idea he began by assessing the opportunity versus risk balance.

Crescendo: Born to Disrupt a Half-Trillion Dollar Industry

Crescendo isn’t just a tech company, it’s a response to decades of broken promises in customer service. But the current approaches to actually disrupting customer service were very siloed. The industry needed to step back and reassess how to transform itself.

Backed by General Catalyst’s company creation fund, Crescendo was formed around a bold thesis: AI could finally transform the $500B BPO (business process outsourcing) industry. But only with a combined solution of human expertise and cutting-edge technology.

Their unique approach paid off and delivered incredible results within a year. Matt noted that as customer care quality increases significantly, the cost to deliver it also decreases.

The early advantage? Crescendo didn’t need to build everything from zero. They partnered with a startup that was already building 80% to 90% of the required tech stack. That team joined as co-founders, allowing Crescendo to move fast and land pilot customers within months.

Betting Big on Outcome-Based Pricing

Crescendo’s pricing model is as disruptive as its technology. While many companies talk about “outcome-based” pricing, Crescendo has taken it to an extreme: if the customer’s query isn’t resolved, or the customer isn’t satisfied, they don’t pay.

This model re-aligns the incentives across the entire support stack: business, supplier, and end-user, resulting in an alignment of motivations. Early customers saw drastic improvements in care quality, alongside meaningful cost savings.

In an industry plagued by siloed bots and endless call transfers, Crescendo’s AI-plus-human model offered a breath of fresh air and quantifiable results. It has transformed how the customer experience will work in the future, while lowering the cost for its clients.

Matt explains that customer service has always been supply-driven and dependent on company budgets. But now, they can afford to open up the channels and talk to customers whenever they want. Customers now have a 5x to 10x increase in engagement with the business.

Customer service has always been a back-end service aspect, but thanks to Crescendo, it is now back in the boardroom since the volume of interactions has been incredible.

Matt cites American Express as an example. In an interview, its former chairman, Kenneth I. Chenault, talked about how the company was all about customer service because it is a premium brand and has built it into its product.

But Crescendo had effectively leveled the playing field thanks to the unlimited customer care it delivered. It threatened the American Express moat.

Building a World-Class Team: Passion and Experience

Matt emphasizes that passion, fire, and enthusiasm exist across generations and dimensions. It can be incredibly powerful if they’re curious and passionate about the opportunity.

Matt’s team includes engineering leaders who built Genesys Cloud, a COO with multiple operations under their belt, and Andy Lee, the founder of one of the largest contact center companies in the world. The Crescendo software is amazingly scalable with fail-safe measures built into it.

Matt explains that it has several features unlike any other AI platform. This became possible because its engineers have extensive experience, having built similar things that have proven to operate at the scale of millions of users.

Matt’s approach as CEO? Optimize for alignment, not command-and-control, since Crescendo has highly experienced talent. As he puts it, managing Crescendo is more like coaching an elite basketball team—high skill, high stakes, and high collaboration.

Raising Capital with Clarity: Milestone-Based Funding

Crescendo has raised over $50M, but not through massive headline rounds. Instead, Matt and General Catalyst agreed on milestone-based tranches, unlocking new capital only when pre-agreed business goals were hit. These included product-market fit and executing the first acquisition.

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This approach helped Crescendo stay focused on operations, not just fundraising. It also created a rare alignment between founder and investor on what value creation actually means. Matt calls it meeting their “value creation milestones.”

Product-Market Fit Came Fast—And So Did Growth

Thanks to the pre-built tech and outcome-first approach, the company hit product-market fit almost immediately. But Matt and his team didn’t stop at organic growth.

They saw a unique opportunity to scale via M&A, a model traditionally associated with roll-ups but now reimagined as a distribution strategy to create more value.

Matt explains the strategy behind using M&A and points out that the BPO and labor market are currently highly commoditized. The game is not just about outsourcing business processes but also about finding offshore labor at the lowest cost. Essentially, it’s an arbitrage.

The Crescendo philosophy is to partner with organizations that are highly skilled operators. Coming from a tech background, Matt talks about how he is constantly impressed by their operational rigor.

Matt’s first acquisition brought not only operational capability but also 200 happy customers, many of whom were quickly transitioned to Crescendo’s platform. The result? Higher CSAT, lower costs, and accelerated market access—months or years faster than a purely organic strategy.

Matt credits their supportive investors who had a clear understanding of the transactional side of things. They helped him think through the execution from a unique perspective to building growth.

Matt explains how they haven’t lost sight of organic growth, but have a complementary approach of acquiring BPOs, augmenting those BPOs with agentic AI, bringing on their book of business, upgrading the customers, and creating significantly more value both for them and for Crescendo, as part of the roll-up.

A Vision for the Future: Service as a Design Choice

From the customer’s perspective, Matt sees a world where customers can interact with a company at any time and get help. They want the interaction to be frictionless and non-frustrating, and they don’t want to waste their time.

This vision has been thrown out by many sellers marketing CX tools, but they haven’t worked. Crescendo has approached the problem uniquely by combining AI with human interactions. It is now exploring the different dynamics of customer support.

As Matt reveals, they are now working with clients who provide reasonably sophisticated home and connected devices and direct customers to support businesses like Crescendo. Customers like to interact with a voice that can provide solutions.

Crescendo eliminates the bad bot experience that routes them to the back of the queue. Then, it sends them callbacks from different-level employees, only to explain the problem again and again. Instead, they get real support, powered by a hybrid of smart AI and skilled human interaction.

CX no longer becomes a frustrating, reactive cost center but a proactive asset. With Crescendo, Matt believes any business can now offer that same level of premium care at scale.

Matt envisions a world where customers can unbox a product, load the app, or enter a QR code. Instantly, they connect to someone who can help them through the installation process. He wants companies to view customer service as essential to operations and worth investing in.

Matt concedes that it is highly challenging for customer service leaders to drive transformation and change at an exceptional level. Integrating consistently evolving AI and technology into their infrastructure is expensive and requires resources.

Matt draws parallels to the rise of contract manufacturing, which triggered a host of Innovations within connected devices because manufacturers didn’t have to set up their production lines to deliver products like baby monitors. Thus, they could quickly get their prototypes into the market.

Matt strongly believes a similar revolution will happen in the customer service vertical. Entrepreneurs and founders will think, “What is my design for service? How do I want it to work?”

Next, they can partner with Crescendo to fulfill the customer service needs of the business instead of putting all the pieces together themselves.

Advice to Founders: Admit What You Don’t Know

If Matt could give his younger self one piece of advice, it would be this: lean into what you don’t know. He notes that one of the unexpected perks of being a founder is the freedom to admit your blind spots and surround yourself with advisors who’ve been there before.

From legal experts to M&A veterans, his “phone-a-friend” strategy has helped him confidently navigate unfamiliar terrain.

Final Thoughts

Matt Price didn’t start with a plan to become a founder. But through decades of working across tech inflection points, from the PC era to SaaS to AI, he developed the instincts to seize the right opportunity when it appeared.

With Crescendo, he’s not just building a company; he’s rewriting how businesses engage with their customers. Judging by the traction and vision, the era of frustration-based customer support might finally be coming to an end.

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

• Matt Price transitioned from corporate operator to founder by recognizing AI’s potential to reshape customer service.
• Crescendo combines AI and human support to deliver outcome-based customer service that aligns business and consumer interests.
• The company reached product-market fit rapidly by partnering with a pre-built tech team that joined as co-founders.
• Milestone-based funding from General Catalyst allowed Crescendo to focus on execution rather than constant fundraising.
• Strategic acquisitions brought operational capacity and hundreds of customers, accelerating Crescendo’s growth.
• Crescendo challenges industry norms with its “only pay for outcomes” pricing model, driving measurable results.
• Matt’s leadership philosophy emphasizes alignment over control and the power of surrounding yourself with expert advisors.

 

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