How Chili Piper's CEO Built a $50M ARR SaaS Company with a Flat Org Structure: Lessons from Alina Vandenberghe's Keynote

What is Chili Piper? It’s the demand conversion platform that powers the demo booking process for companies like Monday.com, ClickUp, and HubSpot. But beyond being a scheduling tool, Chili Piper represents something more radical: a new way of building and scaling SaaS companies that challenges every traditional playbook.

In her recent keynote at SaaS Open (watch the full presentation here), CEO Alina Vandenberghe revealed how she grew Chili Piper to $50 million in annual recurring revenue while maintaining a flat organizational structure. Her unconventional approach offers valuable lessons for founders who are tired of following the same worn-out advice. What makes her strategy particularly compelling is that it addresses the changing expectations of both employees and buyers in today’s SaaS landscape.

The Power of Believing You Can Win

“The most important thing for me when I hire someone in my company is that they have the belief that we can achieve the kind of crazy numbers together,” Vandenberghe explained during her keynote (view the full slide deck here). This isn’t just motivational speaking – it’s a fundamental hiring criterion that has shaped Chili Piper’s entire organization.

Unlike traditional hiring practices that focus primarily on skills and experience, Vandenberghe looks for two core traits: belief in the company’s ability to succeed and a genuine desire to help others. These values can’t be taught, she argues, but they can be identified and cultivated. This approach aligns with what many successful bootstrapped founders have discovered – hiring for attitude and values often trumps hiring for pure technical ability. The Chili Piper platform itself reflects these values, designed to help sales teams convert more pipeline by treating prospects with respect rather than tricking them into funnels.

For founders looking to implement this strategy, Vandenberghe’s approach offers a clear framework. During interviews, probe beyond technical capabilities. Ask candidates about times they’ve persevered against odds, how they’ve helped colleagues succeed, and what drives them beyond a paycheck.

Breaking Down the Flat Organization Structure

The concept of flat organizations isn’t new, but Vandenberghe’s implementation at Chili Piper takes it to an extreme that would make most VCs nervous. “I gave control away a long time ago,” she stated boldly. In her system, decision-making happens collectively, not from the top down.

This structure emerged from her reading of Paul Graham’s essay on “Founder Mode” and Brian Chesky’s experiences at Airbnb. The traditional advice of “hire great people and get out of their way” sounds good in theory, but Vandenberghe found it doesn’t work for founders who have strong visions and particular ways of doing things. Instead, she created a system where self-management thrives within clear frameworks.

The Chili Piper structure operates on several key principles:

• Self-management with purpose-driven teams
• Collective decision-making
• Full authenticity at work (no masks or corporate personas)
• Fluid action-taking based on who’s best positioned to execute

This approach has allowed Chili Piper to maintain agility even as they’ve scaled their product suite. What started as a single scheduling tool has evolved into a comprehensive demand conversion platform with five core products. As explored in this guide to multi-product strategies, expanding your product line requires careful orchestration – something Vandenberghe has mastered through her flat structure.

The $50M ARR Journey: From Point Solution to Platform

Understanding what Chili Piper has become requires looking at its evolution. The company started with a single product – the scheduling solution that Monday.com, ClickUp, and HubSpot now use for their demo processes. But Vandenberghe didn’t stop there.

“We actually had at some point an inbox as well,” Vandenberghe revealed, discussing one of the products they killed. The inbox allowed buyers to see their entire buyer journey and track company interactions. They discontinued it after realizing the insurmountable challenge of getting people to switch from Gmail or Microsoft. This willingness to kill products that don’t fit demonstrates the kind of focus that separates successful SaaS companies from those that plateau.

Today, Chili Piper’s platform includes five core SKUs:

1. Form Routing
2. Chat
3. Team Handoff
4. Scheduling
5. Lead Distribution

The multi-product strategy serves two purposes: cross-selling to existing customers and creating multiple entry points for new ones. This approach to product expansion has been crucial for reaching their current ARR milestone while maintaining cash flow break-even status.

The Numbers Game: Building Predictable Growth

“Numbers can sometimes hide reality, but there are numbers that you can rely on in your pipeline,” Vandenberghe emphasized. Her approach to growth isn’t based on hope or hustle – it’s grounded in data and systematic execution.

When she took over marketing as acting CMO two years ago, Vandenberghe became obsessed with several key metrics:

• ICP (Ideal Customer Profile) identification
• Account targeting and touches
• Pipeline velocity
• First engagement optimization

The results speak for themselves: Chili Piper now books 500 meetings per quarter through their systematic approach. This level of performance doesn’t happen by accident. It requires what Vandenberghe calls a “game plan” – precise activities tracked against pipeline conversion metrics.

For founders wondering about Chili Piper pricing or considering Chili Piper alternatives, understanding this metrics-driven approach is crucial. The platform’s value isn’t just in its features but in its ability to provide measurable pipeline impact. This focus on quantifiable results has helped them compete effectively even as Chili Piper alternatives have emerged in the market.

AI-Powered Operational Excellence Without Losing Authenticity

One of the most innovative aspects of Chili Piper’s growth strategy is their use of AI for operational excellence. Vandenberghe shared how they use AI for ICP identification, account scoring, and targeting – but with an important caveat: “You don’t have to send robocallers to book business. You don’t have to send fake emails.”

Their AI implementation focuses on authentic engagement. They’ve identified specific criteria that indicate propensity to buy:

• Companies with more than 10 sales reps
• High volume of leads
• Complex sales cycles
• Good financial standing

Conversely, they’ve learned to avoid certain characteristics:

• Europe-based companies (longer sales cycles)
• Outlook users (slower decision-making)
• Traditional companies resistant to change

This data-driven approach to customer selection might seem ruthless, but it’s actually more respectful of everyone’s time. By focusing on companies most likely to benefit from Chili Piper, they avoid wasting prospects’ time with solutions that won’t fit. For founders exploring the Chili Piper API or Chili Piper extension, this targeting philosophy extends to their product design – building for specific use cases rather than trying to be everything to everyone.

The Community-First GTM Strategy

“There’s something that remains which is our humanity and our ability to connect with others,” Vandenberghe stated, addressing the elephant in the room about AI and automation. While Chili Piper leverages AI extensively, their go-to-market strategy remains fundamentally human.

Their approach to community building goes far beyond traditional B2B SaaS tactics:

With Employees: Vandenberghe personally helps employees find new opportunities, even outside Chili Piper if that’s what’s best for their growth. This radical approach to employee development creates advocates for life.

With Prospects: No tricks, no fake funnels, no useless eBooks. Every interaction aims to genuinely help, whether or not it leads to a sale. This authenticity has become a key differentiator in a market full of aggressive sales tactics.

With Customers: Support extends beyond deployment. Chili Piper helps customers with success metrics, gets them speaking opportunities, and celebrates their personal milestones. “If they’re sick, we send them chicken soup,” Vandenberghe shared, illustrating the depth of their customer relationships.

With Partners: Creative collaboration beyond standard playbooks. Their partnership with Mutiny, for example, included joint events and influencer collaborations that benefited both companies’ audiences.

The Influencer Strategy That Actually Works

In an era where influencer marketing often feels forced, Chili Piper has cracked the code on authentic influence. “Influencers care as much about audience as we all do,” Vandenberghe noted. “Being creative and helping them get more reach is a lot more important than just cash.”

Their influencer strategy focuses on mutual value creation rather than transactional relationships. By helping influencers grow their audiences and create better content, Chili Piper has built a network of authentic advocates. This approach has generated impressive results, with influencer-driven impressions contributing significantly to their pipeline.

For founders investigating what is Chili Piper and how it differs from competitors, this influencer strategy provides a key insight. The platform’s success isn’t just about features like the Chili Piper login experience or technical capabilities – it’s about the ecosystem and community that surrounds it.

Cross-Selling and Ecosystem Plays

Vandenberghe credits Bob Moore’s book on ecosystem-led growth as a major influence on their strategy. Using tools like Crossbeam, Chili Piper has built sophisticated partner plays that drive cross-sell opportunities across their five-product suite.

“You didn’t build a product, you’ve created an entire industry,” one industry analyst told Vandenberghe. This ecosystem approach means that every customer, partner, and even competitor becomes part of a larger narrative around demand conversion. It’s a strategy that’s particularly powerful for multi-product platforms, where each additional product creates new integration and partnership opportunities.

The Counterintuitive Lessons for Founders

As we analyze Vandenberghe’s keynote and Chili Piper’s journey to $50M ARR, several counterintuitive lessons emerge:

1. Give Up Control to Gain Scale: The flat organization structure requires founders to surrender traditional control mechanisms. This feels risky but actually accelerates decision-making and innovation.

2. Kill Good Products: The discontinued inbox product wasn’t failing – it just didn’t fit the strategic vision. Having the discipline to cut good-but-not-great initiatives is crucial for focus.

3. Hire for Belief, Not Just Skills: Technical skills can be taught; belief in the mission cannot. Vandenberghe’s hiring philosophy prioritizes cultural fit and mission alignment over pure expertise.

4. Help Competitors Succeed: By focusing on growing the entire demand conversion category, Chili Piper has positioned itself as the leader of a movement rather than just another vendor.

5. Measure Everything, Automate Carefully: While AI powers much of their operation, the human touch remains paramount. Technology amplifies authentic relationships rather than replacing them.

Building Your Own “Company of the Future”

For founders inspired by Vandenberghe’s approach, implementing these strategies requires careful consideration of your own context. Not every company can or should adopt a completely flat structure overnight. However, the principles underlying Chili Piper’s success are universally applicable:

Start with Values: Define what matters beyond revenue. For Chili Piper, it’s helping others succeed. This core value influences every decision from hiring to product development.

Build Systems, Not Hierarchies: Focus on creating systems that enable autonomous decision-making rather than approval chains. This might mean better documentation, clearer metrics, or more sophisticated communication tools.

Invest in Community: Whether through influencer relationships, customer success programs, or employee development, building genuine community creates compound returns over time.

Embrace Transparency: The flat structure only works with radical transparency. Everyone needs access to the information required to make good decisions.

Stay Close to Customers: Despite their growth, Vandenberghe remains actively involved in customer relationships. This direct connection informs product decisions and maintains cultural alignment.

The Future of SaaS Organizations

As Vandenberghe noted, “Traditional playbooks of entrepreneurship don’t work anymore.” The younger generation of workers and buyers expects different things from SaaS companies. They want authenticity, purpose, and genuine value – not just features and functionality.

Chili Piper’s success demonstrates that building a different kind of company is not only possible but potentially more profitable. By optimizing for “euphoria at work” rather than traditional metrics, Vandenberghe has created a sustainable competitive advantage that’s difficult to replicate.

For founders considering Chili Piper alternatives or building competing solutions, the lesson is clear: copying features is easy, but replicating culture and community is nearly impossible. The real moat isn’t in the code – it’s in the connections.

Taking Action: Your Next Steps

Whether you’re building your first SaaS product or scaling past your first million in ARR, Vandenberghe’s playbook offers actionable insights:

1. Audit Your Hiring: Are you hiring for belief and values alignment, or just filling seats?
2. Examine Your Structure: What decisions could be pushed down to teams rather than up to leadership?
3. Review Your Metrics: Do your numbers reflect real pipeline health, or are you tracking vanity metrics?
4. Assess Your Community: Who are your true advocates, and how are you investing in them?
5. Challenge Your Assumptions: What “best practices” are you following simply because everyone else does?

The path to $50M ARR doesn’t have to follow the traditional SaaS playbook. As Vandenberghe proved, sometimes the best strategy is to throw out the playbook entirely and build something authentic to your values. In a world where every product can be copied and every feature can be replicated, culture and community remain the ultimate differentiators.

For those ready to dig deeper into Vandenberghe’s strategies, her complete keynote presentation and slide deck provide additional insights. And if you’re looking to connect directly, she promised to accept LinkedIn connections from attendees – just mention “SaaS Open” in your request.

The future of SaaS isn’t just about better products or slicker interfaces. It’s about building companies that people actually want to work for and buy from. Chili Piper’s journey from point solution to platform, from startup to $50M ARR, shows that doing things differently isn’t just possible – it might be the only sustainable path forward.