Scaling the Unscalable with John Eitel

Breaking into a new market is no small feat. It’s a labyrinth of challenges, uncertainties, and endless decision-making. But as with any maze, there’s always a path to the center if you navigate it. 

In this podcast episode, we had the privilege of navigating this complex terrain with John Eitel (current Chief Sales Officer at Demandbase), former Head of Sales at Canva. This company grew exponentially from 500 to 4,000 employees in just a few short years. 

Our conversation wasn’t just a casual chat but a deep dive into John’s journey of spearheading Canva’s foray into the North American market. With insights that range from organizational strategy to the nuances of sales and product-led growth, this episode is packed with valuable takeaways for anyone facing similar challenges.

The Pull of Canva

John had his pick of companies to join but chose Canva, a decision not solely based on its impressive growth, from 500 to 4,000 employees in just a couple of years. 

He explained, “Canva has a certain allure, a commitment to mission and vision that you don’t find everywhere.” John sensed that Canva wasn’t just about revenue and making a difference. 

This became a decisive factor in his move to Canva.

Mission at Hand: Sales, Strategy, and Success

So, what was John hired to do at Canva? 

In his own words, “To carve out new possibilities.” This meant more than just cutting ribbons for a new office. He had to construct the first sales team from scratch and position Canva in the fiercely competitive North American market. And if you’re wondering about the outcome, the team not only met but also exceeded targets, setting a new precedent for what a launch could look like.

The How-To’s and What-Not’s

John touched on several important factors that led to Canva’s success. For starters, he discussed the critical balance between sales and product-led growth. 

He clarified that it was a “chicken and egg situation” but emphasized that a strong product sets the stage for effective sales. Renewals? Those were managed by Customer Success, allowing Account Executives to focus on acquiring new customers.

The dynamics of the buying journey have changed in recent years. “The customer journey isn’t linear anymore,” John noted, hinting a need for a more flexible, adaptable approach to customer acquisition and retention.

The Secrets of Global Market Entry

While the steps in the sales process might appear universal, John Eitel stresses the importance of localized messaging. He warns against importing an “American-sounding pitch” to markets like London or Australia, as it may backfire. 

A sales message needs to be as agile and adaptable as the markets you’re entering. This rings especially true for regions with an aversion to what they perceive as ‘salesy’ American tactics.

The Anatomy of Sales Success

John introduces the concept of a rotational model involving top sellers from the main office supporting the new market. 

These individuals serve as cultural translators, ensuring a seamless alignment between the company’s core values and the local market’s preferences. They bring in the know-how of the parent company while adapting to the local ethos.

John also couldn’t stress enough the value of hiring regional experts when opening a new market. These individuals bring an invaluable local perspective that helps navigate the unique challenges and opportunities each new market presents. The “pitfalls and traps” are best understood by those who have lived and breathed the local business landscape.

Embracing Product-Led Growth in Sales-Averse Markets

According to John, the emergence of companies like Atlassian and Canva, with their transparent sales processes, reflects a global shift toward Product-Led Growth (PLG). These companies are gaining traction precisely because they don’t “sell” in the traditional sense. 

They focus more on treating customers as humans, an approach gaining more and more traction, especially in markets averse to American-style sales tactics.

Sales and Customer Success Strategies During Crisis

1. Shifting Sales Strategies in Times of Crisis

During the early days of the pandemic, companies had to pivot quickly to adapt to the new normal. One such instance was a swift alteration of sales strategies from closing deals to initiating trials and enabling users. This helped maintain business continuity and nurtured potential long-term relationships with customers.

Key Takeaway: Being agile in your sales strategy can help your company survive and thrive in a crisis.

2. Quotas and KPIs: Adjusting to Market Realities

Setting realistic KPIs and quotas is essential for any sales team. During the pandemic, a notable shift was made from traditional sales quotas to focusing on setting up free trials. These adjusted KPIs provided an alternative avenue for the sales team to show their performance and helped keep the business afloat during uncertain times.

Key Takeaway: Tailoring your KPIs to market conditions can make your business more resilient.

3. Empathy as a Sales Strategy

The crisis brought into sharp focus the importance of empathy in sales. A compassionate approach is more likely to yield fruitful relationships when businesses and people are struggling. The team approached their sales pitches not with aggressive targets but with an understanding of their potential clients’ current hardships.

Key Takeaway: Empathy can be a potent tool in a salesperson’s arsenal, particularly during tough times.

4. Agility in Team Structures

The lines between Account Executives (AEs) and Customer Success Managers (CSMs) blurred as both roles collaborated in unprecedented ways. This synergy led to greater unity and effectiveness in reaching common goals, such as onboarding new users and customer enablement.

Key Takeaway: Flexibility in team structures can lead to unexpected but highly effective collaborations.

5. The Importance of Core Values in Crisis Management

Staying true to core values, especially in times of crisis, can be a guiding light. When the going got tough, these values were invoked to make critical business decisions that were strategic and humane.

Key Takeaway: Core values aren’t just words on a wall; they are the principles that can guide you in the darkest times.

6. Accelerated Adoption: Navigating Challenges and Learning on the Fly

The crisis forced the team to quickly adapt and fix breaking onboarding procedures under the stress of accelerated adoption. Learning on the fly became a part of the process, and free users were more forgiving as they understood the circumstances.

Key Takeaway: Crises can fast-track innovations and solutions in business operations.

7. Converting Crisis Into Opportunity: From Free Trials to Paid Customers

The move to offer free trials built a vast pipeline and culminated in a high conversion rate once the crisis started to ebb. This strategy turned what could have been a period of stagnation into an opportunity for growth.

Key Takeaway: Crisis situations can be turned into opportunities with the right strategies.

8. Scaling Beyond the Initial Department: A Case Study

The success with the initial department opened doors for scaling across other departments. This multi-department adoption eventually led to broader, site-wide agreements, demonstrating the benefits of a well-executed scaling strategy.

Key Takeaway: Success in one department can be leveraged for company-wide adoption with the correct scaling strategy.

Navigating the Complexities of “Free” and Rapid Scaling

Q: Is Selling ‘Free’ Products Easier?

A: It’s More Complex Than It Appears

John clarified that selling free products is no walk in the park. The key to success lies in setting the right frameworks and metrics to focus on customer engagement and conversion rather than just customer acquisition. John even suggested that the expectation of future metrics shifting from usage to conversion rates kept the team in check.

Q: Do Customers Lower Their Expectations When Products are Free?

A: Customer Expectations Remain High

According to John, customers expect a thorough sales experience, even when a product is offered for free. The sales process must still add value and be compelling enough for customers to consider implementing your free solution over competitors.

Q: How Important is Adaptability in Sales Organizations?

A: Adaptability is Essential for Scaling

John recounted his experience of rapidly scaling a sales team, emphasizing the importance of hiring a Sales Enablement Leader. This addition streamlined the training process, making it more structured and effective, which was particularly important in remote onboarding.

Q: What Challenges Do Time Zones Pose?

A: Time Zones Can Create Efficiency Bottlenecks

John found that time zones posed a logistical challenge in scaling internationally, mainly when IT support was based in another country. This highlights the necessity of localized support to facilitate smoother operations.

Q: What Lessons Were Learned from Onboarding Remotely?

A: The Importance of Localized Resources and Regular Check-ins

John discussed how onboarding 30-40 salespeople virtually was far from easy. It required regular check-ins, structured Slack channels for communication, and eventually localized IT support to improve efficiency.

The Complex Terrain of Remote Work and Company Culture

Remote work is no longer a luxury or a prospect; it’s the here and now. Start-ups, particularly those in the tech industry, embrace the decentralized work approach. However, while the freedom and flexibility are irreplaceable, the challenges are real. 

Team members wearing multiple hats early on can lead to role confusion. Furthermore, the monotony of a remote environment can chip away at motivation over time. Despite these challenges, businesses that start with a remote-first approach have the upper hand in instilling a solid remote culture from day one.

Micro and Macro Company Culture

Every company has a culture, shared values, and a mission that binds its people. But how do you ensure cultural consistency when your team is scattered globally? The answer lies in balancing a global ‘macro-culture’ and localized ‘micro-cultures.’ 

While the core values and mission of the company should remain unaltered, there is room for local flavors. For instance, an office in Austin may incorporate live music into their gatherings, or the team in France might share local wines during a virtual happy hour. These small touches make a difference in team cohesion and job satisfaction.

Strategic Decision-making in Sales

As a company scales, decision-making gets complex. This involves intricate strategies like defining the sales motion for different market segments. 

Do you offer the same level of attention to a 10-person start-up as you do to a Fortune 500 company? 

By setting clear rules of engagement based on metrics like employee count or annual revenue, businesses can allocate their resources more efficiently. Such strategies can prevent potential bottlenecks and ensure that all customers, regardless of size, receive the attention they deserve.

Building Virtual Communities and Real Connections

Let’s face it: remote work can sometimes feel isolating. 

Companies are getting creative to combat this isolation by building virtual communities. Slack channels dedicated to non-work-related chatter, Zoom game nights, and other virtual team-building activities are rising. And when global travel restrictions eased, the simple joy of finally meeting coworkers face-to-face was unparalleled.

The Road Ahead: Adaptation and Learning

Scaling a remote business involves constant adaptation. Whether it’s pivoting your company’s cultural initiatives to suit a remote setup or overcoming the hurdles of cross-geographical collaboration, the learning never stops. 

But it’s precisely this fluidity and openness to change that sets the stage for a resilient, unified, and successful organization.

From Growth-at-All-Costs to Sustainable Scaling

The last few years have been a whirlwind of change for B2B buying behavior, forcing businesses to reconsider their growth strategies and adapt to new realities. The initial ‘growth-at-all-cost’ mindset has become untenable, primarily due to the rising customer acquisition costs and tighter budgets. Economic uncertainties and longer decision-making cycles are further complicating the landscape. These factors are causing a pivot in how companies view their sales and marketing efforts.

Within this complex scenario, the rise and partial fall of Product-Led Growth (PLG) has been notable. While PLG became a popular strategy, enabling quick customer acquisition and engagement, it also received its share of skepticism, especially when companies over-indexed on it. The dilemma is finding the right balance between PLG and more traditional approaches.

Amidst these shifts, there has also been a change in sales tactics. The most innovative sellers are quickly adapting their strategies to be more empathetic and focused on customer growth, especially when new customer acquisition becomes challenging. Sales Development Representatives (SDRs) are also evolving, equipped with tools that offer invaluable insights into buyer intent, which is essential in today’s volatile market.

But it’s not just about the tools or the tactics. It’s also about adopting a sustainable, scalable, and repeatable model to weather these uncertain times. The focus is increasingly on leveraging AI and other technologies not to replace the human element but to complement it, ensuring that opportunities are matched with the right kind of seller at the right time.


Successfully breaking into new territories and scaling a business is more complex than ever. John Eitel’s insights from his experience at Canva demonstrate the importance of a holistic approach, combining sales and Product-Led Growth strategies. Key to this is a deep understanding of local market nuances, an agile and empathetic sales strategy, and a focus on building genuine customer relationships.

Equally important is the readiness to pivot strategies in times of crisis and ensure that your KPIs and team structures adapt to the current realities. Remote work adds another layer of complexity, emphasizing the need for a solid corporate culture and regular engagement with your team.

As we navigate the complexities of current economic conditions and a shift in B2B buying behavior, a sustainable, scalable, and empathetic approach seems to be the future of sales. It’s not just about numbers anymore; it’s about being human-centric, adaptable, and open to continuous learning.

This multifaceted approach ensures short-term wins, long-term success, and resilience in change.


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