231 Sam Rosen - Scaling Remote Teams: Building Community & Culture through Coworking

Welcome back to SaaS Fuel, the podcast where we explore the challenges and opportunities in scaling businesses and building thriving company cultures. In today's episode, we're diving into the future of work with our guest, Sam Rosen, cofounder and CEO of DeskPass.

Join us as Sam shares his insights on navigating the evolving landscape of workplace flexibility and the rise of coworking spaces. Get ready to rethink traditional office models as we discuss the emergence of flexible leasing, the critical role of culture and transparency in team dynamics, and Sam's vision for a workplace that prioritizes happiness and community.

Don't miss this conversation packed with strategies to fuel your SaaS journey!

Key Takeaways

00:00 On-demand support, productivity system, data trust insights.

03:15 AI insights reveal data gaps in strategies.

10:52 Confidently adapted and maintained perspective amidst uncertainty.

12:43 Respect, autonomy, transparency, trust, and good culture.

16:20 Aggregate diverse workspaces for seamless booking experience.

21:43 Office space is evolving into intentional ecosystems.

25:42 Evolving focus: Coworking software to filling spaces.

29:37 Selling new cooking methods requires mass education.

31:14 Co-working concept challenging to market widely.

35:53 Landlord partnerships offer flexibility; shared risks, rewards.

38:58 Traditional offices aren't optimized for human needs.

42:58 Workplace flexibility crucial for talent retention.

44:10 DeskFest helps understand employees' workplace preferences.

47:59 Humans crave community; virtual can't replace it.

Tweetable Quotes

"Thriving Amid Uncertainty": "For us, we had customers that really believed in us, and we had investors that really believed in us. So it was it was going to them and being honest and being kind of clear about the future." — Sam Rosen 00:11:23

"Redefining Workspaces: We aggregate lots of different operators in your given market. And often that means, aside from some of the big guys, you get, local operators, community operators, people that actually, like, are building a space intentionally in the community near you, which I think is at least the type of space that I really enjoy." — Sam Rosen 00:16:43

Inspired by ClassPass: "We went from a membership model, which became more and more challenging to administer because the business matured and economics and spaces changed, to, you know, instead of selling one off, how do we really focus on teams and, like, predominantly mid market teams where we can, you know, like, where we can, sell groups of people opposed to one off?" — Sam Rosen 00:27:30

Viral Topic: The Evolution of Market Awareness: "So part of it is nothing that we did, and it's just that the market had to learn and be educated, and that takes brute force." — Sam Rosen 00:30:43

"Rethinking the Traditional Workspace": "Traditional office has not been a great setup for everybody forever. And, as this paradigm has changed, building and thinking about the end user and how you optimize around them, I think, is what's gonna lead." — Sam Rosen 00:40:08

"Flexible Work Environments": "What I think companies are doing is they're coming into people's houses and they're replacing it with a dimmer and saying, how much work do you like, how much light do you need?" — Sam Rosen 00:44:28

SaaS Leadership Lessons

Flexibility and Adaptability:

Sam Rosen's journey with DeskPass is a testament to the importance of being flexible and adaptable. Companies initially lost a significant portion of their business during COVID-19 but pivoted from serving individuals to focusing on teams and organizations. Effective SaaS leaders must stay agile and ready to pivot their strategies in response to market changes and shifting customer needs.

Employee Autonomy and Respect:

Building a strong company culture where employees feel respected and autonomous is crucial. DeskPass cultivated an environment where employees were judged on their deliverables rather than their processes, emphasizing trust and transparency. SaaS leaders should focus on empowering employees, fostering a workplace where trust and respect are foundational principles.

Leverage Crises as Growth Accelerants:

Instead of viewing the pandemic solely as a setback, Sam Rosen emphasized using it as an accelerant for growth. This mindset shift helped DeskPass stay focused and double down on their mission. SaaS leaders can draw from this lesson by seeing challenges as opportunities for innovation and growth, leveraging crises to redefine their business strategies.

Value of Customer Relationships:

Rosen highlighted the importance of maintaining strong relationships with committed customers and investors who believed in their vision. SaaS leaders should prioritize building and nurturing relationships with their customer base, understanding their needs, and integrating their feedback into the product development process. This helps in gaining loyal customers and investors who will support the business through ups and downs.

Balancing Technology with Human Interaction:

Despite technological advancements, Rosen underscored the irreplaceability of human interaction and community. Successful SaaS companies should not solely focus on tech solutions but also on creating opportunities for meaningful human interactions, both within their workforce and for their customers. SaaS leaders can foster a more connected and engaged team by balancing remote work technologies with initiatives that encourage collaboration and community-building.