saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by, a serial acquirer of B2B SaaS companies.

In episode #32, Anna Nadeina talks with Kyle, Co-Founder and CEO at Proposify, the online proposal software that gives you the control and visibility you need to better manage your sales document process.

Laying the Foundation: Building a Robust Product

The foundation of any successful SaaS company’s upmarket journey lies in the strength of its product. Kyle emphasizes the importance of continuously refining and enhancing the product to meet the evolving needs of enterprise-level clients. This involves a deep understanding of the target market, identifying pain points, and leveraging customer feedback to drive product development.


Prioritizing User Experience and Scalability

As SaaS companies move upmarket, the focus shifts from catering to small businesses to serving the complex requirements of larger organizations. This transition demands a heightened emphasis on user experience, seamless functionality, and the ability to scale to accommodate the needs of enterprise-level customers.

SaaS companies must invest in developing advanced features and capabilities that cater to the unique needs of larger organizations. This may include enhanced security protocols, robust integrations, custom reporting, and enterprise-level support and service-level agreements (SLAs).

Pricing is another critical component of the upmarket strategy, as it directly impacts the perceived value of the SaaS offering and the ability to generate sustainable revenue. Kyle emphasizes the importance of carefully evaluating pricing models and structures to ensure they align with the needs and expectations of enterprise-level customers.

As SaaS companies move upmarket, the pricing models often need to evolve from the straightforward, one-size-fits-all approach used for smaller businesses to more complex, tiered pricing structures that cater to the diverse requirements of enterprise-level clients. This may involve introducing premium features, usage-based pricing, or custom enterprise-level packages.


Striking the Balance Between Value and Profitability

Pricing for the enterprise market requires a delicate balance between providing value to customers and ensuring the SaaS company’s profitability. Kyle talks about the importance of thoroughly understanding the target market, the perceived value of the offering, and the competitive landscape to set pricing that aligns with the company’s growth and revenue goals.

Positioning for Dominance: Crafting a Compelling Narrative

Effective positioning is crucial in the SaaS upmarket journey, as it shapes the way potential customers perceive the company and its offerings. Kyle shares insights on how Proposify has navigated this crucial aspect of their growth strategy.

Differentiating Through Expertise and Thought Leadership

To stand out in the crowded enterprise SaaS market, Kyle emphasizes the importance of establishing the company and its leadership as industry experts and thought leaders. This can be achieved through strategic content creation, personal branding, and actively sharing the company’s experiences and data-driven insights.

Aligning Marketing and Sales for a Cohesive Approach

Successful upmarket positioning requires a seamless collaboration between marketing and sales teams. Kyle highlights the importance of aligning these two functions to ensure a consistent brand narrative, targeted messaging, and a streamlined customer experience throughout the sales cycle.


Navigating the Challenges

The journey of moving a SaaS company upmarket is not without its challenges, and Kyle shares valuable lessons and insights gained from Proposify’s experience.

One of the key lessons Kyle shares is the importance of carefully timing the expansion of the sales team. He cautions against the common mistake of hiring a sales team too early, emphasizing the need to first establish a strong product, pricing, and positioning foundation before scaling the sales function.


Embracing a Balanced Approach: Growth Hacks and Sustainable Systems

Kyle underscores the importance of striking a balance between growth hacks and building sustainable systems within the organization. While growth hacks can provide short-term boosts, he emphasizes the long-term value of investing in hiring great people and developing robust processes to support the company’s upmarket aspirations.


Head of Growth,