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The DocuSign Playbook: Product Management Strategies for Enterprise Success

Building a successful enterprise cloud product is a marathon, not a sprint. It requires a unique blend of vision, strategy, and perseverance. In a recent conversation on the Startup Project podcast, Court Lorenzini, co-founder of DocuSign, shared his invaluable insights into navigating this complex landscape. His journey, from the initial spark of an idea to a $16 billion market leader, offers a treasure trove of wisdom for product managers looking to build the next generation of enterprise cloud solutions.

The Genesis of an Idea and the Grind to Product-Market Fit:

DocuSign wasn’t born overnight. It started with a simple yet powerful idea: enabling legally binding signatures via the internet. However, the path to product-market fit was a slow and deliberate grind. Lorenzini emphasized the importance of rigorously testing the market’s willingness to pay, even before building a prototype. This crucial step allows product managers to validate their assumptions and ensure they are solving a real problem for their target audience. He also shared a powerful tactic: actively trying to “kill” your own idea by seeking out founders of failed similar ventures. Understanding the reasons for their failures can help you identify and mitigate potential pitfalls early on.

One of the key takeaways for enterprise product managers is the importance of patience. DocuSign didn’t IPO until 15 years after its founding. Building a successful enterprise product requires a long-term vision and a commitment to continuous improvement.

Landing the Big Fish: The Importance of Early Adopters and Strategic Partnerships:

Lorenzini highlighted the pivotal role of early adopters in DocuSign’s success. Landing Microsoft as a client was a game-changer, not through aggressive sales tactics, but through a serendipitous demonstration of DocuSign’s .NET integration. This win provided crucial validation and opened doors to other enterprise clients. Similarly, partnering with the National Association of Realtors gave DocuSign access to a massive user base and significantly expanded their reach.

For enterprise product managers, this underscores the importance of identifying and targeting key influencers and strategic partners. These relationships can provide valuable access to target markets and accelerate adoption.

Building a Moat: Data Integration as a Differentiator:

While the core functionality of electronic signatures might seem relatively simple, Lorenzini revealed the secret weapon that propelled DocuSign to market dominance: data integration. He recognized early on that the true value lay not just in the signature itself, but in seamlessly connecting upstream document creation tools with downstream execution and implementation systems. By investing heavily in robust APIs, DocuSign built a powerful moat around its product, making it incredibly difficult for competitors to replicate their functionality and integrations.

This highlights a critical lesson for enterprise product managers: think beyond features. Focus on building a comprehensive solution that integrates seamlessly into existing workflows and provides tangible value to the entire ecosystem.

The Founder’s Mindset: Adaptability and a Passion for Building:

Lorenzini’s entrepreneurial journey wasn’t confined to DocuSign. He’s a serial founder, driven by a deep passion for building and creating. He shared his experiences with both successes and failures, emphasizing the importance of adaptability and resilience in the face of challenges. His foray into renewable energy and the subsequent failure of his data acquisition company, Metabright, demonstrate the unpredictable nature of the startup world.

Enterprise product managers can learn from this experience by embracing a growth mindset, remaining adaptable to changing market conditions, and constantly seeking opportunities for innovation.

Key Takeaways for Enterprise Product Managers:

  • Validate Early and Often: Test your assumptions and ensure you’re solving a real problem.
  • Think Long-Term: Building a successful enterprise product takes time and patience.
  • Focus on Integration: Seamlessly connect with existing enterprise workflows.
  • Build Strategic Partnerships: Leverage key relationships to accelerate adoption.
  • Embrace Data as a Differentiator: Unlock the power of data integration to create a competitive advantage.
  • Cultivate a Founder’s Mindset: Be adaptable, resilient, and passionate about building.

Lorenzini’s journey with DocuSign provides a compelling blueprint for building successful enterprise cloud products. By focusing on solving real problems, building strategic partnerships, and leveraging the power of data integration, product managers can create solutions that not only meet the needs of their target audience but also establish long-term market dominance.


Nataraj is a Senior Product Manager at Microsoft Azure and the Author at Startup Project, featuring insights about building the next generation of enterprise technology products & businesses.


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