Podcast Summary: B2B Agility™ with Greg Kihlström
Episode #35: Aligning Organizations for Success, with Robert Chadwani, President, DocuSign
Release Date: January 7, 2025

Introduction

In Episode #35 of B2B Agility™, hosted by Greg Kihlström of The Agile Brand, the focus is on organizational alignment and its critical role in driving growth within B2B marketing. The episode features an insightful conversation with Robert Chadwani, the President and General Manager of Growth at DocuSign. Chadwani brings a wealth of experience from his previous roles, including Chief Marketing Officer at Atlassian and leadership positions at eBay, where he contributed to substantial revenue growth and supported significant trading volumes.

Guest Background and Role at DocuSign

Robert Chadwani opens by sharing his diverse background, transitioning from consulting and consumer e-commerce at eBay to enterprise software with Atlassian, and now leading growth initiatives at DocuSign. His passion lies in leveraging technology to empower entrepreneurs and applying growth principles from both B2B and consumer sectors to drive DocuSign’s expansion.

Expanding a Established Brand

Chadwyani discusses DocuSign’s evolution from being synonymous with e-signatures to pioneering Intelligent Agreement Management (IAM), a new SaaS category aimed at redefining how agreements are created, committed to, and managed.

• Mission Evolution:
  “Our mission is really redefining how the world comes together and degrees, you know, making agreements smarter, easier, and more trusted.” [03:35]

• Challenges in Repositioning:
  Balancing the established brand identity with the expansion into IAM poses challenges in changing the company narrative, repositioning products, and managing international market expansions.

• Category Creation Strategy:
  Chadwanni emphasizes the importance of creating a new software category to articulate and name emerging customer challenges—specifically addressing the “agreement trap”, where valuable information is locked within agreements.

  “We call that the agreement trap. And so, you know, one step around thinking about reframing the opportunity for companies and organizations is looking at the next frontier of problems, often creating language that doesn't exist in the world to name that.” [06:25]

Strategic Brand Expansion without Dilution

When asked about expanding the brand organically without diluting its core offerings, Chadwani underscores the delicate balance between authenticity and audacious growth.

• Balancing Reinvention and Authenticity:
  “It feels organic. It doesn't feel like all of a sudden you had another bright idea and it's all the way over here.” [10:12]

• Managing Incremental and Bold Moves:
  Aligning the ability to deliver on new promises while being ambitious enough to consider transformative changes requires reconciling incremental thinking with bold, company-wide bets.

Geographic Expansion and Scaling Challenges

Chadwyani addresses the complexities of scaling digital strategies across various geographies and industries, drawing from his experiences at eBay, Atlassian, and DocuSign.

• Acknowledging the Difficulty:
  “There isn't a go to market leader that I've met who doesn't tell me that they're in the and business versus the or business.” [12:04]

• Prioritization as a Solution:
  Effective resource allocation through prioritization is essential. Chadwani advocates for categorizing initiatives into present and future-focused buckets, prioritizing based on strategic importance, even if it involves making tough decisions on what to under-resourced.

  “I have yet to find a company or team that is successful without going through the painful exercise of making tough choices.” [15:04]

Leadership and Priority Setting

Discussing the role of leadership in setting priorities, Chadwani emphasizes that strategic decision-making should be a collective effort, fostering transparency and shared understanding across teams.

• Strategy as a Team Sport:
  “Strategy and prioritization is a team sport.” [16:48]

• Principles for Effective Prioritization:

  • Progress Over Perfection: Continuously iterate and adapt based on new data.
  • Radical Openness: Maintain transparency in decision-making processes to build trust.
  • Clarity in Success Metrics: Use methodologies like OKRs to define and measure success clearly.

Breaking Down Silos for Product-Led Growth

Chadwyani explores strategies to dismantle traditional silos between product, engineering, data, and operations teams to facilitate a cohesive product-led growth strategy.

• Shared Metrics and Ownership:
  Implementing shared metrics and Designated Responsible Individuals (DRIs) to orchestrate cross-functional collaboration ensures alignment towards common goals.

  “Whenever possible have a North Star metric or a set of metrics that can be shared between teams ultimately meaning know, aligning those goals.” [20:20]

• Enhancing Empathy Through Shared Journeys:
  Encouraging teams to understand each other’s roles in the customer journey fosters empathy and cohesive execution.

Improving Team Health and Collaboration

Addressing team dynamics, Chadwani highlights the importance of foundational models, clear ownership, and reflective practices to enhance team health and collaboration.

• Foundational Models:
  Establishing clear roles (e.g., RACI models) to prevent ambiguity in project ownership.

• Pre-Mortems and Retrospectives:
  Conducting pre-mortems to anticipate challenges and retrospectives to evaluate project outcomes without assigning blame, thereby enhancing team capabilities.

  “We spend a lot of time on not just what we do, but ways of working and how we do it.” [27:30]

The Role of Data and AI in Driving Growth

Chadwyani emphasizes the pivotal role of data and AI in modern B2B growth strategies, advocating for their integration into every aspect of decision-making and operational efficiency.

• AI and Data as Growth Drivers:
  Identifying and implementing AI use cases that enhance data quality, automate processes, and translate into measurable business growth.

  “We spend a lot of time thinking about AI specifically and in our go to market and sales teams. How can we identify use cases that we think can benefit from better data or better automation or better use of AI?” [29:20]

• Translating Data Insights into Business Benefits:
  Focusing on how applied data and AI can lead to tangible outcomes like revenue growth, customer acquisition, and increased productivity.

Maintaining Agility in Leadership

In closing, Chadwani shares his approach to staying agile in his role, emphasizing openness to new ideas and the ability to adapt to new information.

• Embracing New Ideas and Adaptability:
  “Be open to a lot of new ideas that emerge that challenge conventional ways of working and conventional ways of operating.” [33:02]

• Responding to New Information:
  Valuing the capacity to respond to new data and translate it into improved execution and teamwork over having all the answers upfront.

Conclusion

Episode #35 of B2B Agility™ provides a comprehensive exploration of organizational alignment, brand expansion, and the integration of data and AI in driving B2B growth. Robert Chadwani offers valuable insights from his extensive experience, emphasizing the importance of strategic prioritization, cross-functional collaboration, and maintaining agility in leadership. His strategies for breaking down silos and leveraging data-driven decision-making serve as actionable guidance for B2B marketers and organizations striving to become category leaders and achieve optimal results.

Notable Quotes

• Robert Chadwani [03:35]:
  “Our mission is really redefining how the world comes together and degrees, you know, making agreements smarter, easier, and more trusted.”

• Robert Chadwani [06:25]:
  “We call that the agreement trap. And so, you know, one step around thinking about reframing the opportunity for companies and organizations is looking at the next frontier of problems, often creating language that doesn't exist in the world to name that.”

• Robert Chadwani [10:12]:
  “It feels organic. It doesn't feel like all of a sudden you had another bright idea and it's all the way over here.”

• Robert Chadwani [12:04]:
  “There isn't a go to market leader that I've met who doesn't tell me that they're in the and business versus the or business.”

• Robert Chadwani [15:04]:
  “I have yet to find a company or team that is successful without going through the painful exercise of making tough choices.”

• Robert Chadwani [16:48]:
  “Strategy and prioritization is a team sport.”

• Robert Chadwani [20:20]:
  “Whenever possible have a North Star metric or a set of metrics that can be shared between teams ultimately meaning know, aligning those goals.”

• Robert Chadwani [27:30]:
  “We spend a lot of time on not just what we do, but ways of working and how we do it.”

• Robert Chadwani [29:20]:
  “We spend a lot of time thinking about AI specifically and in our go to market and sales teams. How can we identify use cases that we think can benefit from better data or better automation or better use of AI?”

• Robert Chadwani [33:02]:
  “Be open to a lot of new ideas that emerge that challenge conventional ways of working and conventional ways of operating.”

This summary encapsulates the core discussions and insights shared by Robert Chadwani on aligning organizations for success, offering actionable strategies and profound reflections on growth, leadership, and the transformative power of data and AI in B2B marketing.