Cash Out: Inaugural Design Summit

At the beginning of 2023, Bill.com faced a challenge: two large development teams needed to learn how to collaborate and integrate our AP product with our S&E product into one seamless end-to-end user journey. This goal had proven elusive due to differences in how the teams operated and the fact that team members were dispersed across the U.S., making it difficult to leverage each other's strengths.

INITIATIVE:

I proposed a Product Design-led initiative designed to strengthen team collaboration and establish a unified vision for addressing user needs. This initiative focused on improving communication between AP and S&E teams while seamlessly integrating AI and automation to enhance efficiency and user experience.

MY ROLE: Director, Facilitand Workshop Strategist

PARTNERS: Sr. Director of Design for Cash Out & Sr Manager Designer AP

OFFSITE SUPPORT: Product Leaders for AP and S&E

TEAM SIZE: 16 Designers, 2 Researchers, and 3 Design Leaders

Why Now?

Imagine building a car where each designer focuses on a different area: one drafts the exterior, another the interior, a separate designer works on the engine, and someone else handles the tires. While each part is designed, the final product resembles a mishmash of individual pieces that don't flow together, much like Frankenstein's monster.

In car design, the individual parts do evolve, but they do so under the cohesive story and vision of the overall car design. This vision work isn't a comprehensive set of designs from the start but a cohesive, inspirational narrative that guides the process. This storytelling mechanism is currently missing in our approach. With a clear vision, we can accelerate innovative projects that impact the business immediately rather than later.

The initial stages of the workshop are for designers only, as bonding and understanding how to leverage each other's strengths is crucial. PM and ENG partners are brought in consistently to offer context, answer questions, and act as approvers since they will continue to evolve the deliverables. By the last day of the workshop, designers will have a well-developed idea ready for leads to critique, validate, and refine, bringing us ten steps closer than where we are today.

Problem to Solve

Currently, designers struggle to identify opportunities across unfamiliar products and collaborate effectively due to a lack of trust. The Design Summit will enhance cross-collaboration by fostering team bonding in a face-to-face environment, achieving in four days what we’ve been trying to accomplish over the past six months.

Identified Area's of Opportunity

PROACTIVE AUTOMATION

Problem: How do I get better insights into what I don't know; I need my financial system to give a more complete picture of what isn't accounted for.
Goal: Speed to closing the books, reduce in user errors, and increase in user task completion rates

AP & BUDGETS

Problem: how do I track all of my cash management (AP, S&E) so I have a holistic view of my business cash flow?
Goal: Increase spend, and increase X-Sell 10K Shared Units

COMMUNICATION

Problem: How do I communicate inside of the product (processing invoices, chasing receipts, policies etc) which has become time consuming and frustrating to chase down information, get approvals, collect documentation.
Goal: Increase user engagement, Decrease customer support calls

IDENTIFY SUCCESS METRICS

• Increase user engagement by 10%

• X-sell 10K Shared units for AP and S&E

• Increase user task completion rates

• Decrease support calls by 20%

the deliverables

Proactive Automation

TEAM 1: This project aimed to use AI and historical data to provide insights that help users focus on higher risk or unusual bills, speeding up the approval process.

The initial phase uses rules-based logic, with a future phase planned to incorporate more advanced AI insights.

The insights are intended to reduce the time it takes for bill creators to add approvers and for approvers to approve bills, thereby enhancing the overall user experience.

User Communications

TEAM 2: This project aims to use AI and historical data to provide insights that help users focus on higher risk or unusual bills, speeding up the approval process.

The initial phase uses rules-based logic, with a future phase planned to incorporate more advanced AI insights.

The insights are intended to reduce the time it takes for bill creators to add approvers and for approvers to approve bills, thereby enhancing the overall user experience.

Cash Management

TEAM 3: This project aims to track all of the users cash management between AP and S&E so they have holistic view of their business cashflow.

Customers are inundated with Cash in/out documents across several different products where as a dashboard would be a better source of truth for them.

Team must consider the accuracy of automation in the goal of building user trust into the engagements.

WHAT DID WE LEARN?

The Design Summit created a valuable platform for rapid learning, growth, and team alignment. It provided key insights into our designers' processes, methodologies, and strengths while also highlighting areas of dysfunction requiring leadership attention. For example, the summit revealed that many attendees had never experienced a design sprint, introducing a significant but important learning curve.

Key Takeaways and Outcomes

Deepened Process Insights: Gained a better understanding of designers' workflows, strengths, and opportunities for improvement.
Unveiled Areas for Leadership Focus: Identified gaps in experience, such as unfamiliarity with design sprints, that needed attention and support.
Post-Summit Workshops:
- Conducted 6-8 targeted workshops in the weeks following the summit.
- Provided value to both designers and their squads by refining ideas and fostering collaboration.
Growth Through Discomfort:
- Acknowledged that the event’s structure was initially uncomfortable for many participants.
- Feedback confirmed the outcomes were highly impactful, justifying the learning challenges.

This summit ultimately laid the groundwork for better collaboration, stronger processes, and a renewed focus on continuous learning.

Design summit confessional

During the Design Summit, we captured authentic, real-world "confessional-style" moments to document the team's experiences in their own words. These candid reflections offered a glimpse into the highs, challenges, and breakthroughs of the summit, creating a raw and unfiltered narrative of the event. Designers and participants shared their thoughts on the workshops, their personal growth, and the impact of collaboration in a relaxed, conversational format. These moments not only provided valuable insights into the team’s mindset but also served as a meaningful record of the summit’s impact, showcasing the journey of learning, adaptation, and connection in real time.

Meet Kendra, Sr Product Designer

Cash Out: Inaugural Design Summit