Theme 4: Enterprise Organizational Journey
Summary
We’ll blend panel-style discussion, improvisation, business wargaming, and more to explore the dynamics of cross-functional enterprise implementation teams. Our panel of experts—each representing a different facet of the software development lifecycle, including UX, Product, Development, Operations and Sales & Marketing—will be put into situations not of their own choosing that they must resolve in a series of meetings played out before the audience. Each member has their organization’s goals in mind, and their company’s goals in mind, but they don’t always know everybody else’s goals or concerns. Just like back at the office! Participating in this session: - Nafisa Bhojawala, UX Team Lead for Compute, Google Cloud Platform - Kintan Brahmbhatt, Head of Product Management, Amazon Music - David Gatto, Strategic Account Executive, Smartsheet - Dave Sifry, CTO, MyVillage - Wendy Spies, Director of Business Development for Data and AI
Key Insights
-
•
DBNDC’s shift from B2D to B2B requires careful customer segmentation and validation before large investment.
-
•
Technical debt from integrating legacy systems Boneyard and E-Toy is causing outages that threaten customer retention.
-
•
A small, time-boxed cross-functional 'tag team' is preferred for initial exploration of the B2B pivot.
-
•
Government contracts represent a high-risk, high-reward opportunity, necessitating new compliance and legal frameworks.
-
•
Leadership turnover, including the CEO and a key architect leaving, creates instability during critical transition.
-
•
Prioritizing crisis response while maintaining exploration for future growth is essential for strategy balance.
-
•
Machine learning (Project Pavlov) offers potentially unique differentiation but raises privacy and compliance concerns.
-
•
Single sign-on and identity management for B2B customers need additional layers beyond consumer systems.
-
•
Partnership or acquisition can accelerate entry into unfamiliar markets like government or specialized B2B sectors.
-
•
Empathy, respect, and trust within executive teams facilitate civil, productive discussions even under pressure.
Notable Quotes
"We have two competitors: Canine Corp and e-pets, but e-pets is over-diversified, even pet rocks."
"Our consultant says we should pivot from business to dog to business to business—what do we do?"
"We can start small, test and validate quickly with a three-week tag team—one PM, one designer, one researcher."
"Outage caused by technical debt between Boneyard’s VT100 era system and E-Toy’s cloud infrastructure."
"We’re not in the identity business; let’s focus on e-commerce where the growth and customer value are."
"Government contracts are huge but require heavy compliance and long timelines—heads we win, tails we lose little."
"Machine learning could let dogs order just by barking—unique and hard to copy differentiation."
"We have to balance crisis management with long-term strategic exploration to not lose sight of growth."
"Being nice and empathetic at the executive level is critical to get results and maintain trust."
"Leadership is about being a transparent umbrella, shielding teams from chaos while keeping them informed."
Or choose a question:
More Videos
"People and process design are real, real things we have to consider, not just the technology piece."
Alexandra SchmidtEnterprise UX Playbook
December 1, 2022
"The team is passionate, creative, and innovative, building experiences that people love."
Jen Crim Jess Quittner Saritha Kattekola Alex Karr Gurbani PahwaCulture, DIBS & Recruiting
June 11, 2021
"Regularly ask yourself and your colleagues: what are the goals and what are the fears? That’s how you find a path forward."
Christian CrumlishAMA with Christian Crumlish, author of Product Management for UX People
March 24, 2022
"For women, they often won’t apply unless they meet all the bullet points in a job description."
Libby MaurerTreating Diversity & Inclusion in Hiring as a Design Problem
December 5, 2019
"Technology is a tool, not a solution in itself; it needs human input."
Ali Jeffery Sheri ChudowHow DesignOps Helped Enable Wall Street to Work Remotely
October 22, 2020
"Daniel Day-Lewis went so far as to suffer three broken ribs immersing in his role for My Left Foot."
Daniel GloydDesigning From the Inside Out: How Method Acting Can Inspire Design Research
February 12, 2026
"Data is not just numbers; it tells us the story of student learning."
Kristin SkinnerFive Years of DesignOps
September 29, 2021
"Research was completely evaluative and tactical, positioned as serving design by validating wireframes and high fidelity prototypes."
Johanna KollmannInsights-Driven Product Strategy: Get your Research to Count
December 6, 2022
"Momentum in users is like energy in fluid—strong motivation drives fast, decisive movement."
David SternbergUncovering the hidden forces shaping user behavior
July 17, 2025
