Roundtaibles
Roundtaibles is an invitation-only dinner series for senior technology and business leaders who are actively shaping real-world AI strategy. Each dinner brings together a carefully curated group of 25 decision-makers for trusted, peer-level conversation designed to build trust and drive meaningful insight.
Submit your application now
An intimate, invitation-only experience where leaders come together to explore real-world AI strategy over dinner.
Roundtaibles creates space for thoughtful, peer-level conversation focused on the decisions, trade-offs, and realities of building and scaling AI in the enterprise. Attendance is limited and application-based.
Submit your application nowAtlanta - February 5th, 2026
Many organizations have successful AI pilots, but far fewer have operational, scalable AI platforms. This dinner explores the inflection point between experimentation and enterprise reality. Leaders will discuss what breaks as AI moves into production, how platforms, teams, and governance must evolve, and which decisions separate short-lived pilots from durable AI capabilities. The conversation focuses on real lessons learned, not idealized roadmaps. Sponsored by: TBD.
San Francisco - Q2 2026
AI systems fail in ways traditional software does not. Models drift, agents behave unpredictably, data pipelines degrade, and accountability becomes unclear. This dinner creates space for leaders to openly discuss AI failure modes, organizational readiness, and how enterprises are preparing for recovery, oversight, and trust. The focus is on resilience, responsibility, and what leaders wish they had planned for sooner. Sponsored by: TBD.
New York City - Q3 2026
Many AI decisions feel tactical today but carry long-term consequences. This dinner centers on the architectural, data, and organizational choices that will shape enterprise AI maturity years from now. Leaders will examine trade-offs around platforms, tooling, governance, and technical debt, and discuss how to avoid locking the organization into short-term wins that undermine long-term flexibility. Sponsored by: TBD.
Seattle - Q4 2026
AI adoption is reshaping how teams work together across engineering, product, data, security, and operations. This dinner explores how roles and responsibilities are shifting, where new friction is emerging, and how leaders are redesigning collaboration and decision-making in AI-enabled organizations. The conversation focuses on people, process, and alignment. Sponsored by: TBD.
Agenda
Arrival & Mingling
An informal welcome as guests arrive, connect, and settle into the evening.
Welcome & Opening Framing
Opening remarks to set context for the evening, establish shared expectations, and frame the discussion ahead.
Guided Conversation - Round 1
The first facilitated discussion, introducing the core theme and surfacing perspectives from around the table.
Dinner Served
Dinner is served as conversation continues in a relaxed, intimate setting.
Guided Conversation - Round 2
A deeper exploration of the topic, focusing on real-world experiences, trade-offs, and decision points.
Reflection Point (Sponsor)
A brief synthesis of themes emerging from the discussion, highlighting shared patterns, tensions, and questions shaping enterprise AI strategy.
Guided Conversation - Round 3
An open, peer-driven exchange that builds on earlier insights and explores forward-looking questions.
Open Networking & Dessert
Unstructured time for continued conversation and connection.
Closing Reflections
Final thoughts, shared takeaways, and a thank-you to attendees.
Host
Kesha Williams works at the intersection of AI architecture, engineering, and strategy, with more than 25 years of experience designing and delivering complex software and AI systems. An AWS AI Hero, Kesha partners with enterprises and technology leaders to adopt AI responsibly, modernize engineering practices, and build AI systems developers can trust and sustain.
Kesha Williams is the Founder and Managing Partner of Keysoft. Keysoft is a boutique AI consulting agency helping enterprises define their AI strategy, build and govern intelligent systems, upskill their teams, and engage technical audiences with credibility.
Kesha Williams
Keysoft
Supporting leaders shaping real-world AI strategy
Roundtaibles is supported by a small group of technology partners who believe in thoughtful, responsible, and practical AI adoption. Our sponsors participate in the conversation as peers, contributing perspective and insight without sales pitches or product demos.
Attendance & Access
Attendance is complimentary for sponsored dinners, or ticketed when no sponsor is present.
Complimentary Attendance
When a dinner is supported by a sponsor, attendance is complimentary for accepted participants. All guests are carefully selected to ensure a high-quality, peer-level conversation.
Ticketed Attendance
When no sponsor is present, each participant must purchase a ticket to the dinner. The ticket price covers the curated experience, private venue, facilitated discussion, and dinner.
Your questions answered
Apply to Attend
Apply to join a small, curated, invitation-only dinner for AI leaders. This form helps us understand your role and whether the dinner is a good fit. Submitting this form does not guarantee a seat; selected applicants will be contacted by email.
