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 - Q1 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.
Hosts
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
Conference Edition
Bring the Roundtaibles experience to your tech conference.
Conference keynotes and panels introduce big ideas. Roundtaibles makes them stick. Each discussion or dinner takes the core themes of your event and puts them on the table for honest, peer-level conversation about how those ideas actually land inside real organizations.
How It Works
We produce a turnkey Roundtaibles discussion or dinner co-located with your conference. Same intimate format: a curated topic aligned to your event theme, expert facilitation, and a private venue. Your attendees get a standout experience.
What We Handle
Keysoft manages every detail: topic development tied to your conference theme, facilitation by Kesha Williams, and post-event attendee follow-up. Your team focuses on the main event. We handle the rest.
Three Models. Your Choice.
You commission it. We produce it.
Your conference pays a flat production fee. We run a Roundtaibles discussion or dinner as an official premium add-on for your senior leaders, VIP attendees, or top-tier sponsors. Fully branded to your event.
A sponsor funds the discussion. Attendees join free.
A vendor sponsor underwrites the dinner and receives the single-sponsor slot. Attendees are sourced from your conference registration list or through our own application pipeline.
Bundle it. Sell it. We deliver it.
Roundtaibles access becomes a paid upgrade tier on your conference ticket. VIP Pass holders get a seat at the dinner. You handle ticketing. We handle everything else.
Ideal For
Internal summits, AWS re:Invent, AWS Summits, KubeCon, Google Cloud Next, Microsoft Build, Collision, Web Summit, AI Engineer Summit, and similar enterprise and developer conferences looking to offer a curated, senior-leader networking experience.
Inquire about a Conference EditionSupporting 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 purchases a ticket. The ticket price covers the curated experience, private venue, facilitated discussion, and dinner.
Complimentary Attendance
When a conference organizer or sponsor underwrites the dinner, attendance is complimentary for accepted participants. The topic aligns to the host conference theme, and Keysoft handles all production.
Complimentary Attendance
At select conferences, Roundtaibles access is available as a VIP ticket upgrade. Seating is limited and curated. Check with the conference organizer for availability and pricing.
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.
