Most teams track numbers—but few measure what truly matters. In this insightful and practical session, Ken Sipe breaks down how to align organizational goals with measurable outcomes using Objectives and Key Results (OKRs) and Key Performance Indicators (KPIs) that actually drive success.
Ken will cut through the buzzwords and frameworks to show how engineering teams, product leaders, and executives can build a measurement culture that’s both data-driven and purpose-aligned. You’ll learn how to define metrics that motivate, avoid vanity indicators, and establish traceability from daily work to strategic outcomes.
Key takeaways include:
How to craft meaningful OKRs that align technical and business goals
The difference between activity, output, and outcome metrics—and why it matters
Techniques for cascading objectives across teams without creating chaos
How to use metrics as a feedback system, not a weapon
Real-world examples of OKRs and KPIs that improved clarity, accountability, and results
Whether you’re scaling an engineering organization or trying to bring more focus to your current team, this session will help you turn measurement into momentum—and ensure that success isn’t just tracked, but achieved.
Most teams treat incidents as technical failures. Great teams treat them as coordination failures under stress. This session gives engineering leaders a practical incident command system they can apply immediately: roles, communication cadence, decision logging, escalation paths, and postmortems that create learning instead of fear.
When incidents hit, technology matters — but leadership determines outcomes. This session walks through an operating model for incident response that scales across teams and time zones without chaos.
We cover clear roles (incident commander, comms lead, operations lead, and scribe), fast status loops, and decision frameworks that lower risk under pressure. You’ll see practical templates for timeline capture, stakeholder communication, and recovery prioritization.
We also cover the most ignored part: after-action learning. You’ll leave with a blameless postmortem structure that improves systems, process, and team behavior instead of assigning guilt.
Includes realistic scenarios, facilitation techniques for cross-functional pressure moments, and a leadership checklist you can use in your next production incident.
Outcomes:
No panic theater. Just practical leadership patterns that work when production is on fire and Slack has gone feral.
In the fast-paced world of software delivery, we often mistake “management” for “leadership.” Management is about complexity, stability, and the coordination of resources; leadership is about change, alignment, and the inspiration of people. For many tech leaders, the instinct is to manage the code, the deadlines, and the tickets—but great systems aren't built by managed workers; they are built by led innovators.
In this session, Ken Sipe explores the critical shift from a command-and-control mindset to a high-trust leadership model. We will dive into the “Anti-Patterns of Management” that stifle creativity and slow down velocity, and replace them with actionable leadership strategies designed specifically for technical teams.
Building an AI model is the easy part—making it work reliably in production is where the real engineering begins. In this fast-paced, experience-driven session, Ken explores the architecture, patterns, and practices behind operationalizing AI at scale. Drawing from real-world lessons and enterprise implementations, Ken will demystify the complex intersection of machine learning, DevOps, and data engineering, showing how modern organizations bring AI from the lab into mission-critical systems.
Attendees will learn how to:
Design production-ready AI pipelines that are testable, observable, and maintainable
Integrate model deployment, monitoring, and feedback loops using MLOps best practices
Avoid common pitfalls in scaling, governance, and model drift management
Leverage automation to reduce friction between data science and engineering teams
Whether you’re a software architect, developer, or engineering leader, this session will give you a clear roadmap for turning AI innovation into operational excellence—with the same pragmatic, architecture-first perspective that Ken is known for.
What happens when a self-taught programmer with a background in anthropology finds himself leading engineering teams? In this candid, humorous, and emotionally resonant talk, Robert Harris shares his journey from BASIC on a Commodore 64 to building psychologically safe, high-performing cultures in modern software organizations.
Blending fieldwork with frameworks, Robert explores the human side of engineering leadership—imposter syndrome, accidental management, and the painful lessons that shaped his philosophy. Drawing on his training in anthropology, he offers a practical guide to shaping team culture through shared language, rituals, experiences, and artifacts—from flaming pull request beacons to rubber duck onboarding kits.
Attendees will leave with:
•A fresh perspective on leadership rooted in emotional intelligence and cultural design
•Actionable strategies for building trust, accountability, and psychological safety
•A toolkit of metaphors, rituals, and artifacts to transform team dynamics
Whether you’re a reluctant manager, a seasoned leader, or just someone who’s ever stepped on a rake in production, this talk will help you turn dysfunction into culture—and culture into your team’s greatest asset.
Engineering culture is not created by values statements or team rituals. It emerges from
thousands of small signals - who speaks, who hesitates, what gets reinforced, and what
quietly disappears.
Across years of observing software engineering organizations, one pattern appears
consistently: when teams go remote or hybrid, culture doesn’t disappear - informal signal
flow does. The hallways where trust, learning, and psychological safety once formed are
removed, and nothing intentionally replaces them.
In this session, a software engineering leader with formal training in psychology and
anthropology examines why remote teams so often struggle with silence, disengagement, and false alignment - and why most culture initiatives fail to address the real problem.
Using cross-cultural comparison, this talk contrasts engineering organizations with digital communities that have thrived online for decades, surfacing what those cultures get right about feedback, trust, and informal learning.
The core insight is simple but uncomfortable: distance is not the enemy of culture,
poorly designed environments are.
Rather than focusing on tools, mandates, or performative connection, this session
reframes culture as an environment shaped by observable behavior, especially
leadership behavior. Attendees will explore how meetings, async communication, and
everyday leadership moments become the new hallways - for better or worse - and how
teams silently adapt when those spaces fail them.
Participants will leave with:
• A practical lens for diagnosing signal loss in distributed teams
• Clear indicators that silence is masking risk, not agreement
• Design principles for creating “digital hallways” that allow trust, community, and
psychological safety to emerge naturally
• A deeper understanding of how leadership behavior trains culture - whether
intentionally or not
This session is grounded in real-world leadership experience, systems thinking, and
comparative cultural analysis, and is designed for engineering leaders who want to build resilient, high-trust teams in remote and hybrid environments without sacrificing
performance.
Most software engineering leaders struggle for a reason no one talks about.
They were promoted for being great at writing code - and then handed responsibility for humans.
Meetings.
Conflict.
Silence.
Motivation.
Trust.
We quietly expect the same instincts that worked for technical systems to work for people.
They don’t.
In this session, we’ll explore leadership through a systems lens - not as a set of personality traits or management hacks, but as an adaptive human ecosystem that responds to risk, safety, and meaning.
You’ll learn:
• Why silence in meetings is rarely agreement
• How everyday leadership behaviors quietly train teams to wait, escalate, or
disengage
• What makes leaders accidentally become bottlenecks
• Why “helpful” interventions often have unintended consequences
• How human systems learn - even when you’re not teaching
This is not a talk about tools, frameworks, or performance management templates.
It’s about seeing what’s actually happening in your team - and realizing how your own
behavior shapes the system you’re leading.
Drawing on real-world stories from 20+ years in software engineering leadership (and a
background in anthropology), this session gives leaders a language for the invisible
dynamics they’ve felt but never been able to name.
Attendees will leave with:
• A new mental model for leadership
• A sharper lens for reading group behavior
• And a deeper understanding of how to create environments where people actually
think, speak, and decide
No blame.
No buzzwords.
Just a clearer view of the human system you’re already inside.
In moments of uncertainty, teams don’t listen more closely to their leaders.
They watch them.
Across years of leading software organizations - and hundreds of documented leadership
moments - one truth becomes unavoidable: engineers take their emotional cues from
leadership behavior, especially under pressure. Stress, urgency, and fear propagate
through teams not by announcement, but by example.
This talk explores how leaders unintentionally amplify chaos through tone, timing, and
reaction - even when they believe they’re being clear or decisive. Drawing from psychology,
anthropology, and long-term observation of engineering teams, this session focuses on
principles, not tactics: stable leadership rules that hold when incidents, deadlines, or
change collide.
Attendees will learn:
• How leadership behavior becomes a system input
• Why urgency often masquerades as clarity - and how teams experience the
difference
• How trust is like a bank, being deposited or withdrawn during moments of pressure
• Practical ways leaders can become a stabilizing force without suppressing reality
This is not a talk about staying calm for appearances’ sake. It’s about understanding how
human systems react to stress, and how leaders can intentionally reduce noise instead
of becoming part of it.
Leaders will leave better equipped to guide teams through chaos - not by controlling
outcomes, but by shaping the environment in which decisions are made.
“How are you helping unite and bond your teams? What creative team buildings have you tried, both virtually or inperson, to connect the team on both a personal and professional level?”
Join this fun discussion on 12+ creative teambuilding ideas you can give a try to help take your team's connection to the next level! We’ll introduce ideas such as Values Exercises, Wellness Contests, Collaborative Team Development, SkillsBased Volunteerism, and unique games such as ‘Are You Smarter Than a 5th Grader’ that our teams have loved!
In an era where AI tools are reshaping the workplace, effective adoption strategies are crucial for both uncovering potential application and driving tool utilization to influence creativity, save time and drive ROI. This session will shine a light on the specific techniques we used to drive companywide user engagement and utilization of Microsoft Copilot, our internal AI tool of choice.
We will dive into 8+ key strategies that we found impactful in fostering a culture of adoption within our organization. We will discuss ideas such as: identifying Change Champions, conducting training sessions, and leveraging ondemand resources to empower users. Attendees will learn how to create a vibrant community around AI, share success stories, and utilize analytics to track progress and drive continuous improvement.
Participants will leave equipped with actionable ideas to help transform team members into enthusiastic advocates for AI tools. Whether you're a leader looking to enhance your team's capabilities or a practitioner eager to implement change management best practices, this session will provide stops for your respective roadmaps to drive awareness, education and change!
Reliable systems are not accidents. They are designed with explicit operating limits. This session translates lessons from high-risk domains into practical engineering guardrails for microservices: latency budgets, timeout strategy, retry discipline, concurrency limits, and blast-radius controls.
In high-consequence systems, teams define and respect operating limits. Software teams should do the same.
This session introduces an operating-limits model for modern microservices and platform environments. We’ll map common failure patterns (retry storms, cascading timeouts, queue overload, dependency fan-out) to concrete design and operational constraints that prevent small issues from becoming full incidents.
You’ll learn practical techniques for timeout layering, bulkheads, error budgets, load shedding, progressive degradation, and observability signals that reveal approaching limits before customers feel impact.
We’ll also cover leadership practices: how to align teams around reliability contracts and how to enforce guardrails without turning architecture into bureaucracy.
Outcomes:
Yes, we will talk about when your retries are lying to you. And no, adding one more queue is not always the answer.
This two part executive briefing helps leaders, managers, and decision-makers understand the real technologies behind today’s AI movement — in clear, practical terms.
Rather than avoiding key terms, the session translates them: LLMs, RAG, Copilots, Agents, and the Model Context Protocol (MCP) — showing how each fits into the way organizations build and use AI.
Participants gain an intuitive understanding of how AI systems think, retrieve, and act — and how those capabilities are already showing up in tools across the enterprise.
Through relatable analogies, visuals, and examples, attendees will learn how to talk confidently with technical teams, evaluate AI initiatives, and lead with insight and accountability.
The presentation blends conceptual clarity, leadership relevance, and visual storytelling. It’s designed for executives and non-technical professionals who need to grasp how AI fits into their organization’s strategy, operations, and governance.
1.How Modern AI Really Works
Understand how Large Language Models (LLMs) learn patterns from data and generate responses. See why they don’t “know” — they predict — and why context and validation are essential for business use.
2.Retrieval-Augmented Generation (RAG): Making AI Current
Learn how RAG extends an AI’s capabilities by connecting it to trusted enterprise data sources. Understand how this approach keeps responses accurate, relevant, and policy-compliant.
3.Copilots and AI Assistants
Explore how copilots combine AI reasoning, enterprise context, and workflow integration to support human work. See how GitHub Copilot, Microsoft 365 Copilot, and internal copilots assist teams without replacing them.
4.Agents and AI Autonomy
Examine how AI agents can plan, call tools, and make structured decisions using the “Thought → Action → Observation” loop. Understand how this differs from static chatbots — and how to govern it.
5.MCP (Model Context Protocol): Standardizing AI Connections
Discover how MCP enables AI systems to safely discover and use tools, APIs, and data through a shared protocol — simplifying integration and improving control across departments.
6.Security, Guardrails, and Governance
Discuss the emerging field of AI security: preventing prompt injection, protecting data, and enforcing responsible use. Learn how leadership shapes trust and compliance in AI-enabled operations.
7.The Leadership Playbook for AI Adoption
Gain a framework for evaluating AI initiatives.
This two part executive briefing helps leaders, managers, and decision-makers understand the real technologies behind today’s AI movement — in clear, practical terms.
Rather than avoiding key terms, the session translates them: LLMs, RAG, Copilots, Agents, and the Model Context Protocol (MCP) — showing how each fits into the way organizations build and use AI.
Participants gain an intuitive understanding of how AI systems think, retrieve, and act — and how those capabilities are already showing up in tools across the enterprise.
Through relatable analogies, visuals, and examples, attendees will learn how to talk confidently with technical teams, evaluate AI initiatives, and lead with insight and accountability.
The presentation blends conceptual clarity, leadership relevance, and visual storytelling. It’s designed for executives and non-technical professionals who need to grasp how AI fits into their organization’s strategy, operations, and governance.
1.How Modern AI Really Works
Understand how Large Language Models (LLMs) learn patterns from data and generate responses. See why they don’t “know” — they predict — and why context and validation are essential for business use.
2.Retrieval-Augmented Generation (RAG): Making AI Current
Learn how RAG extends an AI’s capabilities by connecting it to trusted enterprise data sources. Understand how this approach keeps responses accurate, relevant, and policy-compliant.
3.Copilots and AI Assistants
Explore how copilots combine AI reasoning, enterprise context, and workflow integration to support human work. See how GitHub Copilot, Microsoft 365 Copilot, and internal copilots assist teams without replacing them.
4.Agents and AI Autonomy
Examine how AI agents can plan, call tools, and make structured decisions using the “Thought → Action → Observation” loop. Understand how this differs from static chatbots — and how to govern it.
5.MCP (Model Context Protocol): Standardizing AI Connections
Discover how MCP enables AI systems to safely discover and use tools, APIs, and data through a shared protocol — simplifying integration and improving control across departments.
6.Security, Guardrails, and Governance
Discuss the emerging field of AI security: preventing prompt injection, protecting data, and enforcing responsible use. Learn how leadership shapes trust and compliance in AI-enabled operations.
7.The Leadership Playbook for AI Adoption
Gain a framework for evaluating AI initiatives.
Leadership isn’t just about making the right calls — it’s about staying steady while everything around you moves fast. From managing tension in meetings, juggling shifting priorities, and fielding last-minute requests, to navigating unclear direction or supporting a stressed-out team, software leaders are constantly pulled in multiple directions. That’s where FLOW comes in: a practical, four-part skillset designed to help you handle pressure, stay grounded in uncertainty, and show up with clarity when it matters most.
You’ll learn how to Focus with Breath, Let It Go, Own Your Part, and Weave FLOW into Your Day through real-world leadership scenarios and peer-to-peer practice designed to reflect the complexity of actual moments you face. These aren't abstract ideas — they’re trainable skills you can use right away to lead with more clarity, presence, and effectiveness. If you’ve been running on adrenaline, reacting on autopilot, or just trying to hold it all together, this workshop will help you become a more nimble, flexible leader who gets the job done — with a whole lot less effort and a lot more ease.
You've basically stopped writing significant amounts of code. AI does it — you check it, direct it, and sign off on it. The leverage is real and so is the uneasy feeling that comes with it. You're now responsible for output you didn't fully produce, at a volume you can't fully review, while leadership pushes for more speed. And nobody — not your org, not the industry — has figured out yet who's actually on the hook when something goes wrong.
Here's the honest truth: nobody has a clean answer yet — not your organization, not the industry, not the people writing the frameworks. So this session doesn't pretend to have one either. Instead, we'll pool what's actually working for people in the room, surface what's already helping teams stay more on top of it, and build something more useful than a handed-down answer. You'll also develop the skill to become calmer and more clearheaded when you're buried in pull requests and competing demands — and when something does go wrong. You'll leave with concrete approaches for navigating the gray zone and more practical ways to handle the pressure of leading when the rules are still being written.
SESSION 4 — Leading When You Don't Have the Answers
How to stay calm and credible in an AI-accelerated world
A few months ago you had a decent handle on what your team was building — or you were building it yourself. Knowing things is how you got here, and it still matters. But now the tools are moving faster than anyone's ability to fully keep up, the output is coming faster than anyone can fully evaluate. Some days that's exhilarating. Other days your team looks to you for answers — and you're not sure you're the right person to ask anymore.
This session gives you a skill to stay functional and credible when the answer isn't there yet — not as a workaround, but as something you can build and rely on. You can use it in the 90 seconds before you walk into a conversation, or in the moment someone asks you something you can't answer yet. Through real scenarios and honest conversation with the people around you, you'll leave more grounded and better equipped to lead from steadiness instead of certainty.
You've gone from writing code to directing AI to write it — in what feels like about six months. The leverage is real, the speed is real, and so is the creeping feeling that you're responsible for more output than you can actually get your arms around. On top of that, your team still needs direction, your calendar is still full, and somehow the work that was supposed to get easier keeps landing back on your desk — and it's costing you focus, capacity, and probably some sleep.
This session gives you a practical framework for making delegation actually stick — to your team and your AI tools. But the framework only works if you can actually let go — of tasks, of control, and of the pull to just do it yourself because it's faster. This is a working session: you'll learn as much from the people in the room as from the content. You'll leave with the skills to hand off work with trust, clarity, and accountability — and one concrete delegation you've been avoiding, with a plan to execute it this week.
Does your life feel like non stop motion with never a moment to chill, as if you're always reacting to shifting priorities? You’re not alone, and it’s time to bring your A-game beyond the code. In this groomed talk, you'll learn how to use similar concepts—roadmaps, backlogs, and more—from your professional life in analogous ways to bring order to your everyday life.
Discover how to transform chaos into clarity by prioritizing tasks like a pro, tackling personal goals with laser focus, and making “fire drills” far less frequent. You’ll also learn how to let go—yes, it’s a skill, not just a mindset—and drop some of the mental clutter that keeps you spinning. Through relatable examples, humor, no-nonsense strategies, and real-world letting go practices, you’ll walk away with tools to get your life dialed in, reduce stress, achieve what truly matters—and still have time for a beer with friends. No debugging required!
Whether you want to effect culture change in your organization, lead the transition toward a new technology, or simply get more out of your team; you must first understand that having a “good idea” is simply the beginning. An idea must be communicated; a case must be made. Communicating that case well is as important, if not more so, than the strength of the idea itself.
You will learn 6 principles to make an optimal case and dramatically increase the odds that the other person will say “Yes” to your requests and suggestions, along with several strategies to build consensus within your teams. As a professional mentalist, Michael has been a student of psychology, human behavior and the principles of influence for nearly two decades. There are universal principles of influence that are necessary to both understand and leverage if you want to be more effective leader of change in your organization.
Being a tech leader means balancing vision, strategy, and innovation—yet too often, the administrative burden of the role becomes a persistent obstacle, especially for those who found themselves thrust into leadership accidentally or reluctantly. If you're a technical expert navigating the transition into leadership, it's easy to feel overwhelmed by information overload, endless meetings, follow-ups, and scattered responsibilities.
In this practical, immediately applicable full day workshop, Michael introduces the Digital Knowledge Management (DKM) Tech Leader Toolbox—a proven approach to taming the chaos and reclaiming your clarity, productivity, and sanity. Leveraging Tiago Forte's “Building a Second Brain” methodology combined with powerful tools like Logseq, you'll learn structured workflows to capture, organize, distill, and effortlessly retrieve critical information exactly when you need it.
You'll discover how to streamline meeting notes, simplify administrative tasks, track decisions and outcomes, hold your self and your team accountable, and build your personal leadership knowledge base. With these tools and techniques, you'll not only master the administrative aspects of your role but transform them into a powerful advantage. Join us and take control of your leadership journey today!
As a tech leader, how can you help your developers take ownership of security without slowing down innovation? Developers are incentivized to prove that systems work as expected—but how often do we ensure they don’t do what they shouldn’t?Security isn’t just a checklist; it’s a mindset. But can your team define what security truly means? How do you measure enough security? More importantly, how do you drive meaningful, incremental improvements in your organization’s security posture without overwhelming your developers?
This session will provide you with a practical, actionable framework to embed security into your development process. You’ll walk away with concrete strategies to help your teams proactively design security in—without sacrificing velocity.
There are certain tech trends people at least know about such as Moore's Law even if they don't really understand them. But there are other forces at play in and around our industry that are unknown or ignored by the ever diminishing tech journalism profession. They help explain and predict the pressures and influences we are seeing now or soon will.
In this talk, I will identify a variety of trends that are happening at various paces in intertwined ways at the technological, scientific, cultural, biological, and geopolitical levels and why Tech Leaders should know about them. Being aware of the visible and invisible forces that surround you can help you work with them, rather than against them. You will also be more likely to make good choices and thrive rather than being buffeted uncontrollably.
I personally believe that the success of an API initiative is at
least largely influenced by the selection and development of the
team that will build and maintain it.
Code-focused developers are not the right starting point. People who
think about information and long-term value capture are more likely
to produce better results. People who actually care about the API
beyond a thin-layer above their code are a great start.
We often say that we are trying to “Build the Right Thing” and
“Build the Thing Right”. But how do you know you are building the
right thing? How are you validating the implementation and the
behavior of the system? How are your business analysts supposed to
verify the API is doing what it is supposed to if your testing
strategy is complicated and code-focused?
In this talk, I will discuss these ideas and more. I will tell you
about a team I put together with no API background that built
what became a $300 million revenue stream in its first few years.
Since the Scientific and Industrial Revolutions, there has been more to know every day. No individual can know it all and we have seen the entrenchment of the specialist for the past hundred or so years. When all of this tacit knowledge was locked in our heads, the specialist was rewarded for knowing details.
In our industry we have seen professionals gravitate to specific languages, specific tiers in the architecture (e.g. front-end vs backend), and specific libraries or frameworks. Sometimes they will even go so far as to list specific versions of specific technologies on their resume.
All of this specialization can be beneficial when you need resources that are deep within narrow confines. The ubiquitous glut of available information no longer requires us to know topics to this level of detail. Market realities are also such that nobody has the budget to employ only specialists any more. Developers have needed to learn to become designers, testers, data-experts, security-aware, AI-cognizant, and capable of communicating with various stakeholders.
When your industry epitomizes unfettered change, you need to rely on generalists, not specialists; synthesizers, not knowledge keepers. How can you attract, hire, and benefit from technologists who identify as problem solving value adders rather than programmers of a specific language? How can you encourage their growth and measure success? Even more, how do you lead them yourself?
In this talk we will discuss the rise of the generalist knowledge worker who creates value even in the face of information overflow and AI.
This one-day leaders program builds practical AI literacy for managers, project leaders, and business stakeholders who need to make informed decisions about AI—without diving into technical implementation. Participants learn the core concepts and current AI landscape in plain language, practice using AI to improve everyday leadership workflows (writing, planning, analysis, and decision support), and leave with concrete artifacts they can use to sponsor and scope real initiatives.
The day is structured around four 90-minute sessions that balance concise instruction with hands-on exercises. Leaders will develop a shared vocabulary (models, assistants, agents, RAG, inference), build an intuition for where AI is genuinely useful versus where it creates risk, and learn a few simple verification habits to improve output quality. A practical workshop segment focuses on turning a real artifact—such as a project update, policy draft, or stakeholder communication—into a leader-ready deliverable with an executive summary, action list, and risk/assumption check, emphasizing clarity and accountability.
The second half of the day shifts from understanding to sponsorship: how to select AI use cases worth piloting, define success metrics, and right-size scope so teams can prove value quickly. Participants work in small groups to complete a use-case canvas and then translate it into a sponsor-ready one-pager that includes constraints, risks, required controls, and measurement plans. The program closes with a lightweight governance and rollout playbook, helping leaders coordinate with technical teams and set expectations for what a reasonable pilot (and a responsible scale-up) looks like in their organization.
AI agents are not just tools for the IDE; they are the new operating system for high-stakes leadership. In this session, Ken Sipe moves beyond the hype of “AI-assisted coding” to demonstrate what it actually looks like to lead and scale with a personal AI agent. From executive briefings and organizational “pulse checks” to automated travel ops and stakeholder management, Ken provides a practical framework for tech leaders to reclaim 20% of their cognitive load.
Everyone talks about AI strategy for their products. Fewer leaders show what it looks like to actually lead with one.
Ken shares his real-world deployment of a personal executive agent that bridges the gap between high-level strategy and tactical execution. This isn't a session on prompt engineering—it is a masterclass in an Tech Leader Operating Model. You will see how an incrementally built system handles morning situational awareness, privacy-safe calendar synchronization, complex travel logistics, and the automation of professional brand building while you sleep.
The Four-Stage Framework for Leaders:
Build: Curating the “Executive Context” (What your agent knows about your roadmap and team).
Trust: The Autonomy Ramp (Moving from “Assistant” to “Agent”).
Delegate: Identifying high-leverage administrative and strategic hand-offs.
Compound: Building a memory system that scales your decision-making.
Live Demonstrations of Leadership Workflows:
The Executive Brief: Beyond email triage—priority surfacing across Slack, Jira, and GitHub to identify organizational bottlenecks.
Stakeholder & Speaking Pipeline: Automating CFP tracking and abstract generation for conferences, while maintaining a consistent thought-leadership presence.
Travel & Logistics Ops: Auto-detecting conference trips, fare watching, and seamless TripIt/Expensify integration for a zero-friction travel experience.
The Privacy Bridge: Managing a personal-to-work calendar sync that protects your private life while ensuring your team has accurate OOO visibility.
Secure Vault Retrieval: Sudo-style authenticated access to sensitive documents and IDs on the fly.
The Nightly Content Forge: How the agent drafts internal memos, blog posts, or project summaries while you are offline.
Strategic Governance:
We will also tackle the critical “Leader-to-Agent” trust design: how to define “Guardrails vs. Guidance,” managing sensitive corporate data, and building a context-rich memory system that makes the agent a genuine force-multiplier for your leadership style.
Outcomes:
A Leadership Mental Model: How to deploy an agent that complements your specific technical and managerial skill set.
High-ROI Automations: A curated list of “Quick Wins” for tech leaders to implement immediately.
Governance & Control: A realistic roadmap for safety, privacy, and control in autonomous systems.
From Intermittent to Continuous: Inspiration to transition from “using AI” to “operating through AI.”
AI agents are not just tools for the IDE; they are the new operating system for high-stakes leadership. In this session, Ken Sipe moves beyond the hype of “AI-assisted coding” to demonstrate what it actually looks like to lead and scale with a personal AI agent. From executive briefings and organizational “pulse checks” to automated travel ops and stakeholder management, Ken provides a practical framework for tech leaders to reclaim 20% of their cognitive load.
Everyone talks about AI strategy for their products. Fewer leaders show what it looks like to actually lead with one.
Ken shares his real-world deployment of a personal executive agent that bridges the gap between high-level strategy and tactical execution. This isn't a session on prompt engineering—it is a masterclass in an Tech Leader Operating Model. You will see how an incrementally built system handles morning situational awareness, privacy-safe calendar synchronization, complex travel logistics, and the automation of professional brand building while you sleep.
The Four-Stage Framework for Leaders:
Build: Curating the “Executive Context” (What your agent knows about your roadmap and team).
Trust: The Autonomy Ramp (Moving from “Assistant” to “Agent”).
Delegate: Identifying high-leverage administrative and strategic hand-offs.
Compound: Building a memory system that scales your decision-making.
Live Demonstrations of Leadership Workflows:
The Executive Brief: Beyond email triage—priority surfacing across Slack, Jira, and GitHub to identify organizational bottlenecks.
Stakeholder & Speaking Pipeline: Automating CFP tracking and abstract generation for conferences, while maintaining a consistent thought-leadership presence.
Travel & Logistics Ops: Auto-detecting conference trips, fare watching, and seamless TripIt/Expensify integration for a zero-friction travel experience.
The Privacy Bridge: Managing a personal-to-work calendar sync that protects your private life while ensuring your team has accurate OOO visibility.
Secure Vault Retrieval: Sudo-style authenticated access to sensitive documents and IDs on the fly.
The Nightly Content Forge: How the agent drafts internal memos, blog posts, or project summaries while you are offline.
Strategic Governance:
We will also tackle the critical “Leader-to-Agent” trust design: how to define “Guardrails vs. Guidance,” managing sensitive corporate data, and building a context-rich memory system that makes the agent a genuine force-multiplier for your leadership style.
Outcomes:
A Leadership Mental Model: How to deploy an agent that complements your specific technical and managerial skill set.
High-ROI Automations: A curated list of “Quick Wins” for tech leaders to implement immediately.
Governance & Control: A realistic roadmap for safety, privacy, and control in autonomous systems.
From Intermittent to Continuous: Inspiration to transition from “using AI” to “operating through AI.”
Two and a half days of insightful sessions, inspiring ideas, and meeting your peers. Learn the skills and methods that will take your organization to the next level.
REGISTER NOW