Keynote Speaking
Real Experience.
Real Talk.
I have led technology at global scale, served a community as its Mayor, and co-founded an AI company from the ground up. When I take the stage, I bring all of it.
No theory. No filler. Just what actually works.
Most technology keynotes are PowerPoint and platitudes. I come to events prepared with real stories, hard-won frameworks, and a willingness to tell the truth even when the truth is uncomfortable. Audiences leave with something they can use.
A career built on real rooms.
Long before "keynote speaker" appeared on my bio, I was standing in front of real audiences, earning their trust and then earning the right to come back.
Vendor Close Events
During my tenure as a senior technology executive, I was a regular presence at large-scale vendor close events, speaking to audiences of hundreds on enterprise technology decisions, platform strategy, and organizational change. Public speaking externally was constrained by my employer. These closed events were where I sharpened the craft.
City Council & Mayoral
Six years of elected office, first appointed and then twice chosen by voters, meant six years of speaking under genuine accountability: council chambers, public hearings, community town halls, and federal partner meetings. I was asked to run for Mayor by the retiring Mayor, fellow Councilors, and community leaders because I had earned their trust by solving the alignment problem others had given up on. When the audience can vote you out, you learn fast.
Oregon Falconers Association & Beyond
As VP then President of the Oregon Falconers Association, I built the coalition that produced the first species downlisting in Oregon history: the Peregrine Falcon. Most people said getting on the ODFW commission agenda was impossible. I recruited the Oregon Hunters Association, Oregon Shooting Association, and dozens of hunting and fishing organizations representing tens of thousands of Oregonians to write letters of support until the commission could not look away. Getting people who don't typically align to stand together for the same cause. That is the same skill that fills a conference room or moves an enterprise initiative forward.
Five talks. Zero filler.
Each talk is available as a keynote (45-60 min), workshop (half-day), or virtual format. All are customized for your audience.
The AI Reality Check
Most AI programs don't fail because the technology is wrong. They fail because the organization isn't ready: unclear ownership, no governance model, pilot-to-production gaps, and vendors who overpromise. I break down the patterns I've seen across dozens of enterprises and give audiences a clear-eyed framework for getting AI out of the lab and into production.
Reliability Is a Strategy
Uptime is not a vanity metric. For organizations that run on digital infrastructure, reliability is a competitive advantage, a brand promise, and an operational obligation. Drawing from maintaining 99.99% uptime at Nike.com, I unpack how the best engineering organizations think about reliability as a business outcome, not a technical checkbox.
Technology That Serves People
What does it feel like to be responsible for technology that affects thousands of people every day? I draw on two very different leadership experiences: running global infrastructure for a Fortune 100 brand, and serving as the elected Mayor of a real community. Both taught me the same lesson. The technology is never the hardest part.
Shadow AI and the Governance Gap
The average enterprise employee is using AI tools that IT hasn't approved, legal hasn't reviewed, and security hasn't assessed. This is not a discipline problem. It is a leadership gap. I walk through the real risk landscape, the governance frameworks that work without killing productivity, and how to move from reactive policy to proactive strategy.
The Platform Trap
Organizations spend years and hundreds of millions on platform modernization, and far too often end up with a new version of the same problems. This keynote digs into the real causes: legacy thinking in new architecture, vendor lock-in masquerading as flexibility, and transformation programs that solve for the org chart instead of the customer.
What working with me looks like.
We Talk
A 15-30 minute call to understand your audience, event goals, and what you need people to walk away with.
I Prepare
Customized slides and examples delivered 48 hours before your event. No generic decks with your logo slapped on.
I Show Up
Punctual, prepared, and adaptable. I bring energy, tell the truth, and stick around for Q&A and side conversations.
Follow Through
Available for post-event fireside formats, executive dinners, and follow-up. Many clients extend into workshops.
Formats Available
Keynote | Workshop | Fireside Chat | Panel Moderator | Virtual | Executive Roundtable
Travel
Based in Salem, Oregon. Available nationwide and internationally.
Speaker Fee
Fees vary by format and engagement type. Contact me for details. I respond personally within 48 hours.
What they're saying.
"I've worked with hundreds of enterprise executives over a 20-year career, and I can count on one hand the people who can walk into a room full of salespeople and genuinely electrify them. Ben Pickett is one of those people. He made a room full of hardened enterprise sales professionals lean forward in their seats, laugh out loud, and walk away remembering exactly why what we do matters. That speech is still talked about. Years later, people from that kickoff still bring it up. If you're looking for a keynote speaker, a thought leader, or someone to represent your brand on stage. Ben Pickett is the real thing."
"I've worked with Ben across vendor partnerships and speaking engagements for nearly a decade. When I brought him in to speak at an invitation-only DevOps workshop for CTO-level executives in Hawaii, he delivered exactly what that audience needed: no theory, no filler, just hard-earned perspective from someone who had lived it at global scale. He was the person everyone wanted to keep talking to when it was over. There is no one I would recommend more confidently for a senior technology audience."
Common questions.
Let's make it happen.
Tell me about your event. I respond personally to every inquiry, typically within 48 hours.