Applied AI + security engineers
People shipping systems where models, agents, identities, and infrastructure collide.
Inaugural gathering
20–22 January 2027
Applied AI × Cybersecurity
SkiSides
Whitefish
Montana
A small conference at 101 Central in downtown Whitefish for the people applying AI to security—on offense, defense, and the difficult terrain in between.
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The premise
Big ideas are only the beginning. Let’s bring them to life.
Security practitioners are exceptional at pursuing difficult problems and developing inventive solutions. Too often, promising work stops before it reaches the people who could benefit from it.
SkiSides brings researchers, engineers, founders, and builders together around one question: how do we turn deep work at the intersection of AI and cybersecurity into products, capabilities, and outcomes that create real value for end users?
3days
Talks+ workshops
Networkingbuilt in
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The space
Built for practitioners
The right people.
Close enough to talk.
Red + blue team researchers
Practitioners using LLMs to attack, defend, investigate, automate, and rethink tradecraft.
Security founders
Builders turning hard technical insight into durable security companies and products.
Venture-backed builders
Operators and investors working close to the frontier—not watching it from a distance.
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The format
20–22 January 2027
Three days.
One continuous conversation.
01
Wednesday
20 JanGather
- Welcome reception
- Opening dinner
Arrive, settle in, and meet the room before the ideas start moving.
02
Thursday
21 JanExchange
- Technical talks
- Shared lunch
A concentrated day of field-tested work, sharp questions, and honest discussion.
03
Friday
22 JanBuild
- Discussion workshops
- Organizer-led hackathon
- Closing dinner
Work through hard questions together, build alongside the room, then close the week around one table.
Before / After
Stay for the mountain
Fresh tracks.
Clearer thinking.
Arrive early or stay late. We’ll be skiing and snowboarding at Whitefish Mountain Resort—optional, informal, and an excellent place to keep a good conversation going.
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Take part
Help shape year one
Bring something
to the table.
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Field notes
What to know
Questions,
answered.
01What is SkiSides?
SkiSides is a small, practitioner-led conference at the intersection of applied AI and cybersecurity. The inaugural gathering brings together people doing the work—across research, engineering, company building, and investment.
02Who is it for?
Applied AI and security engineers, red and blue team researchers working with LLMs, security founders, and venture-backed builders. The content assumes technical fluency and rewards active participation.
03Why keep it small?
An intentionally small gathering keeps conversations candid, makes introductions useful, and lets the full group share meals and experiences together.
04What does a ticket include?
Final ticket tiers and inclusions will be published on Eventbrite. Conference programming includes the Wednesday welcome, Thursday talks, Friday workshops, and the meals listed in the schedule.
05Where is SkiSides?
SkiSides will be held at 101 Central, 101 Central Avenue, in downtown Whitefish. Most conference programming will take place upstairs in Second Story.
06Where should I stay?
We have published travel guidance and a short list of recommended Whitefish hotels on the Travel & Lodging page. Attendees book and pay for their own rooms directly with the property.
07Is skiing part of the conference?
Skiing and snowboarding are optional, informal community time for people arriving early or staying late. Lift access, rentals, lessons, transportation, and mountain activities are not included unless explicitly stated later.
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Conference announcements, speaker news, travel notes, and registration updates.