Updated November 2026
Top AI Speakers for Sales Kickoffs (2027)
Sales leaders want kickoff speakers who go beyond the AI basics: practitioners who have built and sold, and who leave the team knowing what to do on Monday morning and how to think about the change in how customers buy.
All seven are speakers Crimson books. Each entry gives the reason the speaker was chosen, the audience they suit, and a fee range.
The short answer
- Shama Hyder: Sales and revenue teams that need to connect AI to growth and how customers buy now. $30K–$60K.
- Zack Kass: Large kickoffs that want an inside view of AI from a go-to-market leader. $50K+.
- Jeremy Utley: Kickoffs that want an interactive session where reps try AI in the room. $25K–$40K.
- Allie K. Miller: Technology and B2B sales teams that want practical AI use cases. $25K–$50K.
- Brian Solis: Kickoffs with a customer experience theme. $25K–$50K.
- Paul Roetzer: Marketing and sales teams that want a practical introduction to AI on a smaller budget. $10K–$25K.
- Gary Vaynerchuk: Very large kickoffs that want a headline name on the main stage. $200K+.
The top 7 AI speakers for sales kickoffs in 2027
Ranked for sales kickoffs, revenue team meetings, and go-to-market events.
1. Shama Hyder
Best for: Sales and revenue teams that need to connect AI to growth and how customers buy now.
Fee range: $30K–$60K
Shama Hyder is first because she has done the job the audience does. She built Zen Media over 17 years and sold it, and she has advised Microsoft, Adobe, Salesforce, and JPMorgan Chase. She is Professor of AI at the Link School of Business, was named to the 2026 TIME100 Creators list in the Leaders category, and wrote the forthcoming Seven Signals (Simon & Schuster, 2027). Her AI in Action keynote gives sales teams practical moves they can use the next week.
Shama Hyder profileShama Hyder speaking feeCheck availability
2. Zack Kass
Best for: Large kickoffs that want an inside view of AI from a go-to-market leader.
Fee range: $50K+
Zack Kass is the former Head of Go-To-Market at OpenAI and the author of The Next Renaissance (Wiley, 2026). He was chosen because he led go-to-market at OpenAI, so he speaks to a revenue team from go-to-market experience, not only technical knowledge. His keynote explains what AI can do today and what is coming, in terms a sales organization can plan around.
3. Jeremy Utley
Best for: Kickoffs that want an interactive session where reps try AI in the room.
Fee range: $25K–$40K
Jeremy Utley spent more than a dozen years as a director at Stanford's d.school, co-wrote Ideaflow with Perry Klebahn, and co-hosts the Beyond the Prompt podcast. He was chosen because his sessions are interactive and focus on how people work with AI day to day. He fits kickoffs where the goal is for the team to work differently afterward, not only to hear about AI.
Jeremy Utley profileJeremy Utley speaking feeCheck availability
4. Allie K. Miller
Best for: Technology and B2B sales teams that want practical AI use cases.
Fee range: $25K–$50K
Allie K. Miller was Global Head of Machine Learning for Startups and Venture Capital at Amazon Web Services and earlier launched the first multimodal AI team at IBM. TIME named her to its TIME100 AI list in 2025. She was chosen because she shows business teams where AI pays off in practice. Her sessions suit technology and B2B sales organizations that want specific use cases.
Allie K. Miller profileAllie K. Miller speaking feeCheck availability
5. Brian Solis
Best for: Kickoffs with a customer experience theme.
Fee range: $25K–$50K
Brian Solis is Head of Global Innovation at ServiceNow, former Global Innovation Evangelist at Salesforce, and the author of books including X: The Experience When Business Meets Design and Mindshift (Wiley, 2024). He was chosen because he explains how AI is changing what customers expect, which helps sales and customer teams rethink the buying experience. He speaks at a strategic level, so pair him with a workshop if you want tool training.
Brian Solis profileBrian Solis speaking feeCheck availability
6. Paul Roetzer
Best for: Marketing and sales teams that want a practical introduction to AI on a smaller budget.
Fee range: $10K–$25K
Paul Roetzer is the founder and CEO of Marketing AI Institute and SmarterX, co-author of Marketing Artificial Intelligence with Mike Kaput, and host of The Artificial Intelligence Show podcast. He was chosen because he teaches AI to business professionals for a living and keeps his material practical. He is a good choice for a combined marketing and sales kickoff, or a mid-sized team that wants a clear starting point at a lower fee.
7. Gary Vaynerchuk
Best for: Very large kickoffs that want a headline name on the main stage.
Fee range: $200K+
Gary Vaynerchuk is chairman of VaynerX and CEO of VaynerMedia, and the author of books including Crushing It! and Day Trading Attention. He was chosen because he is an operator with a very large audience who speaks about attention, marketing, and how AI changes both. He suits a large kickoff with the budget for a marquee name. His material leans to marketing and entrepreneurship more than sales process.
Gary Vaynerchuk profileGary Vaynerchuk speaking feeCheck availability
How we ranked
We ranked on five things, with the most weight on whether a speaker is a real practitioner who leaves a sales team with something to act on.
- Fit for business audiences
- The talk has to work for executives, managers, and teams, not only for a technical crowd.
- Practical takeaways
- People should leave knowing what to do on Monday morning and how to think about the change.
- Recent stage record
- We look at current keynotes, books, research, and roles, because AI material dates quickly.
- Planner feedback
- What organizers tell us they need from an AI keynote.
- Value for fee
- What the audience gets for the budget, compared with other speakers in the same fee band.
The order is our editorial judgment, not a measurement. Every speaker here is one Crimson books, and the list covers the Crimson roster, not every AI speaker working today. Fee ranges are the listed ranges for an in-person keynote, before travel.
How to choose an AI speaker for a sales kickoff
A kickoff keynote has one job: send the team into the year with energy and a plan. A few decisions narrow the list.
- Decide who the talk is for
- Frontline reps, sales managers, and the wider revenue team need different depth. Tell the speaker the mix.
- Pick keynote, workshop, or both
- A keynote sets direction for the full audience. A workshop gives a smaller group time to practice with AI tools.
- Tie it to this year's plan
- Share your sales priorities, product launches, and customer segments so the speaker can use examples the team recognizes.
- Set the budget band
- Fees on this list run from $10K to $200K+. A typical sales kickoff keynote budget is $25K to $50K.
- Book early for January and February
- Kickoff dates cluster at the start of the year, so check availability as soon as the date is set.
For the full checklist, use the AI keynote speaker selection guide, or see sales kickoff keynote speaker costs and options.
AI speaker fees for sales kickoffs
Fee ranges for the seven speakers on this list run from $10K to $200K+ for an in-person keynote. Four have ranges that start at $25K or less.
| Rank | Speaker | Fee range | Fee details |
|---|---|---|---|
| 1 | Shama Hyder | $30K–$60K | Fee guide |
| 2 | Zack Kass | $50K+ | Fee guide |
| 3 | Jeremy Utley | $25K–$40K | Fee guide |
| 4 | Allie K. Miller | $25K–$50K | Fee guide |
| 5 | Brian Solis | $25K–$50K | Fee guide |
| 6 | Paul Roetzer | $10K–$25K | Profile |
| 7 | Gary Vaynerchuk | $200K+ | Fee guide |
The final quote depends on the date, location, format, travel, and how much the talk is tailored to your audience. To compare offers line by line, use the speaker quote comparison checklist.
Frequently asked questions
Who are the best AI speakers for a sales kickoff?
Crimson's top AI speakers for sales kickoffs in 2027 are Shama Hyder, Zack Kass, Jeremy Utley, Allie K. Miller, Brian Solis, Paul Roetzer, and Gary Vaynerchuk.
Who is the best AI keynote speaker for a sales team?
Shama Hyder ranks first on Crimson's list for sales kickoffs. She built and sold Zen Media after 17 years, is Professor of AI at the Link School of Business, and was named to the 2026 TIME100 Creators list. Her keynote connects AI to growth and to how customers buy now.
How much does a sales kickoff keynote speaker cost?
Fee ranges on this list run from $10K to $200K+. Paul Roetzer is listed at $10K–$25K, Jeremy Utley at $25K–$40K, Allie K. Miller and Brian Solis at $25K–$50K, Shama Hyder at $30K–$60K, Zack Kass at $50K+, and Gary Vaynerchuk at $200K+.
Which AI speaker is best for an interactive sales kickoff session?
Jeremy Utley, co-author of Ideaflow and a longtime director at Stanford's d.school, is the most interactive speaker on this list. Shama Hyder and Allie K. Miller also focus on practical next steps.
How was this list ranked?
Crimson ranked the speakers on fit for business audiences, practical takeaways, recent stage record, planner feedback, and value for fee, with sales teams in mind. The order is an editorial judgment, and all seven are speakers Crimson books.
When should I book a sales kickoff speaker for 2027?
As soon as your date is set. Kickoffs cluster in January and February, so the same speakers are requested for the same weeks. Send Crimson the date, audience size, and budget range to check availability.
Planning a sales kickoff?
Send Crimson your date, audience, and budget range. We will check which of these speakers are open and suggest comparable options. Free to event organizers.
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