Ranking 13 Sales Kickoff Speakers from Best to Worst

I recently attended a fantastic sales kickoff event for my early stage software company. The entire event lasted about a day and our venue was a conference room at the WeWork that we use as our primary office. That event made me think about some of the large sales kickoff events my team produced over the years. While the six of us in that conference room didn’t justify an external guest speaker, it didn’t stop me from thinking about some of the great speakers we might hire in the future as we grow.

With that context, I reflected on the kickoff speakers my team hired over the past 15 years or so and I ranked the ones I could remember. My ranking is based on the fit and impact of their appearance. A bad ranking doesn’t especially mean that they are a bad speaker, it simply means that the magic didn’t really happen that day.

One conclusion that jumps out is that price is not directly related to quality of fit. The number one on the list was probably the least expensive speaker we hired.

An important note about this list: In general, I don’t intend to pass judgement on the speakers’ capabilities. I am assessing our choice vs. the speakers’ capability or value. Some of the choices that are near the bottom of the list might be good ones for you. Where appropriate, I will highlight the reason for the fit or lack thereof.


Gene KranzGene Kranz, NASA Flight Director for Apollo 11 Mission. Grade: A+

Gene was one of those speakers who caught you by surprise. An unassuming, zero-ego gentleman. He showed up and started talking about the Apollo 11 Mission and the audience remained completely silent and at attention for his entire talk until they burst into applause at the end. I believe it was 2005 when we hired Gene, and the timing was important for us. We were about to embark on a near-impossible mission of taking a small software company known for scanning software to become a leader in voice. And for a little while at least, we did it.

walter i-3Walter Isaacson, Historian, Journalist, and Writer.
Grade: A+

Hiring Mr. Isaacson was the brilliant idea of Lori Johnson, who was, at that time, the executive assistant for our CEO. At the time of our kickoff, he had just finished writing the biography of Steve Jobs, and Mr. Jobs had recently died from his battle with pancreatic cancer. I believe that we were the first organization to hire Mr. Isaacson to speak about his book as it was just published. I was struck by his ability to speak flawlessly about the story in incredible detail for 45 minutes without once referring to notes. His delivery was calm and quiet, which seemed appropriate for the somber time. Perhaps most compelling was the story he told about Steve Jobs enthusiastically talking about Siri, the project that we contributed the voice recognition to, just before his death. Several years later, I went to hear him speak about his biography of Da Vinci at Harvard University. This thoughtful, compelling presentation of another brilliant man makes me believe that our speech wasn’t just a flash in the pan.

bill ClintonBill Clinton, 42nd President of the United States.
Grade: A

President Clinton is a divisive character whose legacy is complex, especially with the more evolved view that we all have now on the topic of sexual assault. That being said, he is an incredibly charismatic and brilliant man. His scheduling team initially said that he couldn’t speak at our event, but at the last minute, he agreed to do a presentation over satellite (which saved us a lot on the extremely expensive travel and security requirements for an ex-President). I have done many remote presentations in the past, and I know how difficult it can be to engage an audience at a distance. He made it work and impressed us with his ability to connect complex geopolitical issues of the time with our message as a company.

billy beane-3Billy Beane, Baseball Executive and Author of “Moneyball”.
Grade: A-

Billy Beane is another example of a great fit and a great speaker. Known for his leadership in bringing math into baseball, writing a best-selling book, and most-impressively getting Brad Pitt to play him in the movie version of Moneyball, Billy Beane also happens to be a brilliant man and a compelling speaker. His talk really resonated with our team because we reached that point in our company where we needed an analytical approach to drive growth to the next level. He was well-prepared, approachable, and a real professional.

will i am-3will.i.am, Singer, Songwriter, Producer, and Philanthropist.
Grade: A-

Will was one of the most surprising speakers who we hired during my tenure at Nuance. We had been working with him on a project to voice-enable an innovative smartwatch that he developed. While the watch was panned by the tech press, I think they missed the point. He approached the watch design the same way that a fashion designer approaches clothing design. It isn’t about making a commercial success for that specific item, it is about pushing design forward. His talk was so surprising because he was shy, vulnerable, nervous, but told an incredibly powerful story about growing up poor with a mom who made all the difference. By the time he was done, there wasn’t a dry eye in the house. The other impressive bit about Will is that he brought kids from the inner city into his design studio and completely changed their lives.

colin-3Colin Powell, 65th United States Secretary of State.
Grade: A-

Not surprisingly, the guy who spent 35 years in the military and ended up at the rank of four-star general was prepared for his speaking engagement. Perhaps more surprising was the fact that General Powell was warm, funny, thoughtful, and did a great job connecting the dots between his experience, the current political climate (in 2016) and our business. Overall, he was a solid choice for a speaker.

ray k-3Ray Kurzweil, Inventor and Futurist.
Grade: B+

You may know of Ray Kurzweil as a noted futurist and an early pioneer of AI, but he also had a close relationship to the formation of Nuance. Ray sold his Kurzweil Computer Products business to Xerox in 1995, creating the foundation of what became ScanSoft and then Nuance. It’s hard to get more relevant to the business than that. Ray is also a brilliant futurist (although he has some “out there” ideas), and he presented a compelling case for the future importance of AI. That being said, his talk was a little over the head of some of the sales audience. If he was speaking to an engineering audience, I could see him delivering an “A” speech.

nando-3Nando Parrado, Survivor of Uruguayan Airplane Crash.
Grade: B+

You may not recognize the name, Nando Parado, but you probably recognize his story. Nando was part of the soccer team whose plane crashed in the Andes in 1972. Of the 45 passengers, 16 survived, in part through resorting to anthropophagy (cannibalism). Nando and one other from the group hiked out through the snow-covered Andes for 10 days, saving the lives of the survivors. This was an incredible story, told by Nando with a look in his eyes like he was re-living the crash in real time. While the story was incredible, it wasn’t the best fit for a sales team. I remember everyone leaving the room with the feeling that they needed to go spend time with their families, not go out and sell more.

bruce-3Bruce Jenner (now Caitlyn Jenner), Olympic Gold Medal-Winning Decathlete.
Grade: C+

If my memory serves me correctly, Bruce was the speaker the year after Gene Kranz spoke at our kickoff. The speech was delivered during an interesting dip in her career, bookended by the early days as an Olympic hero whose image was emblazoned on Wheaties boxes across the world, and the reality show star turned transgender pioneer. The speech, delivered in the mid 2000s, was awkward and forced, without a good effort to connect the personal story to our company.

lance-3Lance Armstrong, Former Professional Road Racing Cyclist.
Grade: D

You may sense a pattern that sports personalities are not often the best choices for a sales kickoff meeting. We spent a lot of money on them before we figured that out. When Lance came to our kickoff meeting (before his cheating scandal), there was a small part of the audience that was incredibly excited to hear him tell some riding stories. For the majority of the audience, they didn’t really get it. The best part? I asked him to retweet something to his followers and he did.

michael p-3Michael Phelps, Most Decorated Olympian of All Time.
Grade: D-

Continuing with the athlete theme, we hired Michael Phelps to appear at a kickoff meeting to do a Q&A session with his coach. Michael had traveled in from China the day before and looked totally exhausted (or maybe bored…) during the session. He didn’t seem to know why he was there, and I shared the sentiment.

jason a-3Jason Alexander (The "Donny Clay" version), Actor and Comedian.
Grade: D-

This one was a surprise to me. I am a fan of the irreverent humor of Jason Alexander (best known as “George Constanza” from “The Jerry Seinfeld Show”). It turns out that Jason plays an over-the-top character called “Donny Clay” during some of his appearances. One of his bits included showing up in a long coat, which he removed to reveal an exaggerated, larger-than-life, anatomically correct “nude suit”. About 10 percent of the audience thought it was hilarious, the rest was pretty mortified.

drewDrew Rosenhaus, Sports Agent.
Grade: F

I’m thrilled to say that I had nothing to do with hiring Drew for this speaking engagement. Drew is a famous sports agent who has a brash approach to negotiating gigantic deals for his athletes. The most memorable part of his speech was the moment he asked his girlfriend to stand up and be recognized, as Drew said to everyone “isn’t she hot?” We all felt pretty mortified for her. It could have been a good message about selling huge value, but the delivery was too distracting to make the message stick.

Key takeaways.

My key takeaway from assembling this list is that the most important factor in hiring a speaker is the connection to your message, combined with timing. Our top speakers all captured a special moment in the evolution of our company with a heartfelt message. And hiring celebrities simply because they are celebrities never ends up with a good result. They don’t know why they are speaking to your company, and you won’t know either.


Peter Mahoney
Peter Mahoney is the founder and CEO of Plannuh.  Peter has degrees in Physics and Computer Science and studied Latin for 7 years, and then showed up in the wrong room one day and ended up in marketing.  In his 30+ year career, Peter has built products and led marketing for startups and for multi-billion dollar public companies.  You can follow him on Twitter and LinkedIn.





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