Planning a sales kickoff for 2026? Selecting the right keynote sales kickoff keynote speaker can set the tone for the year ahead, inspiring your team and providing actionable insights. 

Our sales kickoff speakers have diverse backgrounds and areas of expertise that help sales teams succeed – from rejection and resilience, to storytelling for the perfect pitch, negotiation, emotional intelligence, AI, and more. Read on for some top sales kickoff keynote speakers to consider.

Kevin O’Leary – Entrepreneur & Investor

Kevin O’Leary is a Canadian entrepreneur, television personality, and investor. He is best known for his role on the television series Shark Tank, where he evaluates investment opportunities and offers advice to entrepreneurs. O’Leary is also the founder of O’Leary Funds, a mutual fund company, and has authored several books on business and personal finance.

Molly Bloom – Author & Former Poker Host

Molly Bloom is a former Olympic skier turned entrepreneur and author. She gained national attention for running one of the most exclusive high-stakes poker games in the world, which was later the subject of her memoir, Molly’s Game. Bloom now speaks about her experiences and the lessons she learned about risk, resilience, and success.

Zack Kass – Former Head of Go-To-Market at OpenAI

Zack Kass is a global AI advisor and the former Head of Go-To-Market at OpenAI, where he built the company’s sales, solutions, and partnerships teams. Today, he advises Fortune 1000 companies and governments on how to lead in an AI-driven world and collaborates with the University of Virginia to explore AI’s socio-economic impacts. His new book, The Next Renaissance: AI and the Expansion of Human Potential, is available for pre-order now and will be published on January 13, 2026.

Tiffani Bova – Growth, Innovation, and Sales Transformation Keynote Speaker

Tiffani Bova is a growth, innovation, and sales transformation keynote speaker. She is also a two-time Wall Street Journal bestselling author and highly rated podcast host of What’s Next! with Tiffani Bova. As a top business speaker, she has delivered more than 1,000 keynotes on six continents, helping thousands of companies respond to changing market dynamics while developing a customer-centric go-to-market approach.

Rashaun Williams – Entrepreneur & Speaker

Rashaun Williams is a visionary venture capitalist, entrepreneur, and advocate for financial literacy. With over two decades of experience in investment banking, private equity, and venture capital, Rashaun has invested in more than 170 companies and mentored dozens of startups through their growth journeys. His dynamic keynotes cover topics such as financial literacy for the next generation of leaders, entrepreneurship and innovation in today’s economy, and lessons from investing in industry-changing companies.

Margie Warrell – Author & Leadership Expert

Margie Warrell is an author, leadership expert, and keynote speaker who helps individuals and organizations lead with courage and confidence. She is the author of several books, including Find Your Courage and Stop Playing Safe, and has been featured in various media outlets, including Forbes and the Huffington Post.

Daniel Lubetzky – Founder of KIND Snacks

Daniel Lubetzky is a social entrepreneur and civic leader, best known for founding and building KIND Snacks into a multi-billion-dollar brand. He is also the founder of the Builders Movement, which helps people move beyond “us vs. them” to find common ground and build on it together. Daniel is a Shark on ABC’s Shark Tank and the author of the New York Times bestseller Do the KIND Thing.

Matthew Luhn – Storytelling for Business Expert

Matthew Luhn is a storytelling expert and former Pixar animator who has worked on films such as Toy Story and Finding Nemo. He now helps organizations craft compelling stories that engage audiences and drive action.

James Clear – Author of Atomic Habits

James Clear is a writer and keynote speaker focused on habits, decision making, and continuous improvement. His book, Atomic Habits, has sold over 25 million copies worldwide and was the #1 bestselling book of the year on Amazon in 2023 and 2021. Clear is a regular speaker at Fortune 500 companies and his work has been featured in publications such as Time magazine, the New York Times, the Wall Street Journal, and on CBS This Morning and Today Show Australia.

Bill Benjamin – Sales Leadership Consultant

Bill Benjamin is a sales leadership consultant who helps organizations improve their sales performance through effective leadership strategies. He has worked with various companies to develop sales training programs, improve sales processes, and enhance team performance.

Dr. JP Pawliw – Motivational Speaker & Coach

Dr. JP Pawliw is a motivational speaker and coach who inspires individuals and organizations to achieve their full potential. He combines motivational speaking with coaching techniques to inspire sales teams, focusing on mindset, resilience, and achieving peak performance in sales.

Jia Jiang – Expert on Rejection, Resilience, and Goal Achievement

Jia Jiang is a leading expert on overcoming rejection and building resilience. His bestselling books Rejection Proof and viral TED Talk inspire sales teams to embrace challenges and turn fear into action. He teaches practical strategies to help teams stay motivated, persist through setbacks, and achieve ambitious goals. 

Chaunté Lowe – Olympic Athlete & Cancer Survivor

Chaunté Lowe shares her story of resilience, highlighting how overcoming personal challenges can translate into professional success. Her message inspires sales teams to remain focused and determined in the face of adversity.

Kwame Christian – Author & Negotiation Expert

Kwame Christian teaches the art of negotiation, emphasizing the importance of emotional intelligence and effective communication. His strategies empower sales teams to navigate complex conversations and close deals with confidence.

Selecting the right keynote speaker for your sales kickoff can inspire your team and set a positive tone for the year ahead. Consider the specific needs and goals of your team to choose a speaker who aligns with your objectives. 

Ready to book a sales kickoff speaker? Email info@bigspeak.com to inquire.