Why Laughter is a Secret Weapon for Sales Success
By Karry Kleeman
3x SaaS Exited CRO | Board Member | Investor | Advisor | GTM Executive
Scaling Companies. Inspiring Teams. Closing Deals with a Smile.
Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader with a proven track record of driving business growth. Having helped scale multiple companies to successful exits and generating over $1 billion in enterprise value, Karry brings energy, clarity, and momentum to organizations looking to level up their revenue game.
But here’s the twist—he doesn’t just lead with numbers and strategy. He leads with laughter, connection, and the power of human engagement.
Whether he’s building world-class revenue teams, architecting go-to-market strategies, or performing classic rock hits on stage, Karry believes that enthusiasm, energy, and a little bit of humor make all the difference.
- From $1M to $50M ARR at LogicGate
- Led SpringCM’s revenue function through its $270M acquisition by DocuSign
- Scaled Mobius from $3M to over $100M, culminating in an IPO
Looking to drive revenue growth while keeping your team inspired? Let’s connect.
Revenue Growth with a Human Touch
At the intersection of business success and human connection, Karry Kleeman thrives. With decades of experience in enterprise software and go-to-market strategy, he has built and led revenue organizations that have transformed startups into industry powerhouses.
His leadership style? A blend of strategic execution, team empowerment, and a bit of well-timed humor.
- Mobius: Scaled revenue from $3M to over $100M, culminating in an IPO.
- SpringCM: Led revenue function through its $270M acquisition by DocuSign.
- LogicGate: Designed a go-to-market strategy that took the company from $1M to $50M in ARR.
Karry doesn’t just lead teams—he rallies them around a common mission, ensuring alignment, execution, and momentum every step of the way.
When he’s not in the boardroom, you’ll find him on stage, microphone in hand, performing classic rock anthems—because whether in sales or music, it’s all about connection.
Let’s scale your business—and have some fun doing it.
Why Laughter is a Secret Weapon for Sales Success
The Best Salespeople Are the Ones Who Make You Smile.
What if the secret to closing more deals wasn’t just in the pitch, the product, or the pricing—but in the power of laughter?
Laughter Builds Instant Connection: People buy from people they like. Humor breaks the ice, lowers defenses, and makes conversations more engaging—turning stiff sales calls into real connections.
It Diffuses Tension & Creates Trust: Sales negotiations can be high-stakes. The right joke at the right moment can ease tension, create rapport, and transform a rigid discussion into a productive one.
It Makes You Memorable: Think about it—who are you more likely to remember? The salesperson who droned through a pitch? Or the one who made you laugh, leaving a lasting impression?
A Lighthearted Approach = More Wins: From $3M to $100M at Mobius to $270M at SpringCM, Karry has proven that the best sales teams aren’t just the smartest—they’re the ones that keep customers engaged, relaxed, and laughing along the way.
Want to build a revenue team that connects, converts, and closes?
Speaking & Consulting
Let’s Talk Revenue. And Have Some Fun While We’re At It.
Karry doesn’t just share frameworks—he brings energy, clarity, and engagement to every stage. Whether it’s keynotes, workshops, or leadership coaching, he’ll help your team drive revenue growth while making the process engaging and enjoyable.
Keynote Topics Include:
- The Role of Laughter in Sales Success
- Scaling Revenue Teams from Startup to IPO
- How to Create Momentum in Sales Leadership
Available for conferences, executive workshops, and virtual engagements.
About Karry Kleeman
Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader. He thrives at the intersection of business growth and human connection, blending a sharp instinct for scaling companies with a deep passion for people and a commitment to infusing a human touch into the process. He is known for bringing energy and clarity to organizations—rallying teams around a common mission, driving execution, and creating momentum that fuels growth.
With a career spanning decades in enterprise software, Karry has built and led high-performing revenue organizations from early-stage startups to IPOs and strategic acquisitions. He has played a pivotal role in scaling multiple companies to successful exits, generating well over $1 billion in enterprise value. At LogicGate, he architected a go-to-market strategy that propelled the company from $1M to $50M in ARR. At SpringCM, he led the revenue function through its $270M acquisition by DocuSign. And at Mobius he helped scale the business from $3M to over $100M, culminating in a successful IPO.
Karry’s ability to inspire and energize teams is a core part of his leadership. Just as he commands attention and engagement when performing live music, he brings the same presence and intensity to leading teams—aligning them around a shared vision, setting the pace, and ensuring everyone is moving in rhythm toward ambitious goals. When he’s not driving business growth, you’ll find him performing classic rock hits anywhere he can find a live mic.
