ABOUT US
We are Serious About Sales Enablement
Toying With This has a stellar team of subject matter experts in sales enablement, scripting, training design & facilitation, coaching, graphic design and video editing. We are passionate about our work and delighting our clients.
Our Mission
Our mission is to empower commercial organizations to crush quotas with the talent, tools, talk tracks, tech and training needed to excel in sales performance. We strive to drive sales process improvement, enhance go-to-market strategies, and unlock the potential of your teams and cultivate a culture of clear expectations setting, continuous growth and improvement and a frictionless sales process.
Our Values
At Toying With This Idea, our values guide everything we do. These values form the foundation of our culture and guide our decisions, actions, and relationships as we strive to make a positive impact on the success and growth of our clients and our team.
Integrity
Excellence
Collaboration
Innovation
Growth Mindset
Empowerment
Zach Mitchell
Chief Growth Officer
“I had the privilege of reporting to Caroline during my first six months of onboarding at Advisory Board. Caroline's ability to break down sales concepts - specifically finding need - and then teach me to subtly engrain them into my conversations with customers was key to my success at the firm. She helped me break down complex conversations into broke her FIIT model and make sure I had truly found a real problem worth solving for the customer.”
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“Through the milestones of her program, Caroline taught me not just to ask questions, but to dig into what success looks like for my customers and fluidly tailor our solution into that vision of success. I would record different aspects of the pitch - intro/elevator 20 sec, longer extended intro, and closing - and then listen to them on my commute to make sure I had them cold for Caroline to ‘certify’. Once I was through the initial milestones, Caroline shadowed my calls with members and then strategized with me to help control and win my first deals. Now, almost five years later, I still find myself ‘listening for need’ in my conversations with customers! Thanks Caroline.”
Caroline Holt
Founder & Principal Consultant
With a track record of high performance in sales development, sales, account management as well as sales management & sales enablement leadership, I have cultivated a unique perspective that blends firsthand experience with best in class solutions for commercial strategy, playbooks, training and coaching.
My career highlights include spearheading successful product launches, turning around struggling lines of business, and helping my teams and customers shatter revenue targets.
I can incorporate methodologies like Challenger Sales, Sandler, MEDDICC and SPIN Selling, but I've also developed my own approach that allows reps and their managers to coach to the fundamentals of sales any opportunity. SalesBalls™ which is inspired by my passion for tennis and centered on the essential variables you need to keey your eyes on at all times in commercial opportunities: Need, Value, and Decision Process.
Whether you support small teams to enterprise-level initiatives, I truly enable commercial teams with the mindset, skillset and toolset to nurture their growth mindset, while being deeply dedicated to identifying gaps and reducing friction in your sales process to increase your organization’s commercial effectiveness.
“I’m typically described as:
Passionate, A Sales Nerd (I spend an obscene amount of time studying sales), High Energy, and Entrepreneurial.”
AWARDS & CERTIFICATIONS
Brainshark’s Sales Enablement Program of the Year 2021
Brainshark’s Sales Enablement Leader of the Year 2022
Revenue.io’s Top 25 Revenue Leaders of 2022
Certified Professional in Talent Development (ATD) Association for Talent Development
Jason Klein
Your go-to leader for marketing, communications, and content
“If you’re looking for a proven and inspirational leader who can empower your revenue teams to be more productive, effective, and successful, look no further than Caroline Holt. When you first meet Caroline, it’s immediate from the start that she knows her stuff.”
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“I had the opportunity to work with her as she brought on Groove at EVERFI, and I was impressed with how deeply she understood every piece of the foundation she was building to enable repeatable and sustainable growth at EVERFI.
On top of her deep expertise in revenue enablement, she’s also kind, empathetic, and full of integrity. The tech industry needs more leaders like Caroline Holt.”