We Help Build the Mindset, Skillset and Toolset to Elevate Sales.

Three coworkers discussing work at a table. Sales Enablement Services Near Me. Consulting Services to Help Operational Efficiencies in a Company.

At Toying With This Idea, we’re serious about sales strategy and enablement.

Our work drives sales effectiveness, operational efficiency, and revenue generation potential. Reduce friction in your process, develop your team’s skills, supply the right tools and resources for your commercial teams to be successful, then watch them crush their quotas.

Together, we can create the power formula that propels your business forward.

Are you looking to…

Group of coworkers at the office in a meeting. Custom Sales Training

Build or optimize your sales enablement function

OUR SOLUTION:

SALES ENABLEMENT STRATEGY ➔

Woman and IT Tech optimizing a computer. Coach for Sales Teams

Choose or optimize sales technology to gain efficiency

OUR SOLUTION:

TECHNOLOGY OPTIMIZATION ➔

A man presenting to a team at a table. Consulting Services to Help My Team With Sales Playbooks

Onboard, train or upskill your commercial team

OUR SOLUTION:

TRAINING & COACHING ➔

Optimize sales strategy & execution

OUR SOLUTION:

SALES ENABLEMENT STRATEGY ➔

A group of women cheering in a conference room. Caroline Holt Speaking Events at My Organization.

Find an energetic keynote for your next event

OUR SOLUTION:

SPEAKING ENGAGEMENTS  ➔

Woman with blonde hair and glasses at her laptop. How to Get Help With My Organization's Document Sales Process and Customer-Facing Best Practices

Document sales process and customer-facing best practices

OUR SOLUTION:

TOOLS & SALES PLAYBOOKS  ➔

4 people gathered around a computer in an office.

Hire and ramp sales professionals more effectively

OUR SOLUTION:

TALENT ASSESSMENT ➔

Four people gathered around a computer in an office. Consultancy to help my company Ensure your sellers have the messaging and resources to crush their quotas

Ensure your sellers have the messaging and resources to crush their quotas

OUR SOLUTION:

TALK TRACKS & SALES COLLATERAL ➔

Lindsey Boggs

Blonde haired woman smiling. Sales Strategy Consulting Arlington VA

3X Salesforce Top Influencer / VP Sales Development & Enablement at Glassbox / TEDx Speaker / Mental Health Advocate

“Caroline is quite easily the most organized person I’ve ever had the pleasure of working with in the sales training field. From the moment we began scoping our social selling webinar together she was incredibly thoughtful, detailed, and knew exactly what was needed for her sales organization. Caroline was very engaging with both me as well as her sales organization and brought so much value to our planned social selling webinar. It was a delight working with Caroline and hope to work with her again.”

Man presenting on stage. Small Consulting Firm That Specializes in Helping Sales Teams Grow.

Bryan Caplin

Chief Revenue Officer / Board Advisor / Investor

“I had the pleasure of working with Caroline in three roles. Once as a peer where we went head to head as revenue contributors at CEB, then I hired her to analyze and assess the talent of our organization at Axiom Law as we were attempting to build process and build predictable revenue in our mid market team.”

  • “In that role, she used her proprietary talent assessment tool to analyze the effectiveness of each of our staff on about 40 skills, then prioritized the ones that were most important. She then led a series of commercial skills building programs based on the result. From that program, we saw an increase in our win rate the following quarter. We also saw more of our folks hit goal that quarter than the quarter before.

    When I left Axiom for Andela, I brought Caroline there to help lead our Sales Kickoff as a speaker and trainer, and lead a series of commercial skills building programs. Through that process and subsequent work, she also helped us identify some important process gaps, inconsistencies in our talk track as well as management development opportunities to support our longer term growth strategy. Her work helped us justify a more significant investment in enablement for our growth. I highly recommend Caroline's work and have referred her to others. She's thorough, efficient and my team and I loved working with her.”

Here are the highlights of how we will work together, and what we may ask.

Initial Consultation

What challenges are you experiencing or what outcomes are you trying to drive? On what timeline are you hoping to see impact?

1

Recommendations & Pricing

How do these recommendations align with your needs & anticipated outcomes? How does the scope align with your budget?  

2

Proposal & Contracting

Who will be involved, what role will they play and what will they want to see?   How do we work through your purchasing process? 

3

Kickoff

Who else will be involved in development & implementation?  How often shall we meet? What are the metrics we will use to assess impact?

4

Development

Here’s how it’s going for us… Here’s what we need your help with… (e.g., intros, feedback, friction, decisions, edits) Here’s what you can expect to see next… What feedback do you have?

5

Delivery & Rollout

What’s the best format and audience for roll out?  Who should we include to preview? 

6

Followup

How has it gone? What is the feedback? Let’s look at the metrics & impact.

7

Caroline Holt Smiling. Sales Team Enablement Services.

A Message From Our Founder

Caroline Holt

“Welcome! Toying With This is a stellar team of subject matter experts in sales enablement, training facilitation, coaching, and more. We are passionate about our work and delighting our clients. We treat you how you want your commercial team to treat your clients: prepared, engaged, knowledgeable, focused and client obsessed.”