Toying With This Idea

SERIOUS SALES SOLUTIONS: Pitching |  Sales Process Enhancement | Training | Coaching | Management Development | Enablement 

Caroline Holt | (202) 468-6104

Customized Sales Enablement Solutions


For 20 years, Caroline has worked at and with organizations from early stage like Aquicore to global multinationals like Hobsons Education as rep, mentor coach, talent developer and curriculum developer & facilitator.  Her unique background stems from selling research on best practices research in HR, learning & development and sales for CEB (now Gartner) where she read content avidly while selling it.  After 5 years of  scheduling with, pitching, crushing quotas and launching products as a rep selling to CHROs, she began building scalable onboarding and certification curriculum to support CEBs 30% growth run.  As an enterprise sales leader,  she led her team to 200+% performance for new sales and account growth, and built a robust Sales Academy for secondary sales skills training to build on onboarding. As a consultant, she specializes in c-suite engagement, product launches & turning around struggling product lines and enhancing sales skills. Her ability to identify the root causes of an organization's sales challenges and partner to build effective solutions enables her to be a trusted advisor who understands business goals and delivers impact quickly and within budget.  

Training Facilitation & Coaching


Caroline has trained 1000s of prospect- and customer-facing reps and leaders to increase their comfort with sales skills from preparation, elevator pitch, approach, engagement, demo, follow up, negotiation, handoff, upselling, growth to problem customer turnaround.  She is known for her focus on experiential learning through customized role play and activities as well as tools for managers to reinforce skills and increase manager effectiveness.  She begins with key results and metrics to inflect, then builds blended learning solutions with rigorous assessments to ensure both practice and effective application of fundamental commercial and soft skills.  

Her programs receive great feedback because they build skills and increase consistency, not simply imparting knowledge or wisdom.  

Her audiences include:

  • Passionate Founders
  • Sales leaders from front-line to executive team
  • Sales and Customer Success/Account teams
  • Sales engineers and product specialists
  • Business development representatives (i.e., meeting schedulers)
  • New hires of all levels

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Clear Results


Invest scarce sales training dollars effectively on:

  • SalesBalls™ & FIIT™ Proprietary Sales Framework Methodology (includes aligned tools, tactics, sales stages and coaching resources)
  • Classroom Training & Certification Programs on Key Commercial & Soft skills
  • Go to Market Strategy
  • Sales Process Definition and Documentation
  • Product Launch or Turnaround Enablement
  • Individual Coaching for Reps & Leaders
  • Whitelabel 90-day onboarding program for AE/AM
  • Whitelabel 30-day onboarding program for BDA/SDR
  • Whitelabel new sales manager onboarding & upskilling program
  • Talent Assessment & Performance Management

Toying with This Idea solutions inflect:

  • Average price point
  • Conversion or renewal rate
  • Engagement & retention rates
  • Forecasting accuracy
  • Manager effectiveness
  • Net revenue as a portion of sales acquisition costs
  • Opportunity qualification effectiveness
  • Performance consistency
  • Pipeline generation
  • Sales cycle time
  • Scheduled interactions
  • Time to productivity

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Onboarding | Training | Coaching & Management Development | Sales Process Enhancement | Enablement Materials

Toying With This Idea, LLC

Arlington, Virginia 22201, United States

(202) 468-6104


Monday - Friday: 9am - 3pm