Sales trainings and coaching for early-stage founders

Meet Caroline Fay.

Here’s a bit about my background and expertise:

  • I am an exited founder of an equitable hiring startup called Skillist. Our customers included companies like Wayfair, DraftKings, ezCater, Drizly, and Better Mortgage. 

  • After Skillist, I designed go-to-market strategies for new and existing products at Lattice, a Series F startup.

  • Since 2024, I’ve coached and trained over 150 founders, including through incubators like InnovationWorks, Visible Hands, Company  Ventures, and JFF Ventures. 

  • I’m a trained educator via my master’s degree from the Harvard Graduate School of Education, where I studied adult development.

  • Most importantly, I've learned from countless mistakes as a founder, especially in sales, where I struggled with perfectionism and over-preparation. I openly share my experiences with founders, as it creates an open learning environment where founders feel comfortable to confront their own challenges with sales and leadership.

“Caroline has served as an incredible coach to our founders, providing valuable advice and insights about GTM strategy, founder-led sales, and early-stage company building. Her knowledge, guidance, and expertise have been critical forms of support for our founders as they are working towards strategic milestones at the pre-seed stage.”

Justin Kang, General Partner of Visible Hands, a pre-seed VC firm backing overlooked founders

“Caroline ran an amazing workshop on early sales for our founders.  She was knowledgeable, relatable, and took the time to work 1:1 with our founders. Caroline received a perfect 10/10 feedback from our founders, and we can't recommend her enough to any founder who needs practical and actionable advice for sales.”

Jordan Marinkovich, Platform Community Manager, InnovationWorks

Sales Trainings

Topics include:

  • The new principles of early sales

    • How founders can win early traction fast, without sales experience OR a perfect product

  • Building a sales-forward perspective

    • It’s hard to sell if you feel weird about sales. Build a better relationship with selling - no persuasion or mind games required.

  • Booking sales calls

    • Learn how to stand out from the average cold email and book multiple calls per week by authentically connecting with prospects

  • Running sales calls

    • Handle objections, track insights and learnings, and improve your pitch until you hit repeatable sales

Trainings currently offered

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Trainings currently offered ⋆

The Foundations of Early Sales

How do you get the sales flywheel turning? There’s an art and science to selling before you have product-market fit… and getting that right couldn’t be more critical for founders. 

In this training, we’ll cover the core principles of early sales and how to identify, iterate on, and connect with your ideal buyer.

Most sales trainings for founders are built by former enterprise salespeople, but what works at later stages doesn’t work—and can even hurt—early-stage selling. This training is built specifically for getting sales up and running as quickly as possible.

Perfect for founders who need tactical and trustworthy guidance on how to get early sales going. 

I keep it fun and interactive, with time for Q&A, and provide two takeaway resources.

90-minute session, offered in-person or via Zoom

Early Sales Mastery Workshop

In this intensive, hands-on workshop, participants will get everything they need to build a complete system for winning early sales. We’ll go in-depth on:

  • Key principles of early sales

  • How to define your buyer

  • Booking sales meetings

  • Running discovery and demo calls

  • Building a sales-forward mindset

Available as an in-person half-day session or as an online weekly training paced over four weeks.

Building a Sales-Forward Perspective

This workshop breaks down the most common mental barriers that keep founders stuck on sales, and provides concrete steps on how to transform their approach and make faster progress on revenue.

Includes 1:1 support and practical takeaway documents.

60 minute session, offered in-person or via Zoom.

What founders have to say about our trainings

  • This workshop was an absolute gamechanger. Caroline's frameworks make sales feel natural, strategic, and effective.

    Wendy McSparren, CEO and Co-Founder, Admirra

  • Tremendously useful information, broken down into a tactical and actionable format. The approach to looking at sales differently was inspiring.

    Nolan J Sulpizio, CEO and Co-Founder, Clean Plate Innovations

  • Caroline hosted, by far, the most helpful and actionable sales training that I have ever attended -- and I have attended many.

    Kelsey Willock, CEO and Founder, Aura FInance

  • Before I attended this workshop, I would describe sales as a "necessary evil" (half joking). By the end of it, not only had Caroline demystified the process, but she also clearly made the case why it was almost the only thing that mattered getting right.

    Co-Founder, Healthcare Startup

Sales Advising and Coaching for Founders

For select accelerators and incubators, I serve as an go-to-market coach. 

I provide 1:1 customized sales coaching for each founder, meeting them where they are at on their unique revenue journey. 

What makes my coaching especially helpful for accelerator participants is the combination of my sales advising and my personal experience as a founder. I know firsthand how overwhelming and all-consuming the founder journey is – and I share my mistakes and learnings openly.

What founders have to say about my sales advising

  • Working with Caroline was one of the most impactful experiences I’ve had across any startup accelerator. Thanks to her coaching, I walked into every meeting prepared, confident, and with a clear strategy—knowing I had a world-class go-to-market expert in my corner. Caroline doesn't just guide; she equips you to win.

    Ali Bono, CEO and Co-Founder, Pelican Invests

  • With Caroline's mentorship, we were able to objectively assess and pivot sales strategies faster. Ultimately, we closed our first enterprise sales within two weeks of entering the market. We highly recommend any founder, with or without sales experience, to utilize her coaching.

    Valerie Trent, CEO and Founder, Thizo

  • Caroline provided actionable, honest feedback on our go to market strategy and pitch. She fostered a culture of trust and communication which is vital when you want to make real progress and adapt what you are doing for success.

    CEO and Co-Founder, Cleantech Startup

  • Caroline has a unique way of breaking down complex sales processes into very basic terms. I love how passionate and patient she is with her clients and I would definitely recommend her to other founders who need help with their sales cycle.

    Damilola Soladoye, Co-Founder, Bunce

Founders I’ve worked with (including scientists, introverts, activists, and technical experts) have: 

  • 60xed their recurring revenue and counting

  • Increased pipeline of qualified leads by 300%

  • Closed two sales within one month of a pivot

  • Increased sales calls per week by 400%

  • Gained the skills and confidence to tackle founder-led sales

  • Stopped tinkering on their product (you’re ready to sell now - we promise)

  • Learned what to focus on and what to deprioritize when you’re running a pre-PMF startup

Founders don't need sales expertise to hit repeatable revenue.

But they do need advice that works, from someone they can trust.