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.
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.
“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 Training Topics
The new principles of early sales
How founders can win early traction fast, without sales experience OR a perfect product
Winning the mental game of sales
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 ⋆
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.
Managing the Mental Game of Sales
Nearly every founder I speak to has a mental blocker about sales that holds them back from sales momentum. Think: “I’m not ready to sell quite yet,” “I don’t have time,” or “I’m not extroverted enough.”
Just like a professional athlete, every founder must tend to their “mental game” to ensure a win.
This intimate workshop breaks down the most common myths that keep founders stuck on sales, and provides concrete steps on how to transform their approach and make faster progress on revenue.
Includes group and 1:1 support, and a practical takeaway document.
90 minute session, offered in-person or via Zoom.
Defining and Booking Calls with Your Buyer
One of the biggest mistakes early-stage founders make is making assumptions about their customers instead of validating what they actually know.
In this workshop, you'll build a clear buyer hypothesis based on real knowledge. You'll define your ideal customer profile: who they are, how they think, what they actually need, and where to find them.
No more selling to everyone. You'll have the clarity to target only your best-fit buyers.
You’ll also learn proven outreach tactics designed for 2025, when buyers are drowning in AI-generated spam. You'll discover how to tailor your outreach strategy for your customer so you cut through the noise and book five sales calls each week.
Includes group and 1:1 support, and a practical takeaway document.
90 minute session, offered in-person or via Zoom.
Running Early-Stage Sales Calls
You'll master the art of "selling to learn" — running sales conversations that simultaneously move deals forward and generate crucial market insights.
From discovery to objections to closing, you'll learn detailed methods that work and feel natural, not pushy or rehearsed.
Every deal will become a learning opportunity that accelerates your path to product-market fit.
60 minute session, offered in-person or via Zoom.
What founders have to say about our trainings
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