Go from slow sales to major momentum
Repeatable Sales Club
A monthly curriculum and community membership for early-stage founders who want accelerate growth. Learn tactical sales strategies and get the support you need to execute, so you can generate reliable revenue and find product-market fit.
“Caroline is a world-class go-to-market expert. She doesn't just guide. She equips you to win.”
— Ali Bono, CEO and Founder, Pelican InvestsLive October Intensive
⋆
Live October Intensive ⋆
Accelerate your revenue with our Quarterly Intensive
Don’t go it alone. Starting October 26th, we’ll run a live intensive for members, held over three focused weeks. You’ll be guided live through the essential frameworks that accelerate early-stage revenue.
In just six sessions, you’ll learn our GTM playbook and start building your own. We’ll cover:
The twelve blockers to product-market fit
Nailing your buyer definition
Our foolproof framework for booking sales calls in the age of AI
Our proven sales call script that converts and surfaces key insights
Analyzing market insights to reach scale
Join the Repeatable Sales Club to participate in this live, bootcamp-style experience built for fast results. Over three weeks, sessions are held on Mondays and Thursdays, plus optional office hours on Tuesdays.
Over these six live sessions, Caroline will guide you through training and address your questions live. You’ll leave having made tangible progress on each key element of early-stage GTM.
Members have access to call recordings and the video training library all year long, but join now to skip the self-study and get hands-on support to unblock your sales motion, stat.
What founders have to say
What’s included in the Repeatable Sales Club
Live quarterly intensive to learn or refresh your revenue strategy — starts May 18th
Tactical library of step-by-step sales frameworks so you can move from scattered outreach to systematic revenue generation
Weekly office hours so you can tackle roadblocks in real time
Discounted 1:1 advisory support
Thirty-minute intro call
24/7 community platform access so you can share wins, troubleshoot, and learn from alongside of like-minded founders
-
Master and implement foundational early sales tactics
Define your repeatable customer type so you stop selling to everyone and accelerate your path to recurring revenue
Learn proven outreach techniques that actually work for early-stage startups
Build ready-to-deploy GTM strategies that stand out from the noise, build goodwill, and match with your unique customer
Learn how to run sales calls that expose critical market insights and convert buyers who are a good fit
Figure out the pricing, packaging, and closing strategies that make sense for your business model
Uncover valuable market insights from every prospect conversation
-
Sales aren’t moving as fast as you want, but you’re not sure why, and you’re not sure what needs to change most
You are a B2B/B2B2C founder with $0 to $1M in recurring revenue. You can be pre- or post-product, pre- or post-revenue. If you’re B2C, reach out to us to discuss if you’re a fit.
You are ready and willing to talk to customers
You’re on board with the idea that early-stage founders need to lead the sales process
All industries are welcome
You’re not a fit if you’re looking for a quick fix, or you’re wanting to remove yourself entirely from the selling process.
-
The price for the October Revenue Intensive is $450, which includes three months of unlimited access to the community (weekly office hours, access to the course library, et cetera).
$0 to $50K MRR in six months
Two years of revenue closed in one quarter ($250K ARR to $1M+ ARR)
70x increase in repeatable sales
An average 400% increase in qualified sales calls within two months
First two sales closed in the first month of work
Clarified their target buyer, after months of pivoting or scattershot selling
Our approach and methods work.
Clients we’ve supported (including scientists, introverts, activists, and technical founders) have seen results like:
Meet the founder
Caroline Fay helps startups master early sales and find repeatable revenue.
Startups who have worked with her have seen results like $200K-$1M+ ARR within six months, $0-50K MRR in six months, and a 60x increase in recurring revenue.
Caroline co-founded the equitable hiring startup Skillist, which was funded by Flybridge and Strada, and was acquired by Opportunity@Work. She later led a product marketing team at HR tech unicorn Lattice.
She teaches and coaches at organizations like Yale University, NYCEDC, JFF Ventures, Visible Hands, and Blue Ridge Labs at Robin Hood.
She holds a Master’s Degree in Education from Harvard University and serves on the Board of Trustees of Franklin Cummings Tech, a technical college in Boston.
“Caroline hosted, by far, the most helpful and actionable sales training that I’ve ever attended — and I have attended many.”
— Kelsey Willock, CEO and Founder, Aura FinanceCurriculum details
Comprehensive video trainings with accompanying templates and resources
The Tactical Playbook: Step-by-step instructions on early sales execution
How to define your buyer hypothesis
Cold emails in 2025: new best practices and what to avoid
How to use sales calls to uncover insights
How to price early-stage
Common demo mistakes
Follow-up that converts: best practices and common mistakes
How to spot false positives from a prospect
Understanding and implementing the Sell-to-Learn Cycle
The Bigger Picture: Understanding the "why" behind the tactics
Identifying and addressing the key blockers standing between you and product-market fit
Why you should start selling now, even if you don’t feel ready
How much time it really takes to build a critical mass of sales calls
What to do if you don’t know who to sell to
The six myths of early-stage sales
What signals to listen to (and what to ignore) from the market
The Mental Game: Mindset shifts and habits for repeatable revenue
How to build a consistent sales practice
A winning mindset for early-stage selling
Using the Immunity to Change framework to shift your sales habits
Time Auditing Tool for the busy founder who struggles to hit their sales goals
Weekly Office Hours
When you hit a roadblock while working through the curriculum or need help implementing what you've learned, join these live sessions for real-time problem-solving. I'll help you work through specific challenges and you'll leave with clear action steps.
Quarterly Intensive
Once a quarter, we’ll run a three-week intensive on sales, live. The intensive will bring to life everything in my content library through hands-on application, so you'll leave having made meaningful changes to key elements of your go-to-market strategy.
Discounted 1:1 Advising
Book private time so we can go deep on your sales strategy — for a discounted rate.
Live support
FAQs
-
If you are considering becoming a founder, or you have multiple ideas, this will be helpful. You will get exposure to what it really takes to become a founder. You will also learn why the best way to test your concept(s) is by selling early, and how to do so.
I’ll help you swiftly clarify your target buyer hypothesis and test it, so that you don’t waste time building a product that folks just don’t want to buy.
-
No. The course material helps you clarify any and all hypotheses about the market and what they want to buy from them – and swiftly test their viability through real sales outreach.
Without testing them directly with the market, you’ll be spending time with too much hypothetical data and thinking, which is ultimately harmful to your startup’s health.
-
There is no required commitment. However, I recommend that you stick with it for three months so you can get the full value of the content and begin implementing your learnings. Getting in the swing of true founder-led sales takes time, and I encourage you to plan for that.
-
Members can purchase ad hoc 1:1 sessions at a discounted rate. You can transition to a standard advising retainer so we can go further, faster (you’ll still keep access to the membership).
-
If you can’t make it, the live events are recorded and shared in the content library. You’ll get more out of these events if and when you’re able to attend live, but there’s plenty of value in watching the playback.
-
If you complete the curriculum and commit to selling, you will have learned foundational early sales tactics, and will have put them into motion. You will have defined your target buyer, sent authentic outreach messages to them, run conversational and non-sleazy sales calls, and uncovered tons of incredible insights from prospects that will be the building blocks of a repeatable sales playbook.