Stop spiraling, start selling
Path to Repeatable Sales Program
3-month group cohort
Next cohort begins September 16
Founders carry an impossible burden. You need to have a compelling vision, build a great product, maintain runway to keep the lights on, AND drive sales traction. All at once.
When it comes to the sales piece of the puzzle, a lot of the advice founders receive isn’t relevant. This guidance usually comes from well-meaning veteran sales leaders who have only sold after product-market fit. That’s a completely different process.
In turn, founders waste precious months building shiny sales decks or overwrought sales processes, when those things don’t matter quite yet.
What’s more, most sales advice doesn’t just burn your time and runway… it completely ignores the mental game. It doesn’t address how to prioritize sales amongst everything else you’re doing, or how to navigate the emotional rollercoaster and pressure of being a founder.
You need sales help, but it has to be designed for founders like you, who are selling at the earliest stages all while juggling countless other responsibilities.
You’re a visionary, a builder, and now a salesperson!? No wonder you’re overwhelmed.
Let’s get you everything you need to find repeatable, recurring revenue on your terms.
You need tactics that are proven to work for early-stage startups in 2025.
How to define your buyer and what they need (when you have a limited amount of data about them)
How to connect with your buyer in the age of AI slop
How to run sales conversations that uncover insights and close deals (without any persuasion or pushiness)
And you need to clear any hidden obstacles that might slow down your progress:
How to prioritize all your other opportunities with selling
How to build a consistent sales practice that pulls in the right number of leads
How to manage the mental game of selling (especially if it’s not your favorite thing to do)
Introducing
Path to Repeatable Sales Program
A 3-month cohort program that moves startup founders from endless pivoting to systematic sales success. Through proven tactics and wraparound support, you’ll find your rhythm and get on the path to repeatable sales.
“This program clarified what it takes to build a company — the reality versus just my own imagination. Understanding how sales conversations can power your entire company and product has saved me a huge amount of time. Now I run sales outreach and discovery way more efficiently. Most importantly, I'm no longer scared of the sales process. I really understand what it takes.”
- Founder, Stealth Health Care Startup
“Before this program, I was making a lot of mistakes and wasted a lot of time. I was chasing the wrong things, like pitch competitions and awards. These things don’t create revenue. I learned from Caroline that the only way to create revenue is through sales. The only way to learn is by using sales for research. Now I’ve figured out who to sell to, and who we should target first. I’m in a far better place with my business because I met Caroline and did this program.”
- Chukwudi Kanu, CEO and Founder, Humblebrag
Hi. I’m Caroline. Here’s a bit about me:
I built this program because I could’ve really used something like it when I was a seed-stage startup founder.
While my startup won customers like Wayfair, DraftKings, and ezCater, finding recurring revenue and undeniable product-market fit was a challenge for a few big reasons:
I simultaneously avoided and put too much pressure on every sales call
We tinkered on elements of the product that weren’t going to impact sales (but we didn’t sell enough to know that)
We overthought our sales motion, wasting precious time, instead of leaning into action
I focused too much on what we wanted to build rather than what the market wanted to buy
Since 2024, I’ve coached and trained over 150 founders, including through incubators like InnovationWorks, Visible Hands, Company Ventures, and JFF Ventures. In my work, I enjoy sharing both my expertise and the many mistakes I made as a founder. In doing this I aim to build an open learning environment where founders feel comfortable to confront and overcome any challenges that are holding them back from progress (we all got ‘em!).
What We’ll Cover
Phase 1: Foundations of Founder-Led Sales
Instead of jumping straight into action, we start with the fundamentals. You'll master the Four Pillars of Repeatable Sales — the core elements that separate founders who struggle from those who build consistent revenue. We'll address the mental game, establish your sales rhythm, and ground ourselves in the six key steps to repeatable sales. This foundational phase is short but critical, and will prevent months of spinning your wheels.
Phase 2: Define Your Buyer
One of the biggest mistakes early-stage founders make is staying in the hypothetical about their customers. We'll take inventory of the real knowledge you have about your buyers, and build a clear hypothesis. You'll put a stake in the ground on your ideal customer profile: who they are, how they think, what their real needs are, and where they spend their time. No more selling to everyone. Instead, you’ll have the clarity needed to focus on and target your best-fit buyer.
Phase 3: Build Your Outreach Strategy
With your buyer hypothesis locked in, we'll implement proven tactics so you can book meetings with the right people. You'll learn outreach methods designed specifically for 2025, when nearly every person with an email (including your buyers) is drowning in AI-generated spam. You'll learn how to cut through the noise and generate a steady stream of qualified meetings with best-fit buyers.
Phase 4: Run Sales Conversations
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.
Phase 5: Apply and Iterate
In our final phase, you'll put everything into practice at full speed. We'll tackle your specific roadblocks head-on and iterate on your approach based on the real market feedback you’ve received. You'll dial in the discipline to iterate quickly on what's working and abandon what's not. By the end, you'll have a repeatable sales system that generates a consistent pipeline and the confidence to scale it strategically.
How it works
Live sessions
Weekly live workshops, trainings, and group discussion
Two private 1:1 advisory sessions
Curriculum
3 months of curriculum
Detailed tactics on every step of the sales process
Templates and tools for each stage
Wraparound founder support
Monthly document review
Accountability structures
Slack community
“Small win” challenges and sprints
Role plays and other live experiential exercises
Pricing
$850 per month for 3 months
How we’ll do things differently
Old way: selling off a pitch deck. New way: Conversation-based sales, so you center the buyer, create a real relationship, and learn key market insights that make your next sale better.
Old way: Selling to whoever will buy. New way: Only selling to one repeatable customer type, so you accelerate your time to actual product-market fit and waste less time on customized customer support.
Old way: Spray-and-pray automated outbound campaigns. New way: Hyper-human cold outreach tailored to your buyer’s psyche and needs, so you book more qualified calls faster without wasting thousands of dollars.
Old way: Beating yourself up for wanting to sell but taking longer than you’d like to make it happen. New way: Acknowledge the mental rollercoaster that selling (and generally running a startup) puts you on, and build a sales practice that makes space for you to work through hurdles and obstacles.
What founders have to say about my advising and training
You’re a good fit for this program if:
Your sales flywheel feels slow, non-existent, or just generally painful
You are a B2B/B2B2C founder with zero to one hundred *repeatable* sales – this new way of selling is applicable if you are pre- or post-product
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 (my approach works for any vertical), but you’re an extra fit if you’re mission-driven, as I prioritize serving those startups as much as possible.
You’re not a fit if you’re looking for a quick fix (doesn’t exist!) or you want to outsource sales (not a good idea at this stage).
70xed 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 win founder-led sales
Founders I’ve worked with (including scientists, introverts, activists, and technical experts) have:
FAQs
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I could deliver my curriculum to you in an intense week or two… but in my experience, that won’t set you up for results. I believe that three months gives you the amount of time needed not just to learn my sales methodologies, but to practice applying them consistently.
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At the end of the program, you will have learned foundational early sales tactics, and will have put them into motion. You will have sent authentic outreach messages to your ideal customer, run conversational and non-sleazy sales calls, and uncovered tons of incredible insights from prospects that will make your sales motion more successful. If you want my help at the program’s end, we can continue working together at a discounted rate.
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September 16th to December 5th, 2025. Weekly sessions are Tuesdays at 4 PM ET / 1 PM PST.
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Each week, I’ll share a training for you to watch async, and then we’ll work through the concepts live during our weekly session. If you have to miss a live session, you’ll always be able to watch the replay. It will be available within 24 hours. But more importantly, this program is designed with the understanding that at some point, you’ll get tripped up. I know firsthand that the founder experience never goes exactly to plan. So, I assign homework to enable you to move fast, but I also have built in office hours and workshops to help you apply learnings, mini-challenges to help you get early momentum and confidence, and 1:1s to help you identify and unblock hurdles.
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At minimum, you’ll want to dedicate three to four hours per week to implementing what you’re learning. My honest litmus is that a founder who wants to build recurring revenue should be working on the sales side of the business for about 50% of working hours. If you’re not ready or able to do that yet, it’s okay! We will make progress at a pace that works for you.
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This program covers the detailed steps of making your earliest repeatable sales. Some not have made a sale yet, others may have closed deals, but every cohort member will bonded by their quest to figure out how to sell repeatably to one ideal customer type. We’ll climb the mountain together.
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I’ll be in the Slack daily answering questions so you won’t feel stuck in between sessions.
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If you’re dissatisfied within the first thirty days, I’ll happily cancel your future payments or refund your full payment, less the first month’s non-refundable deposit.