Stop spiraling, start selling

Path to Repeatable Sales Program

3-month group cohort

Next cohort begins September 16

Founder-led sales is hard… and it’s not your fault.

Early-stage founders need early customers in order to find product-market fit… but most sales advice for founders is bad.

The vast majority of advice comes from enterprise sales leaders who have only sold post product-market fit… which is a completely different process. 

As a result, founders waste precious time trying outdated methods, waste money on trainings or staff that don’t yield results, and develop a terrible frustration with all things sales.

Most founders I talk to feel burned by sales investments they’ve made, and disheartened by a lack of real traction. They feel hesitant and overwhelmed. They’re unsure about how to kickstart repeatable sales and feel like they’re spinning around like the Tasmanian Devil.

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 can slow down founder-led sales 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)

Let’s get you everything you need to find repeatable, recurring revenue on your terms.

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.

Introducing

Path to Repeatable Sales Program

“This program clarified for me 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

  • 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: 

Here’s what we’ll cover:

  1. Foundations of Repeatable Sales

Yada yada

  1. Foundations of Repeatable Sales

Yada yada

  1. Foundations of Repeatable Sales

Yada yada

  1. Foundations of Repeatable Sales

Yada yada

  1. Foundations of Repeatable Sales

Yada yada

Curriculum

  • 3 months of curriculum

  • Detailed tactics on every step of the sales process

  • Templates and tools for each stage

How it works

Live workshops

  • Weekly live workshops, trainings, and discussion

  • Two private 1:1 advisory sessions

Wraparound founder support

  • Accountability structures

  • “Small win” challenges and sprints

  • Role plays and other live experiential exercises

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 and 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 building a sales practice that makes space for you to work through hurdles and obstacles.

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

You’re a good fit 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 willing to talk to customers 

  • You are on board with the idea that early-stage founders need to lead the sales process

  • All industries are welcome (my methods work 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).

Hi. I’m Caroline. 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.

FAQs

  • 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.

  • 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.

  • September 16th to December 9th, 2025. Weekly sessions are Tuesdays at 4 PM ET / 1 PM PST.

  • 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.

  • 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. 

  • 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.

  • I’ll be in the Slack daily answering questions so you won’t feel stuck in between sessions. 

  • 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. 

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