Stop spiraling, start selling

Repeatable Sales Membership

A monthly curriculum and community membership for early-stage founders who want to get serious about selling. Learn tactical sales strategies and mental game mastery, so you can generate reliable revenue and find product-market fit.

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.

  • 70xed their recurring revenue and counting

  • 200% increase in calls booked after outbound strategy overhaul

  • Closed two sales within one month of pivot and refreshed outbound strategy

  • Increased pipeline of qualified leads by 300%

  • Increased sales calls per week by 400%

  • Clarified their target buyer, after months or years of pivoting

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

My approach and methods work.

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

What’s included

  • 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

  • Bi-weekly co-working hours that help you power through your sales tasks and build momentum

  • Monthly sales practice sessions to get immediate feedback on your approach and increase your comfort

  • Quarterly intensive for members who want to learn or refresh their skills live

  • Tools and resources on the mental game of founder-led sales that help you overcome perfectionism, imposter syndrome, and anything else holding you back

  • Competitions and prizes to keep you motivated and accountable

  • 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

    • Send authentic, tailored outreach messages to your ideal customers 

    • Run conversational, non-sleazy sales calls 

    • Uncover valuable market insights from every prospect conversation 

    • Build a consistent, non-negotiable sales practice

    • You are a B2B/B2B2C founder with zero to one hundred repeatable sales. You’ll get value if you’re pre-product, or even just “founder-curious” 

    • Your sales flywheel feels slow, non-existent, or just generally painful 

    • All industries are welcome (my approach works for any vertical)

  • $195 per month. Cancel anytime.

Hi, I’m Caroline. I’m an exited founder and recovering sales hater. 

I built this 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

We exited our startup because revenue wasn’t repeatable enough.

I became obsessed with understanding what we could have done differently.

I worked in Go-to-Market at a late-stage startup, and studied the feedback loop between sales, marketing, and product. I read everything I could about the differences between early-stage sales and late-stage sales. Ultimately, I started consulting with founders to test what I was learning. 

Since 2024, I’ve coached and trained over 150 founders. I am a Go-to-Market coach for Visible Hands and Company Ventures. I have run sales workshops for JFF Ventures and InnovationWorks.

My theory of change is that startup success shouldn’t just be for the darlings of Silicon Valley or Sand Hill Road.

By training non-traditional founders on how to sell, I help founders who are often overlooked for venture capital to build a business that can sustain itself on revenue alone.

What founders have to say about my advising and training

  • Caroline is a world-class go-to-market expert. Thanks to her, I walked into every sales meeting prepared, confident, and with a clear strategy. She doesn't just guide; she equips you to win.

    Ali Bono, CEO and Co-Founder, Pelican Invests

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

    Wendy McSparren, CEO and Co-Founder, Admirra

  • 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

  • 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

  • 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 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

  • Before I attended this training, 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

Curriculum details

Bite-sized video trainings with accompanying templates and resources

The Tactical Playbook: Step-by-step instructions on early sales execution

  • The six steps to repeatable sales

  • How to define your buyer hypothesis 

  • Cold emails in 2025: new best practices and what to avoid

  • How to use sales calls to uncover buyer 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

The Bigger Picture: Understanding the "why" behind the tactics

  • 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

Live support

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.

Bi-Weekly Co-Working Sessions

Join fellow founders for silent work time dedicated to sales outbounding. You’ll get accountability and camaraderie that will help you build the selling habits that lead to real revenue. 

Quarterly Intensive 

Once a quarter, I’ll run my one-week intensive on sales, live. We’ll meet live for four hours total. The intensive will bring to life everything in my content library through hands-on application, so you'll leave with a defined buyer hypothesis and ready-to-use outreach strategy.

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 also purchase a 1:1 advising package, where you’d have access to the membership plus two 1:1 calls per month.

  • 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.

  • You can cancel your membership at any time. You will not be charged for the following month as soon as you cancel.

  • 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.