Coaching and sales training for early-stage founders, built by a founder who’s been there.

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 worked in product marketing at Lattice, a Series F performance management software. I designed go-to-market strategies for new and existing products.

  • Since starting my consultancy, The Extra Group, 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 and learning.

  • What sets my approach apart is my willingness to share the hard-won lessons from my own founder journey. Sales was particularly challenging for me—I'd get caught up in perfectionism, endlessly preparing instead of connecting with prospects. By being transparent about these struggles, I help founders recognize and work through their own sales obstacles in a judgment-free environment.


After working at a growth-stage startup in Go-to-Market and coaching hundreds of founders, I’m dedicated to helping ambitious founders and teams sidestep sales mistakes and earn revenue quickly without sacrificing their vision.

You don't need years of sales experience to build a well-oiled GTM machine that delivers repeatable revenue.

With sales tactics designed specifically for early-stage companies, healthy mindsets and habits for selling, and a strategy that leverages your existing customer knowledge, you can create a sustainable sales process that feels authentic to you and your unique mission.

Our clients (including technical founders, introverts, policy experts, and scientists) 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

“We went from not knowing where to start to a structured, multi-step approach. 

Now we know how to find leads, how to build effective cold outreach campaigns, and how to approach warm outreach. This all resulted in a 200% increase in our weekly meetings with leads.”

Johar Singh, CEO and Founder, Astra Wellbeing

“The Extra Group has completely transformed my venture and my life.

She has helped me get out of my own way and unlock the best decisions for my company, which has unlocked repeatable sales.”

Jaime-Jin Lewis, CEO and Founder, Wiggle Room

Early Sales Cohort Program

A three-month small group advising and curriculum program

  • 10 participants

  • Cohort runs twice per year

  • Investment starts at $850/month

  • Next cohort starts September 16

Your product or offer is live, but your sales process feels haphazard and inefficient. OR, you’re in the ideation stage and want to get your sales foundations dialed in from day one.

Learn and apply proven early sales practices and receive week-over-week accountability on making true progress.

You’ll get structured live coursework, plus 1:1 attention to build and implement a sales strategy that works for your specific business. 

Ideal for startup founders who are ready to get serious about selling, and have won their first zero to fifty repeatable sales.

  • Weekly sessions, rotating between live teaching, workshops, and office hours

  • Access to all training content, templates, and decks, so you can skip ahead as needed

  • Private Slack community so you’re never left hanging

  • A 1:1 consulting call each month for personalized attention

  • “Small win” challenges, sprints, and homework to keep your momentum and confidence high

Sales Advising and Coaching for Founders

Your fastest path to repeatable sales

You’ve got some traction, and now’s the time to invest in your GTM machine. Or, you’re still in the early stage but you want to move as fast as possible towards revenue.

 You’re seeking hands-on support to increase revenue efficiently while staying true to who you are.

I’ll be your strategic partner and advisor, helping you look across your business and make meaningful changes, fast. I’ll help you elevate every aspect of the business, from your sales funnel, to customer definition, to leadership and organizational support.

Ideal for founders who desire customized 1:1 support from a strategic thought partner, and who have won their first zero to one hundred repeatable sales. 

  • 90-minute deep dive into your business, bottlenecks, and vision

  • Custom recommendations, action plan, and curriculum

  • Bi-weekly 1:1 consulting calls

  • Access to all training content, templates, and decks

Sales Advising for Teams

Build a well-oiled sales process that unlocks repeatable sales and PMF… and makes you and your team feel aligned and empowered, rather than constantly overwhelmed.

This is a fit for founders who have some repeatable sales. You may have hired a team, or are preparing to, and you need to bring more structure (and sanity) to your sales process.

You’re in need of guidance and advising to get everyone rowing in the same direction.

  • Holistic business diagnostic of your business, bottlenecks, and opportunities

  • Custom-designed workshops and trainings for you and your team to get everyone aligned on a go-to-market plan

  • Build strategic recommendations and oversee quality of sales materials and strategy

  • Weekly 60-minute advisory and coaching call 

  • Fixed availability during “office hours” for either live problem-solving, pop-up workshops, or async work

  • Access to my library of sales trainings, templates, and how-tos

  • Integrate into Slack with same-day reply

“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 look forward to working with her more in the future and highly recommend any founder, with or without sales experience, to utilize her coaching.”

Valerie Trent, CEO and Founder, Thizo

xxx

Nini / Ali Bono /