Brilliant at building,
unsure about sales?
You’re in the right place.
Figuring out repeatable revenue isn’t just important to an early-stage startup. It’s existential.
But something is blocking your growth.
Maybe all the sales advice you hear feels outdated, or comes from old-school sales leaders who don’t understand what it’s like to sell at early stages.
Or perhaps the go-to-market guidance you hear just gives you the ick. It makes you feel like you need to abandon your values or personality to find product-market fit.
Or maybe you’re trying to accelerate sales by building out a team. You’re overwhelmed with competing priorities, and you’re concerned your team is building go-to-market strategies that don’t feel strategic at all.
I’m Caroline Fay.
I developed my sales advising practice because it’s what I desperately needed 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
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:
$0 to $600K ARR in six months
Two years of revenue closed in one quarter ($250K ARR to $1M+ ARR)
First two sales closed in one month
70x increase in repeatable sales
On average, a 400% increase in qualified sales calls within two months
Clarified their target buyer, after months or years of pivoting
Gained the skills and confidence to tackle founder-led sales
Stopped tinkering on the 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
“With Caroline’s guidance, we developed an effective outbound lead gen process, crafted messaging that truly resonated, and dramatically accelerated our deals and revenue, closing more than two years worth of revenue in a single quarter and shortening our average sales cycle from 90+ days to under 60.”
Chief of Staff, Seed-Stage BioTech SaaS
“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
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
Repeatable Sales Membership
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.
Ideal for startup founders or teams who are ready to get serious about selling, and have won their first zero to fifty repeatable sales.
Tactical library of step-by-step sales frameworks and templates
Weekly office hours for real-time problem-solving
Bi-weekly co-working sessions for accountability and momentum
Monthly practice sessions to refine your sales approach
Quarterly intensive to build your buyer hypothesis and outreach strategy live
Discounted 1:1 advisory support
24/7 community platform access
Fractional Sales and GTM Leadership
Build a well-oiled sales process that unlocks product-market fit… and makes your team feel aligned instead of 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