We help early-stage, mission-driven startups and leaders find product-market fit and build a healthy team.

Meet the Founder

Caroline Fay

Caroline Fay, Founder and Principal of the Extra Group, is an exited impact founder, a former Silicon Valley product marketing leader, and a coach.

She has built and sold a venture-backed inclusive hiring startup, designed go-to-market strategies and product launches at HR tech unicorn Lattice, and studied career development for the working adult at the Harvard Graduate School of Education. Full bio.

OUR SERVICES

GO-TO-MARKET COACHING AND ADVISING

To reach your revenue goals, you’ve got to sell… but most people hate sales. Our blend of coaching and advising gives you the tactics to successfully market and sell, and provides you with the mindset shifts and accountability to actually make it happen.

FRACTIONAL GTM LEADERSHIP

If you’re seeking product marketing and founder-led sales expertise, we can join your team fractionally. We revamp your GTM strategies, execute and iterate on plans, and educate on tried-and-true best practices along the way.

EXECUTIVE COACHING

We help impact-driven founders and leaders navigate challenging leadership moments and improve performance, all while staying true to their personal values and mission.

TEAM EFFECTIVENESS WORKSHOPS

Without a healthy and aligned team, growth becomes exponentially more difficult. Our workshops build trust, clarify strategy, and teach teams how to engage in conflict and decision-making productively.

COACHING TEAMS AND LEADERS FUNDED BY

TESTIMONIALS

“Working with The Extra Group has completely transformed my business. Caroline understands exactly what an early-stage founder is experiencing because she's been there. She has helped me get out of my own way and unlock the best decisions for my company, which unlocked repeatable sales! I feel more clear and confident than I've ever felt as a leader, and it's all thanks to Caroline.”

Jaime-Jin Lewis, CEO & Founder of Wiggle Room and 2021 Winner of the David Prize

Go-to-Market Coaching and Advising

“Caroline is, without question, one of the best blessings I've received on my founder journey. She leads with compassion and curiosity, asks insightful questions, and shares reflections that expand how I think about my role as a leader. In just three months, Caroline has helped me delegate more strategically and consistently, enhance my fundraising efforts, and communicate more effectively with my team and with potential partners.

Caroline always ensures that I stay in the driver seat of my founder journey, but having her in the passenger seat - pointing out new pathways to explore and keeping me grounded and confident - is invaluable, to say the least.

Working with Caroline has been especially valuable during a season when I have to be ruthless about my priorities, particularly when it comes to fundraising for my nonprofit. Recently I found myself in a pattern of doing work that was urgent, but not important. I knew there was a problem, and Caroline helped me get to the root of it. She guided me through an exercise that helped me understand - and have compassion for - the reasons why it was hard for me to remain focused on revenue-building activities. I also appreciated that I left the session with concrete tools to shift my behavior over time. We've celebrated my behavior changes, small as they may seem, in future sessions too. I've felt so seen and cared for.

I've appreciated Caroline's insights on how to build partnerships with new potential customers, as my nonprofit enters a stage where we're selling our core education offerings to more schools and districts. She's given me actionable feedback on how to strengthen my outreach messages, and has shared specific guidance on how to think about the earliest stages of our sales process. Her insights have helped me focus on what matters most.

Beyond her sales support, Caroline has been a remarkable sounding board on how to build and sustain an organizational culture rooted in care and equity. I tend to default to crafting policies and practices that put my organization before myself, which isn't sustainable. Caroline has tactfully proposed ideas that allow me to care for myself, while still caring for the collective.

I could go on and on about how incredible Caroline is. But you won't fully understand her power until you experience it firsthand. If you're confused about what to do, or if you’re someone who knows what to do, but for some reason, just doesn't get it done - set up a call with Caroline, and share what's really on your mind and heart. You're in for a treat.”

Shawon Jackson, Executive Director and Founder of Vocal Justice

Executive Coaching and Go-to-Market Advising

"Caroline has served as an incredible coach to our founders, providing valuable advice and insights about GTM strategy, founder-led sales, and early-stage company building. Her knowledge, guidance, and expertise have been critical forms of support for our founders as they are working towards strategic milestones at the preseed stage."

Justin Kang, General Partner of Visible Hands, a pre-seed VC firm backing overlooked founders

Go-to-Market Coaching and Advising

Working with The Extra Group has been a game changer. We were so focused on the product that we didn’t take enough time to assess if it was meeting client needs. Thanks to Caroline, we now understand why our customers like our product, and can replicate that success with other customers who fit the profile. She holds me accountable to my main mission: product/market fit. I highly recommend Caroline to early-stage founders.”

Tanay Tatum-Edwards, CEO & Founder, FreeCap Financial

Executive Coaching and Go-to-Market Advising

“The Extra Group’s facilitation was the main reason for the success of our retreat. She brought a perfect mix of professionalism, insight, and warmth to the event. Caroline’s advice, encouragement, and expertise in sales and startups have all been crucial to our success. I highly recommend Caroline if you want to be a more cohesive team, understand your co-workers, and refocus your energy on the work that matters most for your organization.”

COO, Fin Tech Startup

Team Effectiveness Workshops

“Caroline’s coaching got me out of my head and helped me clear the big hurdle of early sales. We have accelerated our sales process and feel more confident in our ability to close sales, even though our product isn’t complete yet. She has helped us tactically build out our GTM strategy. The energy and belief Caroline gives us is inspiring.”

Anthony Lewis, CEO and Founder, Emerge.io

Go-to-Market Coaching and Advising

Caroline has transformed my career. I feel more confident, empowered, and excited about my career because of her coaching. From navigating complex organizational politics to setting better work-life boundaries, Caroline’s work is a strategic layer of support and strategy to make the best decisions for my job and life. Her work elevates my perspective, clarifies my ambitions and challenges my assumptions. I cannot recommend her more highly.”

Becca, Senior Enablement Manager

Executive Coaching

It’s only once I started seeing Caroline that I understood the value of coaching. From running her own startup to working in male-dominated and fast-paced environments, she has rich experience that clearly comes through in her coaching. She has helped me build new habits, build my own confidence, and manage stakeholders. I could go on and on about the new perspectives and skills I've gained.”

Connie, Senior Product Manager

Executive Coaching

You deserve extra.