October 18th, 2021

Meet Athena member Katelin Holloway, an investor, people & culture executive, and belonging strategist. Previously serving as VP of People & Culture at Reddit, Katelin made a conscious transition from operator to investor—eventually launching venture firm Seven Seven Six alongside Reddit co-founder Alexis Ohanian. Together, they are helping entrepreneurs evolve their diversity, equity, inclusion & belonging practices through intentional investments.

Below, read Katelin’s insights on how companies can prepare for the future of work, how she made the leap from operator to investor, and her advice for other women leaders to do the same.

Tell me about your executive journey up to this point.

My executive journey has been long and winding, but deeply rewarding. My first executive position was in 2011 with a small startup called Klout. I was employee #21; I built and developed all People & Culture functions from foundational HR frameworks (HRIS, policy administration, compensation & benefits) to pioneering employee engagement philosophies and cultural structure. I learned so much about myself and how the world of work was evolving. The acquisition of Klout in early 2014 proved these strategic initiatives were effective, as “talent and culture” were listed as primary assets in the purchase.

Just after our acquisition, I had my first child and decided to try my hand at building a different type of company and joined a budding mindfulness software company. A quick year later, I was poached to join Reddit — which would prove to be the most challenging and rewarding executive role of my operator career.

Overseeing the People & Culture teams, we grew the company from 75 to 750 in just 4 years. We were dedicated to cultivating a work environment that was characterized by community, empathy, openness, personal accountability, trust, and mutual respect. We created solutions and frameworks that supported the operating principles of Reddit, enabling us to realize our potential through our most valuable resource — our people. It was during this time that I grew my family and welcomed our second child into the world.

Toward the end of 2019, I made the conscious decision to shift my career yet again. My work in HR inspired a deeper look at equitability and access to wealth. In early 2020, I joined venture capital firm Initialized Capital as an investing partner. And then the pandemic hit. As I reprioritized my career and redefined the impact I wanted to have on the world, I decided to join my old friend Alexis Ohanian as he also turned a new leaf. By mid-year 2020, we’d managed to start a new venture capital firm: Seven Seven Six. We’ve spent the last year investing in phenomenal founders and supporting the development of diverse, inclusive teams. I know that I am exactly where I should be, doing exactly what I should be doing.

You recently transitioned from your operating career into the investing world. What were some of the surprises in that process?

To start, I didn’t expect a pandemic to ravage the world just months after shifting careers! That was a surprise I don’t think anyone expected. It shifted the way we work, the way we educate our children, and the way we connect with our communities.

Pandemic aside, I was surprised at how welcoming the world of venture capital was to me. I don’t have a traditional background in finance. I don’t have an MBA. I didn’t previously work in Private Equity. I’m not sure what I was expecting, but I was very grateful to have so many other investors who made me feel so welcome — particularly female investors.

I was also pleasantly surprised that my thesis around HR translating well to VC was proven to be correct. Early-stage investing is so much about the founders’ agility and their ability to build a great team. Being able to identify strong founders, support their organizational development, and bring my expertise to the arena when founders need it most feels really incredible.

How are you advising your portfolio companies to prepare for the “future of work”?

The future of work is flexible, inclusive, and compassionate. The best way to set our companies up for success in these areas is to work closely with them as they’re building their cultures. From co-creating paid family leave policies to auditing recruiting processes — there is no task too small or too large.

We also lead by example. With our 2% Growth & Caregiving Commitment, we reserve dollars for our founders to prioritize their personal development alongside dollars for them to invest in caring for their loved ones. When someone directly feels the impact of being cared for, they are inspired to create a workplace that does the same for their employees.

Can you talk more about belonging and how leaders can begin addressing it in their companies? Why is it important for the bottom line?

Belonging is a critical component of any healthy, thriving organization. Community has long been overlooked in the workplace, but is truly the glue that binds the company together. When you support each sub-community that interacts with your brand or your product — employees, customers, partners — you create an incredible flywheel of value.

What many people get wrong about community is that it’s a monolith. It is not. Each of us are connected through different parts of our identities and that complexity is what makes a culture or community distinct. When a leader understands how to tap into that complexity, returns (both emotionally and financially) become outsized.

What first steps do you recommend a company take to start building an intentional and inclusive culture? And how can they maintain that culture as they scale?

This is such an incredible (and incredibly big!) question. I usually start by telling founders that it’s never ever too early to start thinking about intentional culture-building. Your first task is to become a cultural anthropologist — to listen and observe and understand what is naturally occurring in your communities at work. How are people engaging with one another? What does it look like when a team has achieved their flow state? What does it look like when a team is struggling?

Understanding your role as a leader in creating culture becomes a critical task. Once you understand where your input and guidance is needed versus where it’s best you let the community develop, you cannot lose. Creating systems and frameworks that enable each person to understand their goals and their accountability in every step of a process is helpful as this development begins to blossom.

How has Athena been valuable in your journey?

I was referred to Athena years ago as I began my learning journey into my own executive development by a dear friend and mentor, Cara Brennan-Allamano. I remember the first call I had with Coco was mind-shifting. She listened to me as I rattled on about HR being the next best thing to happen to boards — and she supported me in testing that theory out.

Since joining Athena, I’ve gone from sitting on no boards at all to a full plate of board positions! I currently sit as a director for three pre-IPO companies, a board observer for two very early-stage venture-backed companies, and participate on the compensation committee for another.

The community that Athena has built and nurtured over the years is pretty incredible. I am so grateful to be a part of this incredible group of women!

What advice do you have for a woman leader who wants to take the leap from operator to investor?

Do it! Don’t wait! The skills and mindset you’ve built to this point are invaluable to founders. You know what success looks like from your operational perspective — now capitalize on that. Your time spent in the trenches gaining very real and very relevant experience is something that any founder, any venture capital firm, any young team needs. And they needed it yesterday.

Athena helps women reach their biggest career goals—rising into the C-suite, joining the boardroom, getting started with investing, or launching their own ventures. Learn how Athena can help you reach your next career goal.



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