Profiles In Venture: Greycroft's Alaina Hartley

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Based in the Los Angeles office, Alaina is on Greycroft’s consumer investment team. Her responsibilities include sourcing, evaluating, and executing early-stage investment opportunities and working with existing portfolio companies.

Prior to joining Greycroft, Alaina worked at Bain & Company, where she consulted across Bain’s private equity, technology & media, and retail practices. Previously, Alaina drove go-to-market and brand strategy initiatives for Snap Inc.’s first hardware product, Spectacles, earning fourteen nominations and six wins at the 2016 Cannes Lions awards. 

Alaina holds a B.A. in Economics from the University of Southern California. She is on the board of the Los Angeles Police Foundation’s Young Professionals Group and an active member of the Junior League.

Frederick Daso: What did you learn about launching products at Snap, given your involvement in Spectacles sunglasses?

Alaina Hartley: The Snap Spectacles launch was a once-in-a-lifetime experience that shaped my perspective on cross-functional work and brand strategy. I had the opportunity to be part of an inspiring group comprised of Snap's product, marketing, and operations organizations. They spearheaded the effort and earned six Cannes Lions awards in the process. Together we solved problems, invented and automated processes, and pulled off some ambitious brand initiatives. Finding ways to institutionalize cross-functional collaboration and bring together interdisciplinary talent within an organization can be a critical strategic advantage. 

From a brand strategy lens, I learned the value of integrated, multi-channel marketing. Many startups I meet in my current role are primarily focused on performance marketing/digital advertising. While that is important, there are other high-impact channels for generating sales and brand awareness. I often encourage the companies I meet and partner with to take a customer-centric and long-term approach to build their brand – digital advertising should be a tactic, not the strategy. 

Daso: From your time at Bain & Company, what essential skills did you pick up that help you daily in your role as an investor at Greycroft?

Hartley: I joined Bain & Company to build my analytical capabilities (e.g., Excel modeling, structured thinking). Bain helped me develop strong financial and operational analysis skills. However, I've been most surprised by how valuable the communications lessons I learned at Bain have been in my current role. 

The advice I was given at Bain that has most informed my work style is to "never come to a meeting with a list of problems – come with a list of potential solutions." This demonstrates that you've spent time thinking about a situation and have a bias for action. Evolving my approach to be more solutions-oriented has enabled me to be more time-efficient, optimistic, and pragmatic with partners and portfolio founders alike.

Daso: What are some counterintuitive lessons you've learned as you've grown your network in the venture ecosystem?

Hartley: When I first entered the venture world, the standard advice I received was to invest in attending evening events, traveling to conferences, and sending outbound emails to build my network. I've learned that everyone has a different style. What works for others might not be the right fit for you. I've found that better use of my time is providing support to companies in our portfolio. The referrals from the portfolio founders I've worked with have been some of the most impactful ways to source new investment opportunities. 

Daso: Did your time at Snap shape your perception of what mature consumer tech companies should look like if they are successful?

Hartley: Snap grew from ~500 to 2,500+ employees during my time with the company. A lot changed during my time at Snap. We moved from working out of apartments on Venice Beach to real office spaces, scaled our user base exponentially, and went through many product iterations. Two things that have remained consistent are Snap's culture and mission. I genuinely believe that a strong commitment to investing in the team and purpose is critical for consumer tech companies to scale successfully. Snap has a direct and fluid culture, so for employees who thrive in that environment, it can be incredibly empowering. Snap's continued commitment to its core mission has driven its user experience (e.g., the app always opens to the camera screen), monetization (e.g., camera-oriented ad units), and priorities (e.g., camera access requires trust – so good privacy controls are mission-critical). Experiencing the impact of Snap's culture and mission has made those two key points I mainly look for in a pitch or diligence process.

Daso: Could you give me an example of how you spend your time helping portfolio companies build their companies? What's the best way you've found to support them?

Hartley: Two areas where I'm personally most hands-on with founders are strategic planning and fundraising. Some of our companies like to workshop their go-to-market plans or financial forecasts with me. Others are looking for help with introductions to customers and other investors, editing pitch decks, and helping structure data rooms. In my experience, the best way for junior investors to help portfolio entrepreneurs is to be responsive, reliable, and well-researched. That way, we can be effective problem-solving partners.

Daso: How do you apply a unique/differentiated touch to closing a deal in your role?

Hartley: I joined Greycroft because I love our team and our style of investing. I've always been someone who prefers environments that are more collaborative than competitive, and Greycroft's flexible approach is differentiated and compelling to founders. We look to syndicate our investments with other investors because we see actual benefits to entrepreneurs having a set of diverse, complementary perspectives and networks around a table. I'm a very transparent, communicative person, and I try to provide as much feedback as possible to the entrepreneurs I get to meet. I think this does help me 'close' deals for the firm – but it's also just the right thing to do.

Daso: Numerous VC associates, such as Caty Rea (Highland Capital Partners), Grace Isford (Canvas Ventures), and Courtney Chow (Battery Ventures), say it's hard to "turn off" when it comes to working. How do you spend your downtime (i.e., not doing anything related to venture!)?

Hartley: To be honest, "turning off" is still a significant development area for me. It can be especially challenging to strike a balance in a meetings-heavy role like venture capital. You have to be disciplined about carving out time between meetings to get work done. Otherwise, you'll need to catch up on in the evenings (e.g., responding to emails, writing investment memos). 

Outside of work, I love to hike, travel, read, and explore museums & restaurants across LA. I also go entirely offline on Sunday evenings to have dinner with my entire extended family. In essence, it's my favorite way to relax and recharge. 

Daso: What's one thing in tech or venture that's not talked about enough, that should be?

Hartley: Many founders tell me that they have been "ghosted" during the fundraising process. As investors, we do receive high volumes of inbound emails. However, I believe that it's essential for investors to be responsive and respectful of entrepreneurs' time and energy. The personal SLAs I've set and strive to meet are responding to all emails from Greycroft portfolio companies within 24 hours, and all other emails within 72 hours. My email is [email protected]. 

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