Tip of the Spear: Dee Dee Sklar, Independent Director at Nuveen

January 29, 2026

By The Artemis Fund
The Artemis Fund believes technology can create prosperity for all. With offices in New York, Texas, Massachusetts, and Nevada, Artemis leads seed rounds for companies creating resilient families, individuals, and businesses across the US.
Tip of the Spear is an interview series highlighting The Artemis Fund’s expert network. In this edition, we sat down with Dee Dee Sklar, Artemis LP and Independent Director at Nuveen Churchill PCAP.

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Q: What was your first job, and what did it teach you about leadership or navigating change?
A: I grew up lower–middle class. I understood the value of money and scaled my first business with other kids in my neighborhood, opening a haunted house and charging $1 admission. This was my first time seeing how small amounts could add up. The power of teamwork and peer to peer support made a lasting impression on me through early experiences: I was later a girl scout, a candy striper, and a competitive gymnast.
While in college, I joined a friend to own and manage Earth Shoe stores in Tennessee. I was in charge of the Nashville location, managing inventory, obtaining financing, negotiating leases, and marketing the business. Earth Shoes became very popular, and we were known in both business and country music circles.
Q: Were there any key moments in your career where you had to rethink the system when you took your next leap?
A: Yes, many times. My entry into finance began through an unexpected connection: one of my Earth Shoes customers was the head of a major commercial real estate asset manager in Nashville. I asked directly if I could learn his business. At the time, there were no women in asset management, but through persistence, I earned a role and quickly moved into the commercial appraisal division of the firm.
In appraisal, I learned to spot overlooked opportunities through data. At 25, I identified a pattern in building permits that led me to ask the president of the company to send me to Bentonville to call on Walmart. There, I connected developers with insurance-company capital in markets where we held exclusive relationships.
For my next big opportunity, I moved from Nashville to New York City to open the US office of an asset manager in Asia. I built a franchise from the ground up, and developed a team culture focused on identifying opportunities and managing risk. Our firm partnered with private equity firms and investment banks, and I helped drive that growth by initiating our certification as a Minority Woman-Owned Business (MWOB). Through these partnerships, I gained experience in distressed asset acquisitions and, importantly, was introduced to securitization finance.
Following a real estate downturn, I joined a team that was hired by N.M. Rothschild to build a global securitization business. This role marked my pivot into structured finance across multiple asset classes and international markets. I moved with our team to WestLB, where we scaled the franchise under WestLB’s balance sheet and liquidity platforms. 
Within two years, I was promoted to Head of Financial Institutions Americas, managing counterparty risk across the region. Under my leadership, we centralized the bank’s alternatives lending and helped pioneer liquidity solutions that became widely adopted across the industry, including subscription finance. I ultimately became Global Head of Funds, responsible for both financing and investing bank capital.
I led the successful sale of the global platform to Wells Fargo in 2012, where I retired as Vice Chairman of Subscription Finance after a 45-year banking career. Today, I serve on corporate boards and in senior advisory roles, bringing a broad lens of experience across real estate, structured finance, and global banking.
Q: You’ve built fund-finance businesses through multiple market cycles. What’s next that others don’t quite see yet?
A:  We are in the midst of significant market shifts. Financing and liquidity solutions are continuing to evolve to meet the changing needs of private equity sponsors and alternative asset managers. Much of the innovation we see today reflects both new structures and adaptations of solutions that have existed for decades, often under different names. What was once considered a GP restructuring to extend the time needed to achieve projected returns is now more commonly structured as a continuation fund or NAV financing.
As managers hold assets longer, both GP- and LP-led secondary markets have expanded substantially and are now widely accepted tools to provide flexibility and liquidity across the market. The industry has adapted quickly, but with these developments come emerging risks, many of which are now being actively recognized and addressed.
Q: What does modernization in finance look like, and what’s still holding it back?
A: True modernization means integrating AI efficiencies while retaining expert judgement to make the best decisions. AI is improving speed and accuracy, streamlining administrative workflows and other core processes. At the same time, fraud is a growing concern, and cybersecurity is becoming an even greater priority as technology adoption accelerates.
Q: Where do you see the biggest opportunities to expand access for emerging managers or underrepresented founders?
A: It all starts with proving scalability, and sustainability will develop in lock step. Founders who earn institutional trust are the ones who can effectively communicate their past experience and why it matters to their strategy. Investors, more than ever, need to be confident in their capital commitments to emerging managers. Access also comes from understanding and connecting into existing ecosystems. Many founders build in isolation, but real opportunity emerges when a company taps into the right infrastructure and becomes embedded in how an industry already operates.
For example, Naborforce can plug directly into the long-term care ecosystem, just as companies like CNote and Work& have positioned themselves as essential solutions within their markets. The Artemis team excels at recognizing and supporting these ecosystem-driven opportunities.
For emerging managers and underrepresented founders, the challenge is not just securing funding, it’s demonstrating the ability to scale. That means clearly articulating strategy, building a structured platform, and establishing market credibility. The greatest opportunity lies in learning to operate at an institutional level while still preserving the authenticity and mission that sparked the company’s founding.
Q: What separates founders who scale sustainably from those who lose focus?
A: Discipline must come before committing resources, especially pipeline discipline. A true business opportunity in the pipeline implies not only interest, but also a defined timeline, internal commitment, and real resource allocation. Managing timing and cash burn is critical. Founders who successfully scale understand what to prioritize, where to focus their energy, and how to build alongside experienced operational leaders.
Q: What makes you optimistic about the next generation of leaders?
A: They aren't afraid to advance their careers. They’re not waiting for permission to grow. They’re proactive, adaptable, and willing to seize opportunities as they arise. The mobility we see today reflects a new level of confidence and self-awareness.
Future leaders also demand multidimensional experience. They refuse to be boxed into a narrow path; instead, they’re curious, eager to learn across disciplines, and motivated to approach problems through multiple lenses. That flexibility and hunger for ideas will make them stronger, more resilient leaders.
I’m especially encouraged by the momentum in women’s networks. There is a growing sense of community and shared purpose, creating a pipeline of confident, well-connected leaders who are increasingly comfortable owning their voice and taking the next leap.
Q: Any trends or founders you’re excited about right now?
A: I’m encouraged by the momentum across our economy. We’re seeing renewed investment in infrastructure, technology, and long-term capacity building. This trend creates opportunities for founders who are addressing and solving fundamental problems, and financing is evolving to satisfy the demand. The next generation of great founders will be the ones who can marry that modernization with institutional trust. People who can scale systems, not just ideas.
Q: What’s the best piece of career advice you’ve ever received?
A: When I was at an inflection point in my career, a mentor once asked me: “Is the view worth the climb?” That stayed with me, and for every important decision over the years, I have reflected on that question. As T.S. Eliot said: "Only those who will risk going too far can possibly find out how far one can go."
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