Making it Rain: Practical Tips from Those Who Do


Dorothy (Dolly) von Hollen is vice president and corporate counsel at Prudential Financial, Inc. She is responsible for the corporation’s intellectual property, overseeing all trademark, patent, copyright, trade secret, and domain name issues. Dolly started her career practicing environmental law and commercial litigation before finding she had a passion for IP law. She moved in-house to serve as the assistant general counsel at Nike, Inc., focusing on intellectual property and domain name issues for the sports and fitness company before moving back home to the East Coast.

Dolly is a dedicated mother who—when unable to find a satisfying library book for her son—wrote, published, and illustrated a children’s book. She has climbed Kilimanjaro, Aconcagua, and Denali, and enjoys reading, sailing, listening to podcasts, learning German, and rooting on the Orioles.

You’ve been extremely successful, holding positions at prominent law firms and with some of the largest corporations in the world.  With that experience, are there any universal keys or attributes you’ve identified to adapting and succeeding in any environment? 

One of the most important keys to success is having the motivation to work hard, be flexible, and have the willingness and eagerness to learn. To be motivated though, you have to like what you do.

I love learning and being challenged intellectually. My background is in trademark/copyright, but in my position I also do a lot of patent work, so I am always learning something new. IP law is constantly growing and changing to keep pace with the digital economy, so it seems there is always something new to learn.

The longer I practice, the more I find I also really enjoy helping clients with their issues—partnering with them to find solutions, teaching them about IP principles. The former athlete in me also likes the occasional competition of trademark litigation. And, the English major in me loves reading a well-written brief.

You’ve had a variety of professional experiences. Can you describe the trajectory of your career and how you ultimately arrived in your position at Prudential?

Before law school, I worked as a paralegal on the Love Canal Superfund litigation, and that sparked my interest in environmental law. While attending the University of Maryland School of Law, I pursued that passion: completing an externship with the National Wildlife Federation, as well as a visiting semester at the University of Colorado in Boulder. I co-edited with a law professor a collection of essays on environmental law while working as a research assistant.

These experiences led me to accept a position practicing environmental law with Gordon Feinblatt, a general practice law firm in Baltimore. While there, a partner with a trademark and copyright practice was looking for an associate to help, and I was more than happy to volunteer. It was a field in which I had always had an interest, despite never taking any IP classes in law school.  That decision to volunteer ultimately shifted the trajectory of my career.

Over the next several years, I found that I really enjoyed IP law. I recognized that New York was the place to practice IP law, so I accepted a position at a large IP boutique in the city. My practice there focused primarily on trademark litigation and disputes for large consumer brands. I learned a lot through the litigation work, but wanted to work more in a counseling type of role. So, I accepted a position at a general practice firm, representing companies in the sports, hotel, and technology industries. This was during the Internet boom of the late 90s/early 2000s, so it was an exciting time to be practicing in that space.

That said, my goal had always been to work in-house, and just when I started looking for a change, an in-house counsel position opened up at Nike on the West Coast. There, I was exposed to a wide variety of complex and cutting-edge issues. Ultimately, when I learned of an opening at Prudential, I knew that it was the opportunity I’d been waiting for back home on the East Coast and all of my experiences prepared me well for the position.

Given where you are now and what you have learned, is there anything you would have done differently early on?

I don’t think I would change anything. It is funny to me how everything can make sense in hindsight. When you look back, all the decisions you made seem to prepare you for where you are, even if you did not consciously make those decisions at the time. One glance at my résumé reveals a very diverse set of experiences—transitioning from environmental law to intellectual property law with experience working in boutiques, general practice firms, and in-house. But there was a reason behind every move. Every position gave me a different set of skills and experience, all of which I draw on in my current role. So, while I may not have realized it at the time (and I’m sure it was not consciously intentional), I was following my constant desire to try new things and learn as much as I could. In all of those positions, I was collecting skills and knowledge that I apply today.

What advice do you have for someone that wants to position herself for in-house employment?

Develop an expertise, understand your client’s industry, and get as much client contact as possible so that you can learn to speak to non-lawyers. You need to be able to understand the business concerns and goals, and explain complex legal concepts to them in 2-3 sentences.

If you see an opportunity that is not exactly what you hoped for, be willing to try it. You never know where opportunity will come from or what it will look like, and the most rewarding long-term opportunities might not seem like attractive at first. Be willing to put effort into everything you do; you sometimes may be surprised with the results.

I also believe that gaining as much exposure in terms of the types of clients/industries you represent and the types of work you do—litigation, counseling, agreements—early in your career will pay off when seeking a position in-house. I have worked for two very different companies: a consumer brand and financial services. They are polar opposites in terms of the products, the types of trademarks, the risk tolerance, the regulation, and the corporate culture. But I think the variety in my background prepared me for both opportunities when they came.

With your experience, what advice would you give to someone transitioning from private practice to in-house? Were there any surprises when you first went in-house (or even between in-house experiences) that you wish you had been better prepared for?

Be flexible and open to taking on new roles. I was a trademark/copyright lawyer. And now, in addition to that, I manage Prudential’s patent work. It has opened up a new field to me and kept me engaged and learning, which has been a blessing.

Be prepared to handle a wide variety of matters. Sometimes I feel like my in-house position is like being a utility infielder; you will be asked to handle a variety of issues quickly and you may not always have the time to “dive as deeply” as you do when you are outside counsel.

Be prepared to make a clear recommendation. Business people want to understand the risk they are taking, but they want to understand it in practical terms and they want to know the bottom line, i.e., we see the problem, and we appreciate the risk, but what do you recommend we do? Learn the difference between things that need to be done perfectly and things that just need to get done.  Finally, be prepared for a lot of meetings and administrative work.

One of the biggest challenges for “women rainmakers” is initiating relationships with in-house attorneys. Do you have any advice for those seeking to establish or develop relationships with in-house attorneys? 

It is important to develop expertise and be able to demonstrate that you know a particular area well—copyright fair use, or contract indemnity clauses, or USPTO practice. I have hired counsel who gave a great presentation on a particular aspect of IP law at continuing legal education (CLE) presentations, and I have hired outside counsel that I met at trade organizations. Once, I hired one who asked a good question when I was on a panel and we spoke afterwards.

After you’ve made that initial contact and received that first project, you have to deliver. I work with a lot of outside counsel, and certain individuals tend to become my “go to” people for particular issues, usually because I liked the work they did. Quickly try to understand what your client’s concerns are and what they want, and give it to them. I also will try to test them by giving them different types of projects to see their range, and over time I learn their strengths and weaknesses.

Is there something you know now that you would recommend to “women rainmakers” seeking to be more appealing to inside counsel?  What do you look for when hiring outside counsel?

I use outside counsel for two reasons: 1) because we are a lean department and need extra hands to get the work done, and 2) because we need the expertise offered by outside counsel.

Outside counsel is most useful when they can offer a broad perspective. As in-house counsel, we tend to see the same types of problems through the single lens of our industry. In contrast, outside counsel has usually seen a problem many times and across industries. They know how other parties handle similar situations and can draw on that in advising us. It’s also important that outside counsel deliver a work product that both explains the problem to me (so I can quickly get up to speed and translate it to internal clients) and provides a lot of material that I can use directly with internal clients. It’s also important to have competitive rates, and we like to support minority practitioners.

To be able to do that, “women rainmakers” should develop a broad expertise while understanding your client and their industry. As the client, I understand that we need to develop a relationship, so in the beginning I will work with outside counsel to comment on their work product and train them on our specific needs and preferences. Ultimately, I want someone who can provide me something I can use with internal clients.

Once you have the contact and some projects—don’t be afraid to stay in touch! I do think sometimes the “squeaky wheel gets the grease,” i.e., we give work to counsel we hear from and sometimes forget about the ones that aren’t in contact.

What are fatal mistakes made by outside counsel? 

First, failing to keep the business goals and company style in mind. I have had outside counsel be overly aggressive in their approach. For example, we may not be interested in pursuing litigation, and yet I’ve had outside counsel suggest filing suits at the drop of a hat when that is just not what we want to do.

Second, continuing to make the same mistakes in work product. I spend a lot of time editing work in the beginning of a relationship, but if over time the work product continues to require me to do a lot of work—it’s not helpful and doesn’t save me time.

Third, suggesting approaches that just won’t work in our industry/corporate culture – particularly with recordkeeping and overly burdensome processes. We are thinly staffed and have a lot of competing demands, and sometimes a particular issue is not as urgent to the business people as it may seem to the lawyers. As an outside lawyer, I used to wonder why it sometimes took in-house counsel a while to get back to me on something that seemed important/urgent. Now I understand! There is just a lot going on.

Finally, not being responsive and not staying in touch.

About the Author

Jordan A. Arnot is a partner with Partridge & Garcia, an IP firm in Chicago.  She can be reached at 312.634.9502 or

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