Pamela Webber is Chief Operations and Marketing Officer at 99designs, where she heads up the global marketing team responsible for driving customer acquisition and increasing lifetime value of customers. She is passionate about using data to derive customer insights and to find “aha moments” that impact strategic direction. In her role at 99designs, Pam has penned many guest posts and bylines for marketing and small business publications, from and Marketing Profs to SmallBizDaily, Small Business Opportunities and She has also spoken at several major industry events and startup conferences, from the World Growth Hacking Forum and Lean Startup 2017 to Opticon and San Francisco Small Business Week.

In addition to her experience as a marketer, Pamela brings a host of first-hand experience as an ecommerce entrepreneur and working with fast-growing startups. Prior to joining 99designs, she foundedweeDECOR, an ecommerce company selling custom wall decals for babies’ and kids’ rooms, and also worked as an executive marketing consultant for True&Co, a successful ecommerce startup specializing in custom-fitted women’s lingerie. 

Earlier in her career, Pam served in various corporate strategy and marketing positions with brands Borden, eBay and its subsidiary, PayPal, Inc. A resident of San Francisco, Pamela received her BA from the University of Pennsylvania and a MBA from Harvard Business School.  

1. How has your life experience made you the leader you are today?


I am the oldest of four girls, so was born into positional leadership. While that does not always translate into successful leadership, it did give me a built-in team with which to practice. I was the one who often helped the littlest sibling and had no choice but to be the first to “break barriers” such as asking to borrow the car, applying to college, etc.


2. How has your previous employment experience aided your current role?


I’ve worked in big companies, small companies, and even started a company myself. Working in a big company helps me hone in on strategy, vision, and communication. Working in a small company helped me learn how to execute efficiently. And, starting a company gave me the empathy I need to support the over half a million companies that have used 99designs to get their business off the ground. It really was the perfect basket of experiences for my current role as Chief Marketing and Operations Officer.


3. What have the highlights and challenges been during your current role?


Work always has its ups and downs. The highlights of my time at 99designs have been the launch of our new brand, accelerating new customer growth rates, and watching my team grow into bigger roles. The lowlights were transitioning from an operating model that was driving growth at the expense of profit to one that was driving profitable growth. That transition required changing a lot of people’s jobs, including my own, and communicating this is the better way for the longevity of the company. Fortunately, we have come out from the other end of that. We have people in the right roles, and doing the right things to drive profitable growth.


4. What advice can you offer to women who want a career in your industry?


My biggest piece of advice is work with great people. I know this is easier said than done. But, like parenting and siblings, early managers and colleagues shape formative experiences. Not only can you learn from their experiences and their style, but they will likely be around to support you as you move on to other opportunities.


5. What is the most important lesson you’ve learned in your career to date?


Build a great reputation and great opportunities will come your way. This is a bit of a different take on the business adage “it’s all about who you know”. While there is something to be said for “it’s all about who you know”, if those you know are good people who tout your skills, you will be highly sought after and have many opportunities from which to choose.


6. How do you maintain a work/life balance?


I have a young son so it is important to me that I maximize quality time with him. I do this by committing to no more than one evening away during the week (unless I have business travel). I make few plans on weekends and if I make them, they are generally last minute.


Additionally, I bring my gym bag to the office and am not shy about going for a work out at 2pm if it’s what works best for my schedule (earlier in my career I wouldn’t dream of working out outside the lunch hour). I try to fit that in 2 days per week.


7. What do you think is the biggest issue for women in the workplace?


I think the biggest issue is unintentionally supporting negative stereotypes. I found myself saying the other day “does that sound too ‘female’ ”? I sometimes need to remind myself that it isn’t just the responsibility of men to stop assuming stereotypes, women need to stop acting stereotypical and I need to do my part.


8. How can we encourage more women to start their own business?


I think funding female founders is one of the easiest ways to encourage more women to start their own business. Amongst 99designs customers, we’ve seen males are 2x more likely than women to raise over $100K in entrepreneurial funding. It takes money to start and run a business. Solving the funding problem sets the stage for a lot more females to take the risk.


9. How has mentorship made a difference in your professional and personal life?


Most people think of mentors as a specific individual who sits guides you throughout your career. They are generally accepted to be more senior than you. I think of mentorship more broadly. For example, I’ve had different types of mentors at different points in my life. Some of my most impactful mentors are a group of female friends I met in business school. We’ve been meeting regularly for 15 years to discuss professional and personal issues. Another mentor is a more seasoned colleague I met while working at eBay. It’s difficult for one mentor to meet all needs at all times so I encourage women to think of mentorship not as an individual but as a group of people the make-up of which might change over time.


10. Which other female leaders do you admire and why?


I admire Sheryl Sandberg who seems to have done it all. Not only is she fabulously successful professionally, but she finds time to build impactful organizations outside of work such as Lean In and OptionB.


I’m also big fan of Oprah Winfrey. I love her rags to riches story and am also inspired by her efforts to give back to the arts and education.



11. What do you want to professionally and personally accomplish in the next year?


I have just taken on Operations at 99designs so, professionally, my goal is to successfully transition my role and my team to our new organizational structure. It is to ensure we have alignment on our goals and are clear on who is responsible for what. Additionally, I am building my mentorship network amongst other COOs. So, my other goal is to seek outside advice/guidance from other COOs. I have met with two thus far and plan to schedule at least three more.


Personally, I have a lot of house projects that need to be done. For example, my goal is to replace all of our window coverings which are in bad shape by mid-summer (that probably sounds very “female” 🙂 )


12. What are the top three tips you can offer to an entrepreneur starting out?


As an entrepreneur myself, I offer these tips from experience

1.     Expect it will take 2x as long to get things done, and costs 3x as much as you expect. I was given this advice when I started my company and I cannot tell you how true it is!

2.     Don’t be shy about seeking expert advice, or asking for help. You don’t know what you don’t know.

Pick three (reasonable) things you want to accomplish everyday. Particularly when you are feeling overwhelmed, focusing on three things will give you a sense of accomplishment and the motivation to keep going    

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