Erin Halper, Founder, The Upside, Flexible Career Executive Talent Agency


Erin Halper is the founder and CEO of The Upside, a company that helps corporate professionals transition into more fulfilling, flexible career paths as consultants and independent contractors, matching their clients with companies in need of on-demand executive talent. Erin’s company is making a difference for the 43 percent of highly qualified women with children who leave careers or off-ramp for a period of time due to the constraints of a holding a traditional career. Learn more about Erin and The Upside in her interview with Like a Boss Girls.

erin halper founder ceo the upside
Erin Halper, Founder/CEO, The Upside
 Name: Erin Halper

Company: The Upside

Job Title: Founder and CEO

Lives in: New York City

Originally from: Spartanburg, SC

Your superpower: I can create opportunities out of thin air. Pow!

Name a woman in history that you admire & why:

I admire Oprah Winfrey because despite having everything going against her – race in the 1960s and 70s, gender, abuse, a broken family – she became one of the most successful and influential people in the world. To top it off, she uses her success to influence positive change. She is proof that we have no excuse for failure. (And she’s also proof as to how successful a flexible career can be!)

Quote/piece of advice that you live by:

Follow your passion first and foremost. Then the money will come.

What inspired you to start your current venture?

I started The Upside after seeing so many exceptional women struggling between the limiting choice of working full-time or not working at all, especially after starting families. I enjoyed a successful and fully flexible career as an independent consultant in the investment industry and thought, “Why aren’t more companies capitalizing on this talent pool of high-achieving professionals that want a better work/life balance?” So I created The Upside to match businesses with best-in-class consultants, independent contractors and freelancers, for the benefit of all.

What are you and your company doing to make history today?

The Upside is changing the way that working works. Work culture is shifting and the freelance movement is growing rapidly. The people have spoken – we now know that our work doesn’t need to be difficult, inflexible or limiting in order to be fruitful. We know it isn’t necessary to sit behind a desk for 10 hours a day in order to be productive. The Upside is one of the pioneers leading the charge. We are educating businesses as to how flexible career options offer their employees a better work/life balance, and we are encouraging diversity and maximizing productivity for the companies we work with.

What is one thing you and your company have accomplished that you are most proud of?

I’m proud to be a female founder, pioneering an industry that, until now, has been so fragmented that it felt non-existent. I get calls every week from women thanking me for even trying – let alone succeeding – at this business. I’m fueled every day by all of the positive feedback we receive, and I’m beyond proud of that as well.

erin halper the balance flexible career
Pictured: Erin Halper enjoying her work/life balance

What is one project you are currently working on that you are most excited about?

We are starting to speak at conferences, which enables The Upside to get our message out to a much larger audience than we have been able to reach before. It’s exciting to have the infrastructure, knowledge and confidence to be able to speak about the future of work on a much bigger scale.

What, in your opinion, is one of the biggest challenges facing your industry today?

Educating businesses about the future of work is one of the biggest challenges we face. We try to encourage businesses to embrace these cultural shifts, and we teach them how to implement changes into their corporate culture. All of this takes time. The concept of a flexible career is still relatively new, and some industries are very resistant to change and slow to move. It’s our job to overcome that challenge by continuing to frame our message in a way that conveys how making these changes will be beneficial to the business and their workforce.

What is a trend in your industry that you foresee becoming popular in the future?

Flexibility is absolutely a trend we will see in the future of work – it has already become desirable amongst many people in the workforce. Slowly, flexibility is being embraced by employers as well. I foresee a future where the majority of the workforce is flexible in some way, shape or form.

What is one of the greatest challenges you have personally faced at this job? (Or if you’re willing, share a story of a time you screwed up & how you recovered!)

In the beginning stages of The Upside, I made a mistake that I never plan to repeat when we sent our first consultant out for a client meeting. She was the perfect fit and it was the perfect client, but the meeting didn’t go as well as I’d expected. As I received a play-by-play from our consultant, I began to realize that our client had been expecting a pitch, whereas our consultant had been expecting an interview.

These are two very different approaches. Whereas an interview is a back-and-forth exchange with the candidate responding to the client’s questions, a pitch requires the candidate to actively sell themselves to the client without being prompted.

This made me realize that I needed to train every consultant how to approach their client meetings. Not everyone – even those who are rock stars in their field – know how to pitch a client with confidence. After I made this realization and adjusted accordingly, I’m happy to report that our consultant landed every client we sent her to from that point forward!

What were you doing before your current role? 

I spent the majority of my career in the alternative investment industry, with a focus on marketing. Because I developed this unique niche, I was able to transition my career into an independent consultancy, and I spent 7 years helping investment companies market their funds. I felt very fortunate to be able to enjoy balance in my life and a fully flexible career as I got married and started my family. That inspired me to help others achieve this type of career!

What is one piece of advice you’d like to give to other female founders & change-makers?

Perseverance will be what separates the winners from the losers. Don’t give up!

Are there any resources you have discovered that you would like to share?

I’m obsessed with Google Docs, Sheets, Forms, etc. It’s so obvious, but I am grateful for these free platforms from Google (thank you!) that enable us to collect information and share files from anywhere with anyone. It’s just one of the many elements that has kept my company’s overhead costs way down.

Fun fact about yourself:

I’m a painter and I plan to paint professionally in my next chapter, whenever that may be!

If your company is currently hiring or looking for partnerships, where can readers go to find more information?

We are always looking for amazing consultants and high-level freelancers for The Upside and for our clients. If you’re interested, go to our website (link below) and create a profile. This will upload all of your information into our database, and we’ll be able to include you when we search for client matches.


Connect with The Upside & Founder Erin Halper: website / Instagram / LinkedIn.