Woman of Impact: Erin Halper, Founder and CEO of The Upside

by Solange Lopes | Apr 11, 2018 | Career

Our Woman of Impact feature presents women who are breaking barriers in their careers, businesses and lives. These women are inspiring us to do our best work and live our best lives. Today’s feature focuses on Erin Halper, founder and CEO of The Upside, a new kind of agency that aims to change how working works in America.

Erin Halper is the founder and CEO of The Upside which matches businesses with best-in-class flexible, scalable and on-demand talent. After consulting for more than 7 years, she noticed that there was no existing company successfully connecting the absolute best independent contractors with businesses that could benefit from diverse, high-achieving consultants and freelancers. Acknowledging this gap in the market, Erin decided to combine her instinctual matchmaking skills and consulting expertise to help others gain flexibility and independence in their careers, while also helping businesses acquire top talent that can flex and scale with their evolving needs. The result is The Upside, a new kind of agency that aims to change the way working works in America. 

I met Erin at the 2017 Women at Brown conference this year, during a workshop she was teaching. Her presentation entitled “How to be successful in 10 years” amazed me with its unique insight, wealth of information, and proven strategies. This is a continuation of the conversation started then…

Hi Erin, tell us a bit about you and what you do:

I was a consultant in the alternative investment space for 7 years. During that time, I started my family and tended to my first son who needed two heart surgeries. Thankfully he is totally fine now! But there was a time when he needed constant care. I was already a consultant, and it was beneficial to juggle my son’s medical needs with my work. During that time I always wondered: “How would someone be able to handle this situation if they worked full-time and had little flexibility and limited time off?”

I saw a lot of my friends, even those with Ivy League degrees and major careers, really struggling with balancing full-time hours and having a life outside of work, as well as being there for their kids. They would feel guilty missing a few hours of work to go to their kids’ kindergarten graduations. I just don’t believe in that, especially if you’re a high-performing employee. A lot of them were either struggling full-time or dropping out entirely, but not because they wanted to. They tried to make the best out of it, but the current work culture as we know it failed them. On the flipside, I saw the benefit that my clients gained from having me as an outsourced, scalable, director-level marketing professional that could flex and evolve with their changing needs. That’s when I saw the opportunity for a win-win business model.

Tell us about your business:

I started my business as a talent agent initially, aiming to represent a select number of high-caliber consultants and make a fee off of their work. However, in one week I received more than 200 emails from professionals wanting to work with The Upside. That’s when I pivoted the business to be 100% client-driven where we source professionals from our network based on demand from businesses. We are quickly gaining a reputation for being the number one resource for businesses  to find best-in-class consultants and independent contractors with a white-glove, concierge-style service that’s rarely seen in today’s world of high-tech algorithms and job boards. We’re not a job board, or a job platform. We actually hand-hold our clients and consultants, negotiate on behalf of both, provide market rate expertise and provide robust productivity reporting once the consultant begins work. As for the talent, they don’t have anything to do but show up and kick ass.

Additionally, from a fee structure, we don’t charge any more than other comparable services. Yet clients receive that premium, white-glove service that many people still want.

Can you give us a few tips as to how women like myself can become consultants?

The first thing to do is to find your focus. Most companies don’t need generalists because they already have them. You have to dig deep into your resume. What makes you special? What can you do better than anyone else? We had for instance, a woman who had a great career in marketing. However, we already had plenty of people with the same qualifications. So we had to ask her, “What do you do that no one else does?”We had to basically eliminate 90% of her capabilities, to focus on the 5 or 10% that could make an impact. We ended up helping her land a consulting gig where she put in 2.5 hours a week for $10,000 a month to help a fledgling company gain explosive growth.

You should do your research on rates as well. I always go with an hourly rate for hands-on, roll-up-your-sleeves work, which lends itself to a win-win arrangement for both client and consultant. For more strategic work, we recommend a bespoke, hybrid rate arrangement, especially when a consultant is developing ideas and strategies that will result in a company garnering millions of dollars.

As for personal business development, your first step should be to reach out to every person you ever worked with. People are not likely to work with strangers. They would rather work with someone that an existing employee would vouch for.

What does a typical day look like for you?

As a business owner, I’ve learned to block out time. Wednesdays and Thursdays for instance, are my typical days to go in the city and meet with clients. Mondays are my office workdays, usually for 9 hours straight. Once my kids are off to school at 8am, I’m sitting at my desk, and I basically do not move from that spot until the 5pm work whistle blows. It’s my day to write articles, perform business development research, catch up with my contractors, speak to the press, follow up on older emails, etc. It’s not always glamorous; however, this is the guts of the business, the hard part that nobody wants to do but it has to get done. Everyone wants to see me walking through the city, meeting at Hearst, Bloomberg, and all these fancy companies but that’s only a fraction of what it takes to run a multi-faceted business like The Upside.

Even though I have full flexibility, I still have to respect it, and use it to avoid burning out. There are days when I’m just done physically and mentally, and so I turn off the computer and spend time with the kids and family, or run errands  at 3pm. This business is a long-term play and I cannot risk burning out before we have the type of traction we’ve set out to achieve. It’s too great of a business and there are too many people depending on it! I learned a while ago that working all day and all night is just unhealthy. At 5pm, I just put the phone and computer down, even if I’m in a zone with work. At some point, you have to set limits.

What would you have done differently in your career or business?

In my career, I don’t think I would have done anything differently. I think half strategically, half accidentally, I made the right moves. Being an independent consultant while I started my family was the absolute best thing I ever did. I kept my career in a nice holding pattern, while making money and being there for my son who really required my time. You don’t predict these things, I thought I was going to have a healthy baby but I didn’t. It also helped my marriage and allowed me to travel with my family. I was afforded this opportunity accidentally because I was working in an industry that was forward-thinking and appreciated the type of work I did.  That was a happy accident, and I have no regrets. Everything I would categorize as a mistake, I learned from.

In my twenties I had a different business altogether and brought on a partner that I relied on to help grow the business and help combat burn-out. I learned that business partnerships are like marriages. Unless you bring in a partner who is the yin to your yang, it’s not worth it. It just doesn’t provide the value you need. If you’re the creative person, you need an operations person. If you’re the math person, you need the marketing person. And so on.

As women entrepreneurs, what is your advice to raise capital?

Start with friends and family who will not necessarily breathe down your neck. I have invested in friends and family rounds for women-run businesses I truly believe in, and they don’t hear a word from me.

Also, don’t raise outside capital, especially VC money, unless you really need to. Too many women are valuing themselves by the amount of capital they raise. Not every company needs that kind of capital immediately. There are ways to grow organically first. Just because you raise VC money doesn’t mean you’re going to succeed. And if you don’t raise VC money, it doesn’t mean your business model isn’t valid. We need to stop putting so much emphasis and “popularity” on VC money.

Also, once you raise capital, you have a boss, which totally defeats the whole work-life balance concept for me. Once you have an outside investor, you have deadlines and commitments. I specifically designed my business model to avoid this. It would be nice to have an influx of capital, but ultimately, it’s not necessary. My business will grow on its own because the model was designed for organic growth.

How do you scale a business organically?

First off, you can bootstrap your business. I haven’t bought anything new in a long time, for example. It’s about adjusting your lifestyle. Make what you have work. Invest in yourself.

Secondly you can consult on the side. If you can land one great consulting client, then you can bring in a layer of income to keep yourself afloat while you pursue your business.

Finally, you can design an alternative revenue stream to compliment your main business model.

What is your superpower?

My superpower is creating opportunities out of thin air. No one was doing what I was doing, and I decided to create something out of nothing. This is not a recruiter, a staffing agency, or a headhunter. And it’s not a job board or a matching algorithm. This is something completely new, and I have to explain the concept to people all the time. The fact that the freelance movement is growing like it is, and no one was doing a great job connecting businesses to the best of the best freelancers was an opportunity that I had to seize.

What networks would you recommend to other working women?

It really depends on what you’re looking for. Ellevate Network (https://www.ellevatenetwork.com/) does a good job at covering all age ranges and Dreamers and Doers (www.dreamersdoers.me/)is amazing for millennial-minded entrepreneurs. Work Bigger (https://www.facebook.com/groups/workbigger/) is a wonderful resource for women beginning to break out on their own.

In any of these networks, you have to be a giver for them to really benefit you. Always give more than you take, and opportunities will start to come your way. We all win when we help one another succeed.

Any questions for Erin? You can leave them in the comments, or contact her on the following channels:

LinkedIn – Instagram – Facebook

As seen in:  IdeaMensch – CIO – Thrive – AmexOPEN – LinkedIn

Thanks so much Erin!

To Your Success,

The Corporate Sister.