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Advancing Women in Corporate Leadership Spotlight: Hollie Heikkinen, iWorker Innovations LLC

Hollie Heikkinen is the CEO & Founder of iWorker Innovations and Thought Leader for the advancement of independent worker equality.

A lifelong entrepreneur, Hollie has founded 8 businesses over the past 25 years and brings a keen (and deeply personal) understanding of the myriad policy challenges and obstacles presented by the gig economy. She is an expert advisor to national associations and a tireless advocate for common-sense reform, bringing her fight to the halls of Washington, DC and the board rooms of Fortune 500 aggregators and insurance giants alike. In 2017, Hollie launched an innovative insurance brokerage designed specifically around meeting the unique needs of independent workers. She is currently partnering with national firms and associations to connect gig workers with bundled, portable packages that leverage the strength of their growing numbers and provide key protections and safety nets they are currently denied in government programs. Hollie’s empathy for serving all people and passion for life is contagious and brightly shines through everything she does.

Below are some of her thoughts when it comes to the advancement of women in corporate leadership.

How important is gender diversity to your company, and what value does it bring?

Gender diversity is important to iWorker Innovations in a number of ways, some of which you might not expect. Since the company has a female founder, it sets a different dynamic right from the start: gender diversity has to include ensuring men are also represented in iWorker’s leadership. From a go-to-market perspective, we’re designing and selling products and services that ALL independent workers need, regardless of gender – so I think it’s important for our team to reflect the diversity of our consumer base.  And as a start-up, the team is working in an intense environment that requires everyone to constantly stretch and adapt and take risks. There’s simply no room for siloed or sexist thinking – we need all hands on deck, and all hands are considered equally valuable.

How has your personal experience as a female executive helped shape your company’s diversity and inclusion practices?

As a serial entrepreneur, I think my experiences are a bit different from female executives in a traditional corporate setting. I have always been “the boss” and run my own businesses. As a result, I’ve never felt passed over for a promotion or seen opportunities given to less-qualified people. However, I have experienced discrimination when trying to land meetings or close a business deal. As a woman I sometimes have to work harder to prove my professional knowledge, subject-matter expertise, and leadership capabilities—something I find frustrating not only because it’s wrong, but because it unnecessarily slows down the speed of business. And like most women, I’ve occasionally encountered men who are dismissive or condescending because of my gender. Those experiences have definitely helped shape the culture of iWorker Innovations. I am absolutely passionate about making sure everyone in the company has a voice and is treated with the utmost respect—zero exceptions. I believe in the value and dignity of all people, and the very nature of our business is about serving universal needs of all people - regardless of gender, socioeconomic background, race, religion, or any other label some might try to apply. If you don’t believe in the de facto inclusion of all people, there’s simply no place for you at iWorker Innovations.

What do you think needs to change in order to increase female representation in leadership positions?

I think both men and women have some work to do on this front. There is simply no excuse for sexist attitudes that undermine or de-value what women bring to the leadership table. The “old boys’ network” still opens doors for some people and not others; fortunately it’s a network that is coming undone, and men can help speed up that process by calling out other men when they see bad behavior, and by mentoring and championing female and male colleagues alike. For women, taking charge of their own careers and developing an entrepreneurial mindset is key, even if they are operating in a traditional corporate environment. Research consistently shows that men are more willing to take risks and feel confident pursuing promotions they’re not fully qualified for, while women tend to hang back and wait for an exact fit. Coming from a start-up mindset, I know that business is often unpredictable and risky, and some of the biggest successes require pushing yourself past what you think you’re capable of. I’d love to see more women have that level of confidence in themselves and be willing to go after opportunities that stretch their current skills and experience levels. When that happens, I think we’ll see more women stepping into leadership positions.


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