Activate, don’t wait – lessons on leaps from Allie Fleder

Read about Allie's leaps and how to proactively manage your career journey by creating your own opportunities rather than waiting for an invitation.


We had the pleasure of interviewing Allie Fleder, COO and Co-founder of SimplyWise. We talked about her experiences working at an NGO, moving to the UK to explore career options, starting a luggage delivery business, and then moving back to the US and co-founding SimplyWise (with lots of exploration and steps in between). A recurring theme for Allie was the tension between waiting for opportunities and proactively putting in the effort to…

·      Take your seat at the table

·      Explore new opportunities

·      Speak up and out on issues that are important to you

Take your seat at the table

Allie’s first boss once pulled her into her office to ask her why she was always choosing a chair in the corner at the team meetings and not sitting at the main table. Allie thought that was ‘her place’ and would take notes furiously, despite not being asked to. Her boss told her that was the first and last time someone would tell her to take a seat at the table, and that she needed to continue to advocate for herself because no one else will. Instead of waiting for permission or someone to tell her it’s ok, since then, Allie has become an advocate for herself, knowing that she should take a seat at the table and that she belongs there just as much as anyone else. She learned in that moment to not wait for someone to define her role but to stake a claim for what she wanted her role to be (respectfully and appropriately, of course).

Explore new opportunities

Allie took a big leap going from chief of staff to the head of the NGO she worked to changing teams and projects and helping roll out the internet in Cuba. While she stayed within the same organization, the skill set required, opportunity, job description, and team were completely different. Leaps don’t always have to be to new industries or organizations or geographies, while Allie was still based in the US at the same organization, changing roles was still a huge leap for her professionally and cemented her interest in the tech sector. She decided to continue to pursue tech when she moved to the UK for graduate school, but wasn’t sure in what form. Allie made the most of her student status to meet with people, shadow them, and work on different projects to identify opportunities, ultimately finding her way with a startup. And similarly when she exited that startup, she followed the same process to share her goals with others, attend events, and ultimately found an opportunity to cofound SimplyWise. By exploring widely through shadowing, networking, and her research, and by not waiting for someone to come to her with the perfect job or opportunity (or taking the first role that came her way), Allie knew that when she found SimplyWise, it was the right leap to make.

Speak up and out on issues that are important to you

Lastly, Allie has been an outspoken advocate for issues of DEI for women in tech and LGBTQ+ people in tech, especially as a founder raising capital. The issue is huge, 40% of entrepreneurs in the US are women, yet only 2.3% of VC funding is going to women-led startups. Allie was reticent to speak out at first, hanging back on advocacy, assuming someone else might be the voice for these topics. When she realized that she wasn’t seeing any progress on challenges she was facing, she realized she had to be the one to ‘break the ice’. Once she started sharing her personal experiences with DEI in tech at conferences and other forums, she realized she was the person that other people were waiting for – she described how women have approached her after conferences sharing their own stories and appreciating Allie’s courage. Regardless of what issues and topics are important to you, Allie’s journey highlights that being vulnerable and using your platform to raise awareness for issues or challenges can be a leap of its own.

Allie’s journey and leaps across sectors, industries, and countries provide examples of the value of proactively guiding and managing your leaps and decisions. When Allie found herself stuck or ‘waiting’ for an opportunity or guidance, she was lucky enough to receive it from her mentors early on, and then channeled that into proactively exploring new roles, countries, and companies. And when she waited for someone else to advocate for her, she realized that she had to step up. Regardless of the shape or nature of your leaps and decisions, proactively managing and taking those leaps, rather than waiting for change, are critical to managing your career trajectory.

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To leap or not? Steps to prepare for and make the most of change

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Out, about, and to – three different types of leaps and where they might take you