Crushing It: Advice from a C-Level Alumni

Great careers start with a community. For Bob Reish, community arrived when he joined Orr Fellowship in 2009—and it hasn’t left him since.

Today, Bob Reish is the Chief of Staff at AboveBoard in New York City, a mission-driven startup intent on flipping the executive search model and helping those from underrepresented groups gain access to executive career opportunities. 

As Chief of Staff, he’s a “jack of all trades” with his hands in several areas of the business; including operations, customer success and marketing. As a member of the LGBT community, Bob works daily toward a mission he believes in and has a lasting impact on his colleagues, clients and company.

But let’s go back to the beginning.

In 2009, he graduated from Notre Dame with a degree in Finance and began his professional career as an Orr Fellow with Angie’s List, now Angi. After completing a corporate finance internship while in school, Bob was curious and excited to experience entrepreneurial life at a high-growth startup. 

His experience at Angi was certainly exciting, to say the least. He had the opportunity to work directly with Angie, CMO, and Scott Brenton, the founder of Orr. He learned so much about their approach to business and professional growth. Not only was he learning directly from founders, but by the time Bob left Angi to pursue his MBA at Wharton, he gained cross-functional experience in roles spanning operations, sales and marketing in just four years. 

Bob is fond of his Orr experience – both the career  opportunity and the connections he made with friends and mentors have been meaningful to his professional and personal development. Given this history and growth, he has some advice to share with Orr’s current and incoming Fellows. 

Live in the moment and recognize that you’re always learning.

As Orr Fellows, we value growth highly. With that in mind, it’s easy to fall into the trap of focusing on what’s next and forgetting to be present. For example; during his first rotation in Angi’s call center, Bob recognized that he wasn’t excited about the position. He was so focused on the possibilities of his next rotation that he didn’t realize all that he was learning about the customer and product, which would prove to be incredibly valuable down the road. He likely wouldn’t have been as successful at Angi without that foundational experience, and even today refers back to some of his insights from that time. There’s so much you can take away from any experience.

Do your job, do your job well, then ask for more responsibility.

This is some key advice Bob received from Angie. As ambitious, recent grads, it’s tempting to want to take on all different kinds of roles and responsibilities so you can prove your potential. Yet, having realistic goals and focus is critical to achieving growth. Trying new things is certainly encouraged; but again, learning takes time and experience. If this is your first job out of school, it’ll be good for you to spend time performing well in a new role so that you’re more prepared to take on new responsibilities. Regardless of the company or position, Bob has a saying, “Good things come to those who are crushing it.”

It doesn’t have to be perfect.

This may seem odd to current Fellows – all of whom are fresh from an environment where everything had a grade – but the truth is, sometimes things just need to be good enough to get started. That’s not to say you shouldn’t give your full effort, but it’s more about quieting the imposter syndrome that you’ll face as a young professional. You’re going to make mistakes, one way or another. And that’s okay. If you’re afraid to fail, then you’ll never be brave enough to try things that could lead to great success. This is the best time in your career to take chances in an attempt to push an idea, a project or even the whole company forward.

Your network is everywhere, and you should take advantage of it. 

Orr Fellowship is a unique postgraduate experience. Orr alumni were in your shoes, and they’ve seen the fruits of their time in Orr – they can’t wait to share it with you. As an Orr Fellow, you have dozens of Orr alumni who would love for you to ask questions, for advice, even for mentorship. The network is there and eager to help, so don’t be afraid to reach out.