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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
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Jonno White

7 Questions with Rob Napoli
7 Questions with Rob Napoli

Name: Rob Napoli

Current title: Founder of Rise Up Coaching and Co-Founder and Board Member at Hapday Group

Current organisation: Rise Up Coaching and Hapday Group

An accomplished trainer, speaker, entrepreneur, business, and career coach based in Brooklyn, NYC. Originally from the Midwest, my journey has taken me from my hometown in Kansas City, Missouri to New York City by way of Milan, Italy. My career started in recruitment within Fortune 500/Forbes 100 companies before moving to Milan, Italy to pursue a Masters in International Multi-Channel Marketing, where I also spent two years working for a global e-commerce startup and coaching professional American Football. I moved to New York years ago and have to work for a large global corporation before transitioning over to training and development for startup and growth-stage founders.

Currently I run 2 businesses; Hapday Group, a US GTM company that helps startups enter and scale in the US Market through Sales as a Service. Rise Up Coaching is a training and development business that works with companies on creating and scaling entrepreneurship and innovation through scaling and hiring.

7 Questions with Rob Napoli

1. What have you found most challenging as a leader of a small or medium enterprise?

To be honest, what has been most challenging for me is availability. I want to be on all the time for my team and give as much as I can, which at times leads to me saying 'yes' to everything. With this comes a high level of stress and anxiety and I forget to focus on time for myself and time to spend with my wife and friends/family.

2. How did you become a leader of an SME? Can you please briefly tell the story?

My career started out in the recruitment industry where I was staffing software developers into Fortune 500/Forbes 100 businesses. After 5 years, I met who is now my wife in Des Moines, Iowa when we decided to move to Europe as she wanted to pursue a Masters Degree. She told me she doesn't do long distance so, I packed up, left my job, sold my house, and we moved to Milan, Italy where I got my Masters in Marketing from MIP Graduate School of Business at Politecnico di Milano, coached professional American Football, and started working for an e-commerce startup where I helped them scale globally.

I moved back to the States in 2017, went through an accelerator program, switched careers back into recruitment, built out a team, left to go back to a startup, got fired, and then started my two businesses. I knew I wanted to work with startups to help them scale and grow and used the lessons I had learned the hard way to help. Since I moved to NYC I have coached and mentored at about a dozen accelerators and have been exposed to many types of companies and lessons that we use to help other companies enter with less barriers.

3. How do you structure your work days from waking up to going to sleep?

I try to keep my work down more fluidly as I used to be super rigid. Wake up around 7 am. From 7:30 - 12:30 pm is time dedicated to my clients and work in Europe. 12:30-2 pm is my time for personal development, gym, clearing my inbox. 2-7 pm is for my US work/clients, content creation, and my own training + practice my workshops/training/ etc. I tend to end my work week on Friday at Noon and try and shut off work for the rest of the day and then I work for about 2-3 hours on Sunday morning over coffee setting up for my week and taking a couple coaching calls before my wife gets up and then I shut it all off to spend the day with her. That Friday self-care and Sunday prep has led me to more productive weeks and work.

4. What's the most recent significant leadership lesson you've learned?

That it is okay to ask for help. I used to think that as the leader I needed to have all the answers when in reality, I needed to give myself the grace to ask for help.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

So many books have had different impacts but the biggest one of late was Who Not How... really being intentional on who to delegate or bring in to do the things I or the org is not able to be more productive and effective. This has led to better work delegation and more intentional growth for our team vs what others say you should do when building. And we use these lessons when we train and coach our clients and that has made a huge impact on a number of orgs.

6. How do you build leadership capacity in an SME?

Curiosity - reading and listening to great content
Content Creation - sharing my challenges, wins, and lessons on social and listening and discussing with other leaders on those lessons.
Growth - I am always looking for new ways to innovate and scale, I am not set on a one-way approach, I am always intentional and adaptable which has led me to grow and grow fast.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

We brought in a number of interns throughout the end of 2019 and 2020 to help in our growth but also to give back and teach. In about a 7-month time span we brought in 8 interns and every one of them left the organization and got BIG-time job offers; Tencent, Facebook, JPMorgan, Motorola, etc. One of them even impressed one of our clients so much, the client asked, and we agreed for them to hire him.

For me to see folks who come to our organization, whether for a short or long term period, and use that to truly grow and take their careers to the next level is what it is all about. I don't expect everyone we bring in to spend their whole career with us. What I expect, is that for however long we have them for, they make an impact or our org and we make an impact on them.

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