Get to Know Your Top Ops Superstar 2022: Penny Penati

Ops professionals are the dexterous and dynamic unsung stars of their organizations and fields, the ones on the frontline of the effort to find better, more efficient, and more enjoyable ways to work. They’ve never been more important to their organizations than today, in the wake of changing market dynamics and unforeseen social disruption.

The work these folks are doing could mean the difference between survival and long-term success. Yet ops teams still somehow don’t seem to receive the recognition they deserve.

That’s why this year we launched our first ever AdaptivOps Top Ops Superstar Awards. We asked the greater operations community to tell us who is doing the most innovative and influential work within the operations space. The nominations poured in, and from them, five finalists were selected.

This year’s winner from that group of five: Penny Penati, Head of Operations at Helm!

Penati began her career as an Operations Specialist at Apple. After diving into the world of startups, she quickly worked her way up to Head of Operations at Helm. She has held multiple Chief of Staff positions and is now a mentor to many.

We wanted to get to know Penati and learn how she found her way to a career in operations, how ops is different (or the same) in massive companies versus startups, why mentorship is so important to her, and more.

AdaptivOps: In addition to your full-time role as Head of Operations at Helm, you also mentor multiple people and were nominated for an award for Mentor of the Year from City University. Why do you devote your extra time to mentorship? Why is it so important to you?

Penny Penati: Mentorship is extremely important to me. As a lost individual in school, and consequently in university, I was surrounded by my peers who knew exactly where they wanted to go into — and it was only in one area: banking.

I went to career fairs at university that were centered around big corporations in finance, leading me to just follow the pack and convince myself that this was the area I wanted to build my career on.

After interviewing at banks, and of course being rejected, I was demotivated, confused, and had no one to turn to. Whilst my peers were getting jobs at big banks around me, I still didn’t have an idea of what I wanted to do, and was “left behind,” which takes a toll on your confidence.

Through my own research and hard work, I then made specific decisions that would ultimately lead into the startup world and finding my passion. I’m able to confidently say, “I love what I do and what I’ve built my career on.”

I know that there are other people out there that may be as lost and confused as I was, not knowing where to start or where their passion lies, and ultimately their confidence would be at rock bottom. With this, it’s my mission to try and help as many people as I can, because I can sincerely empathize with how they are feeling.

AdaptivOps: What initially drew you to a career in operations?

PP: I began my startup career working as an events intern at Startupbootcamp FinTech. I loved working on all types of events, from hackathons to workshops to events that had 500+ people. I learnt an incredible amount, including how to operate a truly successful accelerator whilst managing and exceeding expectations of multiple stakeholders.

During my time as an intern, there was one person who was a true inspiration and ignited this passion of operations in me: Edwina Johnson, at the time COO of Startupbootcamp FinTech. She was running the programme (from managing the startups, partners, mentors, and investors) smoothly and efficiently, with the utmost calmness. It felt as if I was watching a conductor of an orchestra, and it was at that point that I knew I wanted to go into operations.

AdaptivOps: What is one thing you wish you knew earlier in your career that you know now?

PP: Ask questions, be curious, and challenge. Great ideas come from everywhere, no matter if you are one of the most junior people in the business, or the most senior.

If the answer is, “We’ve always done it this way,” question it. Is it still the best way to do [x], or is there an even better way? The world is continuously changing, and no business wants to be left behind, so always question.

AdaptivOps: You’re an active member of several operations communities. Why do you think they’re so important?

PP: A couple of different reasons: Firstly, there’s a tendency that startups don’t invest heavily in operations as much as they do marketing or engineering (understandably so). Therefore the community is there to help you solve a problem you are currently going through by providing a different perspective or making you think about it in an alternative way.

Secondly, it helps you stay up to date with what others are working on. As an example, an operator in a 50-person startup may be working on something that isn’t relevant to you as of yet because you are in a smaller company, but you know that when you hit a certain mark, that is something you should be aware of.

Lastly, I’m a big fan of learning and developing, so being surrounded by absolutely brilliant minds makes me continuously stay on my feet and grow.

AdaptivOps: You went from a giant, very public company to startup land. What’s different about ops in those environments? What’s the same?

PP: Two completely different worlds, I must say! Of course, in a company like Apple, their processes are remarkable, and it’s something to admire. However, there are various similarities to working in ops in two different worlds: always iterating and improving, and keeping in mind that operations is the backbone of a company.

AdaptivOps: Let’s talk nuts and bolts: What’s your best tip, trick, or hack that’s helped you in your operations roles?

PP: Write everything down, conduct retros, and read articles and listen to podcasts.

Part of working in operations (amongst many) is: process optimization and change management. Process optimization is probably the “easiest” out of the two, and a recent article from The Smooth Operator has outlined it perfectly. Change management is the harder of the two: questioning and poking holes in their process, potentially getting them onboard with a new software, and changing the way they operate whilst not stepping on people’s toes.

It’s not easy, but as operators, the team are your customers, as they are going to use the “end product.” Therefore, get their buy-in, embed them into the process, let them lead on the imperfections, and stay quiet and listen. Retros are a good way to get their feedback, and so you continue to iterate until they are happy with the end product.

AdaptivOps: What’s next for you? What does the future hold?

PP: COO is the dream, and whilst I’ll continue my journey on getting there, my mission still remains to help as many people as I can. So if anyone is struggling to either kick off their career or get to the next level of their career, in either operations or data, feel free to reach out to me.

Penny Penati is the Head of Operations at Helm and the first recipient of the AdaptivOps Top Ops Superstar Award. Find and follow Penny on LinkedIn, and join the AdaptivOps Community to stay in touch with your operations peers!