Topics: Careers, Business, Health & Fitness
**David Nebinski** (0:05)
Hey, friend, it's David Nebinski here in Brooklyn, here at the Portfolio Career Podcast, here to help you take ownership of your career and design a life that you want to live. This conversation is with Olivia Leavengood. We first got connected through the Chief of Staff world years ago and have stayed in touch since. In fact, we saw each other a few months ago when I hosted a Chief of Staff event in San Francisco. As a reminder, I host events for Chiefs of Staff in New York. You can learn more about my events at achievestaffpodcast.com which is another podcast that I have as well.
In this episode, we talk about Olivia's career after leaving her Chief of Staff role, how her work has evolved from a fractional Chief of Staff to consulting, what she is doing in building now with helping founders with founder-led sales, a specific document that you could create that could help you stay of top of mind for your career and much more. You can learn more about the podcast and my learnings through newsletter at davidnebinski.com/newsletter. Excited for you to build and grow your portfolio career. Here we go with Olivia. What's up? What's up? What's up? I haven't done a Zoom podcast interview or a virtual podcast interview in a while, so I'm excited to do this. It's great to see you. I know I haven't seen you in it. Well, I saw you in person a couple of months ago, and now we're reconnecting virtual.
We, last time we got together, we were just really, we both were really fired up about things.
**Olivia Leavengood** (1:27)
Good moment in life.
**David Nebinski** (1:29)
Yeah. What do you remember about that conversation?
**Olivia Leavengood** (1:36)
I think we were both at a crossroads moment where we were both in our fractional journeys, discovering where we wanted to focus more of our time and energy and create expertise, almost niching down, which I'm seeing as a really big trend that's needed in the fractional space because there are so many people moving into fractional.
You have to be an expert in something or you have to have a niche. So that was the center of our conversation, was our unique viewpoints on the world and how we deliver that for a client. And we were both kind of moving from exploring lots of different things and our own sub-niche of professional expertise, mine being chief of staff in yours, community building. But that was something that was a good seedling moment where we got to have a real IRL conversation where we were totally pressure testing ideas that then we went through the summer and actually brought to clients.
**David Nebinski** (2:35)
Yeah. So you're saying that you have started to niche down more, and that's been going well?
**Olivia Leavengood** (2:47)
Yeah, I'm very bullish on that. So to anyone that wants to get into fractional, my biggest piece of advice is actually not to say you're a fractional CMO or a fractional chief of staff.
That is very general, and it means that your network doesn't really know who to send your way. Instead, saying specifically the pain that you're solving and for who, business world and even the startup world where I've spent all my time, is huge. Am I working with Series A companies that are going through hyper growth in SaaS, or am I doing scale ups, or am I working with tiny seed stage companies that are building AI products? There's all of these different mini markets you can be in, and the more focused I've found that I pitch myself or tell people in my network, the more traction and signal I see. So I actually have a list of things that I don't do, and I'm like, I am not all of these things, and sometimes that helps people go, okay, she's not these things, this is what she is.
So just really niching down and finding your voice, because there's plenty of opportunity when you're fractional. You don't need to work with hundreds of customers a year. You might need to work with 10, and that's great. So you just need 10 customers that really have your problem and you can solve it.
**David Nebinski** (4:17)
And so are you saying that like founder that sales, that's the kind of like focus and the niche? And if so, like what's what's kind of the pain there?
**Olivia Leavengood** (4:31)
So for me, it's that. But my journey brought me from a full time chief of staff and then bootstrapping my own business to jumping into the fractional world where I went and served many CEOs as a fractional chief of staff. And I loved that experience. I did that for about two years and served five different CEOs across that. I learned a lot. And I think from a startup perspective, when you're working with smaller startups, being fractional helps you diversify your risk a little, especially the really early stage. I love working with Seed and Series A and was able to cross pollinate a lot of different ideas that were happening between the different founders and what was happening in that current moment. But seeing how everyone was doing it, I think it made me better at my job.
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