What It’s REALLY Like to Work for Jenna Kutcher

Jenna Kutcher 

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February 25, 2019


Meet Kyle the podcast producer for the Goal Digger Podcast and what it's really like to work for Jenna Kutcher.

I am so excited to introduce you to the newest member of Team Jenna Kutcher and the girl who has been rocking The Goal Digger Podcast behind the scenes as our podcast producer. When my sister told me she was moving on in her journey I was sad to see her go, given all the success she helped bring to this show, but I was also excited to get back to being just sisters again! After an overwhelm of 500+ applicants in just a few hours, Kylie’s application stood out and I just kept coming back to her and knew she was the right pick to fill the role of podcast manager for the show. In this episode, we’re digging into her new role, what her journey has looked like and how she ended up on Team JK, and what the interview process was like… Because you know it wasn’t typical! She also shares her tips for managing a podcast and how to make Google Docs your best friend, and I dig into the process of vetting, hiring, and training a new employee so you can incorporate some of what I learned as you grow your team, too. So what’s it REALLY like to work for me? Press play on the player above for the full scoop.

Meet Kylie

Kylie’s journalism degree and love of storytelling set her up for some wild professional experiences… None of them in a newsroom. Her first job out of college was a spokesperson position, touring her home state of Maine in a bright green car blogging and vlogging about financial literacy for the 18-to-25 crowd along the way. At the end of her one year term, a friend sent her a picture of a pack of Oreo cookies with the group One Direction on the front. Nabisco and One Direction were looking for a “tour correspondent” to travel the country, go to One Direction concerts, and blog/vlog the experience for fans at home. It seemed like a long shot, but Kylie jumped anyway and submitted her video audition and ultimately landed the (dream) job. She spent four full months touring with One Direction, working with a major agency on a massive national account, and creating content for a devoted and engaged fangirl audience.

When the tour ended, Kylie went back to Maine and headed the digital media department for a financial tech company. While the job gave her the confidence to sit at a table with “suits” and built her resume in the corporate world, she kept her eyes open for her next big thing. Kylie launched her own YouTube channel which eventually caught the attention of the local pop radio station. She started collaborating with the DJs on video projects, getting paid in concert tickets and special access to events with her favorite music artists. When one of the founding co-hosts of the radio morning show announced she was leaving after 19 years, Kylie was invited to hang out on the air while the station searched for her replacement. After her first show, Kylie was offered the position of co-host of The Q Morning Show.

For three years she started her day at 4:30 in the morning, hanging out on air with the station she grew up with, connecting with listeners, working on her comedy routine, and having the time of her life. When her fiance’s career brought them to New York City she started her search for the “next big thing” again. After 9 months of working part time a country radio station while interviewing for corporate marketing and digital media positions, the perfect opportunity presented itself when she was looking in all the wrong places. Enter: The Goal Digger Podcast.

Application and Interview Process

I’d never hired for a position online before but I knew I needed someone really good, with a specific skillset, who I could interview and hire ASAP. With maternity leave only a few months away, I posted the opening for the podcast manager position on LinkedIn and shared the info once on Instagram Stories and Facebook. Within four hours I had over 500 applications through LinkedIn. I was looking for some specific keywords when reviewing the applicants including broadcast, social media, and work from home experience, and of course, podcasting. Kylie had heard about the position through a friend and applied the same day I posted the job.

I talk a lot about hiring and investing in your team, and in going through this process with Kylie I fully understand why some people are hesitant to do it. It’s a lot of pressure, you feel like you have to ask the perfect questions, and the interview process can be time consuming and overwhelming. If I learned anything from hiring Kylie, it’s trust your gut. I had spoken to three other women who all experience in the podcasting space, but as I sifted through the impressive applicants, I kept coming back to Kylie’s application. Her years in radio, her director level digital media experience, and unique skill set was ideal for the position. If I hadn’t been on a such a tight deadline I like to believe I would’ve expanded the process and done a formal Skype interview with formal questions, but as a CEO I know when to trust my instincts. Kylie and I hopped on the phone to talk big picture goals and then more specific details about her experience. She says although she was a little nervous, the conversation was simply that: a conversation about our goals to see if they aligned. After a chat with Drew that night, I ultimately decided to hire Kylie for the podcast manager role, as well as another woman named Brooklyn for an entirely different position. Within four days I had made my first official hire for The Goal Digger Podcast!

Onboarding and Training

Since Kylie was entering at a really crazy season for my business, I wanted to make sure we trained and onboarded her in the best way possible. This was the first time I invested in training like this. I flew her out to Duluth so she could meet with Kate and I in person for training, but also so she could see where we’re from and what life is like for us. Kate and Kylie met at a coffee shop and worked a full 8 hour day breaking down all the systems Kate had created for the show. An in-person training meant Kylie could ask questions as they went along and could see Kate in action. The second day of training was more of a work session. Kate delegated some tasks to Kylie so she could get familiar with the processes by actually walking through them herself, not just seeing them performed or reading Kate’s notes.

One resource we developed for Kylie (and for whoever may join the team in the future) is a bank of screen flow videos and Google Docs that explain some of the more technical processes. In the first few weeks Kylie was on her own with the show, she referred to the video library for tasks like updating the website with ShowIt, composing a new blog post inline with our branding standards, and reporting ads to our agency.

Kylie’s New Systems

Kate, and before her Caitlyn and I, created plenty of systems to make the podcast go and GROW. Kylie joined the team and immediately learned our systems, and then adapted them to her own workflow, and added new items to improve efficiency of the show. Kylie is a huge fan of all things Google Docs, and when she identified that certain processes were clunky, she analyzed them by dumping everything into a Google Sheet.

So much of what we were doing was tracked through the email inbox and Kylie wanted to get out of the inbox. Graphics for the show, for example, are actually a multi-step process. We request a headshot from our guests, the photo is emailed back to us (or sometimes it takes a few more asks). Then Kylie sends the photos, titles, and episode numbers to our designer Olivia, who then sends back a big batch of graphics for the blog and social media. All of this was previous tracked in email. The only way to know if graphics were ready was checking emails and the Google Drive folder where they were ultimately saved. Keeping track of that process was clunky, so Kylie incorporated it into a larger content tracker document that contains every item that needs to be completed for every episode. The release date, title, guest, blog slug, descriptions to our audio editor, graphics, videos, social media captions, guest follow up and MORE are all in one concise document with check boxes for when each task is complete. Take a step back and look at the processes you’re managing through email. If you’re frequently using the email search bar or trying to remember if that key piece of info came in, create a content or task tracker for your own business.

More from This Episode

What surprised Kylie the most about the job of being the podcast producer and my business? What am I actually like as a boss? (I promise I didn’t pay her to say nice things!) And most importantly, what were her first impressions of the tiny Duluth airport? I am so excited for you to get to know Kylie, the girl behind the show, and to have a discussion about the hiring process and how I chose to invest in this new team member so that you might incorporate some of my learning experiences into your own hiring process. Press play on the player above for the full episode!

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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