How to Grow Your DREAM Team


A little over a year ago, I had zero semblance of a team, to this day, my team is always growing and evolving but I want to talk you through the process I’ve been on in growing my dream team in terms of assistants, associates, contractors, and employees! It’s been such a process growing, finding, and training the right people for my team but today I want to break down who is on my team, how it works for me, and what to look for when you’re hiring.

First things first: at some point in your business, you’re going to hit your capacity. You can’t grow, you’re overworked, and you’re spinning your wheels. I was there, I remember it quite well, but I was also SO resistant to hire anyone. Before we can dive into this episode, you have to start to shift your mindset – seriously, you have to or you’ll find yourself an hour from now still spinning the same wheels.

Why are we so worried to trade money – a renewable resource, a token of exchange, for time? Time is something we will never get back, our time should be our most coveted resource and yet we often let money hold us back from getting the help we need.

Before we dive into my current team, make sure you download my “5 Questions to Ask Yourself Before Outsourcing” guide to help you in your own team building journey!

My Brand Manager: (Salaried)

Caitlyn: back in episode 7, Caitlyn and I talk allll about how she came into my life (persistence) and how she made the leap and sold her business so she could be full time on my team. Caitlyn’s role started as email support and has really transitioned to her overseeing the entirety of the brand, the direction, and she will be helping lead the team as it continues to grow.

One big change we are working through is getting Caitlyn out of some of the smaller tasks so she can help more in terms of content creation, a lot of things take her hours, so we are looking at how to streamline and systemize in a new way to get her more freed up to create!

My Tech Guru: (Hourly Contractor)

Danielle: Danielle has been on my team for a little over a year, she’s brilliant and manages allllll the complex tech behind my launches. She’s the woman who handles all the stuff that scares the living daylights out of me and we were connected through a mutual friend.

One big change with Danielle is that she also started as email support and then we started getting more complex. I realized how I was underutilizing her brilliance and so she grew her team with Stephanie to help with the support inbox and launch support so that she’s freed up to work on next level stuff like funnels, complex campaigns, and more of that tech stuff. I asked Danielle awhile back the stuff that excites her and fires her up and we realized we could go a lot deeper with her current position and give her more flexibility as she transitions with baby!

My Community Manager: (Hourly)

Alex: This is a brand new role and one I am SO excited about. Alex started to transition onto my team very gradually. Ya wanna know how? She took my courses and I watched her grow, implement, change. She’s absolutely driven, she’s excited, she WANTS feedback, she’s a dream package. I first offered her a spot assisting my associate photographer Courtney this season so she can get wedding experience, then she shot a wedding with me, and when she asked for feedback I knew I needed to seal her into team JK in a new way.

Alex helps manage the multiple Facebook groups that we manage for my courses, she hops in and supports the students, boosts morale, encourages and inspires people, and is creating seamless systems for top-notch service. She’s the overall heart in terms of serving and it takes some of the pressure off of me to be logged in and answering questions 24/7!

My Associate Photographer: (Paid Per Job)

I never became a photographer with the thought of having an associate photographer but when Courtney came around, it changed things for me. We can do double the work, serve double the clients, and she has such a similar personality and shooting style, I am thankful she can help me serve more JK brides! We realized we were turning down a ton of inquiries and generating loads of referrals so when Courtney approached me about working for me, we started to work out how it would look and what that would look like!

Other Contractors We Use: (Based on job)

  • Facebook Ads: Kerry on Episode 058 talks through how we work together and what that looks like!
  • Copy Writing: Ashlyn on Episode 006 talks through how we team up for launch copy and web copy and how she serves the JK brand.
  • Web Design: Jennifer Olmstead on Episode 002 continues to serve my business with her incredible design and she’s always popping in to make sure everything is on brand and beautiful.
  • Image Editing: I’ve worked with the same photo editor for years and I outsource a portion of each wedding to her. She takes such great care of my photography and I still get to edit what I love!

When it comes to hiring:

  • Get very clear on what you need and if you’re willing to train someone on those skills or if you need someone with experienced. Look at where you are best serving your business and what’s holding you back from doing that and then start to craft a position.
  • Places you can find employees: upwork, Fiverr, Facebook, groups like The Rising Tide Society, at your church, in your community, at your gym.
  • Ask for referrals, I’ve never had to do an open application process because I’ve always been able to work off of referrals, which has served me SO well.
  • Set expectations and facilitate feedback. One of the biggest issues when it comes to team is not setting clear expectations and not fostering a workplace that allows for feedback, if you start with a feedback culture, it will be far easier than trying to create one later on.
  • Create a team culture! Whether you email once a week or check in hourly, create a culture that allows for your team to feel seen, heard, and appreciated. We use SLACK to chat back and forth throughout the day and everyone knows what the priorities are.
  • Start small, work big. Too many people want to have a giant team but they can’t even find the right VA. My team has grown and evolved over the year but it continues to grow and while I’ve never spent more money in my life, I’ve also never made as much money.


Goal Digger episodes mentioned in this episode:

Creating an Unforgettable Brand with Jen Olmstead
How to Pack a Punch with Words with Ashlyn Carter
How to Hire the Right Virtual Assistant with Caitlyn Jeffery
How to Make Facebook Ads Work for You with Kerry Swetmon

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  1. Katie | Katie's Kronicles says:

    Wow this is great! Thanks for sharing!!!!!!! It’s so great to know the team didn’t just magically grow overnight. You had to work hard and they seem to have came into the picture at just the right time!

    Katie |


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