Client Case Study: Summer Deepe, Owner of Summer’s Sweet Shoppe

Meet Summer Deepe, Creative CEO of Summer’s Sweet Shoppe, a thriving cookie education business serving hundreds of students through her two flagship memberships: Next Level Cookie Club and Cookie Classes to Cash.

When Summer first reached out, she was running her entire business solo after letting go of her previous team — but she was drowning in the overwhelm of trying to be both the visionary and the integrator. Together, we got her back on track to having the creative freedom she craved, while scaling her business in a meaningful way.

You can read the summarized version in this post or watch the full video below.

Overwhelm Was Keeping Summer’s Sweet Shoppe Stuck

Summer started teaching cookie decorating after over a decade as a custom cookie decorator. What began as helping fellow cookiers learn the craft evolved into two successful memberships teaching both decoration techniques and business skills.

But by 2024, Summer was at a breaking point.

After letting go of her previous team due to a lack of ROI, she was managing everything herself:

• Writing every email, sales page, and social media post
• Creating workshop slides and marketing materials
• Managing launches entirely solo
• Handling all project management and strategic planning
• Tracking zero metrics because there was no capacity left

If that sounds exhausting, that’s because it was. The truth is that with a business of Summer’s size, there’s no way to grow doing it all alone. 

“I could make a list all day long of the things I needed to do. I need to write this sales page, create this graphic, do this and that. I could literally spend the whole day just making that list over and over. But what I lacked was direction on actually doing those pieces.

I felt overwhelmed before I would even get to the doing part. I would get overwhelmed by the process of figuring out what to do first, which was most important, where to put my efforts.”

Summer needed help, but she couldn’t figure out what to do next without a little support first. 

Why Summer Was Hesitant to Invest After Bad Experiences

Like many creative CEOs who’ve been burned before, Summer was hesitant about adding someone else to her team. She worried about:

• Whether someone outside the cookie industry could understand her business model
• Making another expensive mistake with no return on investment
• Finding someone who truly understood online membership businesses
• The risk of another team member who couldn’t deliver results

“The investment piece was big. When I had let my other people go, it was because the ROI wasn’t there. At the end of the day, my litmus test is: is this person going to be able to help me move the needle in my business?”

But during our discovery call, Summer realized something important: she didn’t need someone who could decorate cookies — she needed someone who understood her customers and could help translate her vision into actionable systems.

THAT is what she needed to move the needle forward. 

“I realized very quickly that it didn’t matter that you don’t know how to bake or outline and flood a cookie. It was about the messaging to the customer. You could come from a true customer’s point of view, which actually helped me even more.”

The Transformation: From Solo to Strategic Partnership

After nearly a year of working together, we completely transformed how Summer’s business operates — and more importantly, how she feels running it daily.

Launch Results That Actually Move the Needle

One of the biggest challenges for Summer was having time to sit in the visionary’s chair, instead of the integrator’s chair. With this new mental space cleared up, we were able to create a strategy that resulted in successful launches:

• Before: 20-30 conversions per launch, doing everything solo 
• After: 67 people joined Next Level Cookie Club, 50 joined Cookie Classes to Cash

“We had 67 people join us in our Next Level Cookie Club launch in March, and then 50 people joined us for Cookie Classes to Cash in April. It was a huge increase — the biggest numbers I’d seen since I presented at CookieCon a couple years ago.”

Strategic Messaging Overhaul

We also worked on how Summer connected with her audience in a way that felt authentic, but still funneled them in the right direction:

• Moved from vague, general messaging to specific, direct communication
• Implemented data tracking to see what actually worked
• Created repeatable launch frameworks instead of starting from scratch each time
• Developed clear value propositions for each membership

“We really focused on our messaging, especially in our social media and emails. Being really direct instead of being overarching and general.”

Team Building and Systems

But it didn’t stop at marketing. We also built a system that laid the foundation for a new team:

• Hired the perfect VA with the right skill set for the business
• Implemented Asana for project management across the entire team
• Created clear role definitions and accountability structures
• Established efficient communication systems

“Having our virtual assistant, and having you help hire her and set up those tasks — I think you quickly realized within a few weeks what we needed from a VA and what they could do. You saw the operations part of the business and knew what we needed.”

Event Planning and Execution

We even took this strategic partnership on the road! For Summer’s events, we:

• Created a comprehensive CookieCon plan, her yearly convention booth plan and execution strategy
• Facilitated on-site support for networking and customer conversations
• Created timeline management for all event logistics
• Conducted post-event analysis and customer insight gathering

“Having you there physically to help be part of it was huge. To have someone there that could talk confidently about what we offered, who felt comfortable answering questions about my memberships even though you haven’t decorated a cookie — that was priceless.”

What Summer Gained After Hiring Operational Support

Beyond the tactical improvements, Summer gained something invaluable: a thinking partner who could take her ideas and turn them into reality.

“I have a vision for what I want something to look like, but all those steps to get there — I usually don’t care about those details. I want to get to the fun part of the end goal. Having someone come alongside you and say ‘we’re going to bring this to fruition’ is huge.”

This shows up in practical ways:

• Quarterly planning sessions to set realistic goals
• Idea evaluation to determine if projects align with business objectives
• Resource assessment before committing to new initiatives
• Strategic advice on timing and execution

“I can follow directions really well. A lot of times that’s all I need — someone to say ‘Summer, you’re going to do A, B, and C, and then D is going to be your vision.’ I can do that.”

The Result: The Creative Freedom She Always Longed For

“I feel supported, hands down. That’s the word I keep thinking of. I’m not running the ship on my own. I have help — other people working towards these goals as well.”

As far as what Summer would say to a fellow CEO considering hiring an OBM: 

“I would say, do it. I needed to hire somebody to tell me what to do, because it can get overwhelming. If you’re like ‘I need more management help, I need more operations help of how to operate this ship’ — then definitely the OBM is the way to go. You can always try it and see. What do you have to lose? Because probably what you’re doing now isn’t working for you.”

Summer’s Sweet Shoppe now runs smoothly, allowing Summer to focus on what lights her up: teaching cookiers how to turn their passion into profit.