But what if there was a way to reclaim your time, build systems that actually serve you, and create a more peaceful, professional backend to your business?
Listen to “84. How HoneyBook Helped Jackie Klein Scale Her Business After Teaching” on Spreaker.
From Classroom to CRM
Jackie didn’t start out in the online business world. In fact, she spent years as a teacher before COVID reshaped everything.
“When the pandemic hit, I realized I could retire early from teaching,” she told me. “And I thought, ‘Okay, let’s try something different.’”
She explored the corporate world, realized it wasn’t for her, and eventually found a freelancing course that introduced her to virtual assistance. That’s where the seeds of her new business were planted.
But like many of us who come from non-tech backgrounds, she didn’t start out knowing what a CRM even was.
“I saw someone in a Facebook group mention HoneyBook,” Jackie said. “They were offering a deal—six months for $1 a month. I jumped in and started teaching myself everything. I set up my first automation, tested it… and nothing happened because I didn’t trigger it properly!”
We both laughed at that moment because every solopreneur has a similar story—where you dive into a tool, hit a wall, and feel like giving up. But Jackie didn’t. Instead, she kept going and eventually turned her trial-and-error experience into a business helping others master what she had to learn the hard way.
What Is a CRM (And Why Should You Care)?
For those unfamiliar, CRM stands for Customer Relationship Management. Think of it as the digital command center for your business. Your leads, contracts, invoices, scheduling, and communication—it all lives in one place.
Most of us have used tools like Calendly, Dubsado, or Notion to patchwork our client systems together. But HoneyBook takes it a step further by housing everything under one roof. As Jackie puts it:
“HoneyBook is the spine of your business. It keeps everything running behind the scenes so you can focus on serving your clients.”
She’s right. I personally use HoneyBook in my business, and I couldn’t imagine life without it. From sending proposals to collecting payments, it eliminates the endless back-and-forth emails and sticky notes scattered across my desk.
Jackie explained how CRMs help solopreneurs show up more professionally and save time by automating repetitive tasks—like scheduling, follow-ups, and even sending reminders to clients about invoices or onboarding steps.
“You’re not automating the relationship,” she emphasized. “You’re automating the processes so you can give your energy back to the client.”
The Teacher-Turned-Tech Coach
One of the most powerful things about Jackie’s story is how she’s infused her teaching background into the way she supports her clients.
She doesn’t just set things up for you—she teaches you how to understand and own your systems.
“My membership breaks things down into bite-sized videos so you’re never overwhelmed. I scaffold the learning just like I would in the classroom—step by step.”
Her HoneyBook Success Network is a community for women solopreneurs who are ready to stop Googling everything and start building confidence with their systems. Members get access to trainings, Slack support, tech tickets for personalized help, and weekly office hours to get real-time guidance.
“I want women to know that they don’t have to spend hours trying to figure out one automation,” Jackie said. “They can ask, get help, and move on with their day.”
Game-Changing Automations in Honeybook
Jackie broke down a few of the key workflows every solopreneur should consider building inside HoneyBook:
- Inquiry to Booking Workflow
Set up an automated flow so when someone books a discovery or strategy call, they immediately get a confirmation, prep questions, and reminders—without you lifting a finger. - Recurring Invoices
No more chasing payments. Automate monthly retainers or recurring packages and eliminate those awkward “Hey, just checking in…” messages. - Client Onboarding
Build a seamless sequence that sends welcome packets, next steps, and kick-off call scheduling after the client signs the contract. - Post-Project Follow-Ups
Use HoneyBook’s conditional automations to check in with clients if they don’t respond—or even send a survey or testimonial request once a project ends.
“You can build a mini virtual assistant into your business,” Jackie said. “It’s about designing systems that give you your time and energy back.”
Mapping Your Process (The First Step)
If you’re just getting started, Jackie recommends grabbing a pen and notebook (yep, going old school) and writing out your current client journey—from the moment someone inquires to the final payment.
Ask yourself:
- Where are the gaps?
- What are you repeating over and over?
- What can be automated or simplified?
Then, focus on just one offer or service at a time. Build one solid workflow before trying to automate everything at once. Burnout doesn’t lead to better systems—it leads to breakdowns.
The Honeybook Membership That Makes It Click
Jackie’s HoneyBook Success Network isn’t just another tech membership. It’s the support system she wishes she had when she was starting out. It’s for solopreneurs who know they need systems but don’t want to waste precious hours piecing it all together.
Inside the membership, you get:
- Step-by-step tutorials for all things HoneyBook
- A private Slack channel for ongoing support
- Access to Jackie’s personal tech ticket system (she’ll literally test your automations for you!)
- Weekly office hours and group coaching calls
“The biggest value is having a second set of eyes,” Jackie explained. “Because we see our systems the way we intend them to work—not always how they actually function.”
It’s Not About the Tech—It’s About the People
Toward the end of our conversation, Jackie said something that really stuck with me:
“Automations are not impersonal—they give you space to be personal.”
That’s the whole point of systematizing your business. Not to become a robot. Not to remove the human connection. But to create space for deeper, more intentional service.
When your backend is organized, your mind is clearer. You stop leaking energy on tasks you hate. You show up better for your clients. And that energy radiates through your brand.
Want to Know Where You Stand?
Jackie has a 2-minute Systems Audit Quiz at hellojackieklein.com/quiz that will show you whether you’re a:
- Scrambling Entrepreneur
- Almost Automated
- Or Systems CEO
From there, she’ll guide you to your next step, whether that’s booking a call, joining the membership, or getting support with a build.
Final Words of Encouragement
If you’re feeling overwhelmed by tech or scattered in your business, know this:
You don’t have to figure it all out on your own.
There are people like Jackie who’ve walked through the confusion, who’ve tested the automations a dozen times, who know exactly how to help you simplify and get back to doing what you love.
So take a breath, write out your workflow, and just start with one system.
You deserve a business that flows—and support that helps you get there.
Check out Honeybook for yourself, see how it works for you, and let Jackie know if you have any questions. Check out Jackie’s work at hellojackieklein.com.
- 86. Building a Bold Brand Identity That Lasts with Christi Cooper - September 19, 2025
- 84. Streamline Your Systems: How Jackie Klein Uses HoneyBook to Help Solopreneurs Simplify and Scale - July 22, 2025
- 83. Hormones & Hustle: Navigating Business in the Midlife Transition with Vika Teicher - June 13, 2025
