10 Systems that will make you a Killer Business Manager

10 Systems that will make you a killer business manager - stacy kessler.001 copy 2.jpeg

My bad business management days

When I started my first business I had these grandiose visions of being the most organized business owner ever. My business partner took the lead on operations and so I let him set up all the tools and behind-the-scenes systems.

Then, six months in, our business partnership went south and I took over the business solo. I was left to figure things out and I had to do it fast. Our business was up and running and tax day was right around the corner. I struggled to get oriented to (and even find logins for) what he had set up. I didn’t know where to begin figuring out where he left off.

Overwhelm set in and a lot of things fell through the cracks.

I never did dedicate the proper time to figure everything out and instead just addressed stuff when I had to.

I always felt angst around my business disorganization, but I used the business partner breakup as an excuse to never get things in proper order. I ended up settling for being a kinda shitty business manager.

The impact of not having my shit together

Because I hadn’t set up or maintained things the way I should have, everything became more difficult. Let me give you a few examples.

Bad financial Management

Every year at tax time I was scrambling to wrangle together the financials for the year. Because they weren’t readily available to look at and analyze on a regular basis, I wasn’t in tune with what was really going on with the numbers of my business. I knew I wouldn’t be happy with them and avoiding them seemed like an easier path at the time.

However, this kept me from being an informed business manager able to take action based on results and actually improve things.

Bad customer lead management

I didn’t have an organized way to keep track of business inquiries and was horrible at remembering to follow-up with people.

Since only a small percentage of people are ready to become a customer on the spot (the rest need to be nurtured and followed-up with), I was missing out on a lot of business sales.

Bad scheduling management

When someone wanted to schedule a tour or book a meeting with me, the process involved long email chains going back and forth about schedule availability. Times would often get double-booked when responses were delayed and I’d have to ask people to switch meeting times.

This was a huge waste of my time and did not set a good impression.

Reality check

I never felt good about how I was managing the business. I was embarrassed, but was in denial about how much it was affecting my business results and holding me back from growth. It wasn’t until I got approached by someone who wanted to buy my business two and half years later that I really saw the situation for what it was.

I had been managing my business like no one would ever see or care about the behind-the-scenes, but if I wanted to sell, that’s exactly what would happen - a long due-diligence period of digging into all the dark and scary nooks and crannies of my business that I didn’t want anyone to see.

It was the reality check I needed to whip my ass into shape.

Lessons Learned

When I was running a million miles a minute to build my business, setting up some systems just seemed unnecessary for where I was at. What I didn’t realize was that setting up these systems before they seem necessary is the perfect time to do it.

Early on, you have more time to learn these systems and the setup is so much simpler with a newer, smaller, leaner business.

The small amount of money I saved because I was too cheap to pay $10 a month for a CRM software was NOT WORTH IT. That small investment of time and money would have paid dividends in the long run.

So, I decided to do things completely different when I launched this business.

I figured out how to be a good business manager and researched and set up the best tools to help me do that.

And I’m gonna let you in on all my secrets so you can be a better business manager than I was for my first business.

Simple systems that will make your business better

I’m going to make this super simple and tell you exactly what I would do if I were to start from scratch again. The worst part about getting this stuff setup is figuring out where to start, what’s important, and which ones are the best to use.

I’ve already done this tough work for you and have chosen 10 that are easy to set up, won’t break the bank, and can grow with your business.

So learn from me and build it right from the start, or wherever you’re at. The longer you wait, the harder and more complicated implementation gets. Don’t get stuck in a rut like it did, MAKE TIME FOR THIS.

Here are the top 10 systems that I recommend to help you manage your business like a beast.  

  1. Business Bank Account ($0)

    For some reason this gets a lot of people stuck, yet it’s literally THE EASIEST THING TO DO. Open a separate and dedicated business checking account and get a debit card.

    Trust me, it makes everything else easier including financial reporting, analysis, and tax prep along with just having the mindset that you’re running a real business.

    Best of all, it’s free and easy. I suggest opening an account where you already have your personal checking account. Most banks will setup the account under your same account login so you can quickly and easily move money between your business and personal if you need to add funds, pay yourself, or reimburse yourself for something.

    As a sole proprietor, all you need is your social security number and driver’s license.

  2. Credit card processor (2.9% + $0.30/transaction)

    A lot of business owners want to just operate in the land of cash and checks. It great to not have to pay a fee, but it’s just not realistic for most modern businesses.

    The small percentage of money you have to pay for this service more than pays for itself by not wasting your time depositing checks and reminding customers to pay (some of which never will).

    I suggest Stripe. It can be integrated into most anything you’re using to sell and track financials. If you’ve ever purchased something online and entered your credit card information - this is the same kind of user experience that Stripe provides.

    Some people also use Paypal. The fees are the same, so it’s just personal preference. I use Stripe everywhere but have a Paypal account if someone prefers to pay that way.

    If you sell goods or services in person, you’ll want to get a Square credit card reader to process payments on the spot. There are better options for very high volume businesses, but for everyone else, Square will be your easiest option.

  3. Accounting software ($9/mo)

    Choose a bookkeeping software like Xero (what I use) or Quickbooks and link it to your business checking account and credit card processor. All of your purchases, payments, and fees will automatically filter in and you just need to “reconcile” them (aka. tell the software what kind of purchase or sale it was).

    You’ll want to spend a little time setting up your Chart of Accounts in a way that makes sense for your business. This is essentially just how your revenue and expenses are categorized. The IRS recommends certain classifications for business expenses, but you are not required to categorize things this way. I recommend you do it in a way that enables you to analyze your numbers in a way that’s useful to your business and allows you to stay organized.

    With Xero, you also can email any invoice attachments or photos of receipts to your account with a unique email address for your account. When you reconcile your payments, just find the right file and attach it to the purchase and voila! you no longer need to hold onto a shoebox full of receipts.

  4. Mileage Tracking ($0-$6/mo)

    Using a mobile app like Mile IQ makes tracking your mileage a breeze. It automatically detects when you’re driving and tracks the miles, then all you need to do is go into the app every so often and categorize the drives as personal or business.

    You can also do this in a good ole spreadsheet using Google Maps to calculate your miles, but I think $60/year to track unlimited drives and not have to waste time calculating it myself is totally worth it (It’s free for under 40 drives per month).

  5. Scheduling Tool ($0-$25/mo)

    Acuity is an amazing online appointment scheduling software I use. I'm continually blown away by how easy they make it to set automations for my business. I didn't realize how much time I was wasting doing mindless office tasks until I experienced the power of Acuity and have never looked back.

    MY FAVE FEATURES: Customize Availability by Appointment Type | Collect Custom Client Info & Post-Meeting Feedback | Setup Auto Emails & Reminders | Integrates Seamlessly with Squarespace

    Also, if you use Squarespace, it’s free for their mid-tier product! Otherwise, their free lowest tier or inexpensive mid-tiers will fit your needs.

    Setting this up early on may not seem necessary, but it makes it SO much easier to manage things as your client base grows and your schedule gets busier if you’re already all set up. I decided to set this up from the beginning and I’m so glad I did.

  6. Customer relationship management ($10/mo)

    I avoided using a CRM system for so long because they seemed cumbersome and overly complicated. Enter Less Annoying CRM. The name says it all. They take out all the other bells and whistles that most businesses don’t need in order to simplify the experience.

    Use this to track who you’ve been talking to and where they are in the decision-making process to hire you. You can set reminders to follow-up and log your email communications with each individual so they are all in one place.

  7. Email Management ($29/mo)

I’ve used Mailchimp, Campaign Monitor, Covertkit, and other email management tools. Even though some of them are free, Covertkit wins hands down and I gladly pay a small fee each month.

It is simple to use, well designed, and I just love their message and how they treat their customers.  

FAVE FEATURES: Easy User Interface | Set Rules & Automations | No Duplicate Subscribers | Subject Line A/B Testing | Simple Form Integration with Squarespace

8-10. Domain ($1-$15/yr), Website ($12-$46/mo), G Suite ($5-$10/mo)

For as little as $1-$15 per year, there’s no excuse to not buy your own domain name. I recommend Namecheap.com.

If you’ve got a normal business without any super special needs, I recommend you only get your domain here (don’t use them for hosting, SSL Certificates, or email management). For those I turn to Squarespace (website includes hosting and SSL Certificate) and G Suite.

I’ve used Wordpress, Wix, Strikingly, and Squarespace for websites and Squarespace wins as my favorite by a landslide. Using Squarespace allows you to have control over your website without being a developer and create something beautiful without being a designer. Even if you decide to hire someone to help you but need to make a quick change yourself, you can easily Google search how to do pretty much anything in Squarespace and get a quick answer instead of waiting on a designer or developer to do it.

At only $5 per month (one year free through Squarespace), G Suite makes you a way more legit-looking business. No more @gmail.com emails. You’ll look way more professional and established with an email address that ends in your domain. You can also setup powerful website analytics among a host of other stuff within G Suite.

Key Takeaways

As entrepreneurs, we all want to just focus on our craft and while that’s important, it’s also important to schedule time to get this boring stuff done (actually some of the setup I found quite enjoyable!). This upfront time investment saves you so much time in the lon-run, and once you grow and get busier, it gets harder to implement or change this stuff.

So, do it when it seems a bit like overkill so it’s done and you don’t have to think about it when you grow. Everything will just work seamlessly.

Your goal is to feel like you have all your shit together, even behind the curtain (and yes, even if you never intend to sell your business). If you don’t, this can block your growth (like it did mine) without you even realizing it.

If you find yourself making excuses like I can’t do X until I have Y done, then you need to do these things now.

Here are the positive impacts you should experience from implementing these 10 systems:

  • Look more professional

  • Stay top of mind with leads and get more referrals

  • Make tax time easier

  • Make decisions based on real-time numbers

  • Save time

  • Reduce stress

  • Be setup for growth instead of being held back

  • Have the mindset of a real, legit business (super important!)

Here are the top 10 systems that I recommend to help you manage your business like a beast:  

  1. Business Bank Account ($0) - Go to your existing bank

  2. Credit Card Processor (2.9% + $0.30/transaction) - Stripe & Square (Free processing on $1000 with this link)

  3. Accounting Software ($9/mo) - Xero

  4. Mileage Tracking ($0-$6/mo) - Mile IQ (20% off with this link)

  5. Scheduling Tool ($0-$25/mo) - Acuity (free premium account trial)

  6. Customer Relationship Management ($10/mo) - Less Annoying CRM (Extra month free with this link)

  7. Email Management ($29/mo) - Covertkit (one month free)

  8. -10. Domain, Website, G Suite - Namecheap.com ($1-$15/yr), Squarespace ($12-$46/mo), G Suite ($5-$10/mo).

Build your kick-ass business

If you found this helpful you should also download my free Step-by-Step Checklist to Build Your Kick-Ass Business below. I walk you through my Foundational Five™, the essentials I believe every entrepreneur should have figured out in order to be set up to succeed.


10 Systems that will make you a killer business manager - stacy kessler.001 copy.jpeg


I only promote things that I have personally used and feel good about recommending. If I won't use it, I won't tell you to. By purchasing Mile IQ, Acuity, Less Annoying CRM, Square, or Convertkit using my unique link above, I receive some sort of compensation for helping to spread the word to you about their awesomeness, so thanks! This helps enable me to continue to provide you with the best free resources to help you build a business you love.


stacy kessler - pathfinding strategist

Hey There!

I’m Stacy, an entrepreneur, strategist, and adventurer dedicated to helping entrepreneurs figure shit out and build kick-ass businesses.

You are meant to do important and amazing things in this world and I’m here to help.


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