Organization at the Core of Your Business

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Fractional Chief of Staff

Administrative Support for ongoing day-to-day business or for launching and running a program or digital course

Digital Organization including inbox, calendar, and filing systems management

Public Speaking and Workshop Facilitation for Groups

Behind PIT Assistant



Pain in the What?
Alexander the Who?

While my son, Cecil Agent (on the right), may be the showrunner of the biz and of my life...

I, Alexander Agent (pictured left, that's me), founded Pain in the Assistant to explore every system, strategy, and tool that business owners might need to make life easier while they:​

  • Increase revenue
  • Save time
  • Eliminate stress
  • Prioritize a healthy life-work balance

The name Pain in the Assistant is fun, quirky, queer, and maybe a little cringey... like I am! And although it (hopefully) elicits a smirk and maybe even an eye roll if I'm lucky, the name Pain in the Assistant also illuminates one of the worst nightmares an entrepreneur can face:

If your systems don't allow you to efficiently delegate to an assistant or other team member, your operations, your revenue, and your business as a whole will not be able to scale anytime soon.

P.S. Every product, digital course, workshop, and service we offer is structured and built around five pillars:

Illuminate, Empower, Advocate, Connect, and Create.


"The Marie Kondo of the digital world."

"Before choosing Pain in the Assistant, I was feeling anxious, being bombarded by a lot of junk emails. Now, my email box is much more manageable. I see every important email first, I am able to get through ALL my emails in a short period of time, and I actually find joy in checking my emails now!!

"Alexander is friendly, masterful, and efficient in saving me time and eliminating the nasty spam mail that clogs up my inbox. Pain in the Assistant works digital magic!!"

Lee Anne Davis
CEO, Brand Concierge


"Language and solutions that are custom-fit for their blessed recipient."

“Before working with Pain in the Assistant, anything and everything tech-related was a slow, crucial car accident that happened every day without end. Alexander basically solved 95% of the tech issues I've been having for at least the past six years. In one session! He's smart, affable, and efficient!

"Pain in the Assistant has REBUILT MY WORLD, and now does ALL THE TECH THINGS for my business with a wizardry I am FINALLY starting to understand."

Jeff Jacobson
Leadership Coach, Author
The Kind Point


"I finally have more time and freedom to better support my customers."

"I was feeling overwhelmed, uneasy, and behind. I needed someone who could help me get organized and Pain in the Assistant overdelivered. They helped organize my operations, manage my calendar, schedule my meetings… if you need competence, organization, and professionalism, stop your search! I can offer no higher recommendation than Alexander.

"Alexander has always had my best interest at heart. I trust him emphatically with my business and with ME! His energy is electrifying-- Alexander is so much fun and is the epitome of joy and excellence."

Tiffany Slater
CEO, Sr. HR Consultant
HR TailorMade


"You leveled up both my processes and my mindset around business."

"Pain in the Assistant set up scalable workflows for my coaching business and much more! I didn't anticipate that how they organized my Google Drive cloud storage would help me level up my mindset around my whole business. 

"The design work Pain in the Assistant did on my key business documents leveled up how my services are perceived. One potential client said "ooooh, pretty!" and then enrolled for a six-month engagement."

Tara Robertson
DEI Strategy Consultant
Tara Robertson Consulting


Previous Clients

Make More, Work Less

A free, biweekly newsletter outlining the creative journey to financial freedom and true life-work balance.

What you can expect:

  • Curation of my favorite articles, videos, and software from all around the world wide web
  • Actionable tips on increasing profits, productivity, joy, and free time
  • Fresh, 100% true stories that you might find insightful, inspiring, or painfully, comically relatable.

Let's Get It (Together)

Aha! We've made our way to the crossroads. Sometimes a decision is the exact kick-in-the-rear that we need. There are no wrong choices as long as we make progress.

Contact us if you have any questions, or you can buckle-down (or buckle-up, depending on what’s motivated you to come this far) and take one of two first steps to regain your freedom as an entrepreneur.