Our mission
Making skilled, human-centered support accessible to entrepreneurs so they have the capacity to rest, refocus, lead with purpose, and do the work that truly matters to them.
Hi there,
Thanks for stopping by and venturing here to learn more!
At Pain in the Assistant, our clients choose to work with us every day, and we take that daily recommitment to heart! We're a team of real people who bring our full selves to every task at hand (and we try to be pretty fun to work with too). Our approach is team-based and software-agnostic, meaning we meet each client where they are and collaborate to build around how they actually think, work, and grow.
Our work typically falls into four areas (you can learn more about these here):
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Classic Admin & Operations,
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Sales, Business Development & Client Management,
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Content & Marketing, and
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Virtual Events & E-learning.
Some clients come to us for digital organization coaching. Some need our support embedded alongside their existing team. Others have trusted us to help them hire and grow — and we've grown in capacity right alongside them.
We're doing this work at a moment when it matters more than ever. The pressure on individuals and small teams (think: increasing workloads, burnout, and the cacophony around AI) is sisyphean at best. But we don't back down, and we have what Sisyphus did not– a team.
Let's get it (together),
Alexander
Founder and CEO, Pain in the Assistant
Why PITA, & why today
Pain in the Assistant began as an educational resource during the COVID-19 pandemic, created for virtual assistants and administrative professionals whose work shifted remote almost overnight.
Backed by years of remote experience in the tech and entertainment industries, PITA quickly became something more — a rallying point for diversity-empowered professionals and creative leaders who are ready to streamline their workflows, expand their capacity, and build sustainable systems rooted in equity, efficiency, and ease.
Our clients are mission-driven, equity-minded, and ready to build intentional businesses that actually feel good to run.
In September 2021, we welcomed our first administrative support client and the world unfolded for us from there.
Pain in the what?!
Pain in the Assistant — or PITA ("Pee-tah," like the bread) — is delightfully human and intentionally fun and cheeky. The name speaks to something not often discussed but nonetheless true: delegation is hard, asking for help doesn't always come naturally, and administrative work can be a real pain in the a**...and typically isn't what gets most people out of bed in the morning! That's okay. It's what gets us out of bed. (And if you're that type of person, maybe you should apply to join our team!)
The name also reflects something deeper. PITA proudly holds space for queer and inclusive joy, business rooted in care and collaboration, and an energetic, values-driven rebellion to the traditionally gray world of admin and operations. We aim to attract colorful, equity-minded humans—and gently repel anyone clinging to outdated business ideas about who deserves to lead or be heard. Our systems are built for everyone, but especially those who’ve had to build their own way.
Support you've been looking for
Now, PITA offers monthly administrative support services, digital organization coaching and consulting, and keynotes and workshops on best practices for entrepreneurs navigating AI and the digital age.
Consider our services a thoughtfully unconventional blend of personal assistant, executive admin, chief-of-staff, and systems-savvy COO.
We exist because burnout is real, capacity is finite, and everyone deserves a team in their corner.
Our vision
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Administrative support is recognized as the skilled, human expertise it has always been.
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As AI reshapes every industry, we believe the future belongs to those with emotional intelligence and discerning, contextual judgment. We are not afraid of any tool that allows us to serve our clients better.
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We are building a team that feels taken care of, a client community that feels seen, and a business where success is always shared.
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In twenty years, Pain in the Assistant will still be the place that finds exactly the right person for exactly the right problem, every time.
Core values
Every goal, project, and decision at Pain in the Assistant aligns with our core values, and every system we build for clients is infused with the following principles. Consider them our operational compass and the soul of our support.
Create
We’re builders at heart. With a constructive & creative spirit, we love making things that are not only useful and beautiful but also transformative—whether it’s a workflow that saves you hours or a new tool or framework that feels more aligned with how you uniquely do things.
Creating is about crafting a life (both personal and professional) worth living: one with structure, freedom, and growth.
Every project is an opportunity to build thoughtfully, to forge new pathways for ourselves and our clients, and to lay the foundation for something meaningful and lasting.
Certified LGBT-owned Business Enterprise
Certified Disability-owned Business Enterprise
Member of the National Association of Productivity & Organizing Professionals
*Any forms of discrimination, hate speech, racism, misogyny, queerphobia, or threatening of safety or security will be called out and will not be tolerated under any circumstances. If these behaviors are exhibited during a project, the contract is subject to immediate termination without refund.*
Our team
The delightfully human support you've been looking for
The PITA team is made up of skilled, passionate professionals who actually love this work. We come from diverse backgrounds across admin, operations, sales, marketing, content, and events — and we show up as whole people, not just robots. We are curious, reliable, and genuinely invested in the success of every client we serve. When you work with one of us, you get the expertise of all of us.
Alexander Agent
he/they
Curious. Experimental. Kind.
Likes: Volleyball. Nintendo. Cecil.
Founder & Digital Organization Expert
Alexander has always been fascinated by how technology can make life simpler and calmer. Growing up in a household shaped by ADHD and disorganization, Alexander learned early how much stress clutter — digital and physical — can create.
Alicia Klepper
she/her
Creative. Reflective. Supportive.
Likes: Family. Sourdough. Sticky notes.
Administrative Support Specialist & Copywriter
Alicia Klepper is an Administrative Support Specialist & Copywriter at Pain in the Assistant, where she brings clients’ voices to life through purpose-driven writing. Her work bridges the client’s message with their audience’s experience, creating moments where vision meets diction to make a lasting impact.
Cecil
he/she/they
Happy. Smart. Food-motivated.
Likes: Sunny spots on the floor. Cozy blankets. Getting two breakfasts.
Emotional Support Mascot
Adopted in 2020 after being found in the sugarcane fields of South Louisiana, Cecil is a constant reminder to stop and smell every single flower.
Follow along @suddenlycecil on Instagram.
Our team is growing...
interested in joining us?
We are good people who love this work, and we're always looking for more people like us! Bright, organized, and detail-loving minds (especially those with good energy and a knack for keeping things running smoothly) who find joy in assisting others and quelling chaos...to the front!
Experience in administrative support is a plus. Curiosity, integrity, and a good sense of humor are non-negotiable. All backgrounds and identities are welcome.
If joining Team PITA sounds like your kind of adventure (with just the right mix of sticky notes and strategy), then we hope to hear from you soon.
Who we support
Entrepreneurs and professionals across industries who are passionate about what they do and who they serve.
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Seasoned professionals who have been building their business for years, and are ready for their systems to finally catch up, and
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Emerging entrepreneurs earlier in their journey and wanting to build it right the first time.
What they share is a desire for real support without the commitment of a full-time hire.
Our clients come to us usually with a single problem first: an inbox that's out of control, a filing system that needs building, or simply a business that's ready for its next level. What they discover is a team that knows their industry, answers their questions, and brings a network of resources they can actually use.
Where we shine: We align with your purpose and your passion. We are good people helping good people.
"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 always has 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 and Senior HR Consultant
HR TailorMade
A Real Peach to Work With
"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 and Brand Concierge
Promoventures
A Real Peach to Work With
"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 you organized my Google Drive cloud storage would help me level up my mindset around my whole business.
"The design work you 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
A Real Peach to Work With
"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 Facilitator and Author
The Kind Point