“The Calm in Our Chaos”

Do you thrive in fast-paced environments where the phrase “other duties as assigned” is not a warning, but a lifestyle?

Do you send holiday cards every year? Do you know Stephen Covey’s quadrants by heart (or at least pretend convincingly)?

Does your love language scream Acts of Service?

Then keep reading. Everyone else may exit quietly.

Who You’ll Be Supporting

You’ll be the right hand to Jackie, our Founder — a brilliant, overloaded executive who is tired of:

• Back-to-back calendar chaos
• Inbox purgatory
• Realizing she forgot her makeup bag 5 minutes before an evening event
• And discovering on Friday night that she has 17 client meetings next week

She needs a handler.

A mind-reader.

A human steel trap.

A bringer of coffee.

A slayer of chaos.

If that thrills you… excellent. Let’s continue.

We thought it made sense to give you an additional perspective on this job. For that, we asked our new Chief of Staff, Laura, to chime in.

From the Chief of Staff:

“We’re looking for a true Type A personality—someone who thrives in a high-paced, high-functioning environment and genuinely gets fired up by challenge. This is the kind of person who never says ‘overwhelmed,’ but instead says, ‘Bring it on—I can’t wait to dig in and make a difference.’ It takes mega-high energy, both mentally and physically, a love for being organized and detail-oriented, and a sense of fun along the way. This role isn’t for the faint of heart—but for the right person, it’s incredibly exciting.”

Who You Are

• High-energy, high-capacity, high-standards
• Backbone + polish
• Loves structure but thrives when the day blows up
• In-person, every day, no exceptions
• Proudly Type A
• Sees chaos and whispers, “Not on my watch.”

Bonus points if:

• You have never missed a holiday card year
• You’re the friend people describe as “scary organized.”
• Your soul will not let details slip

$50,000 - $80,000 yearly

Examples of what you'll need to do:

Command the Inbox

• Draft replies Jackie can fire off in seconds.
• Own outcomes — not just “mark unread” and hope for the best.

Architect the Calendar

Stephen Covey would weep tears of joy.

You’ll create:

• A weekly plan
• A daily Top 3 (yours + negotiated final version)
• Buffer space
• Travel sanity
• Deep work blocks

If you know Quadrant 3, great. If you don’t, Google it — initiative is part of the job.

Pivot Gracefully (and Often)

A random Tuesday may include:

• Booking a car to Pittsburgh because driving wastes productive time
• Delivering kids’ gym clothes
• Running to her house for an outfit
• Protecting the evening event prep window
• Finding the exact right nail polish shade
• 
  

If this sounds beneath you, you are beneath this job.

Be the Bridge Between Jackie’s Work + Life

Expect:

• Dry cleaning coordination
• Wardrobe rescue missions
• Liaising with household staff
• Organizing her office like The Home Edit
• Guarding her Saturday morning Christmas-card-designing time

At a large corporation, this is two roles. Here, it’s one. Wear it proudly.

Possess a Memory That Terrifies Others

• You’re the person who remembers birthdays, passwords, deadlines, and that one thing someone said in Q2.
• You don’t just solve problems — you prevent them.
• If a calendar looks tight, you fix it before Jackie feels it.
• Mind-reader energy required.

Problem Avoidance > Problem Solving

• Solving problems is good, preventing them is elite. In the event that they do arise, we solve them with overwhelming execution and with as little emotion as possible.

We believe in common sense. Radical, we know.

• Experience in providing executive-level support in a fast-paced environment.
• Ability to manage complex calendars and prioritize tasks effectively.
• Proven track record of maintaining confidentiality and discretion in all matters.
• Strong organizational skills with a keen eye for detail and accuracy.
• Excellent communication skills, both written and verbal, to liaise with internal and external stakeholders.
• Ability to anticipate needs and proactively address potential challenges.
• Experience in coordinating travel arrangements and managing logistics efficiently, including booking transportation and accommodations for executives and their families, as needed.
• No fear of saying "no," having difficult conversations, or being disliked.

Pennywise Tax Strategies is built on a simple belief: small business owners deserve better tax advice—and better tax experiences.

We are a growing firm focused on raising the standard in small business tax accounting. That means thoughtful preparation, real planning, and professionals who care deeply about the work and the people behind it.

We live by four core values:

• Find the Truth
• Figure It Out
• Be Curious, Not Judgmental
• Take Our Job Seriously, But Not Ourselves Too Seriously

We’re scaling intentionally—our team, our systems, and our impact. We value people who take ownership, ask good questions, and want to be part of building something that actually matters.

If you want to do work you’re proud to sign, serve clients you respect, and grow into deeper responsibility over time—we’d love to hear from you.

Compensation details: 50000-80000 Yearly Salary

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