Our Mission
We honor skilled operators and anchor visionary leaders.
Entrepreneurship is one of the most powerful forces for human creativity and freedom. Yet too many brilliant visionaries find themselves buried in operational chaos, unable to focus on what they do best.
We believe every festival and event organizer deserves to experience the relief of systems that actually work—where the complex becomes straightforward, vague ideas transform into clear action plans, and your shoulders can finally unclench.
Smooth Operator Company Timeline
Year
Company Evolution
2017
Ashlee leaves her operations role at a financial services consulting firm to start A Squared Online. Her dream is autonomy to mold her career around her family’s needs. The company focuses on general operational management for small businesses.
2018
Ashlee graduates with her MBA from Georgetown University, and A Squared hires its first team member. Ashlee learns about delegation through great mentorship and making a lot of mistakes.
2019
Ashlee has her daughter Averee and hires her first team members (including Jennifer Dale, who’s now our Team Captain) to provide direct client service rather than just internal support. The company begins specializing in process and system strategy.
2020
A Squared navigates COVID alongside its clients, grateful to already be operating virtually.
2021
Ashlee publishes her first book: “Eureka Results: How Entrepreneurs Can Turn Their Best Ideas Into Reality” (she swears it will be the last for a while). A Squared stops providing direct administrative work and begins virtual assistant recruitment services when clients ask for help in finding people who operate like we do. Ashlee has her second daughter, Alexee.
2022
Ashlee completes several large process reorganization projects for companies undergoing significant change and system work, proving out her model in larger contexts.
2023
Ashlee begins work as a fractional COO for a client and articulates her philosophies and methodologies into the first iteration of what is now the Smooth Operating System. The company begins to lay the groundwork for scale and hires COO-level staff to provide strategic support alongside Operations Managers who can implement those strategies.
2024
The A Squared team works with their first event companies and falls in love with the industry. The company survives a difficult year both personally and professionally.
2025
A Squared Online rebrands to Smooth Operator. The company officially plants its flag as a specialist in event companies and integrates AI into its approach.
This is our commitment to you:
We’re your island of peace in the storm of event operations. You don’t need to become a systems expert or figure out delegation on your own. Just answer our questions, and we’ll handle the rest.
When systems decide what happens in your business, we make sure those systems create sustainable profit, genuine relief, and the freedom for you to focus on creating extraordinary experiences.
We succeed when you feel supported, clear, and calm—when you can finally breathe deeper knowing someone truly has your back.
Smooth Operator Team Manifesto
Our mission is to amplify the impact of good people doing good work in the world. Our manifesto articulates why we’re here, and each team member signs it as they join. If you work with us, we want you to know this foundation, too.
I believe and commit to the following as a member of the Smooth Operator community:
- I believe that my work as an integrator is meaningful and that the ripple effects of my work can carry forward for generations, even when I cannot see my own impact.
- I recognize that my work is not just time spent but a reflection of my character; I will do my work with honesty and integrity.
- I honor the uniqueness of creatives, neurodivergent entrepreneurs, and energetic big-picture thinkers, and am dedicated to building systems that work for them.
- I honor the beauty of my unique talents and gifts.
- I agree to care for our clients personally and speak the truth, even when it is hard to hear.
- I agree to pursue shalom (thriving and wholeness) for every human being that I interact with through my work at Smooth Operator.
- I will be relentless in wrestling chaos into order for my clients and will do the hard thinking for them.
- I will be so reliable that my clients know they can trust everything I say. I will do what I promise to do, when I promise to do it.
- I will communicate proactively with my clients so they never have to wonder or ask for updates.
- I recognize that I can expect to be honored and valued in my work here, and I have the power to speak up if that ideal is not reached.
Your brilliant events deserve bulletproof operations. We extract the chaos from your mind and build systems that work for you. We take our work very seriously as a major component in our contribution to the flourishing of the world.
If these values speak to you, we’d love to connect:
By the Numbers
(last updated September 2025)
Managers placed
(staff and contractors)
*Our other projects have been consulting or systems strategy without Ops Manager placement
Meet the Team
Ashlee Berghoff
Founder and CEO
Ashlee Berghoff is an MBA and systems strategist with the mind of an architect and the heart of an entrepreneur. She started her company in 2017 on a quest for freedom and autonomy.
Entrepreneurship is one of the most powerful tools we can use to take back our time and express our deepest strengths, but Ashlee quickly discovered that growing a business beyond yourself is far from automatic. In fact, making the transition from ‘being’ the business to building something beyond you can be harder than getting started in the first place.
So, what’s the solution? Ashlee discovered that entrepreneurs need solid workflows, operational strategy, and someone in the trenches to get things done.
They need just a bit of a COO’s brain, documented systems magically extracted from their brains, and an operations pro in the co-pilot seat who they don’t have to manage. From that discovery and her experience supporting over 100 entrepreneurs, Ashlee created Smooth Operator – a done-for-you program to give entrepreneurs every element they need without having to shell out for a team of internal hires.
Ashlee’s entrepreneurial philosophy is codified in her book “Eureka Results: How Entrepreneurs Can Turn Their Best Ideas Into Reality” and draws heavily from her background at Georgetown University, long-term relationships with clients, and in-depth research of hundreds of business owners. It is an essential field guide for anyone who struggles with overwhelm and shiny object syndrome.
You don’t have to become a productivity nerd to bring your best ideas to life, but you’ll get there faster when you have someone like Ashlee in your corner.
“When my team and I were maxed out in our capacity to meet our ambitious goals, we knew we could get there with a better workflow system and the right person to help us implement it – in real time. Ashlee Berghoff was my first choice because she is the only person I know with the systems experience, the understanding (and empathy!) of workflow challenges small to medium biz owners face, and the heart to roll up her sleeves and work alongside us to implement the changes. In just 4 weeks, Ashlee came in like an angel of mercy and provided immediate relief to our team, while spearheading a new system to organize our communication and SOP system, our document filing system, and our daily workflow. The big, hairy conundrum for small teams who need better systems is “when the heck do we make time to learn how to make more time?” With Ashlee, you get the best of both worlds; immediate relief and upgraded systems for the long haul. Needless to say, Ashlee gets my highest endorsement. She’s amazing at what she does, and (total bonus) a super cool person.”
Kevin Rogers
Founder and CEO of Copy Chief
Jennifer Dale
Team Captain
Jennifer has worked virtually for 20 years in Business Development & Project Management. She has a Degree in Business Management and has assisted many small business owners with organizing time & resources, creating processes, and implementing software systems.
Her experience includes team building (recruiting, hiring, training); process creation, operations management, and system development & documentation.
Jennifer joined A Squared Online in February of 2019 as a Client Success Manager. She has led the recruiting department for the entire organization, and now manages the in-house operations manager team. She has enjoyed helping her clients get organized, grow, and reach their goals.
In her down time, she keeps in touch with her four grown kids, watches college football and basketball, and works on her goal of reading 100 books per year.
Brian McMahon
Prospect Specialist
From selling gum in 7th grade to founding a successful online health business, Brian McMahon is a natural-born entrepreneur driven by a passion for leading others. With over a decade of management experience and knack for sales, Brian leads through active listening and understanding. His entrepreneurial spirit sparked early and continues to fuel his commitment to providing clarity and direction to his clients both professionally and personally.
Katrina Kopeck
Client COO
Katrina is a dynamic chaos wrangler with an eclectic background organizing small businesses, entrepreneurs, and corporations. As an operations strategist, Katrina believes that true innovation and freedom often arise from the safety that structure provides.
She has worked in operations and content in a variety of industries including brand, media, marketing, wellness, and tech, giving her a broad view to support your business. What sets Katrina apart is her intuitive understanding of people and her ability to transform big ideas into tangible results.
Katrina is based in Boulder, Colorado.
Nikki Aragon
Client COO
Nikki Aragon has over 15 years of experience working with small businesses and nonprofits to bravely implement new approaches in the workplace. Driven by a desire to help businesses discover the joy that can be found at the intersection of vision and systems, she would love to learn about where you want to take your business and work together to build a strategy and implementation plan to get you there.
Nikki lives in Denver, Colorado and works with clients all over the country. In her free time, she loves to travel to new places and go camping in the Rocky Mountains.
Our Operations
Managers
Over 40 people have passed our vigorous vetting process (we call it The Gauntlet for a reason) and are ready to be matched with clients who need a unicorn. Our Four Pillars of world-class performance for these folks are: rock-solid reliability, ownership over their own work and capacity, proactive communication, and relentlessness in wrestling chaos into order.
All of our Operations Managers are located in the United States, and paying them a sustainable, livable rate is a core part of our model.
