Business Lunch Podcast: Stop Hiring Operators. Start Building Systems.

Host: Roland Frasier
Guest: Ryan Deiss
Date: March 26, 2026

Overview

This episode tackles a common pain point for entrepreneurs and business owners: the desire to find the perfect “operator” to handle the day-to-day of their business, so they can focus on being a visionary. Roland and Ryan explore what an operator actually is, why the default solution of “just hire a COO” is often a mistake, and why systemizing your business should come before hiring high-level operators. They break down the nuances of operator roles at different organizational levels, highlight the dangers of premature or inappropriate hiring, and offer actionable steps—and some hard truths—on building scalable, founder-independent companies.

Key Discussion Points & Insights

1. Defining “Operator” and Its Role

• The term “operator” is used loosely and can refer to multiple roles depending on company need and scale, from assistant to COO.
  • Ryan (02:25): “Operators and organizations come in a number of different shapes and sizes depending on where they are within the org…a personal assistant and an executive assistant—they’re an operator for that person at that level.”
• Most entrepreneurs confuse the need for a COO with needing someone to “do what they don’t want to do,” but this is risky and rarely works out.
  • Ryan (03:33): “How many times [have] we heard that, ‘I think I need to go hire a COO’ and it’s always a fricking train wreck.”

2. Organizational Structure & Operator Levels

• Not all “operators” are created equal; titles matter and skills must match level of responsibility. The risk of over-promoting is high.
  • Roland (04:01): “We have a tendency to accidentally take a bookkeeper and call him a CFO…or a project manager and call them a COO, and that’s not going to really help us.”
• Operator roles exist at every level: project manager, operations manager, director, VP, COO, each with distinct functions.

3. Operator vs. Visionary CEO

• The CEO is (in theory) responsible for transmitting vision, but in practice, much of the “vision” comes from the board—especially in larger organizations.
  • Roland (08:25): “Set the vision? That’s absolutely the function of the board. The CEO is to implement the vision of the board.”
• Ryan and Roland spar on this point, highlighting subtle differences in entrepreneur-led vs. board-led companies.
  • Ryan (09:33): “I would absolutely disagree with you on the vision part because I think that vision by committee is a trainwreck, man…if the board disagrees and the CEO’s like, ‘Well, I think you’re wrong,’ then the CEO’s gotta go. The board’s not going anywhere.”

4. What Operators Really Do

• The core function of an operator: build process and structure; assemble teams and resources; hold people accountable to objectives.
  • Ryan (07:01): “They build process and structure around what the business needs, then hire the team…and hold them accountable to achieve the desired objective.”
• Operators focus on “B to Y”—the practical implementation of the “A to Z” vision.
  • Ryan (12:50): “That’s the distinction…of the operator—so the B to Y person.”

5. Common Pitfalls: Mistakes in Hiring Operators

• Many founders want an all-purpose operator, but mostly just want out of day-to-day. Without clarity, this is a recipe for disaster.
  • Ryan (13:41): “What they’re basically saying is I want somebody to do all the stuff I don’t want to do, which can be dangerous.”
• The danger of hiring or promoting the wrong person (internal “Peter Principle”).
  • Roland (25:40): “To stop that internal Peter Principle thing and also provide you with some defenses to the people in the company that say, ‘Hey, I’d like that promotion.’”

6. Crucial First Steps: Building Systems Before People

• Step one is systematization—create at least the kernel of an operating system before looking for operators.
  • Ryan (14:44): “I would actually say step one, even before [defining the role], is you’ve got to have some kind of an operating system in place already…most CEOs are so in the weeds, they don’t know up and down.”
• Hiring an operator to “fix all this stuff” without engagement from the CEO is doomed.
  • Ryan (16:06): “It’s better if there’s like the kernel of some kind of an operating system there that now an operator is coming in and optimizing it.”

7. Hiring Process: How to Attract and Evaluate Operators

• Clearly define both the role and the qualifications needed.
  • Roland (25:40): “If two is to clearly define the role, I think three is to clearly define the qualifications.”
• The search will often require recruiting, networking, referrals, possibly a recruiter or fractionals—and takes longer than you want.
  • Ryan (24:01): “It’s a combination of going out and networking and hitting people up on LinkedIn, getting out into circles that you don’t know, asking around…painfully expensive [recruiters]…but I think that this is an important enough hire.”
• Avoid looking for entrepreneurial personalities in operator roles—they’ll clash with founders.
  • Roland (23:30): “You really don’t want an entrepreneur as an operator. I think they’ll end up competing with you.”

8. Operator Titles & When to Hire Up

• Most smaller businesses don’t actually need a COO; start with project or operations managers.
  • Ryan (21:21): “Shockingly, a lot could be accomplished with a project manager.”
• Only when complexity and scale demand, move to higher-level hires.
  • Ryan (32:10): “There’s a good chance that the things you don’t want to do fall in a couple of categories…and usually less expensive than more generic high level executive level operational talent.”

9. Why This Matters: Exit & Saleability

• Businesses run by founders are less saleable; systematization (and operator leadership) increases valuation and owner freedom.
  • Roland (33:05): “If you want to have a quality of life and grow your company, you’re going to have to have an operator that’s in there and it ideally isn’t you…”

Notable Quotes & Memorable Moments

• Ryan (02:25):

  “Operators and organizations come in a number of different shapes and sizes depending on where they are within the org. So that was kind of the first distinction…you may not need to go out there and hire a COO.”

• Roland (04:01):

  “We have a tendency to accidentally take a bookkeeper and call him a CFO…That’s not going to really help us because we need more sophisticated people that have completely different job descriptions and functionality in those roles.”

• Ryan (07:01):

  “They build process and structure around what the business needs, then hires the team and…holds them accountable…”

• Roland (23:30):

  “You really don’t want an entrepreneur as an operator. I think they’ll end up competing with you.”

• Ryan (24:01):

  “It’s a combination of going out and networking and hitting people up on LinkedIn…It is a combination of getting out into circles that you don’t know…hiring recruiters which are painfully expensive…But it is an important enough hire.”

• Roland (33:05):

  “If you want to have a quality of life and grow your company, you’re going to have to have an operator that's in there and it ideally isn't you if you are the CEO or the founder…”

Practical Steps: Actionable Framework (with Timestamps)

1. Choose/Create an Operating System (14:44–16:27)

   • Before hiring, figure out the fundamentals of how your business runs.
   • “It’s brutally difficult to bring somebody in from the outside and have them kind of build up and define your company’s operating system when they don’t know anything about the way that anything’s structured.” (14:44–15:02)

2. Define the Operator Role and Desired Outcomes (14:36–16:27)

   • Precisely describe what you want this person to do. Don’t just dump tasks you dislike.

3. Set Clear Qualifications (25:40)

   • List skills, past roles, and required experience level.

4. Search Strategies (29:09–30:11)

   • Use networks, recruiters, fractionals, content marketing, awards.
   • “Referral, fractional, recruiter/search, content, networking…that’s kind of five ways that you might set about trying to find that person.” (29:54)

5. Start Small Where Appropriate (21:21)

   • Don’t default to C-level; project managers or directors often suffice until the business scales.

6. Avoid Unfit Promotions & Entrepreneurial Personality Clashes (25:13, 23:30)

   • Prevent internal “Peter Principle”; don’t put entrepreneurs in operator roles.

7. Invest Time—Start Now (30:11–31:55)

   • Building relationships and pipelines for operators takes months, not days.

Final Thoughts

Roland and Ryan make a compelling case for prioritizing systems over personalities: systemize first, hire later, and build organizational clarity at all levels. They stress that most companies overcomplicate the “operator” notion and that getting very clear on roles, responsibilities, and culture is the path to a scalable, saleable business.

Have Questions?

Send your questions to businesslunchpodcast.com/ask and the hosts will tackle them in future episodes.

For more deep dives on scaling, operations, and entrepreneurial freedom, listen weekly to Business Lunch with Roland Frasier!