How Great Operators Turn Complexity into Growth with Jennifer Goldman
Episode 133: This week, Kyle Van Pelt talks with Jennifer Goldman, Founder and Strategic Operations Transformer and Integrator at My Virtual COO. Jen is an operations expert with 30 years of experience helping 1,000+ service businesses to thrive.
Jen talks with Kyle about what it really takes to run a profitable, scalable advisory firm. From defining what makes a truly great operator to navigating the messy middle of firm growth, Jen shares practical insights on constellation thinking, building operational leaders, and making hard profitability decisions. She also dives into the emotional and structural crossroads firms face as they scale, the evolving role of technology and AI in operations, and why clean data and strong systems still require human ownership.
In this episode:
(00:00) - Intro
(03:33) - Jen's money moment
(06:39) - What it takes to be a great operator
(08:55) - How "constellation thinking" works
(12:19) - Balancing SOPs with creativity in operations
(14:42) - The profitability challenges in the growth process
(16:57) - What determines whether you should build or join a platform
(21:42) - How Jen utilizes AI in her work
(23:01) - Why AI can't replace CRMs
(27:27) - Why it's important to have clean CRM data
(32:36) - What it takes to build a process for advisors and investors
(37:35) - What Jen looks for when engaging with advisors
(39:53) - Jen's outlook on the future of the financial services industry
(42:51) - Jen's Milemarker Minute
Key Takeaways
Think like an operator. Great operators don't work in silos. They practice "constellation thinking"—understanding how a change in one area (people, process, technology, profitability) impacts the rest of the organization. Sustainable growth comes from seeing those connections before making decisions.
Progress beats perfection when scaling a business. Operators must act with imperfect information and accept small failures along the way. Waiting for perfect data or perfect conditions slows growth. Progress, iteration, and course correction are what move firms forward.
Your growth path depends on how well you've built your team. When firms hit major crossroads, whether to scale into a platform or join one, the deciding factor is often people. Leaders who develop decision-makers and future executives create optionality—those who don't often feel stuck or fatigued.
Systems create stability, but creativity keeps operations moving. SOPs and structured processes are essential for consistency, but operators must also stay flexible and creative when reality doesn't follow the playbook. Balancing structure with adaptability is key to running a resilient firm.
Quotes
"Your data is so important. It's telling you stories. If you don't keep it clean, it's not going to tell you what you need to do next with the business." ~ Jennifer Goldman
"Businesses cannot scale unless they're constantly and continuously improving. It doesn't have to be a heavy lift. Just shine a light, make a small change, and keep going." ~ Jennifer Goldman
"This clarity around data and understanding, pulling it together, and using it effectively is so important. It allows you to have more touch with the people around you, whether it's clients or the advisor teams." ~ Jennifer Goldman
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