ON THE RECORD
Brock Thompson on leadership, alignment, and improving performance operations
Brock Thompson
Senior Vice President | LendingTree
Steve Rafferty
CEO & Founder | ActiveProspect
Brock Thompson is a technology and operations leader in insurance and performance marketing, currently serving as Senior Vice President at LendingTree. With leadership experience across companies including QuoteWizard, Drips, and Contact Cubed, Brock has built and rebuilt high-performing sales and call center operations while helping organizations adopt new technologies, acquisition channels, and compliance strategies. Known for his practical approach to problem solving, Brock focuses on aligning people, process, and data to drive measurable performance improvements. A frequent industry speaker and panelist, he regularly shares insights on the intersection of lead generation, insurance marketing, AI adoption, and consumer behavior.
SR:
Brock, you’ve built and rebuilt sales and call-center operations across multiple companies. When you step into an underperforming operation, what are the first non-negotiables you assess and target to improve?
BT:
Honestly, I wish there were an easy answer that everyone could take back, plug into their machine, and assess their position and health—but that doesn't exist. Every business, while generally impacted by the same core themes and issues, has nuances that make assessment more a practice in patience than a pursuit of perfection. After all, we're not in the business of perfect.
Perfect often blocks progress. Lesley Higgins, in the final episode of Ted Lasso, drops a great knowledge bomb regarding perfection: “Human beings are never going to be perfect, Roy. The best we can do is to keep asking for help and accepting it when we can. And if you keep on doing that, you'll always be moving towards better.” Let’s use this premise (we’re building for “always better” instead of perfect), along with the general sense that themes will be known/common/logical, but solutions are nuanced.
The first thing that MUST be evaluated is ourselves. The book The Four Agreements tells us the third agreement is to remove assumptions. Let's start here: What biases and assumptions am I bringing in based on my current understanding of this situation—company, people, product, tech, telephony, etc.? What are the things I think I know? Start by challenging yourself to enter without bias; take the time to truly understand what is going on, respect the burden of leadership, and shut up: listen, observe, and document.
The things we often believe to be the issues are only the symptoms, and it takes a deeper understanding to diagnose before treatment can begin. Honest reflection, followed by critical thought, will empower us—and those we depend upon—to target a resolution. If we give ourselves an honest, ego-free self-evaluation as we enter a new system, we can remove the assumptions that limit our understanding. Coupled with listening, we can ask the questions that truly matter, apply critical thought that goes beyond superficial symptoms, and diagnose root causes down to the DNA of the business.
We start with the basics:
- What am I solving for (my “f of x,” if you will)?
- What are my measures of success that tell me I hit or missed?
- What am I putting at risk with this solution/path?
- Is there an easier, more direct path to accomplishment?
From there, the fun can start.
Major Dick Winters, made famous in the book Band of Brothers by Stephen E. Ambrose and the HBO miniseries of the same name, stated 10 principles of leadership. I’ll spare readers the regurgitated list here, but Major Winters’s first principle is that leaders lead from the front; they say, “Follow me.” But it doesn’t end at the front. Leadership is done with people throughout the organization—leadership, management, rank and file, and even customers, where applicable. This is accomplished by asking:
- Does everyone understand the mission and vision? Is there even a mission and vision?
- Are stakeholders informed? Do they have access to the information and systems necessary to do their jobs?
- What is the general culture: innovative, accountable, transparent, or fear-based?
- How are decisions made, and how are they determined to be failures or successes?
Organizations I’ve seen successfully build, rebuild, or repair fractured areas are the ones that—like you—come in honest and can be honest with themselves. Strong rebuilding starts with clear leadership: leadership that’s present, thoughtful, and aligned around a shared goal.
First, take an honest look at where things stand. Then define the objective clearly. From there, work backward to identify the steps needed to get to square one. When everyone understands the goal and the path to reach it, teams can move forward—toward better—with focus and confidence.
SR:
You’ve led teams through AI adoption, new acquisition channels, and constantly shifting regulations. What have you learned about getting people to buy into change before the results show up?
BT:
I feel really bad calling out Mr. Gabric this way, but bro… we all told you in ’95 that we were 100% going to have calculators in our pockets when we were adults, so we didn’t really need to know algebra inside and out. (To be fair, we were WAY off with the Beanie Baby retirement plan.)
Little did any of us know, not only would we have a calculator, but also a movie theater, concert hall, all the information in the world, a shopping mall, and, for many, an immediate hotline to love—I feel like I’m channeling some inner Doc Brown from Back to the Future right now. Ultimately, innovation is happening every day, and it’s not magic. Often, it just takes an ear to hear it (I know how that reads).
If we listen to the feedback our customers give us, they will define the areas required for growth. Like foreshadowing in a movie, watching and listening to the gripes of people—society, companies, customers, employees—defines the frustrations people experience and points directly to gaps within organizations. And gaps create opportunities for solutions and revenue.
It all starts with identifying the problem and potential solutions. Tied to the answer above, if you understand what you are solving for and the ultimate outcome, and work backward from there, you’ll walk past methods to solve your problem—but you’ll also walk past their applications and limitations. Where you end up is often where you should begin.
Let’s take AI, for example. It has everything: regulation, shifting sands, hype, an unproven track record, resource dependency, changes in organizational approach, cultural implications, and uncertainty. The closest hype cycle we’ve had recently was Barbenheimer—or I suppose now it’s Dunesday coming this December. But just because something enters the zeitgeist aggressively doesn’t mean everyone could or should be doing it. It generally means that, along with it, will come fear, doubt, objection (often just for the sake of objection), and misuse.
No one wants to be the first through the wall; that person or company is usually left pretty beat up. All this noise creates friction in adoption and application. So how do you navigate?
- Remember to lead from the front; leaders say, “Follow me.”
- Define your f(x): what are you solving for, and what are your measures of success?
- Don’t try to solve everything at once. Have a plan that covers broader applications, but pick a single use case.
- Speak to each stakeholder or decision-maker individually and honestly listen.
- Build your case. Your gut may define the test, but the data will define the direction.
- Address concerns. Mitigate or isolate the risks—define what they are and understand them transparently.
- Build alignment through transparency and small, testable wins.
- Be honest with your results.
This isn’t a magic trick. Tell people what you’re going to do and why it benefits the organization, and build from there. If it doesn’t work, make sure you fail forward. If you have documentation and a clear understanding of what you’re solving for and how you failed, you still learn.
I tell my kids all the time: don’t bring me a problem—bring me a solution. I can’t do anything with a problem, but I can absolutely work with a solution. Even a bad solution is clay on the wheel that we can mold. Failure is the same; if you fail the right way, you still make progress—as long as you learn, adapt, and adjust.
In the AI implementation scenario:
- Engage in conversations about what you are solving and why.
- Define the objective and expected outcome.
- Have individual conversations about how the test or application will evolve from concept to reality.
- Define the points of friction and develop solutions to mitigate or isolate them.
Once you have buy-in, build the case, keep transparency at the forefront, and ultimately share in the win. But be ready to accept the loss on your shoulders if needed. Positioning something as risk-free makes it easier for people to support a new idea. When the downside feels limited, resistance drops. It’s interesting how quickly objections fade once there are real results to point to—or at least clear accountability in place. Wins build confidence. Ownership builds trust.
SR:
Can you walk us through a time when removing complexity, not adding more tech, drove the biggest performance lift?
BT:
I’ll be completely honest: most of my builds, repairs, resurrections, and growth come from non-complex, non-technical solutions. Most of it starts with removing assumptions and listening. You can identify pretty quickly where the cracks are. From there, start by walking through the general outline of the business.
Sun Tzu says in The Art of War that if the general’s direction is unclear and the soldier makes a mistake, it’s on the general; if the direction is clear, it’s on the soldier (paraphrased).
- Is there a clear, identified direction?
- Are there clear, understandable goals and measures of success?
- Does everyone understand their role, the role of those immediately around them, and the common goal/target?
- Do we have the right measures and data to assess the situation, the complication, and the resolution?
- Are we consistent in feedback, leadership, accountability, and direction—or are we chasing shiny butterflies?
I had a hitting coach back in the 1900s who fixed my swing without changing my mechanics or stance. He simply broke down my mental approach and opened my mind to the fact that my objective was the exact opposite of how every pitcher would pitch me. And since that approach was such an ingrained part of my DNA, I would react without thinking—pure muscle memory.
To become the hitter I wanted to be (and be respected by pitchers), I had to approach the game differently. I had to learn the geometry of arm angle and release point. I had to look at hand and finger placement and, ultimately, see every pitch into the zone. Once my mental approach changed, my average jumped, my position in the lineup jumped, the respect I commanded from the opposition increased, and my confidence grew.
We took a similar approach—different tactic—last year. We’ll call the rep Jenny to keep it simple. Jenny was good: professional and dependable, but she never got “better.” We used every typical approach with Jenny to improve the areas where we wanted her to grow. We’d see upticks and regressions and ultimately knew there had to be a better way. There wasn’t a technical solution here, and there wasn’t a performance management solution needed. There was simply a need to challenge our assumptions and take a different approach to maximize Jenny’s abilities.
We started looking deeper at the data—well beyond the superficial stats used to measure performance—and looking for trends within the trends: solutions inside the assumptions. And we saw it. We finally saw the path. We were walking with Robert Frost and decided to take a left 😉 In doing so, we unlocked something unique: the same problem we’d faced 1,000 times before—same theme, same needed outcome—but this time we sat with the patience and presence of the moment, challenged our assumptions, and recognized a unique (now replicable) solution that benefited the company, the customer, and our carrier(s) alike. And Jenny’s confidence skyrocketed.
Growth happened naturally, but something else happened too: momentum. Through confidence and momentum, weakness became strength, strength became stronger, and the targets we set as measures of success became bygone metrics—we had to raise the bar across the organization.
As stated above, start simple:
- Do you know what you’re solving for, and do you have the data and views needed to achieve it?
- Do you have clear feedback, communication, and accountability?
- Is there consistency, balance, and understanding in objectives—and when/why they move?
SR:
The insurance and lead-gen ecosystem is being reshaped by compliance, AI, and consumer behavior shifts. What strategic blind spot do you see most leaders missing right now?
BT:
We as people LOVE absolutes. We love to believe that because it is, it always is; because it is not, it never will be; and because it happened before, it will happen again. Yes, those who don't learn from history are doomed to repeat it—but that’s more a repetition of themes than a replay of exact events.
Too often, we weaponize the past. I can’t tell you how often I hear this, even from the most successful and seasoned people. I used to have thick, luscious John Stamos hair—glorious and flowing, like a majestic steed across the plains of the Wild West. Now, after decades of hearing “we did this before and it didn’t work” or “that doesn’t really fit my/our/the business” or “that never works,” it has turned my Uncle Jesse locks into an almost stark white head of hair—and not Roger Sterling’s handsome white.
First, don’t weaponize your past—and look twice at people who want to. Experience should inform better questions, not shut down new thinking. If someone uses their history to block discussion instead of exploring it, pay attention.
In the mid-’90s, I was working at Camelot Music in Canton, Ohio. It was a music store, like Sam Goody. We sold everything: cassette tapes, CDs, VHS, DVDs, LaserDiscs, inflatable furniture, T-shirts, and even a small section of records and 8-tracks. The number of people who came in looking for a specific movie on LaserDisc still shakes my faith in humanity and makes me question whether we’re living in a simulation. Fox Mulder would have closed this X-File. No, I’m sorry—we don’t have Armageddon or City of Angels on LaserDisc. No, we don’t sell a new laser for said “disc.” Could I interest you in the DVD or even the VHS instead?
It was clear these folks jumped onto the bandwagon without doing even light research on the application, advancements, or limitations. They went chasing waterfalls—which we were explicitly told not to do—and in the end, they paid for it twice.
This is a pattern throughout history: AC vs. DC, Pony Express vs. telegraph, Zune vs. iPod. The pattern isn’t new. What’s usually missing isn’t ambition. It’s alignment.
To improve alignment, understand your “why,” “what,” and “how.” Determine whether your why and what are clearly solved, and you’ll get a clearer picture of where you’re going. Sometimes you’re just too far ahead of the game and people aren’t ready (Marty McFly at the Enchantment Under the Sea dance). Other times, you’re not on board out of spite. Remove assumptions.
SR:
Last question, Brock, across LendingTree, Quote Wizard, Contact Cubed, Drips, and beyond, you’ve lived at the intersection of technology and human behavior. What principle guides you when you're deciding where automation should stop and real human interaction should begin?
BT:
Where do people start and machines stop—or vice versa? I’d like to say somewhere between Edward Furlong, Linda Hamilton, and Robert Patrick. Or I suppose the more modern generation would call it Tony Stark.
A brilliant mentor of mine—a man I’ve known for 20 years and spent countless hours building solutions, refining solutions, and rehabbing businesses with—once told me, “Your gut drives the test; the data drives the decision.” He and I learned a lot along the way, and we still practice these principles today:
1) Always assume you are wrong. You are the cause of the miss—effectively remove any preconceived assumptions.
2) Define the test, define the measure of success, and understand the variables.
3) Test, measure, and evaluate objectively.
4) Add a variable, a challenger, or a feedback loop.
5) Determine your path.
It’s no secret. They teach every kid this in school: use the scientific method. Test your hypothesis. Accept that you might be wrong. The real lesson wasn’t just memorizing facts (mitochondria are still the powerhouse of the cell). It was learning how to form a theory, measure it, adjust, and move forward based on evidence. Start with something raw—a rough idea, clay on the wheel. Shape it. Test it. Refine it. Then go create.
I’m no Edgar Cayce—I can’t sleep my way into prophecy—but you better believe there isn’t anyone better at building today for tomorrow. Lastly, don’t look too far ahead or get stuck staring at the ground, afraid to fail—you’ll miss the glory of the here and now. Paraphrasing Bruce Lee: it’s okay to be present for a minute while you survey the paths ahead and listen.