Rob Hamilton
@robertc-hamilton.bsky.social
Executive Vice President of Sales, Roundstone Insurance | Motivated Pathfinder | Accountable Leader in Sales Strategy and Performance | Driving Results in Self-Funded Captives | Enthusiastic Foodie
Down quarter? That’s just game tape.
Great sales teams don’t panic, they tighten the fundamentals. Clear playbook, higher activity, better conversations. And they hold each other accountable because the goal is points on the board, not protecting egos.
Markets swing. Winners adjust. Simple.
Great sales teams don’t panic, they tighten the fundamentals. Clear playbook, higher activity, better conversations. And they hold each other accountable because the goal is points on the board, not protecting egos.
Markets swing. Winners adjust. Simple.
How elite sales leaders drive growth in down quarters
The playbook for leadership under pressure is rigor, innovation, and mindset.
www.fastcompany.com
December 19, 2025 at 1:20 PM
Down quarter? That’s just game tape.
Great sales teams don’t panic, they tighten the fundamentals. Clear playbook, higher activity, better conversations. And they hold each other accountable because the goal is points on the board, not protecting egos.
Markets swing. Winners adjust. Simple.
Great sales teams don’t panic, they tighten the fundamentals. Clear playbook, higher activity, better conversations. And they hold each other accountable because the goal is points on the board, not protecting egos.
Markets swing. Winners adjust. Simple.
Rugby taught me this: you don’t rise to the occasion, you fall to the level of your training.
The wins came from the ugly reps in the mud, not game-day hype.
The wins came from the ugly reps in the mud, not game-day hype.
4 Lessons Athletics Taught Me About Entrepreneurship
I learned how to win and lose on the mat, and those lessons are the foundation for how I build and lead teams.
www.inc.com
December 11, 2025 at 1:53 PM
Rugby taught me this: you don’t rise to the occasion, you fall to the level of your training.
The wins came from the ugly reps in the mud, not game-day hype.
The wins came from the ugly reps in the mud, not game-day hype.
Success isn’t complicated. It’s the basics done every day.
Prepare the night before. Show up early. Stay calm. Do the job right. Follow up. Take notes. Keep learning. Respect people’s time. Do what you said you’d do.
Prepare the night before. Show up early. Stay calm. Do the job right. Follow up. Take notes. Keep learning. Respect people’s time. Do what you said you’d do.
December 9, 2025 at 1:16 PM
Success isn’t complicated. It’s the basics done every day.
Prepare the night before. Show up early. Stay calm. Do the job right. Follow up. Take notes. Keep learning. Respect people’s time. Do what you said you’d do.
Prepare the night before. Show up early. Stay calm. Do the job right. Follow up. Take notes. Keep learning. Respect people’s time. Do what you said you’d do.
You can’t lead from empty.
If you’re drained, it shows in every decision and every result. So, pushing harder isn’t the answer. Showing up sharper is.
The team never needs a hero that's running on fumes. They need someone steady enough to see the next move clearly.
If you’re drained, it shows in every decision and every result. So, pushing harder isn’t the answer. Showing up sharper is.
The team never needs a hero that's running on fumes. They need someone steady enough to see the next move clearly.
Why leaders can't run on empty
Entrepreneurs often face burnout, and it’s critical to address it early and often.
www.fastcompany.com
December 4, 2025 at 1:16 PM
You can’t lead from empty.
If you’re drained, it shows in every decision and every result. So, pushing harder isn’t the answer. Showing up sharper is.
The team never needs a hero that's running on fumes. They need someone steady enough to see the next move clearly.
If you’re drained, it shows in every decision and every result. So, pushing harder isn’t the answer. Showing up sharper is.
The team never needs a hero that's running on fumes. They need someone steady enough to see the next move clearly.
Some organizations talk about impact. Urban Community School delivers it.
Their work with kids in downtown Cleveland is the real thing, and every year at their fundraiser, you can see the difference they make.
If you’re supporting someone this Giving Tuesday, they’re worth it.
Their work with kids in downtown Cleveland is the real thing, and every year at their fundraiser, you can see the difference they make.
If you’re supporting someone this Giving Tuesday, they’re worth it.
December 2, 2025 at 1:48 PM
Some organizations talk about impact. Urban Community School delivers it.
Their work with kids in downtown Cleveland is the real thing, and every year at their fundraiser, you can see the difference they make.
If you’re supporting someone this Giving Tuesday, they’re worth it.
Their work with kids in downtown Cleveland is the real thing, and every year at their fundraiser, you can see the difference they make.
If you’re supporting someone this Giving Tuesday, they’re worth it.
If you want to know what really holds a community together, look at who opens their doors before sunrise.
November 29, 2025 at 1:07 PM
If you want to know what really holds a community together, look at who opens their doors before sunrise.
If there’s one week built for giving credit where it’s due, it’s this one.
We’ve gone from a few dozen broker partners in 2016 to several hundred today. That kind of growth only happens when people trust you enough to bring you in and push you to be better.
We’ve gone from a few dozen broker partners in 2016 to several hundred today. That kind of growth only happens when people trust you enough to bring you in and push you to be better.
November 25, 2025 at 1:35 PM
If there’s one week built for giving credit where it’s due, it’s this one.
We’ve gone from a few dozen broker partners in 2016 to several hundred today. That kind of growth only happens when people trust you enough to bring you in and push you to be better.
We’ve gone from a few dozen broker partners in 2016 to several hundred today. That kind of growth only happens when people trust you enough to bring you in and push you to be better.
Gratitude’s simple.
I'm grateful for the sales team that shows up, grows, and wins the right way. For the leadership crew that solves problems and scales without ego. For a culture where people feel safe to grow and speak up. And for my health, so I can keep leading with energy.
I'm grateful for the sales team that shows up, grows, and wins the right way. For the leadership crew that solves problems and scales without ego. For a culture where people feel safe to grow and speak up. And for my health, so I can keep leading with energy.
November 21, 2025 at 1:08 PM
Gratitude’s simple.
I'm grateful for the sales team that shows up, grows, and wins the right way. For the leadership crew that solves problems and scales without ego. For a culture where people feel safe to grow and speak up. And for my health, so I can keep leading with energy.
I'm grateful for the sales team that shows up, grows, and wins the right way. For the leadership crew that solves problems and scales without ego. For a culture where people feel safe to grow and speak up. And for my health, so I can keep leading with energy.
If your customer experience gives people chills, it’s probably not for the right reasons.
November 14, 2025 at 1:08 PM
If your customer experience gives people chills, it’s probably not for the right reasons.
If you think Marketing just “makes things look pretty,” you haven’t met this team.
They don’t just create content; they create momentum. The way they work with Sales, use tech, and keep things moving is top-notch.
No egos. No silos. Just good people doing great work.
They don’t just create content; they create momentum. The way they work with Sales, use tech, and keep things moving is top-notch.
No egos. No silos. Just good people doing great work.
November 12, 2025 at 1:21 PM
If you think Marketing just “makes things look pretty,” you haven’t met this team.
They don’t just create content; they create momentum. The way they work with Sales, use tech, and keep things moving is top-notch.
No egos. No silos. Just good people doing great work.
They don’t just create content; they create momentum. The way they work with Sales, use tech, and keep things moving is top-notch.
No egos. No silos. Just good people doing great work.
If you’re “too busy” to make progress, you’re not leading; you’re just spinning.
You can’t outwork chaos. You have to outfocus it. Cut the noise. Kill the meetings that don’t drive decisions. Say no to what doesn’t move the mission.
You can’t outwork chaos. You have to outfocus it. Cut the noise. Kill the meetings that don’t drive decisions. Say no to what doesn’t move the mission.
An Epidemic Of Distraction: How Focused Leaders Create Momentum
In a world defined by an epidemic of distraction, the most focused leaders are creating momentum, one deliberate choice at a time.
www.forbes.com
November 10, 2025 at 1:36 PM
If you’re “too busy” to make progress, you’re not leading; you’re just spinning.
You can’t outwork chaos. You have to outfocus it. Cut the noise. Kill the meetings that don’t drive decisions. Say no to what doesn’t move the mission.
You can’t outwork chaos. You have to outfocus it. Cut the noise. Kill the meetings that don’t drive decisions. Say no to what doesn’t move the mission.
We talk a lot about resilience in sales, but let’s be honest, it’s starting to sound like a cover for burnout.
When teams are told to “push harder” without the tools, clarity, or space to recover, resilience stops being strength and starts being survival.
When teams are told to “push harder” without the tools, clarity, or space to recover, resilience stops being strength and starts being survival.
The Resilience Paradox: How It’s Fueling Workplace Burnout
Burnout isn’t weakness—it’s a design flaw. True leadership means fixing systems, not testing endurance. The era of resilience rhetoric is over; change is overdue.
www.forbes.com
November 7, 2025 at 1:13 PM
We talk a lot about resilience in sales, but let’s be honest, it’s starting to sound like a cover for burnout.
When teams are told to “push harder” without the tools, clarity, or space to recover, resilience stops being strength and starts being survival.
When teams are told to “push harder” without the tools, clarity, or space to recover, resilience stops being strength and starts being survival.
Sales isn’t about products. It’s about people.
You can have the best tools in the world, but if your team can’t read a room, they’ll miss the moment every time.
You can have the best tools in the world, but if your team can’t read a room, they’ll miss the moment every time.
November 5, 2025 at 1:35 PM
Sales isn’t about products. It’s about people.
You can have the best tools in the world, but if your team can’t read a room, they’ll miss the moment every time.
You can have the best tools in the world, but if your team can’t read a room, they’ll miss the moment every time.
Everyone wants a sales machine. Few want to build one.
It’s not magic; it's a process. Define the stages, track the numbers, hold people accountable. Then do it again. If you can’t measure it, you can’t improve it. And if you can’t repeat it, it’s not a process; it’s just a lucky streak.
It’s not magic; it's a process. Define the stages, track the numbers, hold people accountable. Then do it again. If you can’t measure it, you can’t improve it. And if you can’t repeat it, it’s not a process; it’s just a lucky streak.
November 3, 2025 at 1:54 PM
Everyone wants a sales machine. Few want to build one.
It’s not magic; it's a process. Define the stages, track the numbers, hold people accountable. Then do it again. If you can’t measure it, you can’t improve it. And if you can’t repeat it, it’s not a process; it’s just a lucky streak.
It’s not magic; it's a process. Define the stages, track the numbers, hold people accountable. Then do it again. If you can’t measure it, you can’t improve it. And if you can’t repeat it, it’s not a process; it’s just a lucky streak.
Thirty years ago, marketing meant catalogs and trade shows.
Now it’s data, precision targeting, and digital ecosystems moving faster than most can explain… including me. I only get half of what our marketing team says, but I know brilliance when I see it.
Now it’s data, precision targeting, and digital ecosystems moving faster than most can explain… including me. I only get half of what our marketing team says, but I know brilliance when I see it.
October 31, 2025 at 12:53 PM
Thirty years ago, marketing meant catalogs and trade shows.
Now it’s data, precision targeting, and digital ecosystems moving faster than most can explain… including me. I only get half of what our marketing team says, but I know brilliance when I see it.
Now it’s data, precision targeting, and digital ecosystems moving faster than most can explain… including me. I only get half of what our marketing team says, but I know brilliance when I see it.
A few years back, our CSI Team helped an employer save $40K by finding waste others missed.
No buzzwords. No fluff. Just people who know their stuff and aren’t afraid to dig in. That’s what real self-funding looks like: teamwork, accountability, and results that stick.
No buzzwords. No fluff. Just people who know their stuff and aren’t afraid to dig in. That’s what real self-funding looks like: teamwork, accountability, and results that stick.
How the CSI Team Helped One Employer Save $40,000
We introduced the Roundstone Cost Saving Investigators (CSI Team) to help employers optimize the value of transparency and control. The CSI Team is always looking for ways to help employers maximize their self-funding benefits by providing cost saving solutions that can be implemented into their health plan. We want to share one of our most […]
roundstoneinsurance.com
October 29, 2025 at 12:15 PM
A few years back, our CSI Team helped an employer save $40K by finding waste others missed.
No buzzwords. No fluff. Just people who know their stuff and aren’t afraid to dig in. That’s what real self-funding looks like: teamwork, accountability, and results that stick.
No buzzwords. No fluff. Just people who know their stuff and aren’t afraid to dig in. That’s what real self-funding looks like: teamwork, accountability, and results that stick.
Tough markets don’t break teams; they expose them.
Rugby taught me that when the scrum’s collapsing, you see who’s really got your back. Sales is the same.
Own the numbers. Stay disciplined. Lead from the front. You don’t win by dodging the hit; you win by driving through it together.
Rugby taught me that when the scrum’s collapsing, you see who’s really got your back. Sales is the same.
Own the numbers. Stay disciplined. Lead from the front. You don’t win by dodging the hit; you win by driving through it together.
October 27, 2025 at 12:38 PM
Tough markets don’t break teams; they expose them.
Rugby taught me that when the scrum’s collapsing, you see who’s really got your back. Sales is the same.
Own the numbers. Stay disciplined. Lead from the front. You don’t win by dodging the hit; you win by driving through it together.
Rugby taught me that when the scrum’s collapsing, you see who’s really got your back. Sales is the same.
Own the numbers. Stay disciplined. Lead from the front. You don’t win by dodging the hit; you win by driving through it together.
Legacy isn’t built by what you say; it’s built by what you’re willing to risk.
The best teams I’ve been part of, in business and on the rugby field, won because they trusted each other enough to take smart risks and back each other up when it got messy.
Play to win. But play for each other.
The best teams I’ve been part of, in business and on the rugby field, won because they trusted each other enough to take smart risks and back each other up when it got messy.
Play to win. But play for each other.
Your Leadership Legacy Depends On What You’re Willing To Risk
Landon Ashworth, as revealed in my recent interview, offers a profound case study how to create a leadership legacy by taking risks and being vulnerable.
www.forbes.com
October 24, 2025 at 12:47 PM
Legacy isn’t built by what you say; it’s built by what you’re willing to risk.
The best teams I’ve been part of, in business and on the rugby field, won because they trusted each other enough to take smart risks and back each other up when it got messy.
Play to win. But play for each other.
The best teams I’ve been part of, in business and on the rugby field, won because they trusted each other enough to take smart risks and back each other up when it got messy.
Play to win. But play for each other.
Health costs are up 40–50% in a decade. Most employers still have no idea where the money goes.
Self-funding changes that. You see the data, control the costs, and keep the savings.
At Roundstone, we make it happen. Not easy. Worth it.
Self-funding changes that. You see the data, control the costs, and keep the savings.
At Roundstone, we make it happen. Not easy. Worth it.
Breaking free from rising health care costs
Discover how self-funded insurance solutions help mid-sized businesses cut costs, gain control and offer employees stable, improved benefits.
www.crainscleveland.com
October 22, 2025 at 12:08 PM
Health costs are up 40–50% in a decade. Most employers still have no idea where the money goes.
Self-funding changes that. You see the data, control the costs, and keep the savings.
At Roundstone, we make it happen. Not easy. Worth it.
Self-funding changes that. You see the data, control the costs, and keep the savings.
At Roundstone, we make it happen. Not easy. Worth it.
Data doesn’t lie, but your expenses do.
You can’t talk your way out of rising benefit costs, but you can analyze your way through them. The smartest teams use data to see where their plan is bleeding and how to fix it fast, so treat benefits like a value engine. Use your data. Get results.
You can’t talk your way out of rising benefit costs, but you can analyze your way through them. The smartest teams use data to see where their plan is bleeding and how to fix it fast, so treat benefits like a value engine. Use your data. Get results.
Use Data Insights to Cut Employee Benefit Costs and Improve Savings in a Self-Funded Plan
Highlights Rising employee benefit costs threaten your company’s bottom line. Measuring and analyzing your healthcare data allows you to understand where your highest healthcare costs are occurring and how to mitigate them, which can improve the savings of your self-insured plan. With Roundstone’s Area to Impact (ATI) reports, employers can compare their costs to national […]
roundstoneinsurance.com
October 16, 2025 at 12:35 PM
Data doesn’t lie, but your expenses do.
You can’t talk your way out of rising benefit costs, but you can analyze your way through them. The smartest teams use data to see where their plan is bleeding and how to fix it fast, so treat benefits like a value engine. Use your data. Get results.
You can’t talk your way out of rising benefit costs, but you can analyze your way through them. The smartest teams use data to see where their plan is bleeding and how to fix it fast, so treat benefits like a value engine. Use your data. Get results.
If your pitch starts with data and ends with price, good luck closing.
At Roundstone, I’ve seen numbers prove value, but stories make people believe. One client moved to self-funding after hearing how another business saved big and improved benefits.
Data informs. Stories close.
At Roundstone, I’ve seen numbers prove value, but stories make people believe. One client moved to self-funding after hearing how another business saved big and improved benefits.
Data informs. Stories close.
Why Storytelling Is an Entrepreneur's Most Powerful Soft Skill
Data shows that storytelling is crucial for transforming scrappy startups into billion-dollar brands. Here's how to sharpen your skills.
www.inc.com
October 15, 2025 at 12:12 PM
If your pitch starts with data and ends with price, good luck closing.
At Roundstone, I’ve seen numbers prove value, but stories make people believe. One client moved to self-funding after hearing how another business saved big and improved benefits.
Data informs. Stories close.
At Roundstone, I’ve seen numbers prove value, but stories make people believe. One client moved to self-funding after hearing how another business saved big and improved benefits.
Data informs. Stories close.
91% of customers say their last interaction defines their entire experience.
We focus on the close, but the real test comes after. A quick follow-up once turned a onetime client into a lasting partner. Not because of price, but because we showed up when it counted.
We focus on the close, but the real test comes after. A quick follow-up once turned a onetime client into a lasting partner. Not because of price, but because we showed up when it counted.
Why the final moment of a customer journey matters more than the rest
Customers judge an experience largely by how they felt at the most intense moment — good or bad — and at the end. But are CX leaders designing experiences for this cognitive bias?
www.customerexperiencedive.com
October 14, 2025 at 12:08 PM
91% of customers say their last interaction defines their entire experience.
We focus on the close, but the real test comes after. A quick follow-up once turned a onetime client into a lasting partner. Not because of price, but because we showed up when it counted.
We focus on the close, but the real test comes after. A quick follow-up once turned a onetime client into a lasting partner. Not because of price, but because we showed up when it counted.
You want a #sales machine? Stop flying blind.
Scorecards + metrics killed the chaos for us; we finally saw who was performing, where deals stalled, and how to fix it. Same with customers: ignore feedback and you stall. Respect the signals and you scale.
Scorecards + metrics killed the chaos for us; we finally saw who was performing, where deals stalled, and how to fix it. Same with customers: ignore feedback and you stall. Respect the signals and you scale.
October 10, 2025 at 12:47 PM
You want a #sales machine? Stop flying blind.
Scorecards + metrics killed the chaos for us; we finally saw who was performing, where deals stalled, and how to fix it. Same with customers: ignore feedback and you stall. Respect the signals and you scale.
Scorecards + metrics killed the chaos for us; we finally saw who was performing, where deals stalled, and how to fix it. Same with customers: ignore feedback and you stall. Respect the signals and you scale.
Health insurance costs are out of control: drug prices, regs, consolidation… all squeezing employers. We don’t dance around it.
Instead, we show them how to get control, measure results, and see real savings. Because sales isn’t about dodging the pain. It’s about solving it.
Instead, we show them how to get control, measure results, and see real savings. Because sales isn’t about dodging the pain. It’s about solving it.
October 8, 2025 at 12:22 PM
Health insurance costs are out of control: drug prices, regs, consolidation… all squeezing employers. We don’t dance around it.
Instead, we show them how to get control, measure results, and see real savings. Because sales isn’t about dodging the pain. It’s about solving it.
Instead, we show them how to get control, measure results, and see real savings. Because sales isn’t about dodging the pain. It’s about solving it.
Some leaders want playbooks. I want teams that can figure it out.
Stability = accountability. Agility = urgency + curiosity. Lean too hard either way and you stall. Get the balance right, and you build a team that delivers no matter what’s thrown at them.
Stability = accountability. Agility = urgency + curiosity. Lean too hard either way and you stall. Get the balance right, and you build a team that delivers no matter what’s thrown at them.
Stability And Agility: Why Modern Leaders Must Master Both
Stagile leaders anchor in purpose while adapting with speed—meeting followers’ need for hope, stability, compassion and trust.
www.forbes.com
October 6, 2025 at 12:14 PM
Some leaders want playbooks. I want teams that can figure it out.
Stability = accountability. Agility = urgency + curiosity. Lean too hard either way and you stall. Get the balance right, and you build a team that delivers no matter what’s thrown at them.
Stability = accountability. Agility = urgency + curiosity. Lean too hard either way and you stall. Get the balance right, and you build a team that delivers no matter what’s thrown at them.