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
When I hired Steve Sullivan back in 2017, I knew he had the right mindset. Now he’s the first two-time Sales Person of the Year in Roundstone history.
February 12, 2026 at 1:51 PM
When I hired Steve Sullivan back in 2017, I knew he had the right mindset. Now he’s the first two-time Sales Person of the Year in Roundstone history.
Sales doesn’t reward certainty. It rewards movement.
Too many teams wait for the perfect pitch, timing, or conditions. Possibility thinking is what drives growth: move with intention, learn in the field, prioritize action over hesitation.
Momentum beats perfection every time.
Too many teams wait for the perfect pitch, timing, or conditions. Possibility thinking is what drives growth: move with intention, learn in the field, prioritize action over hesitation.
Momentum beats perfection every time.
From Making Sense To Taking Steps: Possibility Thinking In Leadership
Possibility thinking helps leaders move forward without certainty, turning clarity into motion through attention, agency, and small steps.
www.forbes.com
February 10, 2026 at 1:21 PM
Sales doesn’t reward certainty. It rewards movement.
Too many teams wait for the perfect pitch, timing, or conditions. Possibility thinking is what drives growth: move with intention, learn in the field, prioritize action over hesitation.
Momentum beats perfection every time.
Too many teams wait for the perfect pitch, timing, or conditions. Possibility thinking is what drives growth: move with intention, learn in the field, prioritize action over hesitation.
Momentum beats perfection every time.
Sales leadership isn’t built in the inbox.
If you spend your day just reacting to emails, you’re doing reps on the wrong machine. Busy doesn’t equal strong.
The best sales leaders set the plan, coach the team, and stay out in front.
If you spend your day just reacting to emails, you’re doing reps on the wrong machine. Busy doesn’t equal strong.
The best sales leaders set the plan, coach the team, and stay out in front.
Why The Best Bosses Are Moving Beyond Inbox Leadership
Email now causes—and pretends to fix—workplace dysfunction. This article explains why inbox leadership fails and what effective leaders do instead.
www.forbes.com
February 3, 2026 at 1:07 PM
Sales leadership isn’t built in the inbox.
If you spend your day just reacting to emails, you’re doing reps on the wrong machine. Busy doesn’t equal strong.
The best sales leaders set the plan, coach the team, and stay out in front.
If you spend your day just reacting to emails, you’re doing reps on the wrong machine. Busy doesn’t equal strong.
The best sales leaders set the plan, coach the team, and stay out in front.
Ideas are cheap. Execution wins.
In sales, nobody buys the theory, they buy results. Momentum, closed deals, and consistent delivery beat fancy thinking every time.
Buyers don’t care who talked best. They care who got it done.
In sales, nobody buys the theory, they buy results. Momentum, closed deals, and consistent delivery beat fancy thinking every time.
Buyers don’t care who talked best. They care who got it done.
How Change Makers Communicate Differently Than Thought Leaders
Leadership credibility comes from action. Here’s how communication differs between thought leaders and change makers and why intent now matters more than insight.
www.forbes.com
January 26, 2026 at 1:08 PM
Ideas are cheap. Execution wins.
In sales, nobody buys the theory, they buy results. Momentum, closed deals, and consistent delivery beat fancy thinking every time.
Buyers don’t care who talked best. They care who got it done.
In sales, nobody buys the theory, they buy results. Momentum, closed deals, and consistent delivery beat fancy thinking every time.
Buyers don’t care who talked best. They care who got it done.
Kicking off a podcast series with something simple.
On New Year’s Eve, I shared a 16-minute podcast with our team. No hacks. No grind culture. Just clear thinking on how to be successful and present at the same time.
On New Year’s Eve, I shared a 16-minute podcast with our team. No hacks. No grind culture. Just clear thinking on how to be successful and present at the same time.
How to Become Limitless in the New Year
Podcast Episode · Kwik Brain with Jim Kwik · 12/29/2025 · 16m
podcasts.apple.com
January 22, 2026 at 1:37 PM
Kicking off a podcast series with something simple.
On New Year’s Eve, I shared a 16-minute podcast with our team. No hacks. No grind culture. Just clear thinking on how to be successful and present at the same time.
On New Year’s Eve, I shared a 16-minute podcast with our team. No hacks. No grind culture. Just clear thinking on how to be successful and present at the same time.
If your purpose never costs you a deal, it’s not real.
Purpose in sales shows up when you walk away from the wrong customer, say no to bad-fit revenue, or push back instead of taking the easy win. That’s uncomfortable… and that’s the point.
Purpose in sales shows up when you walk away from the wrong customer, say no to bad-fit revenue, or push back instead of taking the easy win. That’s uncomfortable… and that’s the point.
Why Purpose Requires Making Leaders Deeply Uncomfortable
Purpose fails when leaders protect comfortable systems. Doug Conant fired 300 of 350 leaders to make culture as consequential as earnings at Campbell.
www.forbes.com
January 20, 2026 at 1:08 PM
If your purpose never costs you a deal, it’s not real.
Purpose in sales shows up when you walk away from the wrong customer, say no to bad-fit revenue, or push back instead of taking the easy win. That’s uncomfortable… and that’s the point.
Purpose in sales shows up when you walk away from the wrong customer, say no to bad-fit revenue, or push back instead of taking the easy win. That’s uncomfortable… and that’s the point.
Sales goals aren't hit by big New Year's talk. They're hit by habits.
Don't vow to "crush quota." Become the rep who owns 2 uninterrupted prospecting hours every morning… no excuses.
At Roundstone, we stay sharp with straight talk & accountability.
Don't vow to "crush quota." Become the rep who owns 2 uninterrupted prospecting hours every morning… no excuses.
At Roundstone, we stay sharp with straight talk & accountability.
New Year’s Resolutions Fade. Developing Habits Create Real Change
Why New Year’s resolutions fail and what works instead. How habits, identity and sustainable systems drive personal and professional growth long after January fades.
www.forbes.com
January 13, 2026 at 8:01 PM
Sales goals aren't hit by big New Year's talk. They're hit by habits.
Don't vow to "crush quota." Become the rep who owns 2 uninterrupted prospecting hours every morning… no excuses.
At Roundstone, we stay sharp with straight talk & accountability.
Don't vow to "crush quota." Become the rep who owns 2 uninterrupted prospecting hours every morning… no excuses.
At Roundstone, we stay sharp with straight talk & accountability.
Let’s be honest: the U.S. health insurance system is a mess.
It’s confusing, expensive, and exhausting for employers and employees. But, we don’t have to just “live with it.”
It’s confusing, expensive, and exhausting for employers and employees. But, we don’t have to just “live with it.”
January 8, 2026 at 4:33 PM
Let’s be honest: the U.S. health insurance system is a mess.
It’s confusing, expensive, and exhausting for employers and employees. But, we don’t have to just “live with it.”
It’s confusing, expensive, and exhausting for employers and employees. But, we don’t have to just “live with it.”
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.