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.
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.
From class clown to #Salesman of the Year! Sam Walters has been with Roundstone for 11 years, consistently delivering solid number year after year.
Big results, bigger personality. Congrats, Sam!
Big results, bigger personality. Congrats, Sam!
September 18, 2025 at 12:48 PM
From class clown to #Salesman of the Year! Sam Walters has been with Roundstone for 11 years, consistently delivering solid number year after year.
Big results, bigger personality. Congrats, Sam!
Big results, bigger personality. Congrats, Sam!
When I joined #Roundstone, we were 28 people with big ambitions.
Now we’re 180 strong and the #growth, culture, and innovation behind it have been some of the most rewarding parts of my career.
I shared this journey, lessons, and what’s next in my UnCAGED interview. Excited for where we’re headed.
Now we’re 180 strong and the #growth, culture, and innovation behind it have been some of the most rewarding parts of my career.
I shared this journey, lessons, and what’s next in my UnCAGED interview. Excited for where we’re headed.
August 21, 2025 at 2:26 PM
When I joined #Roundstone, we were 28 people with big ambitions.
Now we’re 180 strong and the #growth, culture, and innovation behind it have been some of the most rewarding parts of my career.
I shared this journey, lessons, and what’s next in my UnCAGED interview. Excited for where we’re headed.
Now we’re 180 strong and the #growth, culture, and innovation behind it have been some of the most rewarding parts of my career.
I shared this journey, lessons, and what’s next in my UnCAGED interview. Excited for where we’re headed.
#RosettaFest2025 is days away!
Denver will be buzzing with leaders driving transparency, fiduciary responsibility & employer-led #healthcare change. Excited to join the conversation. If you’ve been waiting; now’s the time.
Denver will be buzzing with leaders driving transparency, fiduciary responsibility & employer-led #healthcare change. Excited to join the conversation. If you’ve been waiting; now’s the time.
August 21, 2025 at 2:17 AM
#RosettaFest2025 is days away!
Denver will be buzzing with leaders driving transparency, fiduciary responsibility & employer-led #healthcare change. Excited to join the conversation. If you’ve been waiting; now’s the time.
Denver will be buzzing with leaders driving transparency, fiduciary responsibility & employer-led #healthcare change. Excited to join the conversation. If you’ve been waiting; now’s the time.
Busy seasons don’t build culture; they reveal it.
At Roundstone, we’re entering one of our most intense stretches. What matters most now? Lifting each other up. #Mentorship, support, small check-ins: that’s what keeps teams strong when the pressure’s on. #Leadership #TeamCulture
At Roundstone, we’re entering one of our most intense stretches. What matters most now? Lifting each other up. #Mentorship, support, small check-ins: that’s what keeps teams strong when the pressure’s on. #Leadership #TeamCulture
August 16, 2025 at 12:52 AM
Busy seasons don’t build culture; they reveal it.
At Roundstone, we’re entering one of our most intense stretches. What matters most now? Lifting each other up. #Mentorship, support, small check-ins: that’s what keeps teams strong when the pressure’s on. #Leadership #TeamCulture
At Roundstone, we’re entering one of our most intense stretches. What matters most now? Lifting each other up. #Mentorship, support, small check-ins: that’s what keeps teams strong when the pressure’s on. #Leadership #TeamCulture
Great #leadership isn’t built in big moments. It’s shaped everyday.
Every interaction is an exchange; a piece of your life traded for something.
Make it count.
Lead with purpose.
Set the tone.
The future is just a string of interactions you have to build into something meaningful.
Every interaction is an exchange; a piece of your life traded for something.
Make it count.
Lead with purpose.
Set the tone.
The future is just a string of interactions you have to build into something meaningful.
August 1, 2025 at 12:08 PM
Great #leadership isn’t built in big moments. It’s shaped everyday.
Every interaction is an exchange; a piece of your life traded for something.
Make it count.
Lead with purpose.
Set the tone.
The future is just a string of interactions you have to build into something meaningful.
Every interaction is an exchange; a piece of your life traded for something.
Make it count.
Lead with purpose.
Set the tone.
The future is just a string of interactions you have to build into something meaningful.
#RosettaFest2025 is almost here!
Excited to join the conversation in Denver and share how group captives give employers the power to cut costs, stay flexible, and build smarter, people-first health plans. #SelfFunding #EmployeeBenefits
Excited to join the conversation in Denver and share how group captives give employers the power to cut costs, stay flexible, and build smarter, people-first health plans. #SelfFunding #EmployeeBenefits
July 29, 2025 at 2:30 PM
#RosettaFest2025 is almost here!
Excited to join the conversation in Denver and share how group captives give employers the power to cut costs, stay flexible, and build smarter, people-first health plans. #SelfFunding #EmployeeBenefits
Excited to join the conversation in Denver and share how group captives give employers the power to cut costs, stay flexible, and build smarter, people-first health plans. #SelfFunding #EmployeeBenefits
Saw this at the gym where I workout regularly: “No matter what ails you, WORK.”
Not just about fitness; it's about showing up. In work, in life, in everything. Some days it's about passion. Some days it's about discipline. Just #KeepGoing. #WorkEthic
Not just about fitness; it's about showing up. In work, in life, in everything. Some days it's about passion. Some days it's about discipline. Just #KeepGoing. #WorkEthic
July 26, 2025 at 12:50 AM
Saw this at the gym where I workout regularly: “No matter what ails you, WORK.”
Not just about fitness; it's about showing up. In work, in life, in everything. Some days it's about passion. Some days it's about discipline. Just #KeepGoing. #WorkEthic
Not just about fitness; it's about showing up. In work, in life, in everything. Some days it's about passion. Some days it's about discipline. Just #KeepGoing. #WorkEthic
Fully insured plans = rising costs + zero #transparency. At @roundstone.bsky.social, we help employers break that cycle with a smarter, data-driven approach to health benefits.
#SelfFunding #Healthcare
#SelfFunding #Healthcare
July 25, 2025 at 12:18 AM
Fully insured plans = rising costs + zero #transparency. At @roundstone.bsky.social, we help employers break that cycle with a smarter, data-driven approach to health benefits.
#SelfFunding #Healthcare
#SelfFunding #Healthcare
Happy #InsuranceNerdDay to the data crunchers, risk whisperers & claims wizards keeping it all running behind the scenes.
You make sense of the chaos and somehow make it look easy. Stay curious, stay nerdy. We see you. #RiskManagement
You make sense of the chaos and somehow make it look easy. Stay curious, stay nerdy. We see you. #RiskManagement
July 18, 2025 at 12:47 PM
Happy #InsuranceNerdDay to the data crunchers, risk whisperers & claims wizards keeping it all running behind the scenes.
You make sense of the chaos and somehow make it look easy. Stay curious, stay nerdy. We see you. #RiskManagement
You make sense of the chaos and somehow make it look easy. Stay curious, stay nerdy. We see you. #RiskManagement
You can’t fake #culture and you can’t force people to care.
That’s why being named a Top Workplace again means so much. It’s real feedback from our team, not a PR boost.
At Roundstone, we work hard to make this a place people want to be. And that shows up in how they show up. #Leadership
That’s why being named a Top Workplace again means so much. It’s real feedback from our team, not a PR boost.
At Roundstone, we work hard to make this a place people want to be. And that shows up in how they show up. #Leadership
July 14, 2025 at 12:25 PM
You can’t fake #culture and you can’t force people to care.
That’s why being named a Top Workplace again means so much. It’s real feedback from our team, not a PR boost.
At Roundstone, we work hard to make this a place people want to be. And that shows up in how they show up. #Leadership
That’s why being named a Top Workplace again means so much. It’s real feedback from our team, not a PR boost.
At Roundstone, we work hard to make this a place people want to be. And that shows up in how they show up. #Leadership
This week, I joined the Roundstone team to cheer them on to first place at the Skeeball competition! This was the second first-place finish in two years. Couldn't be more proud of this team inside and OUTSIDE of the office!
#Roundstone
#Roundstone
July 2, 2025 at 1:34 PM
This week, I joined the Roundstone team to cheer them on to first place at the Skeeball competition! This was the second first-place finish in two years. Couldn't be more proud of this team inside and OUTSIDE of the office!
#Roundstone
#Roundstone
Imagine every dollar you save on #HealthInsurance going straight back into your business.
That’s what happens when you're self-insured, manage your own claims, and implement smart #CostContainment strategies.
That’s what happens when you're self-insured, manage your own claims, and implement smart #CostContainment strategies.
June 24, 2025 at 12:51 AM
Imagine every dollar you save on #HealthInsurance going straight back into your business.
That’s what happens when you're self-insured, manage your own claims, and implement smart #CostContainment strategies.
That’s what happens when you're self-insured, manage your own claims, and implement smart #CostContainment strategies.
30 years in #sales #leadership taught me this: the best deals I’ve ever made weren’t with clients; they were with the people I mentored.
Sales is a high-stakes industry. But #mentorship? That’s where real growth happens. For them and for you.
Sales is a high-stakes industry. But #mentorship? That’s where real growth happens. For them and for you.
June 12, 2025 at 12:25 AM
30 years in #sales #leadership taught me this: the best deals I’ve ever made weren’t with clients; they were with the people I mentored.
Sales is a high-stakes industry. But #mentorship? That’s where real growth happens. For them and for you.
Sales is a high-stakes industry. But #mentorship? That’s where real growth happens. For them and for you.
75% of CFOs say rising #healthcare costs threaten their bottom line. As expenses climb, companies must rethink benefits – exploring value-based care, alternative funding, and innovative solutions will balance costs and help employee well-being.
April 2, 2025 at 3:25 PM
75% of CFOs say rising #healthcare costs threaten their bottom line. As expenses climb, companies must rethink benefits – exploring value-based care, alternative funding, and innovative solutions will balance costs and help employee well-being.
Rising #healthcare costs hurt both employers and employees. #WellnessPrograms, #telemedicine, and better plan designs can help. How is your company managing costs? #EmployeeBenefits #CorporateFinance
March 25, 2025 at 1:28 AM
Rising #healthcare costs hurt both employers and employees. #WellnessPrograms, #telemedicine, and better plan designs can help. How is your company managing costs? #EmployeeBenefits #CorporateFinance
80% of CFOs and CHROs say balancing rising healthcare costs with employee demands for better benefits is a constant battle. At #Roundstone, we’re helping companies take control with self-funded #HealthInsurance. By using key metrics like PEPY, businesses can save and make smarter decisions.
March 19, 2025 at 1:15 PM
80% of CFOs and CHROs say balancing rising healthcare costs with employee demands for better benefits is a constant battle. At #Roundstone, we’re helping companies take control with self-funded #HealthInsurance. By using key metrics like PEPY, businesses can save and make smarter decisions.
Curious about #CaptiveInsurance? This alternative plan lets businesses create – essentially – their own insurance company, offering more control over risks and the ability to customize coverage. For those with the right risk profile, it’s a game-changer for cost savings and #financial flexibility.
March 15, 2025 at 7:01 PM
Curious about #CaptiveInsurance? This alternative plan lets businesses create – essentially – their own insurance company, offering more control over risks and the ability to customize coverage. For those with the right risk profile, it’s a game-changer for cost savings and #financial flexibility.
Peer Coaching is a cost-effective way to drive engagement & innovation. To make it work:
✅ Define coaching as guidance, not pressure
✅ Train employees in active listening & feedback
✅ Set clear, measurable goals
✅ Foster trust for open discussions
Is your company embracing these strategies?
✅ Define coaching as guidance, not pressure
✅ Train employees in active listening & feedback
✅ Set clear, measurable goals
✅ Foster trust for open discussions
Is your company embracing these strategies?
March 14, 2025 at 3:35 PM
Peer Coaching is a cost-effective way to drive engagement & innovation. To make it work:
✅ Define coaching as guidance, not pressure
✅ Train employees in active listening & feedback
✅ Set clear, measurable goals
✅ Foster trust for open discussions
Is your company embracing these strategies?
✅ Define coaching as guidance, not pressure
✅ Train employees in active listening & feedback
✅ Set clear, measurable goals
✅ Foster trust for open discussions
Is your company embracing these strategies?
#RUBootcamp is officially over!
While I'm sad to say it's finished, it was a wonderful experience with great people! Learned – and laughed – a lot! #Growth
While I'm sad to say it's finished, it was a wonderful experience with great people! Learned – and laughed – a lot! #Growth
February 19, 2025 at 2:14 PM
#RUBootcamp is officially over!
While I'm sad to say it's finished, it was a wonderful experience with great people! Learned – and laughed – a lot! #Growth
While I'm sad to say it's finished, it was a wonderful experience with great people! Learned – and laughed – a lot! #Growth
