Contact: 800-206-5030

Business Hours Sales:
Mon-Fri 8am-4pm
Pacific Time
Ext. 2

Mon-Fri 5am-5pm
Pacific Time
Ext. 3

Mon-Fri 6am-3pm
Pacific Time
Redtail Technology > Redtail Advisor Hero: Greg Hammond and Scott Iles
Advisor Hero logo

We start the conversation by exploring your purpose, because once you have a central purpose, your financial decisions become a whole lot easier.”


Greg Hammond and Scott Iles
Hammond Iles Wealth Advisors logo
Greg Hammond and Scott Iles

Two Heroes Who Coach Purpose Across Multiple Generations

When posed the question of what one superpower they would choose if they could, Greg Hammond and Scott Iles agreed they’d love to have a Time-Turner like Hermione Granger used in Harry Potter and the Prisoner of Azkaban. As Greg indicated, “To be able to multiply the number of client conversations we could fit in a day would be amazing”.

While no one’s gifted these advisors a Time-Turner, through their focus on helping clients recognize and reach for purpose across multiple generations, they have effectively managed to multiply the number of meaningful client conversations in which they can engage.


The individual career trajectories of both Greg Hammond and Scott Iles dovetail nicely with the principles they now work tirelessly to instill in those who have placed trust in them as financial advisors.

After college, Greg moved to Washington, D.C., where he worked for a law firm in accounting, later moving to public accounting for eight years. When he and his wife had their first daughter and moved back to Connecticut, Greg decided it was time to make a career change as well. He felt a pull to do more for clients than taxes only, so he joined what was then Kelly Financial Group in 1999 as a licensed assistant and learned the business from the ground up.

Scott also had other career plans growing up. When he got married, his mom gave him a note he’d written as a child: “When I grow up, I’ll be president of a bank and I’ll do a good job”- his dad was a banker. Scott began his career in P&C insurance in 1987, later transitioning into banking, which was a dream until he found that he too felt like he should be doing more for people. He went briefly back into life insurance, September 11th happened, and that’s when he wound up working at Kelly Financial with Greg. He left a steady paycheck at the same time the stock market was literally going crazy but knew quickly he’d found a home and a purpose that was for him.

With several years of friendship under their belts and a shared vision for the purpose of their careers, Greg and Scott acquired Kelly Financial when its founder retired in 2005 and rebranded it in 2012 to Hammond Iles.

Greg Hammond
CEO, Financial Coach
Scott Iles
Vice President, Financial Coach
Hammond Iles Wealth Advisors

  • 11 employees
  • 1,204 clients
Greg Hammond and Scott Iles

“Creating Clear Paths to Purposeful Living”

Making a meaningful difference is what we’re up for. Being acknowledged for doing that is really powerful. When people say things like, ‘I could never have done it without you,’ or ‘You saved our family from ruin,’ it’s so powerful.
– Scott

Having thoughtfully made career changes themselves after a significant number of years spent pursuing different paths, Greg and Scott each recognized that they had valuable experiences and advice that they could share across generations.

Greg indicates that all their client conversations begin and end with purpose and that this makes Hammond Iles a little different. As he says, “we’re all earning, we’re investing – but what is it all for? That’s what we try to focus our clients’ minds upon. After all, once you have a purpose, it’s easier to make decisions on investments, purchases, etc. That said, no matter the amount of money you have, it can’t buy you a purpose, and it can’t buy you happiness.”

Scott expands upon the firm’s ideas about purpose specifically as it relates to those just getting started in their careers. “With younger people, a lot of times you have your life or job laid out for you and then you’re stuck, just dropped into a 401(k) and kind of left out there with no further guidance. That would have been me until I realized there was more for me than that. Changing required leaving a comfortable job I was doing well in because it didn’t fulfil me. That can be a challenge for a lot of people.

Scott also points out that families don’t talk across generations about money that often, which can leave younger generations to figure things out for themselves and older generations unaware of opportunities to help those they love. And, in short, those conversations that don’t happen don’t help. Scott says, “The older generation doesn’t want to burden their kids, so they don’t tell them anything. The sandwich generation doesn’t want to talk to the older generation because they feel like the older generation will think they are after their money. Younger members may not want to talk about their student loan or credit card debt. Most of us come from a place of caring, but money is a hard conversation to have. We want to be able to stimulate those conversations, to be able to facilitate.

“As part of this, one of our big endeavors for this year is the ‘family meeting’ – what would it look like if all family members are together in a small room and fighting for one another. Everybody thinks everybody else is fine because they don’t necessarily know the struggles of their family members. Grandparents would probably prefer to help you while they are alive and will get to see it. It’s facilitating these types of conversations while at the same time teaching kids that it’s ok to talk about money that we are excited about.”

Giving as purpose

Each generation has its own challenges. People in my age group, the sandwich generation, are caring for elderly family while having kids in college. Then the younger generation is battling different things. We have a lot of experience in that, but one of the things is just getting conversations started.
– Scott

At the firm’s core is the value of giving back, which naturally flows into the way they deliver financial advice. When Greg and Scott took over the firm, they continued the tradition of hosting an annual client appreciation dinner. It was during one of these dinners that they took a step back and thought about how they could utilize this well-attended event to truly be a catalyst for change. After much consideration, Scott and Greg adopted the Connecticut Children’s Medical Center as an organization they’d like to support. Since that day, their firm has matched client donations, dollar for dollar, to the non-profit, pediatric acute care hospital.

2020, of course, saw a huge increase in the number of individuals and organizations that would benefit tremendously from the charity of others. When COVID-19 hit, some of their clients who were fortunate enough to be unaffected financially by the pandemic asked for guidance on how they might use their stimulus checks. Scott and Greg’s advice was simple—think of those who were greatly affected by the pandemic. They encouraged their clients to donate to charities who were providing much needed aid during the crisis, or to support people or causes they were passionate about.

Further, they launched a campaign focused on food relief, primarily at the local level, matching contributions in this endeavor as well. In the end they helped raise around $25,000 which they matched for local food banks and similar organizations.

At the end of the day, their mission is clear: to help their clients identify their purpose and see how their finances fit into helping them meet it. As Greg says, “We consider ourselves financial coaches, not just financial advisors. Coaches not only guide you, they encourage you on to accomplish what you may not think is possible”. With their multigenerational focus on purpose, empowerment, and generosity, Greg and Scott accomplish at least some of what possessing a Time-Turner of their own would allow them to do: they are inspiring and empowering their clients to have further conversations with all the generations of their own families in order that they each might work most fruitfully toward both their individual and common purpose. Even if they as advisors are not a part of each of these conversations, the coaching they provide helps families approach financial discussions confidently and with care for one another.

Do you know an Advisor Hero who uses Redtail?