Tom Butterfield, Executive Creative Director, Masterworks

Share this article:

Share on facebook
Share on twitter
Share on linkedin
Listen to This Interview Text to speech converter

Sometimes, the most fantastic interviews are right under your nose. Tom has been a long-term family friend, and everything about him – from his eclectic dress sense, to his warm charisma, to his enthusiastic speech – is flamboyant and fascinating.

I interviewed Tom and his wonderful wife Gill in their home in Bermuda, where Tom has dedicated the past 34 years of his life to the preservation and curation of Bermudian art at the Masterworks Museum. Tom’s passion for the endeavor has lead to Masterworks having a huge number of high-profile Bermudian paintings, their own gallery and various annual events which celebrate Bermudian art and culture – and below you will find out how he accomplished all this!

You can read Tom’s full biography here


Tom: Six months ago. I started to think, “My God!”

I had my first job at the age of ten as a caddy, and here I am at seventy-two and all my friends have pretty much retired, and I still enjoy what I am doing every day. I am not retiring. I am just now graduating.

Jamie: Do you work in sales currently?
Tom: I do.

Jamie: Has it been pretty consistent across your career?
Tom: Yeah. Every day is a sales job. You are selling to people to motivate them. So you have got to do that part. You have to raise funds. You have to buy paintings. You have to build a building or whatever it may be. There has just been sales and sales and sales.

Jamie: What have you found most fulfilling about your sales career up to this point?
Tom: To this point, I do not know if I have found any one thing most fulfilling. Maybe it’s the idea that you are selling a concept. Here is this concept. We’ve got this idea. We are going to repatriate some paintings and then from that concept you are going to sell an educational component to it. Then you are going to sell a building, a museum, and then you have to bring people into your world.

You’ve got to bring them into your sphere because the sale is not made with just monetary reward in mind. The sole motivation of the sale is having people believe in the dream or the cause that you are selling.

There are no dividends to offer in charity. So people are giving out of the goodness of their heart. They are marrying into what you see, and so there needs to be a cause.
I am sure that I have the record right. When we were doing the campaign to build the Masterworks building, I knocked on approximately five hundred doors. Knock, knock, and I used to ask, “Will you support me?” Three hundred and eight-five people said, “Yes, we will,” and about a hundred and fifteen said, “No. I do not think so. It is not my thing.”The ratio was good, but there was a lot of sales pitching because you are on a big multi-million dollar campaign and some people say, “I would like to do it, but all I can do is offer you $500.”

So you think, “Okay. Well, you know, no amount is too small.” That is the one thing that I would say to anybody when you are selling. But if you ever get a response, even if it would appear to you to be a brush-off, you have to take it, and roll with it, and have people feel included, because that person could come back and take $500 and turn it into $5,000 or $50,000. My sources of funding will remain anonymous, that is for sure because they are one or two people who are still very much alive. But there is one gentleman who once said, “Oh, all you are going to get is $15,000 from me. That is gonna be the max. Promise.” He rounded the corner to $200,000 and then to £300,000, the other day. You never, ever know.

Now in today’s age, where a trillion dollars are misspent here and a billion dollars there, I realized that what I am talking about, relatively, is peanuts. But that is really not the point. The point is getting into a sales mode and going to bed at night thinking, “How will I do better tomorrow in terms of the sales pitch?” and waking up with that kind of things very much yet in mind.

I guess the reward is seeing it all happen. You know, we started off with twelve little paintings arriving in the middle of August, and you have got to go out there and sell.

Suddenly, you have jumped from the cliff, and you got to figure out how you are going to land because I did not have any spreadsheets. We did not have a bank plan. We did not have any of that. We just had, “We are going to borrow some money. We are going to make it happen.”

For sure, it was the right way around because if we had said that we were going to build a building and then populate it with paintings, we would have been sent to the funny farm. We would not have worked at all, in terms of a sale.

As soon as you had some concrete evidence that there were visitors in Bermuda who came over to see the art, people could catch onto it. The interesting thing to me was that the selling aspect was much easier for me for residents of the States, Canada, and England because they all come from countries with national focuses on art collections. I do not like to use the word national for us because we are a tiny little island. But what I was well-aware of, in this tiny little island, we had attracted a whole lot of talent.

Jamie: You talked about selling a dream, and I think a lot of people sell products, whether physical or intangible. How do you go about creating a dream that people can buy into?

Tom: First of all, I think that the number one thing is that you have got to really be passionate and believe in what you are doing. Not be a slick, sleazy suited salesman that does not really believe in their product. You do not believe in the concept of what you are selling because, as you say, there is no tangible product. Here is your product, and he thanks you for your money – it is not that kind of exchange at all. It is an exchange of, “Here is the money. Now get on with the thing that you are doing.” So in terms of, “How do we go about doing that?” it is that we simply wake up every day and say, “What else can we do now?”

The first thing that we had to do was -because there is a whole kind of socio-economic, racial aspect in all of this – to keep in mind that the concept of art in Bermuda was new, in terms of having a permanent collection around it.

We have a population which is 70% black and 30% white. We do not have a nation full of extremely well-off people, and we do not have a government also that gets behind supporting the arts. They were, however, giving little parcels of money for entrepreneurs, and we did not think of ourselves as being even entrepreneurial, but which obviously we were. We just thought of ourselves as a bunch of overzealous art guerillas.

I managed to get the thing up and running in a week.

We really did the art guerilla stuff, because we had no permanent home. We would literally move paintings at night time just to find a new wall somewhere. Someone will say, “I will lend you some space,” and we would move to another place. It was fun.

Anyway, I do think that it has a particular communication skill that what you are saying has a modicum of truth because no money and goods are going back and forth. Some people who sell, sell for universities. They have got something really tangible to sell. You come to our university, this is what you are going to get: four years of the degree that you are looking for.

In our case, now that we are a museum, we are selling memberships. So this is what you are going to get in return for membership. That is one of the things obviously that changed the moment we opened up our door. We did have goods to exchange. We did have something to say. “For twenty-five bucks a year for membership, this is what you get. For fifty, this is what you get. For a hundred twenty-five, this is what you get.”

You have to put various strata of levels of support. We launched a new concept the other day. You could become an ‘art lover’ on an annual basis and much to my surprise, a lot of people said, “We do not want to be an ‘art lover,’ just to show support,” because we have to raise a lot of money every year on a small island to keep the doors open.

Jamie: You mentioned the lifetime value of a client or a prospect of yours as being so important. What advice do you have to keep people on that journey and keep those relations so strong that people continue giving more and more?
Tom: Communication, communication, and communication. I mean when I was a wine salesman, what I would often see that there were people in the company who should know better, and that’s when I realized why the company was moribund and why they wanted me to join it. Because they would come to a Jamie Hamer and say, “Jamie, I’ve got a case of wine for you. Why don’t you buy a case?” and then they would forget about you, and they would go try and sell to someone else.

So, now Jamie is in the corner thinking, “What about me?” and suddenly you are chopped liver. So, as I said, it’s all about communication. I always try and keep my benefactors in the loop as much as possible, and one of the things is that as it expands and not always having a personal secretary, I have been very slow to do this type of thing. That is a skill that Risa, my secretary, is really good at. Because once you make the sale, if you do not follow up, you are not going to make any more sales. It really is about connecting on a concept and keeping people in the loop. It is not necessarily about the amount.

I had an interview the other day, and they said: “How would you treat a $50 donator and a $5,000 donator?” And two of our personnel said, “Absolutely the same.” Yes, we might be a little more elegant with the five thousand, but we will treat them with the same kind of respect and acknowledgement. There is an important word, by the way.

It’s corny, but good sales has love in it. If you cannot show that love in it, in my mind, you are not going to make any sale. Love is a big word.

Jamie: Any strategies you have employed that had been particularly effective in thanking people?
Tom: I had my druthers, I would give it a lot; as many giveaways as I could expressing that. But you cannot, so the only strategy that you can do is to say, “Thank you very much. Will you come back? Oh, and by the way, would you like to bring a friend?”

That gives them something, to be able to say, “I am really proud of the support that I have offered, and now I am going to bring a friend.”

That has helped us big-time, that concept of bringing a friend. The campaign, I do not think in terms of a sales pitch, when we set off that campaign. I think about our return on the investment dollar, and you will have to do the math here. I believe we spent maybe. $1,000 on lunches and dinners, and we raised $8,000,000. It is just one of those brilliant ratios.

Because I am coming back to the whole dynamic of the socio-racial-economic thing, I realized that to sell the concept to a lot of people, I was not able to go to Bermudians alone. I was about to do my first marathon, “Will you give me $10 a mile?” – that would not work. So I went to people “Can you give me a dime a mile, or a nickel a mile?”

We raised a lot of money, and we thought, “Well, I have made some connections here. Plus some names here. So the next year, I did another marathon, and that raised a bit more. In the following year, a little bit more and so on. And then we got into the bike rides. You spent maybe $1,000, and we would raise $200,000 because of all the bikers.

We had one principle, “We buy our own bikes. We pay for our own accommodation. There will be some ancillary costs that will go into it. Who knows what they will be, but we are going to absorb the cost.” The money is to go into the running of the organization. So every other year, when we are doing the bike ride, we have this spike of cash going into the museum.

Now, we have to sell an item which requires us to do $2,000,000 a year to keep the doors open. It is a different element; that is why selling memberships is important. That is why selling annual appeals is important. We have had along the way some challenge grants and that has been brilliant because they allow the truth to be told, and you can raise more on a challenge grant because you are worthy of it.

Again, that is not being a sleazy salesman. I think that telling the truth is the biggest single contributor to a successful sale and if you do not know the answer, then just say, “I do not know the answer, then I will get back to you.”

I have never really fudged around anything. If I do not know it, I just said, “You know, I do not know,” because you are talking to a natural salesperson, and not a natural businessman who says, “It is spreadsheets, spreadsheets, and spreadsheets,” and then, drilling down to the minutiae. I do not do that well. What I do well is understand that we have got a deficit, and we have got to deal with it. If we have got a surplus, great, let’s smoke a cigar. It is pretty simple stuff.

Jamie: What is the biggest difference you have seen between unsuccessful and successful salespeople?
Tom: The ability to communicate is one. Language is a very powerful tool. It is not about English because I think that my level of education sounds more like I came out of grade ten than out of a university. A part of that is because in a presentation for a museum, believe it or not, you need to dumb down some of the wall-text to get the people involved in reading.

In some way that is kind of a carryover of what I do; you will lose your reader if you lay on all these words that no one really understands and nobody wants to know, so they do not read the wall text. Conversely, the same is true if you do not have some power of language when you are out there making the sales, you are going to fall on your sword. So, language is number one.

A clear fad is that when you are knocking on a door when you are selling and doing your homework, who are you selling it to? In other words, my sales pitch to you is going to be completely different, because I am going to try and say, “Well, Jamie, hmm,” and what do I know about him? What might be a soft spot that will get him engaged? What might his interests be?

With the election and pandemics running on an equal footing, and pandemics right now taking a little bit of a higher profile; nonetheless, we have been pitching like crazy.

You cannot leave kids behind and compromise with their education, because that is not going to do them any good when the pandemic is all over, because they will still need it. They will still need to go and join the workforce. They will still need to have life’s experiences.

I think awareness of the world around you is another thing that you need to do when you are selling.

Sometimes, I just pinch myself at the luck that we have had. When we started our campaign for the museum, the world was healing from the 9-11 terrorist attack, and people at first were so shocked that there was no giving whatsoever.

Purses just clammed up instantly. But then as we started to heal, the purses were opening up then because things were becoming buoyant again and they thought, “You know, the best thing that we can do is give something that has a positive influence on the community or society around us.” There was a lot of that. Then in 2008, the purses closed up again, because of the economy, but we had already opened up our museum. So we took a step back, and we did no campaigning.

We did do some campaigning because we were given a matching grant in 2014 of $500,000. So that match we did, and we did $500,000 plus $250,000 on the backside of that $500,000. That was a good campaign. It achieved a very good result.

I think the people love to see challenge grants because there are those that we have approached they are not on the hook for the big one. They are on the hook for a small one and we, the museum, are the beneficiary. That is a relatively easy sale. I do not like doing is trying to beg for money in meetings. I think there is a big mistake here and I do not know how effective it is because I just do not do it. I am an old-fashioned guy. I do not like sitting in large rooms and begging for money. The only way to do it is, in my mind, is face-to-face.

It is not the sale of a product, where there is an exchange, and so ours has to be different. I do not think that you can ever get around that notion. You just have to bite the bullet and suck it up. There are times when I am just absolutely blown away. I am shattered at the end of the day, just selling, selling, and selling, walking people through, taking them on tours. I am trying to build it up. There are days when you just know that you have uttered ten or maybe twelve thousand words in a day; like a teacher.

Jamie: What kind of preparation will you do for meeting someone, and what cues will you be looking for in them in these face-to-face meetings?

Tom: Being a good listener is key. When you are going in to see somebody, and you want to come out with a check in your pocket or a commitment or a pledge or whatever it is, you got to be on your “p’s and q’s” to take a step back. Because it is they who are in charge, and not you. That is the thing that is number one in the preparation part.

Number two is learning a little bit about where they come from. I have met some arrogant dudes around here. I mean really arrogant and you think, “I wonder if they were arrogant in their country or the states or Canada or England? Have they become arrogant because they have suddenly become a big fish in a very small pond and so that they can come across and wield their perceived power and largesse, as the case may be?” and there are game-players like that, and you got to know when you are in the room with somebody who is playing a game.

There are times when I know from the moment I stepped into the door, and someone says, “One cup of coffee,” and I can see on their face that this cup of coffee is going nowhere than the cup of coffee; that in a half-hour’s time, it is going to be, “Tom. Thanks for dropping by. We will see you later.” So, you try and figure out how you are going to get out of there and save some sense of dignity because some people want to strip you down. They want to sort of say, “Aha! So you are coming here for some money. Well, guess what? You are not going to get any. Here is the reason why you are not going to.”

There was one incident that I have never forgotten.

“Well you know Tom, I just came back from a World Golf Tour with my wife. We were on this cruise boat for eighty days. My God! It was costly. Oh, you should have seen it. Yeah, and you want how much? A thousand? We do not have a thousand dollars. We just spent… ”

You cannot get into that argument because ultimately people will give or spend on the things that they so choose to do. So you can take an attitude and come back with a foul taste in your mouth. But again, you are not in the driver’s seat. It is when they tell that long story about how their life is so gloriously opulent and you are not getting a nibble with it. That is when it becomes really insulting.

Jamie: What is the biggest piece of advice you give aspiring salespeople?


Get ready for the “No.” Get ready for it. Be prepared for it. Do not take it personally. Just tell yourself that “No” means simply “Not now.” It does not mean it’s a “No” forever.

It just means “Not now.” Go back to that person. Come back again and again. Samuel Beckett, I think it was; “If you failed, that is great. Fail again. Try again, and then if you do better, that is great. But if you fail again, fail even better. You’ve got to keep trying.” I think that is great advice.

There are little things like that that have affected my thinking. At the early stages, I used to take some of this personally. It does, in some cases, make it more difficult. In some cases, it made it easy and in some cases, some friends would say to us, “We have friends who do not want to meet you,” and that turned out to be a lie. They had friends that they did not want to have to meet me because they knew I was going to make a sale, and those people actually wanted to get involved with the museum, and we eventually found that out, which is kind of a revelation.

I have seen so much of that sort of stuff, and it amuses me. I have my own book about all of this to write eventually because there have been some very funny instances – from selling the concept of an “artist in residence,” or selling our shows overseas. We have done our exhibitions in major cities in North America, and one in London, constantly selling outside of Bermuda where they need to be volunteers, stay with us, hold the course, and help raise funds from overseas.

We had one girl, a lady, who would fly out from California. She would go back, not even the next day, but that night. That is a big step. That is a four-hour flight back. Some of her meetings took four hours.

Jamie: And Tom, if you had your career in sales again, what would you do differently?

Tom: I do not know. It is funny. I mean because I have always done things differently. I have done things that most people would not do in terms of a sale like I do crazy things. I have run marathons in tutus. I have run races in gorilla outfits, and people would say, “Oh there he is, is that Tom? He is just trying to show off again.”

But no. Tom was drawing attention to a cause. Drawing attention, yes, and I was the focal point again. But it was not about me, or that was not the concept of it. The concept was that by tying me to the concept, we are selling a bigger picture. What advice might I give? I really do not know whether I got any because I think that it is every day for me is a new try. I do not think that I have had any one particularly successful thing that I do.

I suppose having a business background would help because you when you are selling and buying, most of the selling stuff has a number quotient to it. There is magic in the banks and loans and products and things. I really do not have any one bit of advice except, “Be prepared.”

I think you truly need to be yourself. “Tom, we are meeting the Queen tomorrow. I want to make sure you have got your high tops on, okay? We are meeting the Queen. Wear your high tops.” I was once a young and pretty crazy guy, relatively speaking. I have carried that tradition on, although, I soften the approach; only for one reason.

I cannot reach my toes anymore because of all the back operations that I have had, having run marathons.

Do I have any regrets about running marathons and hurting my back, given what I cannot do now? The answer is no. I will have no regrets whatsoever because the result of what we set out to do is being achieved.

I will not say it has been achieved yet because we are still selling.

We are still doing great things. When we did this, with this pandemic and the racial protests and all the rest stirs up, the world was going to hell in a handbasket during May, June, and July – I had always wanted to do this long canvas fundraiser. Much to my surprise, I thought by doing this on canvas, maybe five or six hundred feet, it would get into Guinness Book of Records, but it turns out it would not.

What I could say is that it is the longest painting that someone has ever done in Bermuda and maybe even the Caribbean. Now, no one is taking me up on the challenge of the Caribbean, and I have a feeling that if you come up with a line that you think is right, and you keep saying that line, and no one comes back to challenge you, then invariably, there is going to be some truth to what you are saying. That may be your own truth, but it is a truth, and until disproved, it remains just that, a truth.

We came up with this canvas. We painted 250 feet of canvas. It is Bermuda’s longest canvas. We had to cut it back to get it all the way around the room so that we can do various levels. To sell it, I was having trouble with my own staff with friends. The pushback that I was getting on it and what it would do was extraordinary.

So I just thought, “Shit! We are just going to do it,” and I had a couple of young girls who said, “Yeah, Tommy. Let’s go for it.”

We believed in it, and we rolled out the canvas.

It was one of the greatest days that I have ever seen because we saw these nice little young white girls painting with blond hair and blue eyes, panting right next to a Rastafarian dude and nobody was paying any attention to their backgrounds at all. They were just paying attention to the charge in front of them; to be creative, to be community-minded, to be community-spirited, and through the creative energies and spirits, we could, on that one day, in those six hours, be a better community.

You know what? For a short period, we were. Now we go back to our cocoons, but I am hoping that we can sell other concepts like that and do it again.

By the way, Jamie, there is one other thing that I love in terms of sales. Holy shit! This is fun! Because it was a craze of a wine called Beaujolais Nouveau and I used to get on that blower, and I could sell Nouveau better than anyone.

I realized that I had sold an entire sea container of Beaujolais Nouveau. Then I said to the director, “You know what? I could sell another case. Fly them in, and when it arrives, Gosling brothers and all the other competitors will still have theirs out at sea,” and shortly enough, we flew in the second container of seven hundred fifty cases of Beaujolais Nouveau and Gosling Brothers had their container still out at sea. When the ship arrived, they could not sell a goddamn case of it. It just went to waste because the market was absorbed. It was done. It was over. Talk about swallowing the canary. I mean that was an incredible bit of success. That was really selling.

Jamie: Do you have a favourite sales story from your career?
Tom: Here is one of my favourite stories. It has something to do with a David and Goliath kind of outcome to it. Where I am David and the Bermudian bankers, the men in suits, are Goliath, and they did not want us to exist. They wanted us to cease and resist and go away. I will make this as brief as I can. I can embellish it for about an hour because I love telling it.

Our chairman at the time was a Harvard-educated MBA. Also on our board was a Lady Swan, who was the wife of the then-premier. The bank called us up and said, “We would like to see you this afternoon.” We had some debt and a big overdraft, so I knew that this was not going to be a courtesy call. I was as nervous as hell.

My brother George was in town, and he’s an accountant. I said, “George, we get audited every year, no matter how bad the record books, but we get on with it somehow” So, he said, “let me see the books.”

He said, “Well, you know what Tom, as I see it, this is what you have done. You have built up your assets. You have got some cash on hand. You paid your interest on time, and you pay down a little bit of your principal. So, you are going pretty well.”

So Lady Swan and I met the bankers in suits and our chairman from Harvard MBA who was the single largest bankers as well, they were all in the room, and I arrived a couple of minutes late. Before I could say anything, I said to myself, “You could cut the atmosphere with a knife.”


It was tense, so I said, “I do hope ladies and gentlemen, that this is a courtesy call.” The room went silent, and I said, “You know, because I’ve got a feeling, it is going to be a little bit different.”

“So, let me just tell you about the activities of the last year.” I reeled off the four things that we had done, and the floor went silent. The bankers, the man in the suit, he said, “Gosh, you are doing better than the businesses on Front Street. They cannot tell that kind of story. I guess you are going to have to get on with it.”

I said, “Yeah, I guess we are.”

Harvard MBA chairman, Lady Swan, and I take the elevator down onto the first floor. We exit the building, and they both have a cigarette. Harvard MBA man says, “Tom, how the hell did you ever figure that out? I looked at him with a wonderful sense of victory and a glint in my eyes.

“You see, anybody who has an MBA should be able to understand an audit,” I said, and I just walked away. I love the fact that there was just nothing else to say and that to me was our day of victory, and because from that day on, we were on safe ground.

The moral of the story was that the businesses did not want us to go away, and we on the day. Had my brother not been in town for me that audit might have been a different result. But who is winning now?



Do you like this article? Share this article!
Share on facebook
Share on twitter
Share on linkedin

Leave a Reply

Your email address will not be published. Required fields are marked *

Sign up to receive interviews, excerpts & resources from the Exceptional Sales Career

    Download the free guide

    Best Read

    Sign up to Review our Weekly Newsletter
    The Exceptional Sales Career