A Second Master's Degree: What Isaacson, Miller Taught Me

People ask why I say my time at Isaacson, Miller in Boston was a second master’s degree. I mean it literally. I already had one, from the University of Missouri. What I got at Isaacson, Miller was the other one, and nobody handed me a diploma for it.

Some of it should probably go in a book. Here are the pieces of it I can tell now.

It was never only about executive search

I have spent twenty nine years in this business. I started at Isaacson, Miller, sitting next to Arnie Miller. I call my time there a second master’s degree, and I mean that literally, because I already had one.

It was never only about executive search. It was about politics. It was about policy. It was about how the nonprofit world actually works, and the healthcare world, and government. You cannot place the president of a university or the head of a health system without learning how those institutions really function, who holds power inside them, and what breaks them. I got years of that, from people who had spent their careers in it, and I was paid to be there.

Here is what that education actually looked like. I was working a search with Lisa Savereid and she wanted me to start learning how to conduct a reference call. So she brought me into her office and let me sit there and listen while she took one. The reference was Colin Powell.

Nobody sat me down and taught me a method. She simply let me hear how it is done at that altitude: what you ask, what you do not ask, how long you leave a silence, how you get a person of that standing to tell you something true rather than something polite. You cannot learn that from a book and no firm I know of teaches it. I learned it because someone senior thought a young recruiter should be in the room.

That is what I mean by a second master’s degree. Lisa is gone now too.

The reason I saw so much of it was the internet. I was the one in the building who understood what it could do for recruiting, at a time when most of the profession had not decided it was for them. So I became the pinch hitter. When a search was in trouble, I got brought in.

That meant working alongside a great many partners on a great many searches, and every one came with an industry attached. Conservation. Environmentalism. Advocacy. Government. Transportation. Higher education. Health. I was not studying those sectors, I was trying to fill a hard job in each of them, which turns out to be the fastest way to learn how anything really works.

And sometimes what I did for them was simply put the search on the internet.

The other thing I did was build. I put together an internal research resource for the recruiters to work from, a place where what we knew about sectors and institutions and people actually lived instead of sitting in one person’s head. Eve Porter Zuckerman and I worked on that together.

Word got around. A partner mentioned it to another search firm in town that needed the same thing, and they called me. One slow summer, the couple of months when everyone is on holiday and the searches that were going to close have closed, I spent building theirs.

Here is the part I had not thought about in years. I was doing all three at once. Still on the Isaacson, Miller payroll part time, building a research system for a second firm, and filling technology searches for a third. Three firms in one summer, early in my career, and I went straight back to Isaacson, Miller when it was over because I was not going anywhere.

That same summer I also worked for Mark Woelters, a former Isaacson, Miller partner who had started his own firm doing technology search. His offices were in Faneuil Hall. I went in as an associate and filled technology roles for him: programmers, engineers, the people who build the thing rather than run it. So while I was building a research system for one firm, I was recruiting the kind of people who build systems for another.

I had never done anything like that before. I learned it by doing it, because somebody needed it and I was the one who would try. That is the part of the second master’s degree nobody would have predicted, and it is the part I have used every day since.

That is where ExecSearches came from. Not a business plan. A thing I kept doing for colleagues until it was obviously worth doing on purpose.

Two groups, one building

Something worth explaining about that firm. There were two distinct groups inside it, Arnie’s and John’s, and they worked together. The project I was originally hired for was a joint one, a partner from each side. That is unusual. In most firms the practice groups guard their turf. There I was handed straight across the middle of it, which is how I ended up working for so many different partners so quickly.

One of them was Manny, with whom I worked a great deal and from whom I learned higher education fundraising, which is its own discipline and nothing like corporate development.

We ran a Director of Athletics search and I went out to the University of Connecticut for it. Manny paid me a compliment I have not forgotten, which was that my knowledge of sport was doing real work on the search. He did not follow it himself. I did.

I knew the background of the athletic director we were looking at because he had come from the University of Maryland, and I had followed Maryland basketball since I was a boy. My brother went there.

That was the programme, and the era, of Len Bias. He was the best player I ever watched, and I watched him from close range. My brother and I were at Cole Field House the night Bias threw down a dunk directly over where I was sitting. I saw him play against Michael Jordan when Maryland met North Carolina, two of them on the floor at the same time.

The Celtics drafted him. He was dead within days, before he ever played a professional minute. It is one of the famous tragedies of the sport and people who did not live through it cannot quite be made to understand what it did to Maryland.

So in the meeting I could talk. The athletic directors, the coaches, who had been where and when and what happened to them. I put the names on the table one after another, from memory, because I had been carrying them since I was a kid.

They were impressed. Manny said something like my God, Jay. He had a search to run in a world he did not know, and it turned out the person who knew it was the one doing the outreach.

That is why he took me onto the United States Olympic Committee search, and why I went out to Colorado with him to their headquarters. A search at that level, and I was there because of Maryland basketball.

The head of the USOC gave me a pin for the Salt Lake Olympics. I still have it.

None of that was professional knowledge. It was a childhood spent watching a team because my brother went to that school. And it mattered, because search is not only method. It is knowing the world a candidate comes from well enough to have a real conversation with them. Everything you have ever paid attention to is eventually useful. That is not a motivational sentiment, it is a fact about this job.

Penn, and a week

Upstairs there was a corner that belonged to John Isaacson. Karen Alphonse sat in it, and so did Sean, his associate and a friend of Karen’s. Karen took the senior work. Sean carried the rest, and I helped him on a great many of them. I also worked a search with John himself.

Those searches are where I learned the education administration world, including K through 12. We ran some very large searches for school systems, and if you want to understand how American public institutions actually operate, try filling a superintendency.

And John was watching. Not obtrusively, but he was paying attention to what I was doing and how, and the firm took it up. That is the thing about a place like that: the good methods travel fast, whoever they come from.

One of those was a major gift officer search at the University of Pennsylvania. It was not a hard job to sell. Penn, a senior major gift role, a high salary. Anybody in that profession would want to hear about it. Sean simply did not have the hours, because he was carrying other important searches at the same time. So I took the outreach.

What I did was not clever. It was only unusual. I went after every major gift officer at a higher education institution in the region, one after another, and I wrote to each of them.

The note said roughly this. You are a major gift officer. You are at an institution near here. There is a senior major gift role open at Penn, the salary is this, and here is a link to a page about the search. Would you like to know more?

Nobody had ever seen that. In 1997 a job description was a document that arrived in an envelope, if it arrived at all, and recruiting ran on the telephone and on who you already knew. I was sending qualified strangers a link and inviting them to go and read it themselves.

I had a candidate pool in a week.

Not one name. A pool. Because I had not gone looking for the one person who might say yes, I had told everyone who was qualified that the opportunity existed and let them decide.

Sean was stunned. So were the others. That reaction is the thing I remember most clearly, because from the inside it had not felt like an achievement. I had written some emails. But they had spent their careers building candidate pools one relationship at a time, which is slow and skilled and expensive work, and they had just watched it happen in a week.

There was a shape to it that I only recognised later. An email that reaches the right person. A web page that holds the real detail so the email does not have to. And then a document, a PDF or a Word file, for anyone who wanted the full position description. Three pieces, each doing the job the others could not.

That stack is now how the entire industry works. In 1997 it was just what I had to hand.

And understand what this search actually was. It was not a hard sell. Penn is Penn. The salary was high. Major gift officers across the region would have wanted to hear about it.

It just needed to be told to the right people all at once. That is what I did, and that is the whole of it. Everything I have built in the twenty nine years since is a larger version of that one sentence.

That is why they kept handing me the difficult ones.

Real searches, start to finish

It was not all outreach. I ran searches end to end with David Haley and with Arnie Miller.

David took me to Washington twice. Once for the National Council of La Raza, which is UnidosUS now, a senior finance search as I remember it. That is where I learned how civil rights and advocacy organisations actually work, how they are funded, and what it costs them to hold their ground.

The second trip was Amtrak, a chief financial officer search. That is where transportation came from. You do not understand a national railroad until you have tried to find someone willing to run its money.

David Haley told me he would be a reference of mine for life. He is on every reference list I give, and he has been for twenty five years. He taught me more about how a search is actually conducted than anyone except Arnie.

And then there was San Francisco. Arnie’s search, with Laura Gassner Otting leading and me helping. A major internet organisation, one that still exists and still matters, whose work was internet ethics. Their chief executive was stepping down and we were finding the successor. A large, serious technology search.

I want to sit with that for a second, because I did not notice it until I wrote this down. In the late nineties I was helping recruit leadership for an institution whose entire purpose was working out how a new technology should behave. Nobody had a phrase for that job. There were no certifications, no frameworks, no degree programmes, and no job board.

Twenty odd years later I built the job board.

The office

None of this was a job description. I moved around the whole ecosystem of that firm and helped with whatever needed helping with. If something was stuck, I went to it. That is how you end up knowing conservation and transportation and academic medicine, and it is how you end up useful to three firms in one summer.

Not in the first year, but not long after I started, they gave me an office. It was right next to Arnie Miller’s.

I do not think anybody announced it or explained it. You are simply put somewhere, and where they put you tells you what they think. I sat next to him for years. I heard how he talked to clients, how he talked about candidates when they were not in the room, which is the real test, and what he refused to do.

That is the office I left from when I finally left.

How it actually ended, and how ExecSearches began

They offered to hire me permanently as an associate. I said no.

Not because I did not want to be there. Because I wanted them to build the website I could see, and to run it as a profit centre rather than a brochure. I had already shown them what putting a search on the internet did. I knew what the next thing was.

Karen Wilcox, one of the partners, told me I was a visionary. Then the firm decided to build a postcard website. Pretty, static, an advertisement for itself.

So I said fine. My partner had just been transferred to Florida, in recruiting, in a job I had helped him get. We were moving. And I kept working their searches from there, over the phone, with Alan Wiley and others, including work for the Robert Wood Johnson Foundation. I did not walk out on anything. I closed out every search I was carrying.

I gave six months notice and told them exactly what I was going to do.

On 1 September 1999 I launched ExecSearches.com.

Their postcard website was not finished. So they asked me whether I would build them a section on mine, and I did. For a while, ExecSearches.com was Isaacson, Miller’s web presence, until theirs was ready.

I do not think they believed I would do it. I said a date and I hit the date. That is the whole beginning of the company.

Isaacson, Miller is also where I met Laura Gassner Otting. She joined me later as the first Vice President of ExecSearches and stayed a couple of years, until she left to start her own firm.

Karen Alphonse replaced her. She has been with me ever since.

That is roughly twenty five years. She is now Vice President, Policies, Regulatory Compliance and Talent Management, carrying two roles at ExecSearches and one at GRC Careers. She is also, this week, the person taking our case to Harvard, which is the sort of thing that only makes sense if you know she has been doing this alongside me since the beginning.

People do not usually stay twenty five years. I did not build a company that people leave.

Why it still matters

I went in to learn executive search. I came out able to build the systems the profession runs on, having spent years inside conservation, government, health, higher education and technology, and having watched people at the very top of the craft do the parts of the work that cannot be written down.

What it all was

Look at the list. Universities. School systems. Academic medicine. Public health. Conservation and the environment. Civil rights and advocacy. A national railroad. The Olympic movement. An internet ethics organisation.

Every one of them is civic infrastructure. The institutions a society runs on and mostly does not think about until they fail.

That is what Arnie taught me the work was for, and it is not an abstraction. It is literally why the industry categories on ExecSearches.com are what they are. I did not design that taxonomy from a marketing exercise. I wrote down the sectors I had been taught, by being sent into them one search at a time, and they have barely changed in twenty nine years.

Arnie Miller is gone. Lisa Savereid is gone. What they did for me cost them nothing except the willingness to let a young recruiter be in the room, and to hand him the difficult ones. I have tried to run every business since the way they ran that floor.

AI governance is the newest piece of civic infrastructure. Nobody has trained for it yet. That is exactly the situation I was hired into in 1997, and I know what to do with it.

Hunt Scanlon Media wrote about what I built, on 16 September 2026. The story of how Arnie told me who they were is here: The New York Times of the Executive Search World.