Who’s That Gal: Tracy Cashman, Senior Vice President and Partner at WinterWyman

Occupation: Executive Search Consultant at WinterWyman
Alma Mater: Connecticut College
Current ‘Hood: South End, Boston

You’ve been in recruiting for a long time! What initially drew you to this career field?

It was a little bit luck and fate. The owner of my firm was seeking to hire recruiters from non-traditional backgrounds (especially teaching), who had the right interpersonal, organizational and self-starter skills. I was certified to teach high school but looking to explore roles in business. I went to an open house at the firm - they weren’t looking to hire a fresh grad but liked me enough to take a chance and the rest is history. I do think in some ways I was born to do this.

Talk to us a bit about a typical day for you. What does being a partner at WinterWyman entail?

I wish there was such a thing as a typical day! It’s all about which searches I’m working on and what stage they are at, but my day can consist of internal meetings with other members of my team, business development calls and meetings, managing current searches and screening candidates, traveling to our NYC office,  and the occasional volunteer activity (my company is very supportive of community development so I got involved with Rosie’s Place through them 9 years ago, and continue to volunteer there for 1 lunch a month).

How has the hiring process evolved since you started?

It’s interesting - while technology has certainly enhanced the process, there is no replacement for the human element in hiring...part of the reason I feel confident in my job security!


What’s the number one piece of advice you give to millennials seeking a new job?

Just like every generation, millennials get stereotyped, so I am not sure I would give them any different advice than anyone else. My one piece of advice across the board would be: sell yourself; don’t wait for the company to sell to you. You’d rather be in the position of having a company want to hire you and deciding if you want them.

For someone aspiring to become a partner at their firm?

In my firm, it’s not just about your performance: billing is important but it’s also how you give back to the company. Aspiring partners are evaluated on their team play, their involvement in company committees, their overall leadership, and their relationships with other groups. They are looking for well-rounded individuals that really demonstrate the company values.

Best moment of your career so far?

I’m not sure there’s one but I really, truly am proud of the deep relationships I’ve built, the departments and companies my work has helped build, and the individuals that I have placed into great roles. I just ran into a candidate on Mothers’ Day out with his family at brunch. I hadn’t talked to him in several years, though he is still at the company where I placed him. We chatted briefly, but then he came over on his way out to tell me how grateful he was and how I had legitimately affected his life. Having someone say thank you like that is really meaningful.

What advice would you give to your 21-year-old self?

Don’t care so much what people think of you and be comfortable in your own skin! I spent a lot of the early part of my career keeping a poker face, not sharing who I was, mostly because I was hell-bent on being taken seriously and felt any whiff of something that was not related to work would affect my credibility. I was the youngest person by far in my company, the first and only one hired right out of college, and I felt I had to play it very straight, especially as a woman. And honestly, I have met with women executives who are much harder to connect with than men, probably because they are thinking the same thing – that they have to be an “ice queen” to be taken seriously. If I could go back, I would have loosened up a little as I know being more myself would have allowed me to strengthen relationships with both colleagues and clients. 

Quick Questions:

Currently Reading: About to start reading All the Light We Cannot See and The Paris Wife for my next (2 separate) book clubs!

Favorite summer pastime: Hanging at West Canton Beach (aka my roof deck), golfing or hitting the real beach on the Cape.

Best meal in Boston: I am usually interested in what’s new and hot, but Giacomo’s South End is my local fave for takeout and Sorellina and Scampo are always on the list. SRV is my new go-to in my ‘hood.

If you could have dinner with any woman, who would it be? There are many, but if we’re including the deceased I’ll say Mary Todd Lincoln - only because I did a major paper on her in college and I’d love to see if I was right in my thesis! If we’re going with living, I might go with Sheryl Sandberg, as I’d be interested to hear more about any changes in thinking she has had after her husband’s sudden passing.