Recruiter Extraordinaire, Samantha Simmons

This week we interviewed Samantha Simmons, Chief of Staff and Talent Strategy Lead at Wayfair. Samantha's work journey on the surface looks pretty straightforward - she has been a recruiter for over 10 years and has seen talent spanning both for-profit and nonprofit industries. But when we took a deeper dive, we realized that Sam's journey is far from perfect. At the nucleus of her career lies a series of calculated risks that many would deem precarious, but would ultimately lead to her advancement and career fulfillment. She's got style, she's got grace, and she's here to tell you to take that risk you're scared of if you want to grow.


Tell us a little bit about yourself.

My story centers on a Southeast and Northeast set of experiences that have played a vital role in who I am and what I’ve been through. I have southern roots from my experience growing up in Central Florida and lived there up until my husband and I moved to Boston in 2012. I’ve been here ever since. My career in the world of talent began in recruiting in Florida and came with me up to Boston - I recruited across a variety of roles and organizations for nearly 9 years.


From an identity perspective, I’m a Black woman and often the only person of color in the room. I’ve gotten used to it. Not in a way that means it’s not uncomfortable or something that I ever forget but in a way that makes it manageable for day to day. At the same time, I remained focused on ensuring that my work contributes to shifting the racial/ethnic “makeup of the room” in the future, not only for me, but also for those coming up behind me.



What led you to your current job, and how did you end up in the field of recruiting?


Initially, I went to school in hopes of becoming a broadcast journalist, which is what I got my degree in. In my senior year of college, I got offered a job as an associate producer at a national affiliate network in Orlando and I turned it down. It was weird because this was precisely what I wanted but it didn’t feel right. So here I am, a senior in college, just months away from graduating and I'm wondering “What am I going to do?” I immediately started to think, “What transferable skills do I have?”


There was this awesome woman in the career services center at my school who pointed out to me that I already had experience working in higher education. I had a few jobs on campus, including one in recreation and wellness, so she recommended I follow that trajectory and then figure it out from there. So when I graduated, I went on to do a contract role at a university in nearby Daytona Beach, where I did facilities management and hosted athletic events at their sports complex.


During this time, I reflected on the work I had already done in college, especially when I was a tour guide working closely with the undergraduate admissions team. There also happened to be an opening for a role at private liberal arts college. I applied for the admissions recruiter role and ended up getting the job. That’s honestly how it began and my first experience in recruiting. This experience was very foundational for me because it helped to shape my understanding of the type of recruiter I wanted to be. I learned that I could pitch and sell them anything but found it more meaningful to have real conversations with people about their interests, ask where they wanted to go in life, and what factors mattered in determining their next step. It was always my goal to make my work more relational than transactional.




What would you say is one of the core differences between recruiting students at a university versus mission-driven organizations and for-profit retail companies?


They’re more similar than you think. Even with corporations, I find that there is a mission-driven element to it, but the way it manifests is more around brand affinity. There is more focus on understanding what they know and how they feel about the brand. Beyond higher ed and nonprofits, all organizations are making sure that they have a clear mission statement and perspective on why their work matters in the world. Employer brand is critical. So, yes, I think they’re pretty similar.



What are the top three qualities one should have to be a successful recruiter?

  1. You need to have a high threshold for rejection. I'm not trying to turn people off from recruiting, but you need to be okay with putting yourself out there, getting a lot of no’s and being comfortable with the unexpected. You have to be able to be resilient, bounce back and have a strong bias towards action and persistence because recruiting takes time.

  2. Curiosity. Whether you're working on a search that focuses on conservation wildlife in Australia or a role in operations and logistics at a corporation, a recruiter should approach every search with curiosity and invest in learning more about the role, the team and if applicable, the organization. The goals here are two-fold: getting a deep understanding of what the hiring manager is looking for and ensuring that you’re knowledgeable about the role itself.

  3. Flexibility. I alluded to this in my first point on rejection but being flexible will allow you to manage the changing tide with ease and make you more formidable in the future. Embrace the change, it’s what makes the work interesting and fairly, it can also make it tiring but I wouldn’t have it any other way.


Have you ever received work-related advice that you felt was misguided?

I consider myself a futurist. Almost every career change I have made has had a few concerned critics, questioning if what I was about to embark on was safe for my career. For example, when I decided to leave my last firm, I had a couple colleagues tell me that I was taking a risk by moving into a sector that I had minimal work experience in and recruiting for roles that I hadn’t recruited for before. I know that this advice was more centered on the fear that I could fail and looking out for me, but to me, it wasn't the right advice to adhere to.

With any career transition, you have to know what you’re walking into and weigh it all thoughtfully. If you feel like taking on a new role is the best thing for your career, recognize that it might mean taking a leap so do your research, so you’re making a smart gamble.

As a Black woman what is a valuable lesson that you can offer to other BIPOC women who are interested in recruiting?


Be clear about your limits. Whether it be in recruiting or other areas of talent, you quickly realize that you will be giving away a lot of yourself to do this work because it all centers around people. You have to learn quickly how to balance that out. You have to actively prioritize yourself and your family, and consider how you refuel for the energy that you're going to need to go into another day of work.




Can you share with us a time when you decided to take care of your mental, physical, and/or emotional health because of work? What tips or tricks can you share with our community that has helped you recharge?


In those situations, I've been fortunate to have surrounded myself with a group of people who can see what I can't often see in myself because I am too far into my stress. When this happens, there are visible signs of physical and sometimes mental distress, so having those people in your life who can be very honest and say, 'Hey, are you sure you’re okay?” or that they’re concerned is crucial. Even if you don't want to hear it, their advice and questions will linger, and eventually, it will force you to confront it.


It's also important to say 'no' to things. I often look at my calendar and realize that I should cancel a meeting or an event because there is too much on my plate. You have to be comfortable with that and letting go of the guilt that is usually associated with this is also essential too.


Are there barriers that women of color face in the field of recruiting?


In my experiences, I think there is but think this extends to any field beyond recruiting to be honest. For example, I’ve noticed how I have been put on the spot to give my opinion on a topics (sometimes related to DEI, sometimes not), and when this happens, I only ever speak for myself, but I know that others see me as a representative for all black women and I just cannot be that.

I am not a spokesperson for everyone that looks like me.

I don’t think it's ever done intentionally; it's just one of those situations where people of color by some sort of default are seen as representatives for the groups they identify with and it comes with tremendous pressure. People naturally have biases, despite their best efforts not to, and the best thing you can do is invest in learning how to be more self aware and check in with yourself regularly to question if bias is at play in your decision-making (especially in hiring!).

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