Episode Summary
If you are satisfied with the company where you work, its culture, and the people around you, and you do not want to leave it but want something new, you can change your role and even move to a completely different sector within the same company. In addition, you can explore other opportunities based on what motivates you.
But how do you identify what motivates you, and how do you identify the gaps you need to fill for your next role in order to be successful?
In this episode of Taking the Lead, Samantha DeStefano, VPII of Enterprise at Upwork, explains how you can figure out how to identify what motivates you. In addition, she explains how to develop your career successfully. Samantha and our host Christina Brady discuss the importance of motivators in career development and combining external and internal networks if you’re looking to change careers, and how to prepare for your next role.
Guest Profile
- Name: Samantha DeStefano
- What she does: Samantha is the VPII of Enterprise at Upwork.
- Company: Upwork
- Noteworthy: Samantha started her sales career as an IC, selling to organizations, both within the staffing industry as well as in the enterprise and the healthcare space. She spent almost 11 years in human capital management, moving through different roles. Today she is the VP of Enterprise Sales at Upwork, where she builds connected teams that create positive impact. As a leader who believes in creating opportunities for people and investing in their growth, Samantha co-founded LiftUp, where women in tech feel seen in their experience, connect authentically with each other, and grow in their careers together.
Key Insights
- Your career development depends on you. Samantha spent almost 11 years in human capital management at CareerBuilder. During that time, she changed roles nearly every two years and accepted new challenges and opportunities. According to Samantha, while the career development program at an organization is important, a large part of it depends on the individual. "Don't be fooled; just because a company might have a fully baked career development program, career development is also super unique. It isn't one-size-fits-all, and so, although there are going to be specific things, if you're on a track and you know where you want to go, there are skills, and there are things that you should be learning and developing to get you ready for the next job. But there are also individual things and things that, of course, make you unique that you either need to work on or lean more into. There could be things that you're bringing to the table that others aren't, that makes that opportunity more for your taking."
- If you want to develop your career, first find out what motivates you. While developing your career, you should know what you want to achieve because it will impact your success. People are motivated by different things, and that will indicate the next step. Samantha notes it is important to understand and be able to articulate what your motivator is and how you will get there. "Some people are motivated by title and responsibilities; some people are motivated by compensation; some people are just purely motivated by upward mobility and the challenge that you take on by going into new roles. And so, I think that I always knew, and I think it's important to identify what's important to me, and that might look different in the different seasons of your life too. And so, depending on what you have going on within your personal life or your professional life, those two things can influence what your next step looks like."
- Ask for what you want. If you want to progress or change your current role that you have mastered, you have to make an effort; no one will do it for you. If you openly say what you want, the chances are that you will get it. As Samantha says, if you show interest in something that is not your primary job, you will show that you are ready to learn more, and that is the first step toward your development. "I've been given the feedback; in my prime years where I was really moving fast, like every year-and-a-half to two years, I remember ending every skip level meeting asking for very direct feedback. What feedback do you have for me in pushing me to get constructive? A lot of times on the skip levels, you'll get the good stuff, and I'm looking for the constructive; what can I be working on? And the feedback I got there was like, never stop doing that — if you keep seeking to understand what you could be working on. And then, of course, the application is really important. So, having a really high application, getting that feedback, and then doing something about it in a way that you can showcase, 'I can take feedback, and I can grow, and I can develop on my own through the feedback that you've provided me,' is huge."
Episode Highlights
How to Identify What Motivates You?
“I’ve done that in multiple different ways. Sometimes I wasn’t sure too, but that’s where I leveraged mentors; I leveraged peer groups. I’m a big observer, so if I didn’t know what was next for me, how do I go and do ride-a-longs? If I was unsure about management, can I find some leaders that I trust or that I admire and see what they’ll let me come and sit alongside? I remember I very vividly wrote along on team meetings; I tried to weasel my way into some one-on-ones. How can I see what it looks and feels like to be a leader for more than the viewpoint of being the person on the team? And so, observing and identifying and taking that in to see what fits with you, what motivates you, and what excites you, is really important.”
Combining External and Internal Networks While Moving in Your Career
“There are ways to leverage your external network; it was super critical in my own career development. It’s using your external network; it’s using your internal in-company network, but there are ways to get experience and explore. Go explore what else is out there. If you’re in sales, and marketing intrigues you, find a mentor in marketing — not just a mentor internally at your company at marketing, but find one externally as well. And the reason I think external is so important is you want someone to give it to you straight that isn’t drinking the same Kool-Aid, isn’t working every day at the same organization, who’s going to help you see around corners, and give it to you straight on what it’s like to do those roles. Leveraging that external, identifying someone externally, as well as internally, you can gain experience, and you can gain observation. You can get a good sense of, ‘Is that path, maybe it’s a whole different path, but is that more fit for what I want to do and where I want to?'”
How to Identify Gaps for Your Next Role?
“It’s identifying, for myself, what am I not deeply knowledgeable about when I became a VP? And then, how do I dive into becoming deeply knowledgeable about that? Not just for now, so it’s helping me swim now, it’s helping me drive proficiency now, but it’s also preparing me for my next role. And so, you could apply that to any job; if you’re a BDR, and you’re looking to become an AE, how do you build a relationship with your AE where on a couple of deals, you’re seeing it through a full cycle? So, you’re not only dropping over the opportunity but, ‘Hey, this one, I feel really great about, can I see this through the negotiation, through the signature on the MSA?’ So that you can drive that experience and get one foot ahead or one step ahead before the promotion is even here.”
