EPISODE 643: Why Oracle is a Premier Women in Sales Employer with Tiffany Taylor

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Today’s show featured an interview with Tiffany Taylor, Group Vice President Sales Development, from IES Premier Women in Sales Employer Oracle. Read more about the PWISE designation and program here. The interview was conducted by Gina Stracuzzi, IES Women in Sales Program Director.

Find Tiffany on LinkedIn.

TIFFANY’S ADVICE:  “Voice your expectations, your aspirations, but also where you need help. Whether you are looking to move from covering maybe smaller accounts to enterprise accounts, it’s important that you’re great at covering the small accounts, but you got to let someone know that you’re interested in covering the enterprise accounts so that they can connect you with the opportunities and the people that are going to help you get there. If you have an interest in being a sales leader, you have to be a great seller. But it’s important that you let someone know that you have aspirations to be in leadership so that you can begin taking on some of the projects, some of the work, some of the mentorship that’s going to help you build those muscles and that competency so that people can see you in that role.”


Gina Stracuzzi: I am very honored to have Tiffany Taylor. She’s the group Vice President of Sales development at Oracle, and she is a powerhouse. I cannot wait to have a further conversation, if I’m being honest, because she, as Fred said, she was part of our round table of PWISE companies, and she will be featured in the report that will be coming out very soon. Welcome, Tiffany.

Tiffany Taylor: Thank you, Gina. I’m really excited to be here and thank you, Fred, for allowing me an opportunity to be a part of this great platform.

Gina Stracuzzi: Before I get into a deep conversation about what we’re going to talk about, I’d like you to tell us a little bit about yourself, maybe how you got into sales and how you got to be where you are today.

Tiffany Taylor: I will give you the short version. I guess first a little bit about me. I am a mom, and so as a woman in sales and a mother, that’s always a consideration for me. I’m a native of St. Louis, Missouri, and so about 12 years ago I relocated to the Northern Virginia area. Also, around that time I transitioned from a career in pharmaceutical sales to a career in IT sales. It was really one of the best decisions of my life, being a part of this sales industry and IT.

Gina Stracuzzi: Tell us a little bit about your particular job, because it really plays into the whole idea of PWISE and what makes a company a great employer.

Tiffany Taylor: I guess I’ll take a step back and tell you a little bit about how I have evolved in my career. I started at Oracle in 2013. As I mentioned, I transitioned from pharmaceutical sales, so I had an opportunity at Oracle, a unique opportunity, because most employers look for people who come from their biggest competitor. I was coming from an outside industry, and so I really appreciated the opportunity to learn and grow in the business, but I started off as a federal seller. Then my career transitioned, I went to work for a partner, also in the federal business. I got to understand the behind the scenes contractual and then also the structure and strategy that goes into making a deal profitable.

Then I had an opportunity to come back to Oracle as an application sales manager, and then I was afforded an opportunity to lead a small piece of our business development organization as a director. Then in 2019, I was promoted to Group Vice President. In my current role, I lead all of enterprise business development for North America cloud infrastructure. That includes industry verticals ranging from government and education, to healthcare, to financials, to manufacturing and transportation, you name it.

Gina Stracuzzi: That’s impressive. Well, you work with some of the young new candidates that are coming into selling, don’t you?

Tiffany Taylor: Yes, I do.

Gina Stracuzzi: I’m sure that things have changed over the last several years trying to onboard in a virtual world. Now probably they’re back in the office. It must’ve been different to go to onboarding in a virtual environment versus having them in front of you where you could talk directly to them. Was that a challenge for you?

Tiffany Taylor: It absolutely was a bit of a challenge. But Oracle has so many resources that we just simply had to think differently about how we onboard and develop people. Fortunately, we had technology on our side, and we have a great team of trainers and managers who were there to support the, we call them business development consultants, throughout their journey from day one. We really just leveraged technology. Also, I think it was really important to set clear expectations for what virtual learning and virtual execution looked like. As leaders, I think the biggest challenge was how do you connect with people who you’ve never met? How do you create a team environment when they’ve never met each other face-to-face? We got really good at finding creative ways to connect people.

Gina Stracuzzi: Well, that’s a nice lead in to being recognized as a Premier Women in Sales Employer, which congratulations by the way, on behalf of Oracle, obviously. What does it mean to you personally and to Oracle to be recognized as a premier employer for saleswomen?

Tiffany Taylor: Well, as a seller, we know that a third-party endorsement or a reference is everything, very valuable. People want to hear how you are perceived and how others experience you. I think meeting the qualifications to have that endorsement is really powerful. However, I would say that we’ve always done the work to check all those boxes. It’s really great to have the recognition and have all that work come to the forefront to be recognized. But the commitment has always been there. This is I believe essentially an endorsement that now helps to give additional credibility to some of the stories that people may have heard about experiences working at Oracle, particularly as women.

Gina Stracuzzi: Talk to us a little bit about what Oracle does to attract women into the sales profession.

Tiffany Taylor: One of the first things that I’ve seen, and whether it be through our, we call it the class-of program or as a sales manager, we go after people. Oracle is not shy. We are not a passive company. We spend time looking for talent. I just came back from a conference in New York called Sisters in Sales. That organization is designed to increase the ranks and mobility of women of color in sales. I think one of the first things we do is we meet women where they are. We participated in that event, but we participate in a number of events. Being in the spaces where women who aspire to be in sales are is one of the first things. That’s really important to show that we have a commitment to creating opportunity for women in sales. I think that’s one of the first things that we do.

Then I think the other thing that’s really important is representation. Our company is led by a woman. When women are looking for opportunity, it’s really important to see people who’ve had a similar or shared experience in those positions that you aspire to be in. Who greater than Safra Catz to look up to? I’m several levels below Safra, but even in my own leadership chain, I am able to see women at the senior vice president level throughout our business development organization. I have three women that I lead across our sales organization. I partner with many women who are at various levels from the individual contributor to the executive level. I think that representation is so very important to reflect the possibility of what a career at Oracle could be.

Gina Stracuzzi: It is great to know that there’s possibilities for your career, because there can be a lot of people at your level, but if you don’t see the opportunity there in front of you, it’s a very good point, Tiffany. What do you see as some of the biggest challenges women face in knowing success in sales? How do you personally address them?

Tiffany Taylor: The biggest challenge in knowing success? That’s a good one. I think it varies for a lot of people. One of the first things I would say is awareness. This ties back into your question about how do we attract people. I think a lot of women, they’re simply not aware of how great a career in sales can be. I know for me, it took me several years into my career to even begin to explore opportunities in sales because my perception of it was not one of value. The awareness is one of the first things that we have to get over. Really spreading the good news, and that’s where attending certain events, but also meeting women when they’re younger. Not even when they’re starting their interview, but even in high school. Talking about these careers, how lucrative they can be, but also the impact that you can have on the communities and companies that you serve. Because I think a lot of women, we tend to be nurturers and we tend to gravitate toward things that we feel like we’re having an impact and we feel like we’re making a difference.

I absolutely feel like I’m able to do that within sales. I think focusing on the impact to people is one of the things that we could do a better job of with branding, the sales role, particularly for women. Then the financial gains are certainly a plus, the financial freedom that comes from it. I don’t know that people are aware of how lucrative particular sales roles can be. But I really think awareness is probably the biggest hurdle. Then when women get into sales, you have to be comfortable being a woman. I think there are many times in my career when I’ve been in a room full of men, and it can feel a little bit different and maybe you feel like you have to show up a particular way to be heard and get past some of the biases that folks may have in those rooms. But what I’ve learned is to just really show up as my myself and step into all the privilege and greatness that comes with being a woman. I feel like I don’t have to be loud to be heard, for example, is one of the things that I’ve learned. Just maintaining that confidence in the fact that you belong in the room, even though it is dominated by men in many instances, is probably one of the biggest things that we have to overcome. I would just say the confidence in belonging is probably another thing that I know. I’ve struggled with it early on in my career, and I know that a lot of other women that I mentor, it’s something that they’re challenged with as well.

Gina Stracuzzi: No, it’s a real thing. We’ve had the Women in Sales Leadership forum for some time now, of which Tamara Greenspan is a faculty member, but we just recently started the Junior Forum, and one of the things that we’ve talked about is learning right away to use your voice and to not be intimidated and to advocate for yourself, because if you don’t flex that muscle early, it becomes a habit that you’re not doing it. Then you see women who are mid-career and they still don’t know how to do it. That is great advice, Tiffany.

What do you see in the women that are coming through your onboarding classes? What do you see them looking for? Have career goals changed or what they are motivated by, do you see that changing?

Tiffany Taylor: I do, actually quite a bit. It’s interesting and a little bit foreign to me, but I’ve learned to appreciate what our early career sellers are interested in. What I’ve found is that purpose is very important to the women that we’re bringing into the organization. To my earlier answer, I believe that fed that, my awareness of what women are looking for now. They want purpose. They want to feel like what they do every day matters. That’s how we get to the point where we have to incorporate what is the value that we are bringing. When I sell you this software, what does it really mean for your constituents, for your customers, for your business? When we’re able to do that, people feel that they are empowering others, which is very powerful.

Then the other thing they’re looking for is money. People want financial freedom. They want to be able to live well. The women that I’m seeing coming up, they value experiences, they value the travel, they value the connection. In addition to the purpose and the money, they want to have balance. Balance in being able to enjoy the fruits of your labor is also something that’s very important. I think there’s not much of an appetite for the road warrior or always-on type of working style that is so prevalent in sales. A lot of people feel like that’s old school and an antiquate way of thinking. I think women today feel like, “Well, why can’t I just be as productive as possible in the allotted amount of time and have a boundary between my personal and my private life?” I think that’s really the expectation now, which I think is appropriate.

Gina Stracuzzi: We hear that a lot, that the new generation coming in, they have expectations of, “This is my life. If you mess with this, you mess with my life.” It’s probably healthier in many respects than the way we approached things, which was, “Whatever you need. Whatever you need, even if it kills me.”

Tiffany Taylor: Absolutely. They are so conscious of self-care, for example. Or we have a thing called a recharge day across our company. But it is essentially something that came out of feedback that we received in employee surveys, and people need time to reset. They demanded it. Because we listen and we really take to heart things that come out of employee feedback, we now have a recharge day. If you feel like, for whatever reason, there’s not that balance that you’re seeking, you can simply take a day, no questions asked. Now, it’s not unlimited, but it is respected. I think there are certain environments where even taking time off feels like you’re…

Gina Stracuzzi: Punitive at some point.

Tiffany Taylor: Like you shouldn’t be doing it. You feel guilty about taking vacation, or you’re always plugged in. This generation, this new crop of women, they have set a hard line in the sand, and saying like, “This is my life and I want to love my work and incorporate it into my life, but it will not be my life.”

Gina Stracuzzi: Good for them.

Tiffany Taylor: I know. I’ve gotten better. I think there’s always something to learn from people no matter where they are in their career journey. I think that perspective is so valuable. I live with two of those younger women, and so I hear it at home as well.

Gina Stracuzzi: Well, I have a 21-year-old as well. It is quite funny sometimes when she’ll complain, she’s in college, but she works. She’ll say something about something in the workplace, and I’ll be like, “That’s just how it is, honey.” “No, that’s not right.” “Yeah, good luck with that.” I think if they come away with an appreciation of how to speak up for what you want and need, but learn that balance of it’s a two-way street, so you got to give a little to get what you need, they could be highly successful.

Tiffany Taylor: Yeah, absolutely. As a leader, what I have learned and really come to appreciate and respect is you have to create a space that allows people to speak truth. Because had we not created a space where people could voice those opinions, and then we actually took action on it, you’d probably just have attrition and not understand why, because we’re not respecting the boundary that we didn’t even know existed with our colleagues. Creating that space for people to speak up and speak truth to leadership, and have leadership be open to pivoting, if necessary, or stopping or starting or extending some behavior, is really important. I know for me as a leader, it’s one of the things that I hold to be very dear, and I consider it one of my leadership principles. But what it does is it creates trust, and this conversation is not even just about attracting women or talent, but top talent.

These people have choices. They have choice in where they are highly desirable for any organization. They build value no matter where they go. It’s really important that they feel like they work in a space where they can trust leadership, and there’s mutual accountability. That’s also something that I think is really important, because, to the point you made about it’s a give and take, with the mutual accountability, I think that’s how that manifests for me. Setting a very clear expectation and getting agreement, and then checking in to make sure that we are on track to hit those expectations. Then if we’re not, how can I step in to help?

If there’s something I can do to step in to help, rather than people saying, “I got it. I’m fine, I’ll figure it out,” we have to create a space where people feel vulnerable enough and they trust you enough to say, “You know what? I’m really struggling with this thing. That’s where we could use some help.” I always tell my team, “Don’t suffer in silence. I want to hear what your challenges are.” But those are the types of things that I believe are making a difference to women not only considering careers in sales, with Oracle specifically, but also staying with the organization.

Gina Stracuzzi: We all know that that’s key, hanging onto good talent. One of the things that we really espouse in the forum is the grass isn’t greener somewhere else. If you’ve got issues and you’re not talking to anybody about them, to your point, if you’re suffering in silence, then no one can help you. It’s not fair to the employer, but it’s not fair to you either, because you’ve got some tenure there and you’re moving forward, but this is frustrating you. If you just leave, you haven’t accomplished anything. There are challenges with every employer. Just like anything else, there are going to be good things and bad things, but you’ve got to speak what you need, as you mentioned.

Tiffany Taylor: I think that’s really important. It is such an important point that you’ve just made. It’s unfortunate that I can predict this sometimes, but what I see happen is people who leave for just the reason that you mentioned. Maybe they didn’t voice their concerns or they suffered in silence, and they struggled and maybe didn’t feel like they had a safe space to say what they needed, or to ask for help. Because in some organizations it is frowned upon to say, “I don’t know how to do that.” But people will leave and they’ll go and get another great job. Then I look at their LinkedIn, and every 11 months or so, they’re changing jobs, because the challenge that was there initially was never addressed. The growth that needed to happen to close whatever that gap was, it was never bridged. I really think it’s important for both the employee and the leader to make sure that those needs are verbalized and addressed.

Gina Stracuzzi: That is absolutely spot on, Tiffany. When I meet amazing women like you, I always think, “Man, if I had somebody like that as my leader coming up, my career might’ve gone different ways,” because I worked in really male-dominated industries and at a time when people could say whatever they wanted to whomever they wanted, and there was no recourse, there was no even a slap on the hand. It wasn’t always pleasant, so it didn’t lead me necessarily to great growth inside of corporations. I feel profoundly lucky for all the women that are working under you, that they get this opportunity to share what they need. It’s a learning process for everyone as things change. Just your face when you said, “Yes, things have changed,” you could see how different classes of new salespeople come in. They all have different expectations and different needs, and you seem like a perfect fit for helping them become everything they can be.

Tiffany Taylor: Yeah, that’s the goal. I definitely feel like the role that I’m in now is a sweet spot for me. I feel like it’s a culmination of everything that I’ve gone through throughout my career journey, both in and outside of sales. I’ve been the benefactor of working for a lot of great women. I’m also a hodgepodge of many great lessons that I learned there. I had one great leader in pharmaceuticals. Her name was Cheryl Shaughnessy. I remember her sitting me down, and this goes back to a point I was thinking about self-awareness and being coachable, and I thought I was doing a fantastic job, but I was very regimented and I guess wasn’t soft enough, wasn’t empathetic enough. She introduced me to the concept of EQ or emotional quotient, emotional intelligence. I’d never heard of it. I didn’t really even understand why it was that important.

She told me, she said, “Tiffany, people don’t care how much you know until they know how much you care.” That was so profound. I’ve used it many times, even coaching leaders that I work with, both male and female, because it’s so important to treat people as people, and have some empathy. You can still have empathy and execute with urgency. That’s my mantra, but that just reminded me of that lesson that I learned early on in my sales career.

Gina Stracuzzi: Clearly, you’ve internalized it and used it, and it has made you very successful, which is wonderful. Well, you have done a fabulous job of representing Oracle, as to why you are all a PWISE company. I can’t wait to see what else comes out of the PWISE collaboration and all the great things we’ll accomplish together. We like to leave our audience with one piece of advice from our guests, something that they can put into place today to maybe further their career or close a big sale. What piece of advice do you have?

Tiffany Taylor: Something that could scale across the spectrum of what you mentioned is speaking up. It’s very important to voice your expectations, your aspirations, but also where you need help. Whether you are looking to move from covering maybe smaller accounts to enterprise accounts, it’s important that you’re great at covering the small accounts, but you got to let someone know that you’re interested in covering the enterprise accounts so that they can connect you with the opportunities and the people that are going to help you get there. If you have an interest in being a sales leader, well, you got to be a great seller. But it’s important that you let someone know that you have aspirations to be in leadership so that you can begin taking on some of the projects, some of the work, some of the mentorship that’s going to help you build those muscles and that competency so that people can see you in that role.

Oftentimes people do see things in us that we may not see in ourselves. It’s because those aspirations and those things that you’re passionate about are coming through. They’re manifesting through you, through your actions, how you interact with people, but it’s really, really important to voice it. I would say no matter what the situation is, just make sure you voice those things. Even in closing a deal, you have to be open and communicate with the customer. If you need something to happen by a certain timeline, and we are all notorious for trying to get the customer to do things on our timeline, but if you want value with that customer, then it’s important that you say, “It would really mean a lot if we could get this done by the 26th. What can I do for you to make that a reasonable ask? Or is that a reasonable ask? How can I help you?” Making sure that your intentions are known is probably the best thing we can do. That goes back to your comment earlier about the importance of advocating for yourself.

Transcribed by Mariana Badillo

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