What REALLY Sets Women in Tech Sales Leadership Apart

Women in tech, believe in yourselves, shoot for the stars. You never know what you might hit. If you don't ask, you don't receive. So if you, if you need that part-time role or you want to craft up a role, you know, be bold, be bold and have the conversation because you can only get a no and you can move on to something else and that's okay as well. And you know, when you think you're far enough, be even bolder in what you're trying to achieve.

Andrea Breen is the VP of Government Solutions at The Objective Corporation. She has over 20 years of leadership experience at global software companies, and she's an absolute champion of women in sales tech. Hi, Andrea.

Hi, Tea. How are you? Good.

Thank you. I'm so excited to have you as our guest today. I know you've been such a great supporter of women in sales tech and anyone who you've mentored or you've worked with and, or they've worked with you over the course of your career is really very fortunate.

Thank you. I appreciate that. That's good.

Look, you've said to me in the past that many of the limitations that people face in their career have actually been self-imposed. And there was actually a time earlier in your career where you were really underestimating your own capability. Tell me a bit more about that.

Yeah, it's an interesting one. And I think it just, it really dawned on me after this event that I really was holding myself back. So. What happened was I was off on 12 months of maternity leave. And at that stage I was an individual contributor in sales and the VP of the region rang me to say that the leader that I would be going back to had left the business, had decided to move elsewhere. And so my initial reaction was, let me have a think about who I know who's out in the market, because I was going to be going back off mat leave in, you know, a month's time, but I was going back 3 days a week. And he said, hold on, that's not why I'm calling. I said, well, why are you calling? And he said, because we want you to consider doing the role. And I said, I couldn't possibly do the role because it's a full-time role. And he said, well, no, we're willing to support you to take the leadership role in a part-time capacity and we'll make it work. So it just made me realize then that, that boundary that I'd put on myself in that I had small children and I was part-time meant that I couldn't take the next step in my career. And I I was the only one that had put that boundary in place. No one else had. So it was a big lesson for me.

Yeah, it sounds like you lacked the confidence to back yourself and maybe even learn a new set of skills.

Absolutely. So, and it was the best opportunity. It taught me a lot going into a part-time leadership role because you really needed to be very, very strategic around your time and the boundaries that you had around your time. So it was a very interesting time for me.

And that's really interesting because, you know, you've built and led high-performance sales teams whilst you were working part-time, and that's really not the traditional path in tech sales. So tell me, what did you put in place to make that work? And even more importantly, you know, what should women be thinking about when they're negotiating flexibility in their own careers?

Yeah, I think for that to work, the key here was to put boundaries around the situation. So. Whilst you obviously need a level of flexibility to the business that you're driving an outcome for, you also need to be, there's a reason you're part-time. So that 3-day-a-week role, I really had to make sure that my team were aware of when they could get me and when they just couldn't and what the mechanism was if there was something drastic that happened in those 2 days that I wasn't working. So it's taught me then to pass that on to others because no one will impose those boundaries for you. You know, I came across a situation in my team the other day where I've got someone working 4 days a week, which is fabulous. I've got lots of part-time people that work across the team. And I'd put a meeting in on a Friday and they'd come back and said, I don't work on Fridays. And I said, well, your diary needs to be blocked out on a Friday and you need out of office on a Friday. So I'm a bit particular about the boundary side of things. And I think the other thing to make things work with part-time leadership or part-time in general is The team needs to be on board and be behind you. They need to understand the boundaries as well and the why, because I was juggling a young family at the same time and you've got to be fair to them as well as the team.

Yeah, absolutely. I think it only works really well when firstly it's well designed and then really supported, not just by the leader, but yeah, respected and supported by the entire team and organization.

Absolutely. It was a really successful period of time for me. So I look back and I feel like I've been very supportive of people doing part-time leadership roles because of that. And I think the more it happens, the more we'll see it across the industry.

Yeah. And you've actually been, well, you haven't been lucky. You've actually created a lot of your own roles as well throughout your career. And I think for, there's a lot of women that I speak to that feel quite stuck in the roles that are available to them. They don't all get that opportunity, like a great leader like you that's offering part-time roles, but how do you identify an opportunity? opportunity to craft a role and then how do you pitch it to the business?

Yes, it is true what you say there. I think I look back at my career, which is quite lengthy now. I've only ever gone into 2 roles where I've come in off the back of someone else being in the role. Every other role I've had has been newly created or a variation on a role. So I think that the role that you've got in mind has to present value and drive outcomes for the business. That is the fundamental outcome. This is why we're here to drive an outcome for our businesses. And a new role or a sort of fairly major modification to a current role, it takes really some time and thought to put behind it. How am I going to quantify the impact that this role is going to have? How's that going to be measured? Why would the business be supportive and under what conditions would the business be supportive of this? And then I pretty much, I mean, we're in tech sales. So I pitched the concept. This is the concept I've got. Here's the why, here's the value to the business. Generally, I've been very successful in those roles eventuating. And sometimes, if not now, the business says, we've got a few moving parts to get into play and then we can move forward on that. So I've done it across multiple businesses because as you get further into your career, that next step that may be very obvious early in your career, for example, you're an individual contributor. You're working for a sales leader. You see that as your next path forward. As you get further into the career, those next steps, they are generally not obvious. So that, that crafting of roles becomes very important for you because then you're satisfied in your role and the business you work for can see the outcome.

Yeah. Love that. And like you said, a lot of these roles don't actually exist until someone is actually proving the value of the problem that they're solving and then go to the You know, go to the business with a business case and it's all about the, you know, the impact and the outcomes, as you said, and not about going and, you know, just getting another headcount.

That's right. I think it's important on that scenario with that business case and so forth that we can get very set in it's about me. But at the end of the day, it's about me in the business driving an outcome for the business. And I think you've got to make sure you come with the lens of what the business outcome will be. Can't, it can't all be about you as much as we'd like it to be.

And, you know, Andrea, your career has been quite unique. I can, you know, you've had 2 really long-term stints with tech companies. So you've stayed long-term and, and I know that they've supported you through the different stages of your life as well. You know, the natural stages that we go through family, you know, then older parents and so on and sort of becoming a bit of a carer as well, but what should women be really looking for in an employer or leader to ensure that then their career can evolve with them?

Yeah. And it's interesting you say that because it is a journey that you go through. Like you say, different things happen in your life along the journey. The one thing for me that stands out is that you need to have value alignment. So I need to make sure I've got a company where my personal values align to the values of the business. That is where I've had the most amazing matches. I've had 10-year-plus stints. And I can see back to the roles that haven't worked out, that value alignment was not there. So when I look back, I think I'm not surprised that those few roles didn't quite work out. The other thing I see here too is that in tech sales, and it's an interesting industry in that salary is often, um, you know, lots of people are very, um, open in their salaries and so forth. And it's an industry like no other from that perspective that I've seen. But I see sometimes people chase the large packages. without looking at what the entirety of that role looks like. So they'll go and chase a really lovely large salary to find that the roles are a bit hollow. There's a lack of support from leadership. There's some cultural challenges. And they're the people that I see that are jumping every 1 to 2 years because they just can't seem to settle. So we need to look at roles in their entirety. It's not all about the money. It's a factor. We've all got bills to pay and lives to lead. But really that value alignment, you know, where that product sits within market, what sort of innovation is sitting in there. What the leadership looks like all comes into play in the decision-making on taking roles.

Yeah, it's all too familiar in our space, isn't it? The attraction of the shiny logos and big salary packages without really getting into one, most importantly, are we values aligned? Will I be supported to be happy and successful and to really carve out the next 3 to 5 years of my career? So really important for women that might be weighing up as well, whether to stay or move on, depending on what's important to to them right now.

It is the other thing I find too, Tia, is that people are quick to jump, jump out of a role. And sometimes I think, you know, you've got to put the effort in to make that role what you want it to be and the outcomes that you want. And I always sort of say, even in my teams, you know, don't complain about the business. You are the business. We are the business. So if we need to drive some change or we need to kind of work on some cultural aspects, then we need to drive the change. No one's doing that for us. So. I think sometimes people jump out of these roles a bit too quickly. I agree.

So win together, we go through the ups and the downs, you know, we're there to stay the, you know, the long course, um, and, and, and weather the, you know, the, the tough battles and, and don't just jump ship the minute something that's, you know, um, not perfectly aligned, um, to what you thought you were signing up to. So, and I think You know, when you've gone through a journey with someone, much like in life, you know, um, I actually said to a hiring manager just recently, I think, you know, when we've gone through something together where we've, you know, we've overcome a situation and then we've come through the other side, it just, it just brings you closer together. You feel more aligned to the business and what you're working towards together as a team. And I think that's really important as well. And you would have seen that multiple times over in a 10-year career span at, you know, one software company.

It is. You've got to build those internal relationships. And I think on the, you know, staying the course scenario, I'm very fortunate. I've got a number of colleagues outside of work that, you know, we can support each other through, through business and different ideas. But I remember her saying to me, because it's not always rosy in a 10-year period, there's times where you would think, is this, is this what I want to keep doing? Is this the place I want to be? Like, it's, it's a natural sort of thing. She said to me, Never, never leave in the tough times when things are terrible, but when things are great, if you still feel the same way, then maybe it might be time to think that you need a different challenge somewhere else. So that was great advice that she gave me. And also, you know, our CEO here where I am now, he said to me, you know, when people have made lots of deposits, he calls it, you know, in their career, when they need to make a withdrawal because they need extra time off or they're just not quite on their game because something else is happening in their life. Then, then, you know, you've kind of got the credits in play to work with, but when you've got very short tenure, it's very tricky when something might impact your life.

Yeah, absolutely. And I think there's a lot of give and take, but then over that time, trust builds. And I have that in my current workplace as well. So, you know, again, we're not, we're not looking at hours, we're looking at outcomes, but we again have that shared journey and experiences. We've got that transparency, that communication, and ultimately the trust. that also helps us to feel well supported to take the time when we need, no questions asked.

Absolutely. I mean, you feel like you can thrive in your career because you need your personal life and your career in sync. You know, I've never seen anyone who's got a horrible personal time really thriving at work. Like they go hand in hand. So we need to try and give people the ability to make sure that they've got that holistic journey. Going well for them. Yeah, I agree.

Andrea, I know that you've mentored many women in tech sales over the time. So what do you think that it takes or separates those that have long successful careers from those who may have suffered, you know, burnout or their careers have stalled or they've lost their confidence along the way just due to, you know, life taking over, maybe needing to take a bit of a A step back or a sidestep just to find that balance.

Yes. And I have mentored a number of ladies along the journey. I love mentoring. I think it's something that I will always do. I think people have mentored me along the way and I get as much out of it as they do from that perspective. I think the only way to achieve balance is to set boundaries. And my, my, my ladies that I mentor have that drilled into them. You don't get balance without boundaries. And when you set the boundaries, it impacts on someone else. Get ready because they're not going to like it, but you've got to stand firm on these things. So I learned the hard way on this a number of years ago. I certainly had let my boundaries drift and I was absolutely headed towards burnout. So it's something that I had, had to work on. And I think the other thing, and I know you're a big proponent of this, Tia, is that your health and wellbeing needs to be a factor. These careers in tech, they get stressful. They get very busy. A number of us are traveling a lot as well. And I think you really do need to focus on being the best version of yourself from a health perspective that you can.

Yeah, absolutely. Actually, that was my advice to, uh, I was speaking to a, um, an account exec who was returning to work this month after, um, her first baby. And, and that was my advice. Like, you know, you're going to go into the office, you're going to commute there and back. You're going to put in a full day's work. But then you've got to switch over. You've got to start thinking about the family. You've got to be organized. You've got to feed them dinner and really think about, you know, how sustainable that's going to be. Like, is that the environment that is best suited to your needs now? She was just comparing, you know, her current work situation compared to what she actually needs. And maybe she needed some more flexibility in the workplace, maybe to be able to work from home a few days. But so we talked through all of that, but also. The number one thing I said is make sure you look after yourself because whatever you do needs to be sustainable. And then you need to also be well supported, but it all starts with you. How are you looking after yourself? And that comes down to what you said as well, putting those boundaries in place, but looking after, you know, how you're eating, how you're sleeping, you know, what are you doing for yourself as well? So it's just not all work and work at work and then work at home.

Yeah, look, that's such great advice to a new mother that's looking at doing that because it's such a big impact in your life for those who've got children there. The other area I think for success, if I look at the mentees that I've had over the years, is that no one's going to take charge of your path and your career other than you.

Yeah.

So I think the ladies that I have mentored that take charge of their own learning and development paths. have really progressed. And I've got one in particular at the moment that I'm mentoring who I said, let's work out a development plan. I want you to draft the development plan, and then we're going to liaise back with your manager as well. And I loved that she came to me with a development plan, not just for her career, but it encompassed her whole holistic personal health. You know, not into a lot of detail on those side of things, but she was thinking about things holistically and I can see. That, that has made her very, very successful. So I loved that approach to a development path that was not just about work.

Yeah, I agree. So, you know, you've been in tech sales for a long time now, and I know things have changed along, you know, over the course of time, you know, and you're a great mentor to others and increasingly seeing more, you know, female and male sales leaders who are mentoring the next generation coming through. But, you know, who's inspired or mentored you along the way? And, you know, how's it helped to shape the leader that you are today?

It's a very easy question for me to answer, Tia, because I have been particularly fortunate with 3 particular people that have been a part of my career. And there's been others on the periphery as well, but 3 really stand out. The first one leads back to, you know, when we started our conversation about me taking on a 3-day-a-week leadership role. Now, that leader that I worked for was so supportive of that taking place, but has ended up being a lifelong colleague and friend to me. Now, Has followed me from a couple of businesses across into the one I'm in now. And he's someone that I can always go to, to bounce an idea off, will give me an honest opinion. And if I'm being a bit out of line on something, he feels he's not scared to let me know. So I think, you know, that realism comes into play with him was amazing. Big supporter of women in tech, which has been good. And another one that I had worked for in the last 5 years or so. He taught me a lot around the people side of things and the soft skills. You know, if one of the team members were really not quite performing where they needed to be, he said, you need to dig in and see if there's something outside of work that's impacting this. Because he said, you'll find that 9 times out of 10, that's the reason why. So very, very good at being very positive, really dealing with what makes people tick and why. And that's not something that I had been exposed to too much. You know, in tech sales, you can get very much into the numbers and the cadence and the KPIs and all the things that come into it, but let's really focus back on the people. So that's been really good for me as a leader to focus on that.

Wonderful. For anyone that's listening that's, you know, wants to get involved with mentoring in their own workplace, how do you go about it? How do you set it up so that it, you know, it There's actually some structure to it and some outcomes to it and benefits longer term. Do you recruit others to get involved as well to get, you know, different perspectives depending on, you know, what area of the business they're working in and how do you get the business to support you?

Yeah. So you do need some structure to a mentoring relationship. Otherwise it can end up in a fortnightly or monthly just to catch up. And that I don't think serves the purpose of what you're trying to do. So first one is I document. Actions and outcomes so that when we get back to that month, I say, now you agreed to do this. Has that been done? So that keeps people on task, which is good. Our organization here now has a structured program where they're matching up mentors and mentees. So that's been, that's been really good. But the other thing for me is there's still a lot of people in tech who are not mentoring, who are not, who are not doing that. I actively go in our business. If I can see people that, that I see that would benefit from a mentoring relationship, I start to do the matches. But the other thing, Tia, is that I've got people now that are quite advanced in their career that I mentor. I get them to be a mentor to someone else. So this keeps the chain moving and keeps it growing.

Yeah.

And I think I said to them, you, you are at a level where you can absolutely be a mentor. And a lot of them sort of look and go, I don't know that I'm experienced enough for that. You are absolutely experienced enough for that. So, and they get a lot out of it. So I quite enjoy. The matching of people. And I think the other thing, Tia, too, is that the mentoring and mentee relationship, it has a time span. And some of my people, I find I've got there and I've said, it's time for me now for you to go to somebody else to get this different experience. And so I'm not scared of letting them go and taking someone new in. I love that.

And for anyone that, like you said, that's considering mentoring and think they don't have enough experience, um, what I learned recently myself was that You only need to be one step or two steps ahead of the person that you're actually mentoring to be able to share your learnings and experiences. So, you know, some of the best sales reps are younger and earlier in their career because they're, and they're great to learn from because they're actually using modern processes, sales processes. And then equally on the other end of the scale, you've got more seasoned experienced sales reps or leaders that can impart on them, you know, tried and tested and no-fail processes that continue to work. And obviously the learnings throughout their careers, aspects of your learning journey, you can turn to different people, young and old. Well, I don't want to say old, but young and experienced.

It's true. Because I mean, if I look at, I generally have a rule of only have 3 mentees at a time because I find any more than that, I just cannot dedicate the time and effort that I want to them, but I've certainly got people at different stages and it's true to you. I learned so much from people who were just emerging earlier in their career about what drives them. And certainly, you know, on some of the tech side and some of the tools, I've learned a lot on, you know, some efficiencies that can be gained in different things. So it's been great for me to keep my skills relevant and valid as well.

Yeah. Excellent. Well, Andrea, I really enjoyed this conversation and I think it's hugely beneficial to hear from like people that have been there, done that, and, uh, and now paying it forward to that next generation, particularly of female, um, females in sales tech. Yeah, I love the work you're doing. It's incredibly inspiring and valuable.

Thank you. I'll look in summary, Tia, look, I think for me, for our women in tech, believe in yourselves, shoot for the stars, and you never know what you might hit.

Yeah.

And, you know, you don't ask, if you don't ask, you don't receive. So if you, if you need that part-time role or you want to craft up a role, you know, be bold, be bold and have the conversation because you can only get a no and you can move on to something else. And that's okay as well. And I think, you know, if I look at, you know, where I am now and the leader I have, you know, he said something to me. He said, if I stopped every time someone told me something couldn't be done in what I've built in our business. He said we wouldn't be anywhere near where we are. So I always say, be, be, be bold. And you know, when you think you're far enough, be even bolder in what you're trying to achieve. And success awaits. It's such an amazing career for our women in tech. We just need more people in tech. And please go out and be a mentor for someone. If anything out of this that they, our listeners and audience see today, you know, go and take the step of being a mentor because it is so much fun.

Yeah. And lift up all the women around you in tech sales, maybe not even in sales, but in tech. They've come into a fantastic industry. We don't want to lose them. We want to promote them. We want to see them be successful and we want to celebrate their wins collectively.

Absolutely. The industry is better for it. All of our customers are better for it as well.

They definitely are. Well, I think we could keep talking for so much longer. Very much a topic that we're both passionate about. And, um, yeah, I love your work, Andrea, and we'll have to do another episode again soon.

Sounds good. Thanks so much for having me on, Tia. I've really enjoyed it.