Gender diversity and inclusion have become increasingly important in various industries recently. However, the finance sector has traditionally lacked gender diversity, with women being significantly underrepresented in leadership positions. Developing and empowering female leaders in finance is not only a matter of equality but is also crucial for the industry's strategic growth. So today, Sayle Hutchison, Chief Financial Officer at 15five, joins us to discuss the importance of diversity in the workplace, empowering women's leadership within an organization, and the need to cultivate the next generation of female finance leaders.
Sayle is an accomplished operations and finance executive with over twenty years of experience in the international high-tech industry. She has a demonstrated track record of implementing operational changes, improving efficiency, and driving growth. In the past, she has held various leadership positions, including Vice President of Finance at ExtraHop, Outreach.io, and Avvo, as well as Director of Finance at Microsoft.
Welcome back to CFO Weekly, where we're talking with financial leaders about how to build efficiency in their teams, create time for strategy, and ultimately get results with your host, Megan Weis. Let's jump right in.
Megan - 00:00:31: Today, my guest is Sayle Hutchison. Sayle is a 25-year veteran of high-growth technology companies, from Microsoft Azure to her current role as CFO at Series C Heart-Centered Leadership Company, 15Five. She has a proven track record of driving operational change, efficiency, and growth evolution. Sayle, thank you very much for being my guest on today's episode of CFO Weekly.
Sayle - 00:00:57: A pleasure to be here. Thanks so much for having me.
Megan - 00:00:59: Yeah. Today we're going to be talking about diversity in the workplace and specifically the importance of developing the next generation of female leaders in finance, as well as the importance of leading with heart. Sayle, this is such an important topic for all of us, and I'm really looking forward to our discussion today. So let's get started. Great. First and foremost, and as always, let's start with you and your story and how you got to where you are today.
Sayle - 00:01:25: Yeah, great. It's been kind of a wild ride. And I will say that I really landed in my first job, I think when I was 26, and it was a startup, although it was a massive startup. So it was a joint venture between Microsoft and Accenture. And we started global from the first day, and I was the hundredth employee. And I started off as a senior financial analyst and I went on a journey with them for 11 years and, went from zero revenue to a billion and a hundredth employee to 10,000 employees. And as part of that journey, we went public, we went private, we implemented Sarbanes-Oxley, we implemented SAP, we had these really big, massive scaling initiatives, and I got a front-row seat. And so I started as a senior financial analyst, and I ended up as the Director of Global Operations.
Megan - 00:02:19: Is that the start of Avanade?
Sayle - 00:02:21: Avanade, yeah. That's a good day. And I also had the good fortune of joining Microsoft after that since and began as one of the first three finance people in Azure in Microsoft, and started when Azure was a couple of racks. And when I left, my CapEx budget was in the billions. So it was a massive scaling effort and cost consciousness bringing cost-consciousness to the Microsoft environment, which was not the software model. So it was a super fascinating experience. And then for my 40th birthday, I gave myself the gift of startups. I really wanted to understand the venture capital world and I wanted something smaller. And I really loved the scaling experience. And I've been in the startup community for the last 10 years and have grown from the head of FP&A to CFO.
Megan - 00:03:17: So what made you want to get involved with startups?
Sayle - 00:03:21: That's a great question. And I think it really has to do with how I value my time and how I want to spend my time. And what I love about startups is finance is such a critical aspect. It's not really a back-office function. The fundraising effort and understanding the unit economics and understanding the competitive landscape and the business model, it's a critical function to the thriving and survival of a startup. And I really love being a part of that. And I really love how directly I can impact our customers and our business. And it's not abstracted in the same way it is in bigger companies. And you're not necessarily a small part of the picture. You're at the table and a big part of the success of the company, which I love being a part of.
Megan - 00:04:08: And today you're the CFO for 15Five, correct?
Sayle - 00:04:12: Mm-hmm.
Megan - 00:04:13: So tell us a little bit about your role and what it is that 15Five does.
Sayle - 00:04:19: Sure. And so I am CFO, but as is the case with startups, you own probably a lot more than accounting and finance. So I own accounting, finance, legal, IT, rev ops, and data. And I think- Oh boy, I've been with them for a year and a half. And it in itself is an HR software that helps connect people in a remote environment and promote and create heart-centered leadership and really is about connecting people and helping managers be effective and creating culture and feedback loops that allow companies to really thrive and create an HR ecosystem of connection. That includes performance management, employee surveys, weekly check-ins, one-on-ones, OKRs, career frameworks, and career hubs.
Megan - 00:05:20: And you mentioned heart-centered leadership. So why is it that that's not the default these days? Why does that seem so hard for companies to grasp and implement?
Sayle - 00:05:32: It's such a great question. For some reason, the corporate cultures that certainly I grew up in had a very narrow allowance for the human being. And it was very work-centric and very focused on compartmentalization. What went on in your personal life didn't impact your professional life. And we focused on work and not necessarily the people involved in the work. It was certainly the school in which I grew up in. And as we've gone to more of this 24-hour life cycle, as we've gone to more of a remote hybrid environment, we're in each other's lives in these deeply personal ways. And I know for my part during COVID, I had people on my team whose kids were right next to them going to school. And so really the separation between work and home is almost impossible to maintain in the modern workplace. And so our personal lives have to play a part in our professional lives. And why wouldn't we want to have as much thought and care in where we spend our days as where we spend time at home? And so I think the demand of the younger generation, which I love, some people complain about millennials and expectations, et cetera. I think, pushing the boundaries of what is humanity and how we show up at work in a humane way. It's a powerful force and I think a force for the good.
Megan - 00:07:01: And can you tell us about your experience in developing female leaders in finance and how you all approach this goal at 15Five?
Sayle - 00:07:10: Sure. That's something that I've thought a lot about and that I've personally had to experience and go through as a person on my own career journey. And there's been a couple of powerful articles for me in the recent future with Show of Presence Now, which is there's a McKinsey study that they do every couple of years. And there's a big gap between men and women in their transition to their first management role. And then there's a big gap in the kind of feedback we receive in between men and women. It's quite a bit different. And so for my own part, making sure that I make time for the women in my life, and invulnerable in my own experience. And what I've navigated as I've grown in my career has been super critical, I think, in normalizing what it is to grow in the workplace as a woman. And the kinds of conversations I have found are not necessarily different, but there is a crisis of worth in the women that I have personally managed in my own journey, being able to fill out your performance review and said, yeah, I did great at that. And here's the impact I had. There's a comfort level that really has to be addressed. I think when you're managing a woman in a way that's different from the men that I've managed in my life. But what I can't do is just have that conversation. What I owe them both is, how do you think about the business model? What's the strategic vision for the company? How do we think about craft and being excellent at our craft? And what I found is that you have to have both of those conversations to do the most service to the women who work for you. And they're not sequential, they happen both. Your IQ is there, your capacity is there, and the ability to understand the business problems and to grow intellectually, it just needs to be met with being able to say out loud, your value, your strengths, and your accomplishments with a fair amount of effortlessness. And that's been a journey, I think, for most of the women that I've managed.
Megan - 00:09:16: Why do you think it is that women have such a hard time being kind to themselves and speaking highly about themselves?
Sayle - 00:09:23: Jeez.
Megan - 00:09:25: I mean, I know as a woman that I have that problem.
Sayle - 00:09:28: Why would they find it easy? Certainly, I come from a very traditional southern family. And in my upbringing, the women cooked meals and cleaned the dishes, and the men sat at the table and smoked cigars and drank brandy. The expectation of me having worse is something I've had to reckon with and really earn from myself. And there are so many societal messages about the role we should play and how we should be of service to other people. There's very little training conditioning support. This is who I am, and this is myself, and this is what brings me joy, and this is what brings me passion for me, myself. And so I think it's a generational journey. Certainly, my mother didn't ask these questions. My grandmother for sure didn't ask these questions. And this is the evolution of becoming ourselves and becoming a whole people.
Megan - 00:10:23: And why is it that we see the difficulty in women moving up into managerial roles? Because I mean, studies indicate that they make great managers. So why is it in finance in particular that we don't see a lot of women moving up, or at least not as quickly as men?
Sayle - 00:10:44: At least not as quickly as men, for sure. Yeah. And it's such a powerful question. And when I think about it in my own opinion and my own experience, if you don't have it by this, I mean, if I don't have the capacity to say, here's what I'm great at, and here's why you should trust me, and here's why I'm going to do great. And I'll tell you this example of a woman that worked for me and she blew my socks off, there was a senior manager position that came open, and it was quite a bit of a leap for her. And what she did was she took me into a room and she said, I know this is a big leap, and I know I'm asking you to trust me on this, but I'm telling you, here's what I'm gonna do to prepare myself, here's why I think I'd be great at it, and here's the risk I want you to take on me. And it was such a powerful moment of her own claiming, of her worth, asking for what she thought she could do, taking a risk, asking for my support, and being truly confident in her capacity to take that role on. I'm telling you, she got the job. And that is the personal journey that I think we need help. We need to help each other, and we need to hold ourselves accountable for that's what it looks like.
Megan - 00:11:58: So do you see with younger generations that the problem is subsiding with women or is it still there?
Sayle - 00:12:05: Yeah, I think it is still there for sure. I know that because we have women's events at 15Five, we did something right before the performance review where it was a claiming your strengths exercise, where we got broken into small groups and had to tell each other what we thought we were good at. And it was a super powerful experience, number one because people really struggled with it. And number two, I still see my highest-performing women consistently ranking themselves lower than I rank them. In the performance review, we have a shared set of questions and they ranked themselves and I ranked them. And two of my highest performers, I had to sit down and say, okay, I'm going to go through this with you and I'm going to show you what I think of you. And let's talk about the struggle for you to think that about yourself.
Megan - 00:12:50: And in your opinion, what are the key attributes of successful female leaders in finance and how can these be nurtured and developed?
Sayle - 00:13:01: Well, I think successful leadership from a craft perspective is pretty gender-neutral, right? If you're thinking about finance and wanting to have influence across the organization and thinking about a CFO or a leadership path, understanding your craft and being that guardian of the business model where you really understand all the ins and outs of what's going on in the business and can help people measure that, you know, that's a craft. And it is easy to default to managing confidence in women and ignore the craft of what it means to be the guardian of a business model. And it's super critical to have excellent craft in leadership. Some of the things that I really look for also are your ability to be influential across your peers. And can you listen and can you contribute and can you hold your own opinion and help shape the conversation? Those things are, what women are super capable of doing. There's no question of capacity for me. The things that I think I have personally struggled with, are to not hold on to difficult decisions and just stay grounded in the business strategy and vision, make decisions, and move on. So what do you need to learn? What did I need to learn in order to give myself that confidence, in order to give myself that comfort that I'm going to do my best and surrender to the best? And the other thing I look for in a leader, irrespective of gender, is do they understand how to deliver feedback. Can they attract and retain high-performing people because they are themselves? can spur and create creativity in others and facilitate conversation. So I think... The specific aspects of what makes a great leader are very, very similar. I think where women can shine, or they are expected to shine, also, is around compassion and creating humanity, and extending the conversation to the whole person. And you can argue about whether that's a fair expectation, but it certainly is a requirement of being a female leader in the moment.
Megan - 00:15:16: And I think as females, we're still expected to take care of families at home. I mean, we saw during COVID that it was the women's obligation a lot of times to step back from her career and do the teaching that was required because the kids were at home. So what can organizations do to make things easier for women that do have families at home?
Sayle - 00:15:41: It's such a great question. It was such a powerful experience for me, both the men and women in my life who had small children during COVID, like, oh, that looked terrible. That looked terrible. And I had to grow in my compassion. And actually, that experience made me a better leader because I find that the more compassion you can have for your people that you know deliver work, the more gratitude, the more loyal you, the more trust, the better their working relationship is, and the more they can be unleashed. And I also, for one, question the gender distribution of tasks and our willingness to sign up for all of this and all of that. It's not for me to judge anybody's individual contract, but the expectation that we can do it all, I think, is toxic for women. And it's always a balance of sometimes I'm a great wife, sometimes I'm a great mother, sometimes I'm a great employee, and sometimes I'm not great at any one of those things, depending on the rhythms of my life. So I think self-compassion in that balance is super critical. And from a workplace perspective, the women I know who have children and especially young children, require flexibility and, happily for the way that we're oriented. We're remote first, so people are in the home predominantly and also we're across multiple time zones. So the idea that you have to work from eight to five, I think it's a super restrictive model for people that have multiple kinds of responsibilities. And I trust the people to juggle what they need to juggle and to ask me when they need grace and to work with them. If you've got a great employee, I'll bend over backward.
Megan - 00:17:21: And how does 15Five prioritize diversity and inclusion in the workforce? And what steps have you guys taken to attract and retain talent?
Sayle - 00:17:31: Yeah, it's D-E-I-B is such a, I struggle with the word. I love all of the pieces and when something becomes a four-letter acronym, I worry about the heart-centered focus on the actual activities that go into creating it. But from a management team, we have a commitment to diversity. We actually have three women on our ELT of seven and a number of people of color. So my hats off to Jim and to David. Having a diverse leadership team has been a priority for them, and that's across the board. And we also have made a commitment to publicly disclose our diversity metrics and to hold ourselves accountable for moving in a particular direction. We have a commitment to move and have representation that reflects the greater population. So that's the metrics. Anything you measure, you can move. And if you don't measure it, you're living in a lack of motivation and a lack of commitment. So we've got a commitment there. The other thing we've done is been very clear on our leveling guidelines and our leveling expectation and the compensation that goes with that. And we don't necessarily have the inequity around pay that some people evolve into because they have that consistency of measure. And we also look to make sure where people are in those bands and to see if we have outliers and inequities that we need to solve, which I have a lot of respect for. And it's still a work in progress for everyone. But I'll say that the kind of commitment and the kind of accountability that I've seen from David and Jim, who are the founder and COO and president, and also from Jenny, who is our Jenny Yang, who's our head of people, this is very important to them. And so I get to participate in that with them. I joined where that was already a mandate and it's something that I believe in personally, so powerfully. And that's where I get away from the concept of DEIB and I get to my personal commitment for the kind of world I wanna create. And for me and the leaders, we've made a commitment that our panel will be diverse of people that we interview and that we focus on the sense of belonging on the other side of, do we have an open and welcoming, and inclusive environment. Do we meet people where they are? Do we allow them to be who they are? And that, I think, is the part of the equation that is really hard to get right, and where most people and most companies miss it. And having been the only woman in the room for 20 years of my 30-year career, the welcoming and the belonging piece is as important as the opportunity.
Megan - 00:20:23: Why do you think that piece is so difficult for companies to get right?
Sayle - 00:20:27: I myself wanting to ask you the same questions. At Avanade, which is a company that was very good to me, I received a lot of career success, that was also extremely male-dominated when I walked in the door and the only company swag I received was a button-up-collared golf shirt. That's a loud statement. When 95% of the men left on Friday every quarter to go play golf and no women were invited, that's a big statement of belonging, and whether or not I'm included in the culture. I think there is a lack of awareness on how these choices really do create belonging. And it is a life commitment from leadership to watch that boundary and to watch who's included and to be purposeful and mindful about it. And it's a hard bit of personal development work that we all owe, I think, to the world we want to create.
Megan - 00:21:24: And how do you ensure that all employees at 15Five, regardless of gender or other factors, have access to equal opportunities for growth and development?
Sayle - 00:21:34: Wow, if I knew that I would be answerable. I can't is the big question. I think there is a commitment to do so and a lot of the work around the structures. But the most powerful impact I think that Jenny and I have as a collaborative force is taking the time to actually reach out to the people and to do the mentorship and the coaching and to create the ERGs and to help create that sense of welcome and belonging and the training in our managers to really examine where we might have implicit bias and where that boundary of what it looks like for a man to be qualified and what it looks like for a woman or a person of color to be qualified, make sure that wall doesn't move and then really hold ourselves accountable for the metrics of are we seeing the right representation of women versus men? How are we seeing the people of color within the organization progress? And what do we need? to do from that data and from that information and take that action piece and hopefully make the impact that we intend and that we want to see?
Megan - 00:22:48: And throughout your career, how have you addressed resistance or pushback within an organization when it comes to promoting diversity? There must be times when you feel like you run into a wall or...
Sayle - 00:23:01: Sure. And there are times when I've personally run into the wall. I think I was so relaxed when I hit the age of 40 and it was no longer the rumor that I was having some kind of extramarital affair with whoever was my boss at the time to receive my promotion.
Megan - 00:23:15: stuff like that is just so ridiculous, but it's like women face that all the time. 100%.
Sayle - 00:23:22: So there's a personal commitment for how I faced it and have faced it. And I used to take it a lot more personally and it used to impact me a lot more. And so I think my personal work has been if that's something that you hold and that's a belief that you hold, then that gives me information about you. It doesn't actually give me information about me. And so holding that internal sovereignty of value and worth, and not getting lost in the opinions of others. At the end of the day, it's been my commitment to my craft and it's been my commitment to my journey and what I want to learn. That has seen me through those roadblocks, and not getting distracted by someone else's prejudices. And that's been a super critical part of my personal development is what somebody else says about me or thinks about me or over talks me or does something that I take as being essentially sexist or discriminatory. It gives me information, but it doesn't give me pain, and When I meet those things, there's sometimes that I get too into my advocacy and I give away my power and I give away my effectiveness of influencing. And I'm OK with that. And finding the right balance between influence and advocacy and still staying in my passionate connection to equality, regardless of race or gender or orientation, how to walk that and still being in my integrity, that's a constantly evolving journey. And as I've become more senior in the organization, I can afford to be more radical. And I also feel called to be so. And that is the way I choose to show up. And I allow the chips to fall where they may.
Megan - 00:25:18: And what advice do you have for other aspiring female CFOs or finance leaders that are listening today?
Sayle - 00:25:27: I think for me, there's a Brene Brown quote or recommendation, which is, to take a one-inch square by one-inch square piece of paper, and write the names on it of people whose opinions you truly respect. And those are the people that you go to when you are struggling with accountability or you are trying to connect to your worth or trying to understand what you have to learn or grow from a situation. And I've been fortunate to have some really amazing, powerful women who I can call when I'm in the question about how to deal with a particular kind of performance management issue or... when I'm struggling with my own sense of conviction or needing to let go of something I'm holding onto and worrying about too much. So think about your square squad. And those are also people when you're in the room and you're getting talked over, you're getting dismissed. Is this person, someone whose respect truly can penetrate me? Is there something that I need to learn from this person? Or do I just disregard it and move on? And having that close side of people who I can turn to has been a critical part of my ability to grow and thrive through adversity. And the other thing I would say is... your personal development of confidence, worth, craft. Stay focused on that and commit to your own journey. And when you get feedback, stay curious and think about whether it resonates with you and discard the rest, at the end of the day, it's your personal, this is your life, right? It's your personal commitment to your life and what excites you and what brings you joy and what makes this life one worth living. That's all there is. It's not necessarily the title or the positional authority. Does this make you wanna wake up in the morning?
Megan - 00:27:25: So last question, what is it that you want your legacy to be? How do you hope to leave the professional world a better place?
Sayle - 00:27:33: Oh gosh, that sounds very ambitious, but I'll say.
Megan - 00:27:39: Sounds like you're already making it happen.
Sayle - 00:27:44: my professional development, to CFO. It's been a very lonely journey, and I am very committed to helping the people that come up behind me or later than me to help them through that journey with some support and some languaging of the emotional experience. And then, of course, women can be successful and be leaders. Of course, we can. Of course, you're brilliant and have the capacity to contribute at the level of anyone else in the room. How can I help you see that as clearly as I do?
Megan - 00:28:25: Thank you very much for being my guest today.
Sayle - 00:28:27: Well, thank you so much, Megan, for having me.
Megan - 00:28:30: Yeah, I really enjoyed speaking with you, and thanks for finding the time to be here with me today and giving back by having this conversation. I wish you and 15Five all the best.
Sayle - 00:28:40: Thank you so much.
Megan - 00:28:41: And to all of our listeners, please tune in next week, and until then, take care.
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In this episode, we discuss:
The significance of diversity in the workplace
Empowering women leadership in finance
Developing the next generation of female finance leaders
Embracing Heart-Centered Leadership Within Finance
Many corporate cultures have traditionally confined employees to a narrow definition of their roles as mere workers, emphasizing strict compartmentalization between personal and professional lives. However, with the evolution of a 24-hour work cycle and the rise of remote and hybrid work environments, these boundaries have blurred significantly. We now find ourselves deeply interconnected in each other's lives on a personal level, making it almost impossible to maintain a strict separation between work and home in the modern workplace.
Our personal lives now inevitably impact our professional lives, and it's crucial to consider our work environment as thoughtfully as our homes. So younger generations demand a more humane workplace, redefining how we show up at work. Heart-centered leadership recognizes the human aspect of employees, creating supportive and inspiring workplaces for personal and professional growth.
“The demand of the younger generation is pushing the boundaries of what humanity is, and how we show up at work in a humane way is a powerful force,” Hutchison said. - 05:20 - 07:00
Empowering Female Leaders in Finance
When it comes to developing women's leadership in finance, Sayle highlights a McKinsey study showing significant gaps between men and women in their transition to management roles and the feedback they receive. To normalize women's growth in the workplace, Sayle believes in having inclusive conversations about business models, strategic visions, and excellence in their craft for both genders. She recognizes the intellectual capabilities of women but emphasizes the importance of confidently expressing their value and accomplishments.
“What I've navigated as I've grown in my career has been super critical in normalizing what it is to grow in the workplace as a woman,” Hutchison said. - 07:01 - 09:16
Nurturing Successful Female Leaders in Finance
Finance leadership is not limited by gender. To succeed, it is crucial to understand the intricacies of the finance business model, effectively communicate, and give constructive feedback, regardless of gender. Foster a work environment that promotes creativity and empathy to attract talented individuals. Empower female leaders by providing them with training, mentorship, and an inclusive culture. Equal opportunities are crucial. Nurturing these qualities can lead to success.
“Women can shine, or they are expected to shine around compassion, creating humanity, and extending the conversation to the whole person,” Hutchison said. - 12:50 - 15:16
Fostering Compassion, Flexibility, and Trust - Women's Leadership in Finance
Organizations can make life easier for women with families by showing compassion for those who deliver quality work. This fosters gratitude, loyalty, and trust, strengthening working relationships and unleashing their potential.
We must reconsider the gender distribution of tasks and the expectation that women can do it all. Instead, embrace a balanced approach, recognizing that everyone has different rhythms in life. Encouraging self-compassion is crucial in maintaining this balance.
“The more compassion you can have for your people, the more gratitude, the more loyal, the more trust, the better their working relationship is, and the more they can be unleashed,” Hutchison said. - 15:16 - 17:21
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