8 Women in Leadership Share Lessons Learned and Advice For Fellow Women in Tech

Women who hold leadership positions reflected on the lessons they’ve learned over their professional journeys and shared advice for industry compatriots.

Written by Lucas Dean
Published on Mar. 08, 2023
8 Women in Leadership Share Lessons Learned and Advice For Fellow Women in Tech
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Tomorrow is International Women’s Day, an opportunity to celebrate the significant achievements in advancing women’s rights around the world and reflect on the many areas where progress still needs to be made. 

Over the past decades, many glass ceilings have been shattered. Significant progress has been made in areas ranging from reproductive rights and representation in positions of power to workplace equality and educational opportunities. Still, the pendulum of progress swings back and forth, and in many ways, these advancements have been uneven — or even taken away. 

The fight for equity and inclusion in the workplace persists in the tech industry. As of 2022, women made up roughly 27 percent of the sector, down from a peak of 31 percent in 1990, according to Zippia. Additionally, only 15 percent of tech company CEOs were women. Last year, as layoffs plagued the industry, women accounted for 69 percent of job losses, according to WomenTech Network. 

Nevertheless, women in tech continue to ascend to leadership positions, blazing a trail for their compatriots in the process. Last year, women comprised 25 percent of leadership roles, a 19.5 percent increase compared to three years earlier, Deloitte research showed. 

Still, these numbers should be a lot higher. As women seek to advance their careers in tech and attain leadership roles, leaders from eight Boston companies shared the lessons they’ve learned as their careers grew, the ways they stay motivated and the advice they have for the next generation of women in tech. 

 

A shot of Formlabs headquarters.
Formlabs

 

Shirley Paley
General Counsel • Formlabs

Somerville-based Formlabs develops and manufactures 3D printers and related software. The company, founded in 2011 by MIT Media Lab students, connects creatives across industries with powerful fabrication tools.  

 

What’s the most important lesson you learned as you grew your career? 

The first general counsel I reported to, Jeff Snider, in his first review of me, told me that I did a great job getting to know the company, meeting with lots of employees and understanding what they each do. Chatting with people and being curious about them is in my nature, so it was funny for me to hear this being pointed out as a positive at work. I realized then that I could use this innate skill as part of my role. Working as in-house counsel, it’s really important to understand the company as a whole, so you can understand where the risks and opportunities are and how they balance each other. It’s also surprisingly helpful to know who to go to when you need to learn details about an esoteric part of the business you need to ramp up on quickly because of an odd legal letter that just landed on your desk.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

I think constant inspiration is a tough — perhaps unrealistic — goal to aim for. But I do stay motivated by the teams around me: the team I’ve built, other leaders at Formlabs and so many of the people I work with cross-functionally. They all push me to do my best and learn every day. I am also motivated by the day-to-day variety of my work. It keeps me on my toes, curious and learning. In terms of motivating others, especially women, I believe in and try to practice genuine positive feedback. If I see something awesome, I say something. People are naturally motivated when they are noticed in a positive light and valued as team members; these are the little bits of fuel that keep us all going!

In terms of motivating others, especially women, I believe in and try to practice genuine positive feedback. If I see something awesome, I say something.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Be unapologetically yourself in the path you choose. Do what you love and enjoy and not what you think will be “the best” thing to do from someone else’s perspective. If you sacrifice yourself for your job, you will burn out quickly and be resentful when the sacrifice didn’t lead you to the goal you had in mind. Enjoying what you do is your own internal sustaining fuel, and it will highlight the best of you.

 

 

The grand opening of Toast’s Omaha office.
Toast

 

Megan Anderson
Chief Customer Officer • Toast

Toast is a cloud-based restaurant management platform that helps boost customer engagement and offers a range of digital tools to hospitality professionals. 

 

What’s the most important lesson you learned as you grew your career?  

An important moment in my career was when a previous boss asked me, “What do you want to do next?” I was still pretty new in the role, and the work was going well, so this wasn’t a career transition conversation but rather him pushing me to think about how I wanted to grow. Simply asking me what I wanted to do next opened up a lot of different paths and ultimately got me where I am now.  

This conversation was helpful in putting my goals on his radar so that he could help me move in the right direction. More importantly, I think it put the agency on me to define my own career goals. I shared what matters to me in terms of the type of work I want to do, how I want to spend my time and what excites me. I’ve come back to this question many times in my career. I’ll ask myself: What do I actually want to be doing? How do I want to spend my time? What skill sets do I want to develop? What is going to give me the most energy while allowing me to put my skills and experiences to the best use? 

When I joined Toast, this question helped me get to know my team. Having dedicated time to discuss goals turns the focus on career development from just a natural progression to a more intentional discussion, which sets us all up for success.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company? 

In my role, I work in a lot of different areas, which is exciting but can be overwhelming at times. For me, a big piece of staying motivated is finding a connection with people. Whether that’s connecting back to our customers, with my direct reports or to the broader customer success team, being connected to people is inspiring for me. I want to know where they’re coming from and what’s going on in their lives. It’s important for building working relationships, strengthening trust and working well together. I encourage all Toasters to think about their work through this lens.

Toast does a great job fostering community. I’m part of ToastHer, our employee resource group for women. ToastHer empowers women in many ways, like hosting networking events, providing resources to further professional development and organizing mentorship programs that pair up women across the business. I will be speaking on a panel hosted by ToastHer in honor of International Women’s Day and Women’s History Month. This event will be specifically focused on how we can help women at Toast build their careers, find mentorship and ultimately define their own paths. 

 

What advice do you have for the next generation of women in tech, and why is this advice important? 

Don’t be afraid to advocate for yourself! This goes back to the idea of knowing what matters to you and how you want to grow your career. Speak up on what’s important to you so that you spend your time doing the things you want to do and using your strengths and passions in the right way. 

Speak up on what’s important to you so that you spend your time doing the things that you want to do and using your strengths and passions in the right way.”

 

Advocating for yourself is so important. It’s OK to acknowledge things that you do well and point to the impact that you’ve had. Often women — and this certainly speaks to me earlier in my career — rely more on other people noticing what we do and the positive outcomes we drive. Sometimes recognition does automatically happen like that, but not always. It’s important to tell your manager about the impact you’re having, highlight your strengths and point to what you’re doing really well. Earlier in my career, I thought self-promotion was bragging, and I think that’s an area that women in particular need to overcome. Highlighting your accomplishments is important when it comes to advancing your career and reaching the objectives you have. You deserve recognition for the great things you’ve done!

 

 

A group photo of the Boomi team.
Boomi 

 

Shawn Maurice
Chief Human Resources Officer • Boomi

Boomi’s integration-platform-as-a-service foundation helps businesses leverage data to build integrated experiences. 

 

What’s the most important lesson you learned as you grew your career? 

Be open to saying yes. Some of the greatest experiences in my career are a result of saying yes, even though I was terrified or felt like I was not the most capable person for the role. Those experiences not only shaped me as a leader but they made me more human.

Some of the greatest experiences in my career are a result of saying yes even though I was terrified or felt like I was not the most capable person for the role.”

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

I am passionate about servant leadership and leading with gratitude. I start each day journaling for five minutes about the things I am grateful for, and I end each day with a review of my day and how I showed up for my team, colleagues and stakeholders to assess how I supported them as a leader. I celebrate the positive, and I write down the things I could have done better or differently so I can adjust the next day. 

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Be who you are. Show up authentically. Take risks. Make change and celebrate.

 

 

Hannah Shipton
Vice President, Customer Enablement • Medically Home

Medically Home provides patients with home-based medical care built upon a decentralized approach and high acuity chassis. 

 

What’s the most important lesson you learned as you grew your career? 

I learned how important it is to expand your scope of experience to a different field, industry or type of role to round out your experiences during a manager training class. A variety of professional experiences pushes you to flex and learn and makes you more prepared to lean into leadership roles where you will be accountable for functional areas where you are not the expert. 

As I reflect on my own journey, the range of experiences prepared me for the role that I have today as the VP of customer enablement at Medically Home. I left my first career of teaching and pivoted to the healthcare industry as a Spanish interpreter at an Academic Medical Center. While in the interpreter role, I learned about Six Sigma Green Belt training, and — not really knowing what I was getting into — I signed up for the certification course. Six years later, I was leading the department as a Six Sigma Master Black Belt. I moved from that role to a position in a consulting firm working with hospitals across the country in clinical operations. Now, in my role, I often doubted my ability to successfully accomplish this work, but I also realized again that I was prepared because of my previous experiences.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

My primary motivation as a leader is the mission of the company to provide exceptional care to patients in the best environment. I am consistently inspired by other women leaders at Medically Home who lead in a genuine and incredibly effective manner through their alignment with our mission. Likewise, I encourage other women leaders to know their value and to lead in ways that are authentic, without changing who they are to reflect their male counterparts. You do not have to modify who you are to be effective and successful.

I am consistently inspired by other women leaders at Medically Home who lead in a genuine and incredibly effective manner through their alignment to our mission.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

My advice for the next generation of women leaders is threefold. Firstly, embrace new opportunities to learn and grow outside of your comfort zone. Secondly, be authentic to who you are as a person and leader. And finally, support other women by being a mentor. 

Women may often doubt themselves more than men in similar roles and feel the need to change who they are to rise in the ranks of leadership. My encouragement to women is to lead with authenticity and to step into new spaces that are uncomfortable so you continue to expand your knowledge, skills and experience to influence from a leadership perspective.

 

 

Dina Elshawaf
Manager, Service Delivery Team (Madrid) • Nexthink

Nexthink connects IT teams worldwide to real-time analytics, automation and employee feedback. 

 

What’s the most important lesson you learned as you grew your career? 

The most important lesson I have learned is that if you have a dream, you need to keep your head up in the sky to chase your targets — one after the other — and keep your feet on the ground to make sure you are running in the right direction toward your dreams. I learned that early in life through my parents, as they taught me to always learn, plan, work smartly and hard, and never give up on reaching for my dreams in my career. Along the way, I’ve learned that failure is only one more trial on the road to success.

That advice helped during all the hard times when challenges would surface. Being a woman in tech, challenges are a bit highlighted, and the harder the challenges get, the harder we need to keep fighting for our dreams.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

Staying motivated and inspired is key to keeping going and succeeding. I always try to make sure I find inspiration in the little tasks that compose our bigger targets. Learning is a very good route to motivation, as the power of knowledge is unstoppable. I always try to inspire others by positivity in my attitude, changing our perspective about a challenge by searching for the good in everything we do and sharing little pieces of information that would personally help them advance in their lives and careers. Always remember that no matter how much we advance in tech, it is mostly about people helping people.

Staying motivated and inspired are key to keeping going and succeeding. I always try to make sure I find inspiration in the little tasks that compose our bigger targets.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Believe in your dreams even if no one else does. Keep learning, focusing on what you are good at and doing it in a better and smarter way. Communicate your goals and targets, as you might find many leaders around you who are willing to help and guide you. Never stop learning and know that the sky is not the limit, but that is where stars are born and shine!

 

 

An employee of The Predictive Index focused on work.
The Predictive Index

 

Suzy ElFishawy
Vice President of Engineering • The Predictive Index

The Predictive Index is a talent optimization platform that HR teams use to predict candidate success and hire the right people. 

 

What’s the most important lesson you learned as you grew your career?

Reflecting on my 29-year career in software — first as a software engineer for many years, then transitioning into technical leadership — I think the most important lesson I learned through experience is that it’s OK to be me. I went to college back home in Cairo, Egypt, in a male-dominated major, computer science, and have been in a male-dominated field for all my career. I have a very engineering-oriented mind, but my personality is very outgoing. I have a lot of empathy, and I care deeply about the people I work with.

When I first got into leadership, I struggled with how to position myself and how I am being perceived. But I learned to be comfortable with how I approach leadership. My team always knows and feels how deeply I care about them and that I will always be a huge advocate for them. I also expect a lot from my team — hard work, dedication, commitment — and I lead by example; that’s how I do my work and give it my all. Diversity is not just about gender or ethnic background but also about how we all have different leadership styles and being OK with embracing ourselves and each other.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

I draw a lot of my motivation and energy from my team. As we set goals together, work hard to achieve them and navigate the challenges that come with leading software development teams and ambitious timelines, I love observing my team grow and helping them through their career growth. I am very motivated to align company goals with team members’ career paths and see us reach personal and companywide objectives together. 

As far as inspiring other women at my company, I have a huge passion for helping women early in their careers in this field. I am lucky to work at a company that values diversity and dedicates time and resources to focus on this area. At PI, we have several employee resource groups, one of which is the Women in Tech ERG. I am proud to be the executive sponsor for that ERG and provide support and advocacy for women in tech at PI.

I have a huge passion for helping women early in their careers in this field.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

My biggest advice to the next generation of women in tech is to truly find their passion. Be curious and try different roles, then home in on what gets you the most energized. Is it a specific area in tech — front end or UI, back end, more SQL focused and so on — or is it more toward process and leadership? Observe others, listen, have mentors, then define your version of what makes you at your best at work and embrace that. 

Finally, never stop learning and growing. There are learning opportunities every single day, and it takes us being observant and keen to self-reflect and apply those learnings to continue to grow and truly enjoy our journey.

 

 

Ashlen Price
Engineering Manager • ActBlue

ActBlue is a nonprofit fundraising organization that connects small donors to democratic and progressive campaigns. 

 

What’s the most important lesson you learned as you grew your career? 

I’ve learned so many important lessons throughout my career that it’s hard to pick one. They are from a combination of advice, experience and watching great leaders lead in their own authentic ways and seeing myself in them. 

The most important lesson is that your career is your career. You have to drive it forward yourself and push yourself to work in ways that may not feel comfortable at first. Your career should fit you rather than the other way around. Don’t compare yourself to others. Instead, pick and choose from what you see others do and craft your own journey.

Throughout your journey, find people who are aligned with your approach and validate the parts of your leadership style you may question. Make those people a part of your personal board of directors. At times, they will point out things that align with what you’re good at and propel you faster toward your goals. Don’t shrink from their observations; ask questions and lean into them. Stay open and curious; your career path doesn’t have to be rigid. Eventually, you’ll get into the habit of seeing yourself through the perspective of this group, and you’ll start to believe in yourself and take more rewarding chances.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

My most influential career moves have been inspired by women, from becoming a developer, starting my engineering career and my first management opportunity to where I am now. These leaders not only saw the work that needed to be done but the potential in me to rise to the challenge. All of my greatest experiences have been led, exemplified and amplified by women. They provided me with opportunities that challenged me to grow. I’m inspired by their strength and how they overcome challenges and move through life. This motivates and inspires me personally and professionally.

As I became a leader in the tech space, I pulled from my own experiences. I make time to get to know the women I lead. I provide opportunities for them to grow their skills and learn to trust themselves. I ensure that I create a space where women can show up authentically and don’t have to compartmentalize other aspects of their lives. 

I make time to get to know the women I lead, and I provide opportunities for them to grow their skills and learn to trust themselves.”

 

For example, if a parent on my team had a rough night with a toddler, they can feel comfortable sharing that with me and working through any support they need for the day. Often just being able to talk about it frees up space for them to get support instead of hiding their humanity.

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Find your champions. Your champions are people who understand your goals and will keep you accountable on your journey. They shouldn’t be folks who unfailingly agree with you but rather an evolving group of people who support you, understand where you’re heading and challenge you. This is a group you can lean on during setbacks, who celebrate your successes and help you talk through your moments of doubts and questions. 

Keep an open mind! Have your plans and goals, but stay flexible and open to unexpected opportunities that arise in your career. Re-evaluate your goals periodically and make sure they continue to align with where you want your career to grow. Recognize sometimes where you are is where you should be, and you don’t always have to focus on the next steps. 

To sum it all up, be accountable to yourself. Find your champions, but your career is still your career. There is no shortage of resources, support and inspiration. Use it all to shape your career and give yourself the grace to figure it out. You will.

 

 

Mainstay team members pose for a photo.
Mainstay

 

Hilary Riley
Vice President of Partner Success • Mainstay

Mainstay’s engagement platform allows colleges and businesses to start and measure conversations.

 

What’s the most important lesson you learned as you grew your career? 

The most important lesson that I learned as I have grown in my career is to be an authentic leader. The lesson came about from an experience I had with a specific manager. When I worked as a director of admissions, this manager would come by my office every morning at the start of the day and ask me the same two questions: How are you today, and what are you forecasting for applications? 

He would listen to my response about how I was doing, but he never engaged in follow-up questions or acknowledged anything that I shared. When I would be in one-on-ones with him or if I went to ask him a question, he would continue to type or multitask and rarely exhibited active listening. This made me feel unappreciated and that what I was sharing was not important. I did not feel like he cared about me as a person. 

I vowed never to be that type of leader based on my experience. I chose to turn this experience into an opportunity for me to elevate my leadership style to ensure that I am intentional with the engagement of my direct reports, honest about their performance and supportive of their motivation in the workplace. I am self-aware as a leader and genuine in my approach to creating a culture of respect.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

I stay motivated and inspired as a leader by keeping connected to my entire team, not just my direct reports. I think it is important to stay linked to the team to keep my ear to the ground and know how folks are doing personally and professionally. It is also critical that I stay rooted in my goals and maintain a positive demeanor. People feed off their leaders’ energy. I tend to focus on the positive happenings and turn challenges into teaching opportunities which keeps me accountable to growing as a leader. My motivation also comes through leading with kindness and empathy for all. 

I look to inspire other women at my company by leading by example and sharing ideas and best practices to support their development. I make myself available to them as well to foster organic mentorship and share my experiences while being an active listening board.

I look to inspire other women at my company by leading by example and share ideas and best practices to support their development.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Stay true to yourself and your leadership style. Learn from the leaders who are role models and also the ones who are not — both will teach you valuable lessons. Be curious; sometimes, your best growth moments come from the breadth of your experience. As you advance in your career, own each and every role. When you have this mentality, you won’t just pick up where others left off. Don’t be afraid to use your voice to advocate for yourself. This advice is important to ensure that women continue to thrive within tech.

As more women enter this field and roles, it is important that there is diverse representation.

 

Responses have been edited for length and clarity. Images via listed companies and Shutterstock.

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