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“Why confidence is the closest thing in this world to magic” with Penny Bauder & Dolly Singh

Confidence is the closest thing in this world to magic. It is also a self-fulfilling prophecy. To become a more confident person, you cannot continue to what you’re already doing. Something has to change. Act confident to become confident. Eventually, the more we practice at things, the better and more confident we become. We all […]

Confidence is the closest thing in this world to magic. It is also a self-fulfilling prophecy. To become a more confident person, you cannot continue to what you’re already doing. Something has to change. Act confident to become confident. Eventually, the more we practice at things, the better and more confident we become. We all have fear, and we all have causes we believe in. It’s our choice which one we allow to win in the end.


As a part of my series about “Lessons From Inspirational Women in STEM and Tech”, I had the pleasure of interviewing Dolly Singh. Dolly is the head of talent innovation and inclusion at ServiceTitan, the world’s leading all-in-one software and operating system for residential and commercial service and replacement contractors.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I was raised in San Jose, California, which is kind of the heart of Silicon Valley. I graduated high school a very long time ago, in 1996. I didn’t really know at the time that technology was going to be an interest or passion point for me, andI went to college to study psychology. When I graduated, I wasn’t 100% sure what I wanted to do. I applied for a few different jobs and ended up working at a recruiting firm with an expertise in technology. That’s how I ended up in tech.

I can’t say that I started out my educational experience with a mission to build technology. I kind of ended up here by accident. But I am very thankful that I did, because I love engineering. Engineers are truly the creators of the future, and they build the reality that we live in. I think that’s really compelling, and the ability to create a world that you want to live in is hugely powerful, inspiring and motivating.

I’m just really fortunate to have been able to grow up in California. There’s such an emphasis on technology as part of our culture, and part of the fabric of California itself.

The ability to impact the lives of real people in a positive way is very profound. All of us now know, especially in this consumer tech economy, how much good technology can change your life. With good technology, you can save lives and do remarkable things in the world. I have a lot of hope for the world of engineering and tech.

Can you share the most interesting story that happened to you since you began at your company?

One specific story that illustrates this is when ServiceTitan participated in the hackathon at the Children’s Hospital in L.A. The hackathon was about bringing professionals and other ambitious people across Southern California together over a weekend to create different solutions that will help children and patients within the Children’s Hospital ecosystem.

We’re really proud of our participation there. It’s a good example of how we believe that what makes STEM, engineering, science and technology so compelling is that you can impact the lives of people in such positive ways. That was a really remarkable opportunity for us, because we got to go outside our traditional day-to-day thinking and really focus on our team’s talents and apply those in a new and interesting way.

What do you think makes your company stand out?

The reason that I was really motivated to come to ServiceTitan is this idea of using technology to help people who technology has kind of missed. The world of STEM, as powerful as it is really is, has been kind of difficult to access in some way, right? Most of what we think of in terms of software as an industry or software as a service is mostly products being made for other technology companies or other Fortune 100 or Fortune 500 companies. It’s big corporations and big tech helping big business.

What I think is really remarkable about ServiceTitan is that it’s using the power of Big Tech to help small business, and it’s helping a segment of the American economy that technology has kind of overlooked. California’s economy is vibrant and rich, and amazing things are happening, but there’s this giant swath of the country that hasn’t seen the same benefits. There are a lot of big, blue-collar industries and workforces that Big Tech hasn’t really helped.

That’s what I think is really remarkable about ServiceTitan in particular: It’s not just about building tech for tech’s sake or to support big business, it’s about using the power of tech to really empower a segment of the economy and a segment of our society that hasn’t seen the same level of progress as we have.

Are you working on any exciting new projects now? How do you think that will help people?

We are really focused on diversity and inclusion, and it’s one of the core values of our corporate culture. One of the things that we’re doing is building out our charter group organizations. These are sometimes called employee resource groups, and they’re community organizations within the company.

The employees self-form and self-manage them. You can think about them like clubs in college or high school, like the band club, chess club, soccer club or whatever. In this case, they’re not organized around an activity, but around a particular community and culture.

So, we have the Black Titans charter group, an LGBTQ Alliance charter group, a Titans for Philanthropy charter group and a few others. These are all important parts of the company, because we’re an engineering and technology company, and we do software, but we have to build and create an office for the real world.

Each of these will have people from technology, engineering, business and sales; they represent the mix of our talent across the organization. What they’re able to do is promote a richness and culture from the bottom-up. You can have top-down leadership, and executives can preach about how important these values are, but the way we think we can bring these values to life is through our actions, not just the things we say.

We believe inclusion does equal innovation. When you have people from similar backgrounds all looking at a problem, no matter how brilliant they are, they all look at the problem from the same perspective. What we really need is a richness and diversity of perspective to help solve problems. At ServiceTitan, we want to keep innovating, which means we need a diversity of thought to keep from stagnating and keep generating great ideas across the organization.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. Are you currently satisfied with the status quo regarding women in STEM? What specific changes do you think are needed to change the status quo?

I am absolutely not at all satisfied with the state of women in STEM. The data would support that we are greatly underrepresented, under-resourced and underappreciated. That’s part of why I think diversity and inclusion as a function within STEM and technology companies is really important.

If engineers are the creators and shapers of the world and the future and most engineers are men, guess what that world is going to be shaped like and who for?. It’s going to be shaped for men by men, right? That’s why it’s really, really critical for women to be involved in STEM, because the world that we will live in is really dependent on how many women we can engage within the industry.

Starting kind of at the advanced high school level, and then all the way through to college, there are less women and girls in STEM fields. Then, including the ones that get into the industry, there’s an even stronger drop off after they enter the workforce. And if you do make it into the STEM industry as a woman, you’re going to face headwinds.

Unless you’re being really studious and working really hard, women will get promoted at a lower rate. It will take longer to get promoted, and you’ll be paid less. You’ll always have to be faced with a room of colleagues that don’t look like you in most cases. And this is going to take a long time, and it’s going to be a generational problem; it’s not something that we can fix overnight.

So, the status quo is really not something that I, or anybody, should be satisfied with. If the world is demographically half men and half women, and we want our daughters to be on equal footing with our sons, then we’ve got to get as close to that 50/50 mix in the creative ecosystem as we can. We’ve got to really strengthen the pipeline for girls going into STEM and developing their interests in science, technology, engineering and math very early on.

In your opinion, what are the biggest challenges faced by women in STEM or Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

I think the challenges that are that are unique to women are kind of obvious, right? Anytime you’re in a minority, you tend to have less power. Women are a minority by a significant margin in the world of tech. So, that’s an uphill climb from day one. All of the infrastructure and ecosystems and processes in a male-dominated organization will have an inherent slant.

It’s similar to some of the things I talked about earlier: it will take longer for women to be promoted than men. Women tend not to apply for a job or promotion until they meet 90% of the requirements, while men will apply with as little as 40% of the requirements.

Ultimately, there are very different behaviors that men and women are taught, and there are very different perceptions of those behaviors from a compliance standpoint. When a man is assertive, he’s a boss. When a woman is assertive, she’s bossy, right? When a man knows what he wants and goes after it, he’s ambitious, and that ambition carries a positive connotation. When a woman is ambitious, it has a negative connotation.

So, there is absolutely a slanted playing field, and that’s the reality of what women face. But that makes us stronger, and it allows us to be more solid contributors to every team we’re on. Hopefully, people will start to notice and that ecosystem will start to change. As companies, we can really fight these disparities and systemic biases.

What are the “myths” that you would like to dispel about being a woman in STEM or Tech. Can you explain what you mean?

I don’t know if there are myths about women in tech or STEM. I think there are perception issues, as we talked about earlier, about women in business vs. men in business or about how different attributes are viewed differently. It’s less about myths and more about slanted perceptions.

What are your “5 Leadership Lessons I Learned From My Experience as a Woman in STEM or Tech” and why.

There are five secrets of success I’ve learned over the years. The following material is taken from my article, “A Former Head Of Recruiting’s 5 Secrets To Success,” published on Forbes.

Pursue Your Goals

Reaching your goals begins by doing your homework. You must know your goals and standards before you can hope to live up to them. For example, if you see a company you want to work for, learn as much as you possibly can about the company’s history, current status and future goals. This knowledge will give you credibility as you engage with the company and its network. Inadequate effort in this stage is why thousands of interview candidates each year fail to effectively answer the simple but critical questions of “What do you know about our organization, and why do you want to work here?”

Learn Confidence

Confidence is the closest thing in this world to magic. It is also a self-fulfilling prophecy. To become a more confident person, you cannot continue to what you’re already doing. Something has to change. Act confident to become confident. Eventually, the more we practice at things, the better and more confident we become. We all have fear, and we all have causes we believe in. It’s our choice which one we allow to win in the end.

Know When to Surrender

Never use the good to chase the bad. Take time to re-evaluate every so often, not only on how you are making progress on achieving your goal but also whether your goal is worth the long-term investment. It’s critical to stay aware of your larger-scale needs and goals.

People who value themselves don’t stay in situations that deplete them of energy and joy. As human beings, we are limited. As with money and time, we have only a limited amount of energy to give. In order to have the greatest impact on the world, we must guard our energy, keeping an eye on how it is spent and how it is replenished.

Be the Driver of your Success.

To achieve success in personal and work relationships, define what success is. Then, bend the world to match that definition. Let’s say you started a new job. After the first few months, you’ve decided you like the team and organization, and you want to continue to invest in the opportunity. In this case, you should take some time to identify where you’d like to be 12 months into the role, and should have professional, and on-going dialogue about it with your superiors. A good leader’s job is to enable your success, and unlock your potential, but they can only do so if you know your goals, and if you are taking active steps in achieving those goals as they align with the company.

Define success in your own terms, and then actively drive others toward that definition of success.

You Get What You Give.

In a highly interconnected world, the foundation you build today will define your success tomorrow. Look for ways to provide value to everyone you can on a daily basis. We all face personal and professional challenges, and regardless of what we see in the lives of others, none of our roads have been paved perfectly smoothly. Those who appear to be lucky in their lot in life are usually those who see every challenge as an opportunity, and consistently seek out ways to turn weaknesses into strengths. It is the energy with which they approach these challenges that begets their success.

What advice would you give to other female leaders to help their team to thrive?

I think that women should have the right to be as bold and fearless and fiery as they want to be as long as they’re respectful of their peers. There shouldn’t be a negative connotation to that. I think that’s more about creating the right cultural tone and teaching all your leaders — that means your male leaders and your female leaders — to be aware of their unconscious bias and the systemic bias that exists in society.

You can’t do that through just lecturing people or giving them learning modules and mandatory training. We do that by really helping people understand each other, and giving them insight into one another’s stories and letting them connect on a deeper level, because that really changes perception.

What advice would you give to other female leaders about the best way to manage a large team?

The first the first piece of advice would be to delegate and create some organization within your, your team. You can’t do it all yourself, so who are you going to deputize? Make sure that you’re developing and that you’re supporting people underneath yourself, letting them learn and grow and make mistakes. Letting them learn how to manage their own team.

Any executive should never really have more than seven to 10 direct reports. Anything more than that, and things start to break down. You should manage your number of direct reports, and then really develop the people and leadership skills of the team that is reporting to you directly. That way, you know they’re able to manage their teams with minimal oversight from yours.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have probably a dozen or so people who have been instrumental in my development, it’s tough to pick just one. But who I’d probably have to pick is Dr. Garrett Reisman ; I am constantly inspired by Garrett’s perspective on life and work, and he is one of the best friends a person could ever hope for.

How have you used your success to bring goodness to the world?

I’ve chosen to focus on Diversity and Inclusion in my current role to help empower more women and minorities in tech.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

If every mid-sized company in California adopted one underprivileged middle school, we would close the diversity and opportunity gap in technology/ business much faster.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Be the change you want to see in the world.” I try to live by this mantra.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Sara Blakely is my dream date for breakfast. I’ve seen her speak and met her briefly, but never had the good fortune of any quality time with her.

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