Our new Chief Technology Officer (CTO) Andra Milender defected from a medical career track before finding her footing on a technology path. Andra is excited to leave her public company comfort zone and bring her talent to the BetterCloud team. She’s looking forward to helping BetterCloud scale and become one of the most reliable solutions that customers use. Andra hopes to build a culture within her team where everyone has a voice and is comfortable using it. We’re excited to have Andra on board and for all the positive change that she’s bringing with her.
Andra has bachelor’s degrees in computer information systems, marketing, and international business from Indiana University Kelly School of Business.
Where are you from?
Originally, I’m from Indiana. I was born and raised in the Midwest, went to school there, and worked in Chicago for the first 16 years of my career. I moved to Atlanta 11 years ago and have been here ever since. I still don’t miss the snow shoveling.
What made you want to pursue a career in technology?
I started out in a pre-med track in school. When I was about to start my clinicals in nursing, I had a professor come up to me and say, “You are not going to make it in the medical field because you have no bedside manner. So, I set up a meeting for you to meet with a professor in the business school. I think you should consider an opportunity in business.”
I met with that professor, who happened to be the head of their IT, or what they called Computer Information Systems, program. At that point I shifted gears and ended up with three different majors out of Indiana University’s business school. I didn’t know exactly what I wanted to do—I focused on technology, international business, and marketing. Then I landed my first job in tech and have been committed ever since.
It was a little more of a journey than a direct mission, and it was all because of a teacher who took the opportunity to invest in his students that initiated my pivot to technology.
What does your role as the CTO entail?
You wear all hats as CTO. Sometimes I’ll wear a strategic hat when I’m building out the technology or business roadmap. Sometimes I’ll wear a business hat when we’re talking about the direction that we want to take BetterCloud. Sometimes I’ll wear the up-at-3 a.m hat when we’re solving a mission-critical issue affecting our platform. I’ll do whatever it takes. I live by the principle “never ask anyone to do something that I am not willing to do.”
The definition of CTO is so broad and that’s what I like about this role! I get to focus on the cool tech stuff, but I also get to focus on the bigger business picture and how that filters into execution.
Before coming here, you were at Discover and then Global Payments, which are both much larger companies. Why did you decide to make the switch to a startup?
It was more about the mission and drive, not necessarily the size, that played the biggest role in my consideration.
Coming here, it was more about, “Do I want to leave my comfort zone?”
What really struck me about BetterCloud didn’t have anything to do with its size. The idea of being able to operate in a private environment for a while was compelling. Working in the public sector for 25 years is exhausting and becomes repetitive. The regulations can really hinder scaling and innovation. I get energy from the execution, not necessarily from managing fires, mastering the art of politics, and placating the day-to-day. At some point, when a company gets big, the execution gets lost in too much bureaucracy and moving at less than ideal speed becomes the norm. You’re not rolling your sleeves up and moving it forward at an exciting pace. So, I thought this was a perfect opportunity to take a different path and get back to the excitement of execution at this pace of business.
The hook, line, and sinker was talking to David [Politis, CEO], Bart [Hacking, CFO], and members of our Board of Directors and hearing their vision for BetterCloud.
What is the biggest opportunity that lies ahead of you in your new role? What is the biggest challenge?
The biggest opportunity is the amount of change that we can effectively manage at pace to get bigger and better. We’ve got amazing talent in the BetterCloud team, and everybody I’ve met has the right mindset: “Let’s build the business. Let’s do it fast. Let’s do it right, not just fast.” And to me, that’s exciting. I’m excited about the energy, the drive to succeed, and the commitment I have seen from everyone I have met to deliver for our customers, our people, and our product.
I’m apprehensive about making sure we’re communicating early, often, and continuously. This growth will require the team to use technology, techniques, and methodologies they may have not had to use in the past. I don’t want to break the awesomeness we have and have people be fearful versus excited about what we’re doing to grow the business the right way for the right reasons. Making sure that happens really comes down to solid communication.
Coming into this role, what are your top three objectives that you hope to accomplish?
Reliability is number one. Reliability includes maintainability, availability, and security, period. If we don’t have that foundation, that’s a problem. Objective one is to make sure the product we sell to our customers is top-notch, always secure, and always available.
The second is being able to do what we do well, do it fast, and do it at scale. I can’t clone the awesome engineers here, but can we leverage them to do higher-level-thinking work so that we can leverage multiple resourcing models. I need to figure out how we should distribute work so that people are using their strengths to their optimal potential and that we’re positioned to win the game by getting scale, getting there faster, and keeping spend in line with growth.
My third objective is making sure that we keep and continue to build a culture where everybody has a voice. I know there can be a propensity of, “Oh, well I’m new, or someone else will figure it out, so it doesn’t matter what I think” as our organization continues to grow. I have a huge problem with that. My expectation is that every person’s a leader regardless of their title. I expect every person to come with a brain to think, challenge, and deliver. I want everyone not to just do what they’re told because somebody said to, but because they understand the “why.” If the “why” doesn’t make sense or they see the wall we are headed towards, I want to foster a culture where everyone feels comfortable raising their hand, asking for clarity, or speaking up.
Technology is not a field known for having many women, especially not in leadership. What does it feel like to be a female CTO? And what has it taken to get here?
I pride myself on not focusing on people’s differences, gender or otherwise. To me, if I’m focusing on the differences, I’m minimizing the focus on the most important part of the equation which is an individual’s potential and capability.
I participate in a number of tech forums including the Women’s Network in Atlanta, which is an organization that focuses on supporting women in technology. I do this primarily to network with colleagues in the technology world I may not otherwise have the opportunity to meet. I also hope to change the mindset of others to ensure we acknowledge all individuals for their awesomeness, regardless of gender. Gender does not drive success— ability and hard work do.
I don’t look at it as, “I’m a woman technology leader,” but I respectfully acknowledge this is something many see as a rarity and motivating, and I respect that perspective. As a leader, I owe it to others to appreciate all points of view, evolve beyond the differences, and mentor/develop future leaders. I came across a saying once that has stuck with me as a guiding principle: the function of leadership is to produce more leaders, not more followers. I strive to enable future leaders of any gender, age, race, religion, etc.
I think empowering more women in technology is a matter of dispelling this as a stereotype in the younger generations, meeting people where they are in their current beliefs/experiences, shifting focus on ability, and reinforcing the belief that anyone can do anything.
What do you do in your free time?
I have three teenagers, so I like to spend as much time as I can with them, or at least as much time as they’re willing to spend time with my husband and me. We will be empty nesters in one year! While we are looking forward to being nagging parents from afar, we realize the end of this parenting chapter is near. We have a family goal to attend a game in every MLB stadium before the kids are gone for good—18 down, 12 to go. Go Yankees!
I enjoy DIY projects, photography, and maintaining a fitness routine.