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“5 things I wish someone told me before I became a CEO” with Robin Fleming CEO of Anvl

Carve out time to read and think. I have found over the years that it’s easy to fill every moment with bits and pieces of life and miscellaneous information. Taking time to just think without music, without emails, messages or social media is rare and it’s important just to be and to think. As a part […]


Carve out time to read and think. I have found over the years that it’s easy to fill every moment with bits and pieces of life and miscellaneous information. Taking time to just think without music, without emails, messages or social media is rare and it’s important just to be and to think.


As a part of our series about powerful women, I had the pleasure of interviewing Robin Fleming, CEO of Anvl. Robin has over 30 years experience in technology delivering Enterprise and eCommerce software solutions. In 2018 she co-founded Anvl, a B2B SaaS software company focused on worker safety. Anvl helps companies predict and prevent workplace injuries and deaths for the front-line worker. Anvl replaces outdated paper processes, checklists and electronic forms with smart digital workflows, rich data analysis, and real-time communication. Anvl’s workflow engine evaluates real-time data and helps companies manage risk at the point where work occurs. Real-time safety supervision drives behavioral change and builds a safety culture that delivers results. Prior to co-founding Anvl, she served as an Entrepreneur in Residence at High Alpha. She has also held technology leadership roles at Angie’s List (now ANGI Home Services), Teradata’s Marketing Applications Division (formerly Aprimo), Match.com, Worksoft and i2 Technologies (acquired by JDA). Fleming is a 2015 TechPoint Tech 25 winner, a Tobias Fellows Alumni, a 2016 Leading Light Award Nominee, a 2017 Ouachita Baptist University Milestone Award Recipient and a past board member of the Women & Hi Tech and Clear Software. Anvl is a finalist for the 2019 Verdantix Innovation Award along with Cummins and was a nominee for the 2019 TechPoint Mira Awards for the new Startup and Innovation of the year categories.


Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I am the poster child for the young woman who didn’t think she could compete with the guys in computer science. I really enjoyed the applied science and computer classes in high school and I was good. But I was better or perhaps more comfortable with writing, drawing and painting. Despite the fact that I tested out of any required science classes for college, I decided to focus on Communications/Journalism with a minor in Art which gave me a broad set of options. About mid-way through college and my scholarship money, I realized that I was going to be living with my parents for a very long time based on the salary I might make in my chosen career. Thanks to excellent coaching from my Mom, I also was realized I really missed science and technology. I ended up landing an internship to help a corporate IT group implement a custom-built inventory control system. I did everything from software setup, database setup, data entry, software testing and end-user training. I made many mistakes as I learned and by my standards today I was terrible, but I loved it all. I decided to stick with my degree and take as many computer-related classes as I could and would try and land an IT-type job and go from there. My friends from the IT department, helped me land my first official technology gig in 1987. It’s been on-the-job training ever since and I have loved nearly every minute.

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

I began pitching to companies — enterprise companies — a few months before we had a product ready. The goal was to sign up early adopters who were willing to engage early, get a deal and help us with product market fit. Problem was that I was literally demoing a set of mock-ups that simulated a product so I really was selling the idea. My pitch deck looked pretty good thanks to some amazing designers, but it lacked substance and I had to give the promise of a product. I was about 4 months in after starting the company and boldly pitching a fortune 20-ish company asking them to sign up to be a paying early adopter. The executives I pitched to seemed intrigued, but the lack of so many things — including a working product put me in a hole I couldn’t get out of at that time. It was totally nuts or brave, possibly both to try and pitch this huge company. But I boldly pitched anyway! I didn’t land any early adopters from those early meetings but hope to go back and land them in the future.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was in a fishbowl (all glass) conference room in a meeting at our venture studio, High Alpha’s office. An identical conference room was next door and both had frame-less glass doors. I had spent a couple of weeks working out of the very conference room I was in, so I was very familiar with the space.The office was super busy and both conference rooms were occupied. My meeting wrapped up and I got up to leave and was heading out of the open door… the open glass door. Except it wasn’t open. I walked right into the closed glass door head first — hard. So hard I was a bit dazed. So hard, that folks in the next conference room and nearby noticed. I was so embarrassed! Fortunately, my hair covered the area on my forehead where the huge knot and bruise was forming. Ironically, I am heading up a safety software company. The lesson I learned from that is to slow down and pay attention especially around glass doors!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

The CEO/Co-Founder role is not a role I had aspired to earlier in my career but after working in so many different software companies, I really wanted to build something brand new, from scratch. I wanted to find super smart leaders with the grit and tenacity needed for a startup, who were aligned in values, ethics and grounded in hard work. In my previous roles, I joined the companies long after their products and services were built and delivered. My role was always to be a change agent to fix and improve operations. I decided that I wanted to apply my 30+ years of experience to build a company that would improve on everything I had learned from years of successes and failures.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Well, as employee one and leader in a small startup it’s a bit of everything and anything day-to-day. The goal is to focus more on the business and driving toward objectives in any way possible. As the CEO of a startup, there is a frequent balancing act between tactical work that supports the daily activities of the team and strategic work planning and executing on those plans. Roles I play include the vision keeper/story-teller of the company, head networker, coach, mentor and pinch hitter to help with daily work activities that helps us advance our goals.

What is the one thing that you enjoy most about being an executive?

I like making decisions and setting the strategy and direction for the team. I enjoy digging into projects, vetting status, progress and providing direction and guidance. I enjoy seeing teams and individuals flourish and grow as they learn from failures and successes.

What are the downsides of being an executive?

It is truly is lonely as an executive, specially when you are a founder of a startup. I like being transparent with my team, but there are always things you cannot even share with your leaders or your board. There are concerns, fears, self-doubt or disappointments that are just too sensitive to share or perhaps transient in nature and inappropriate to share. So, you shoulder those items alone or with your co-founder, advisors, mentors or coaches or perhaps a partner or spouse.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

Being a CEO and Co-Founder of a startup is not glamorous. There are certainly perks of being a CEO and Co-Founder of a startup including just the opportunity to spearhead the building of a business that can make a difference and build jobs. But, it’s super hard work, you are always on, may often be the last person to leave the office, the one who manages and delivers unpleasant news and the one always on the road. I think the perks can outweigh the negatives, but it’s a role that isn’t for everyone.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

I think the expectation that women uniquely give up something to be an executive compared to men is a problem mindset that can set the tone for how women are treated. Being an executive at some companies requires a level of commitment that may limit your personal time, may require unexpected travel and tighter integration of your job into your life. I think there may be a common bias that being an executive harder for women, which I don’t believe is true. Women and men can be caregivers, make a home, raise children and more and still have careers as executives. The one exception is that women have children and time off work and workplace acceptance of this fact makes a big difference. The good news is that parental leave trends for women and men and benefits and policies are starting to make having a family easier for anyone in the workforce whether you have a child, adopt or foster.

What is the most striking difference between your actual job and how you thought the job would be?

Fund-raising was significantly hardener than I imagined. I pitched to over 40 VCs, on average 3 times and in some cases I pitched 4–5 times before getting a No answer. I landed in a good place with $2M in seed funding High Alpha, Rise of the Rest Seed Fund, local entrepreneur Steve Cage and other local Indianapolis angel investors. But, recent studies show that only 2.2% of women CEOs are able to land VC funding in 2018, so I feel extremely fortunate. VC interest after closing our seed round picked up significantly, so discussions venture capital firms is on-going, which I didn’t really expect. I thought that there would be a break in pitching and while I’m not actually raising a round, I’m continuing to pitch and build relationships with potential investors.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

I think the most important trait is being comfortable and confident in making decisions. Many times these decisions will need to be made with the best available information, made quickly and could be pivotal for your company. Along with being decisive is the ability to be or appear to be cool under pressure and animated and excited when you may not feel it. There’s lots of pressure and stress in an executive position and if you don’t handle pressure and stress well most of the time, this type of role might not be the best fit for you. That said, I think it’s possible to grow into an executive role as long as you are aware of areas of growth that you need to focus on and you invest in those areas.

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

Know your values and your why. If you cannot easily articulate what your values are, I would recommend taking time to think about them and write them down. Your values are tied to knowing who you are and provide a good foundation for why you do what you do. And this also indirectly provides a good foundation for your team. One related recommendation is to put yourself in the role of working for your team, that means different things at different times, but ultimately is sets the tone for how a team collaborates and what you can achieve together.

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?

The biggest impact and help I received was from my Mom. She saw a glimpse of the future when she became a proficient user of Visicalc back in the early 80’s. She saw that business operations could change dramatically with technology and those changes opened up career opportunities for her. When I shifted my career focus in college, she encouraged me not to worry about trying to get a second degree. She believed technology was changing so fast that I could just go for it with on the job training and learn everything while software technology evolved around me. That’s exactly what I did and I’m so grateful that she pushed me to take early risks in finding a career that was a good fit.

How have you used your success to make the world a better place?

In my little corner of the world I’ve tried to positively influence young people to pursue their dreams through mentoring, especially for STEM fields. I’ve also coached and mentored more seasoned folks who are working to reinvent themselves for the next level of their career.

On the larger stage, I would like to think that we’re making a positive impact with Anvl. I think helping people make it home safely at the end of the day is beyond a noble mission. We have amazing technology that is applied every day in creative ways to make businesses successful, and more importantly focused on helping companies ensure their workers make it home safely at the end of every day.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Be prepared to work harder than you imagined and be ready to negotiate. As a woman you are going to have to work harder than you ever imagined for reasons that make no sense. Be mentally ready to deal with everything from mansplaining to the frustration of learning that your pay and/or equity is not equal to your male peers. Learn how to negotiate and ask for what you feel is fair and on par with peers.
  2. Carve out time to read and think. I have found over the years that it’s easy to fill every moment with bits and pieces of life and miscellaneous information. Taking time to just think without music, without emails, messages or social media is rare and it’s important just to be and to think.
  3. Freeze your eggs while you are young. If you expect to wait to have a family, think about freezing your eggs. I know it’s still a bit of a lottery ticket, but I wish I had purchased that ticket long ago. Or at least considered it early. If I had maybe I would have kids today. The difference today is that advances in fertility technology are making having children more possible and improvements with frozen eggs are a part of that landscape giving folks more options to overcome fertility issues.
  4. Find a boss that believes in you. I’ve worked for both kinds of bosses and waited way too long to leave some bad situations thinking it would get better. Once you work for someone who sees potential in you, listens to you, challenges you and truly encourages growth, it forever changes your expectations for yourself and your boss. And ultimately working for the right boss can make a huge difference in how you see yourself and directly impact the trajectory of your career.
  5. It’s okay to be authentic. I have mostly been authentic in my career, but there was a stint where I thought I had to be one of the guys at work to blend in and get ahead.It wasn’t me and I wasn’t good at it. I finally realized, I should just be respectfully real.

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

I cannot believe we are still in a situation where pay equity is an issue. My mother lobbied for equal pay long ago in the 70’s and in fact the gap has narrowed but has been stagnant for the last 13 years stalled at women making 80–83% of what men make. It’s not just a salary issue, this also applies to startup equity. According to the latest Carta gender equity study, women founders and CEOs own only 48 cents in equity for every dollar men own. Since women make up nearly 50% of the population, what wonderful things would happen if women were on equal footing with men for pay and company equity? And if the roles were reversed and men were making less than women, would this be acceptable?

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

The Golden Rule — “Do unto others as you would have them do unto you” made a big impact on me and still does to this day. J.T. McAllister was my Mom’s boss and an extremely successful businessman back in the 60’s. I was about 6 years old and one day after school, he called me over to his desk one day and told me that he needed to teach me something very important.He said he needed me to listen very closely. He gave me a beautiful shiny gold metal ruler that he used as sales swag for his customers. He showed me where the ruler had the saying “do unto others as you would have them do unto you.” He explained what this meant and asked me to take care of the ruler and always remember the importance of the Golden Rule. I can’t say that I have always followed the golden rule and I’m disappointed at the times where I haven’t followed it. But in both my personal life and business life the golden rule is a core part of my values. I still have that Golden Ruler and it has a prominent place in my home where I see it everyday.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment 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

There are two women that come to mind immediately for me. Because of their successes, and relevance of their backgrounds to Anvl, I would love to meet these strong business leaders who not only made hugely positive differences in multiple businesses but have also given back to drive positive change on a large scale:

Melinda Gates, co-chair of the Gates Foundation, she’s had an outstanding tech career, and is an outstanding advocate for big changes with STEM, women and diversity. We have big goals for Anvl, and I would love to get her perspective on best ways to drive the needed change.

Shellye Archambeau, former CEO of MetricStream — she had amazing entrepreneurial journey taking on some monumental challenges to transform businesses with amazing success. She’s transformed a business in an adjacent space to Anvl, and I would love to meet her and learn from her journey,

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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