Inspirational Women Leaders Of Tech: Cheryl Porro of Betterworks On 5 Steps Needed To Create Great Tech Products
An Interview With Rachel Kline
Communicate a compelling vision that inspires your team.
Create a culture that drives team collaboration and accountability. Use shared, cascading goals to help ensure everyone is rowing in the same direction.
Currently, only about 1 in 4 employees in the tech industry is a woman. So what does it take to create a successful career as a woman in Tech? In this interview series called Lessons From Inspirational Women Leaders in Tech, we are talking to successful women leaders in the tech industry to share stories and insights about what they did to lead successful careers. We also discuss the steps needed to create a great tech product. As part of this series, I had the distinct pleasure of interviewing Cheryl Porro.
Cheryl Porro is a visionary leader, advocate for diversity and inclusion, and change agent with a proven track record of driving growth in disruptive software companies. As the Senior Vice President of Engineering at Betterworks, she brings her wealth of experience and strategic leadership to the organization.
Prior to joining Betterworks, Cheryl was instrumental in generating tremendous growth during her tenure at Salesforce while growing the company’s nonprofit and education business to hundreds of millions in just 4.5 years. She also scaled Salesforce’s platform quality engineering division, overseeing the growth of a team that exceeded 100 members.
Previously, she played a pivotal role in piloting products to market for healthcare startups Curve Health, where she successfully led the company from seed-stage to an oversubscribed Series A funding round of $12 million in just 18 months. Under her leadership, Curve Health introduced its connected health solution to 65 senior care facilities, revolutionizing the industry with innovative technology. In her earlier role at Thrive Global, she showcased her expertise in enabling rapid scalability and driving innovation.
Beyond her role at Betterworks, Cheryl is dedicated to diversifying C-suites across the tech industry and is actively involved in empowering women and other underrepresented engineers to maximize their leadership potential as a Certified Executive Coach. She served on the board of directors at Amplify, an organization committed to amplifying historically excluded voices in all areas of technology.
Thank you so much for joining us in this interview series! Before diving in, our readers would love to learn more about you. Can you tell us a story about what brought you to this specific career path?
I started off life as a chemical engineer. I love to tell the story of how I moved from chemical engineering to software engineering. I was in Silicon Valley working for a family-owned industrial waste treatment company that built systems to handle silicon chip manufacturing waste. It was the late 1990’s, and I was expected to be to work by 8 am (not a minute late!), but of course, stay as late as I needed to in order to design, configure, and price out systems for deals. Let’s just say the perks at this company were non-existent. I started hearing about the tech companies spinning up and how employees rolled into the office by 10 am and that there were all sorts of perks, even free Odwalla! I was convinced. I left my chemical engineering job and found a role at a small software company. As I like to tell it, I made the shift for the free Odwalla.
It has been said that our mistakes can sometimes be our greatest teachers. 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 am not sure how funny this story is, but it sure is memorable. I will never forget it! I was working at a small startup owned by Amazon. It was an intense time, at an intense place, as it was at software startups during that first internet boom. I was working hard alongside many great coworkers, but there was one senior software engineer in particular who was very difficult to work with. He was verbally abusive and constantly yelling at me and/or accusing me of not doing my job, which was, of course, false. He did it again, this time in a large meeting with many higher-ups present. In the moment, I lost my cool and essentially threatened to beat him up. As you can imagine, this did not go over well! I learned that no matter what anyone else’s behavior is, I can only be accountable for mine. There was no excuse for my losing my cool (and there was no excuse for his verbally abusive behavior). To this day, I work hard to create cultures where people are respectful of one another, no matter the disagreement.
What do you feel has been your ‘career-defining’ moment? We’d love to hear the lead-up, what happened, and the impact it had on your life.
Definitely my time at Salesforce. I had actually been thinking about leaving tech. I was an avid baker and cupcake blogger at the time. I had built up some notoriety and a following. I had gone so far as to find a partner in opening a commercial kitchen for us both to run our bakeries out of. At the same time, I was being pinged by former coworkers that had gone on to Salesforce. This was the very early days of the company. It had no name recognition, but I was hearing great things. As a part of the interview process, I had to signup for a free trial and explore the product. I was super impressed with what I saw. Highly configurable enterprise software delivered in the cloud was a very new concept. Then I interviewed with a bunch of folks. I hadn’t met such a smart, motivated, and nice group of people! I was sold. I remember leaving the long day of interviews feeling super pumped up and a little bit anxious. I wanted the job so badly! Needless to say, I got an offer. I started as a lead engineer and went on to grow with the company over 13 years, leaving as a Senior Vice President. My time at Salesforce had a huge impact on me and my life. I gave birth to my daughter two years into the journey, and the combination of motherhood plus jumping on a professional rocketship made me into someone I would never have imagined.
Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?
As I mentioned, I did consider leaving tech. There were definitely challenges I touched upon, bad company cultures, bad employee behavior, and other struggles along the way. I have a strong creative side to my personality, and I didn’t feel like I was able to utilize it or express my full self in those early days. So I did toy with leaving and got close to it. But changed my trajectory was ending up at the right place at the right time. There was definitely luck involved! But once I became a mom, I had all the drive I would ever need to propel me forward.
Ok, super. Thank you for all that. Let’s shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address? How does your company help people?
Remember those bad company cultures I mentioned? Well, Betterworks aims to give companies and the people that work in them the tools they need to create great workplaces. We all spend a lot of time at work! And most of us care a lot about our work and want to make a positive impact in our workplaces. In order to do that, we need to feel like our work is aligned with the goals of our company, that the great work we are doing is visible, that we are getting the feedback necessary to grow and improve, and that we are challenged in ways that facilitate growth. Betterworks helps companies do all that with easy-to-use but very sophisticated tools.
If someone wants to lead a great company and create great products, what is the most important quality (for example, “determination” or “eye for detail”) that person should have, and what habits or behaviors would you suggest for honing that particular quality?
Really, it’s really a combination of two qualities. You need to have one foot on the ground with your head in the clouds. It’s all about balancing big-picture, visionary thinking with pragmatic, delivery-focused thinking. I recognize that vision is critical to inspire your team and your customer, but you also need to deliver day in and day out.
I coach folks to practice putting themselves 5 to 10 years out. Really think about how things may be different — for you, your team, your company, the customer, the world. It’s not easy to do, especially the further you go out, but it’s fun! When I was at Salesforce, we had a robust 10-year long-range plan, so it was actually pretty easy to think about the scale that the company would be at in 10 years. That inspired a lot of innovative thinking. My other message? You are your habits. Vision is critical but you build your vision one brick at a time. I am a big believer in building strong habits and routines along with strong self-awareness and self-discipline muscle.
What’s a team management strategy or framework that you’ve found to be exceptionally useful for the product development process?
There are a lot of great rituals and practices inherent in agile frameworks that, if applied, can really help teams come together to deliver great products. When building complex software systems, for example, you are guaranteed to face ambiguity, complexity, challenges, hurdles, and roadblocks of all sorts. Two of the critical agile processes that help teams face these challenges are the iterative approach to delivery and retrospectives.
Iterating through the product development process helps remove ambiguity and lessen complexity and risk. Another great side effect is momentum. If you break up a big, daunting effort into smaller chunks, the team can deliver in those small chunks. I find that it really helps maintain enthusiasm and momentum while decreasing anxiety.
Teams learn so much from the retrospective process. I am a huge fan of retros and blameless postmortems to foster continuous improvement and learning. They should not be wielded as a stick or used to point fingers. This is one of the most challenging aspects of leading a cross-functional team to do difficult work under pressure. When things go awry, remember they likely will, it’s human nature to point fingers. This doesn’t help us one bit. We win as a team, and we fail as a team, always.
When you think of the strongest team you’ve ever worked with, why do you think the team worked so well together, and can you recall an anecdote that illustrates the dynamic?
The strongest teams I have worked with are those that share a passion for the problem the company is solving with their products. I once led a team that built products for the nonprofit sector. Many of the employees on the team had previously worked for the very nonprofits that used their products. They were so deeply committed to delivering highly functional, high-quality products for our customers.
If you had only one software tool in your arsenal, what would it be, why, and what other tools (software or tangible items) do you consider to be mission-critical?
In my role leading teams in a remote-first company, it’s my calendar + Zoom! I love connecting with the team, and I spend a good chunk of my day on Zoom in team meetings, project meetings, and one on ones. After that, it’s Slack. Email used to run my day, but now it’s Slack. I love Slack for communicating with my coworkers. Betterworks recently launched a one-on-one tool that I am addicted to! I used it daily. Any time a thought pops into my head, like “I should talk to so-and-so about something,” I add it to the agenda for our one-on-one. It’s great to have one place to track agenda items, store shared and private notes, and track action items. It makes me a much better leader. Finally, I am more and more using tools like Chat GPT to speed up my work. For example, I never start a presentation from scratch, ask I ask for an outline as inspiration.
Let’s talk about downtime. What’s your go-to practice or ritual for preventing burnout?
I have many such practices! I had a pretty monumental shift about 15 years ago when I was suffering from burnout. I had to step away from work for a month to recuperate. In the process, I learned much about what causes burnout and how to avoid it. But I also learned that self-care practices not only help you avoid burnout, they actually help you perform better at work and better enjoy your life. For example, I know that any minute I spend exercising gives me minutes in return for the energy it gives me. Any minute I spend meditating saves me minutes from needless worrying.
Thank you for all of that. Here is the main question of our interview. Based on your experience, what are your “5 Steps Needed to Create Great Tech Products”? If you can, please share a story or an example for each.
- Communicate a compelling vision that inspires your team.
While AI isn’t new, the launch of ChatGPT into the wild has caused a dramatic shift across all industries and functions. No company or employee will likely be untouched by this technology. And if your product vision isn’t incorporating generative AI, you run the risk of being left in the dust. At the same time, it isn’t always possible for one person or one role to fully assess what these major shifts mean for your company and product. It is critical to tap the collective wisdom of your employees in a way to generate innovative ideas quickly. For example, at Betterworks, we recently ran a generative AI hackathon, and we didn’t just leave it to engineers. All employees were able to participate. The winning teams had diverse representation in skills, roles, and geographies. The event was energizing and inspiring, resulting in a slew of innovative ideas for our product. - Create a culture that drives team collaboration and accountability. Use shared, cascading goals to help ensure everyone is rowing in the same direction.
When there is conflict on a team, it is almost always due to misalignment. What is important to you and your function may not be important to another function. It’s the responsibility of team leaders to demonstrate and encourage a collaborative working style that allows everyone to show up at their best. That also means being accountable to your team and raising the flag if you aren’t able to meet your commitments. For example, my team and I partner with the product and design organization. Our chief product officer and I sit down each quarter and agree on shared goals across our team. We then have those goals cascade into our organizations, ensuring we are all rowing in the same direction. - Iterate! Ship early and often to get early feedback and course-correct, as well as drive momentum with energy with your team.
We have embarked on a long-running, complex, and risky effort to modernize our product and technology. This is something many technology companies face at many points in their journey. Very large and very complex efforts can be daunting and anxiety-inducing for the team, often resulting in analysis paralysis. Encouraging iterative delivery and breaking up a large complex effort into smaller efforts is critical for leaders to do. In our case, we did a deep analysis of dependencies and attempted to reduce them wherever possible. Dependencies, and an all or nothing approach, definitely increase risk to delivery. - Build in the rituals needed to deliver with excellence and stick to them, including retrospectives, post-mortems, and feedback designed to help everyone improve.
Vision and culture are critical to the health of an organization and its ability to deliver impact for the company. But without the commitment to day-in and day-out rituals, teams will struggle to deliver.
5. Celebrate! We tend never to stop to celebrate our accomplishments and wins. It’s critical to celebrate and appreciate the work of your team.
Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?
There is plenty of data that shows there are still hurdles for women in tech and in the workplace in general. We have made many strides, but many of our work cultures are built for the status quo and don’t support the needs of a diverse workforce. For example, as a working mom, I benefit greatly from workplace flexibility. For example, I am able to block my calendar for school drop-off or pickup. There are no questions asked! Some companies offer that for employees, but many don’t. The more we can give employees the flexibility to get the work done in a way that works for them, the more we can accommodate the needs of a diverse workforce as well as inspire better performance from all employees.
Thank you so much for this. This was very inspirational, and we wish you only continued success!
