Daniel Waithe’s career in Quality Assurance (QA) began in 2004, when he worked as a QA analyst for Citigroup. Since then, he’s risen rapidly through the ranks and has established himself as a true thought leader in the world of quality engineering. Prior to joining BetterCloud as our new VP of quality, Waithe was a director of engineering at MailChimp.
We recently sat down with Waithe for an informal, but wide-ranging discussion about his career path, the opportunity at BetterCloud, and the future of quality engineering.
Editor’s note: This conversation has been edited lightly for clarity.
Let’s kick things off by chatting about the opportunity at BetterCloud. What excites you about the job and the company?
Ultimately, it was a no-brainer to take the jump to BetterCloud, primarily because of the space that we’re creating. The SaaSOps space is a huge opportunity and the ability we have to shape this space is significant. That was very exciting to me.
Secondarily, I had a chance to chat with [CTO Jamie Tischart] even before he joined the company. It didn’t take me long to say, “Oh yeah, this is a leader I definitely want to work with and learn from.” I felt very much the same with my conversation with [CEO David Politis]. There are a lot of really good humans here who are doing great work and I can learn a ton from them.
Jamie and I talked about how there’s this fork in the road for engineers where you have to decide if you’re going to move into management or write code for the rest of your career. What about the management path was attractive to you when you got to that point?
I’ve had some really great managers in my life and I’ve had some bad ones. I’ve seen what the impact of having good leadership and management can have on me, but also what bad leadership can have on me emotionally, mentally, and my ability to build generational wealth for my family. All of these things can be impacted by your manager.
It was primarily the bad experiences that I looked at and said to myself, “Man, it’s got to be better than this and if I could be better than this for somebody else, I’d want to do that.” That was the catalyst for me to think about leadership and management.
From there, I was driven by the ability to continually help people build their careers and watch people grow, and to watch people who are marginalized break glass ceilings. Being a part of those journeys is the number one driver for why I stay in management.
We talk a lot about mentorships in tech, especially when it comes to creating opportunities for underrepresented candidates. Were there any mentors that helped you get to where you are today? What types of challenges did you face along the way?
I like this question. I often say that Black people in this space are over-mentored. Mentorship is something that is relatively free. I can talk to someone and get advice with little effort and investment, but at the end of the day, will you take the chance on me?
But don’t get me wrong, I value mentorship highly. There’ve been some key mentors for me in my career. The first being when I was working in a bank before I got into QA/Tech, there was an opportunity to do a three-month stint doing some User Acceptance Testing.
They were revamping the whole banking system, and I had a mentor who saw an internal opportunity and said, “Daniel, you should apply for it.” I said that I wasn’t interested, but she replied, “Daniel, I’m not asking you, I’m telling you. You’re going to apply for this thing and go for it.” It was the start to a wonderful career.
That’s great. Now that you’re a manager, how do you build trust with the engineers who report to you?
For me, it’s about transparency and honesty. There also might be a few F-bombs along the way, but the underlying message through them is that I’m going to show you my humanity. I’m not going to code-switch and speak in a way that isn’t normal for people, or authentic to who I am. Leading with honest, real-life conversation and perspective has served me so well over the years. It’sone of the reasons people enjoy working with me;that they know I’m going to give them a good, honest conversation at all times.
When I chatted with [VP of Engineering Lorinda Brandon], she said that her management strategy doesn’t change based on the product, but it might change based on the people. Is that something you’d agree with? And if so, how do you imagine any of your management strategies or approaches shifting to meet the needs of the existing team?
I’m a big fan of Lorinda and the way she thinks, and I agree with that completely. Over the years I’ve filled my management toolbox with a ton of skills and techniques. When I join an organization, I assess and then ultimately take those tools, lay them out across the proverbial desk and ask, “Which of Daniel’s skills and techniques does this team need?”
There are always going to be things that make me the person I am, but what I bring to bear per organization will likely change according to the need. Here at BetterCloud, I’d say it’s still relatively early for me to think about what would be different from a management perspective? I’m still going to be honest. I’m still going to cuss a whole bunch. I’m still going to care deeply about the growth of people.. We’ll see what the future holds and we’ll see where I may need to adapt and change.
That’s great. I know a few engineers whose biggest complaint about previous managers was not getting timely feedback until you get to the point where you say, “Hm, well that would have been nice to know.”
Yeah, totally. I had a manager who wouldn’t even look at you when you walked by them in the hall if they were unhappy with something that you had done. It was always this awkward, horrible experience. In those moments, I would always go back to my desk and start looking for a new job, it’s completely demoralizing..
As a leader, I’ve committed to not letting a moment like that happen when I see someone that I’m managing. I’m never holding back in those moments when I feel like we need to have a rough conversation. If there’s that type of feedback, you’re going to hear from me first. We should be the first ones to talk about it. You shouldn’t hear about it on the “streets” or otherwise.
That’s really interesting. Has your approach to delivering blunt feedback evolved over the years? And how do you do it with engineers who can be very smart but also very opinionated?
Hard conversations are hard conversations. A tough conversation with my kid is just as hard as it is with an adult at work. Having to tell someone they haven’t met certain expectations is always rough.
For me, it all starts with establishing expectations early on. I rely on consistent one-on-ones with my direct reports. In these one-on-ones, we’re calibrating, we’re checking in, and talking directly about performance. There is very rarely a big moment of, “Oh shoot, you did this big bad thing.”
Speaking of teams, let’s talk about how you think about building them. What are some of the qualities in QA candidates and managers that you look for? What traits do you look for that might not be on job descriptions?
For me, when I’m assessing good hires, I look for some key things that I think can survive any of those things. In the world of QA and quality, it’s curiosity above all else. I want to hire people who don’t take things at face value and know how to ask probing questions and get to something deeper.
I hate to typecast people, but I will say generally it’s known that QA people and engineers in general are relatively quiet. Finding those individuals in the QA world who have the ability to speak up and say, “This feels wrong. This should be different,” is absolutely key and critical for the work we’re trying to do. The work of QA is no longer just relegated to the end of the process, where we’re finding bugs because we pushed a bunch of buttons. We’re going further left. We’re influencing technical decisions. Were influencing product decisions. We’re influencing design decisions, so we need to have people who are curious and have different ways of thinking about things.
Let’s talk about those misperceptions of QA. Are there any other ways that your work has changed over the last few years? Are there any emerging approaches or methodologies that you think will be a little more mainstream in the next year or two?
The industry has shifted widely over the last several years. Automated testing has become far more prevalent in the space. There are companies who are making the explicit decision to not have a separate QA function.. They’ve decided to just have their engineers write automated tests and that’s going to be it. This is a shift in the marketplace that I don’t align with, but it is a shift nonetheless.
I am a believer in the idea that automated testing can remove the rote work. It can help organizations scale their testing efforts and ultimately allow for our testers to have the freedom to do exploratory testing and investigate in ways that truly align with how customers use our application. The industry is currently grappling with these approaches and chasing the answer to the questions: Where do manual testers actually fit? Do they still fit? My perspective is that there will always be a need for testers. How we use them will change over time, but there is still a big need for that function and how that role thinks.
Some of the emerging technologies or trends that I’m really interested in right now are machine learning and AI. I want to know how we leverage these technologies to empower automated testing at scale. How do we leverage machine learning and AI to write automated tests for us, how can we tap into true user data, and through AI/ML automatically write new tests and add them to our suites? And because this is an area where I see a lot of automated test practices fall down, I’d like to know how do we use AI and ML to facilitate the maintenance of our test suites to keep them running and viable? Is there meat in the market today or is it just a bunch of slick marketing—and if it’s the former, where can we leverage it?
I’m sure many QA candidates that we want to hire have several options to choose from. Based on your time here, what are two or three things that you’d say to sell BetterCloud to those people?
I think I’d bring my personal experience about learning about where BetterCloud sits in the industry and the lane that we’re creating for ourselves. That’s the same thing that sold me on BetterCloud, so that’s where I would likely start.
Secondary to that is BetterCloud’s quality engineering organization. We’re in a really interesting place right now. We’re putting old and new processes on the table at this point and we’re willing to explore how to do them all better. You have the ability to help us reshape or mature our practices, plus you get to explore new technology. It’s a really good and exciting point in our journey for that type of work.
Also, we are significantly committed to test automation. A lot of companies, to be very honest, will hire someone to do automated testing and within the first three months, they’re just focused on manual testing. It’s kind of a bait-and-switch sometimes, but we are doing pure test automation here. The ability for someone to come in and simply work on code to test code is a big draw and that’s something that I would absolutely leverage.
It’s also nice that you’re not hiring people to write automated tests only to have them automate themselves out of a job.
Oh, certainly not. There’s longevity in this work without a doubt.
A couple of easy (I hope) questions to wrap up our conversation. Where do you see BetterCloud this time next year, and what role do you hope QA will play in getting BetterCloud to where it hopes to be this time next year and into the future?
I think the number one thing that I’m excited to see for BetterCloud next year is just better rooting in our industry. We focus on how people love SaaS, SaaSOps, and the BetterCloud brand. I think that quality engineering has a big part to play in that. Having a reliable product that is delightful to use goes a long way to loving it. That is frankly my number one driver. How do I help make this an awesome experience that ultimately drives stickiness for our customers?
That’s awesome. This question is a real softball, but since we’re still in the middle of a pandemic, what’s a hobby or activity you’re looking forward to picking up when this is all over?
As I think about the world normalizing again, I’m excited to get back into the office. I am not a work from home person. I love office culture. I love seeing people face to face, although I completely value distributed teams. I value our ability to hire in different places and get more diverse talent, but I personally would love to walk into the office again. Well, for the first time. It’d be the first time for me at BetterCloud’s office.
Want to learn more about the interesting and complex challenges that our engineering folks are tackling? Check out our Careers page to learn more about open roles on the team.