Mike McClay has spent the better part of two decades working in Silicon Valley. Here, he chats with software engineer Akash Gupta about the road from Software Engineer to VP, what it’s like to work in digital health, and his best advice to both independent contributors (ICs) and managers.
I'd love to first understand a bit about you personally. What do you like to do in your off time? What’s something most people don't know about you?
I grew up in Orange County, which is pretty suburban, so that afforded us a lot of time outdoors as a family. A life goal of mine is to do a solo hike of the John Muir Trail. The route starts in Yosemite Valley and heads south to Mt. Whitney. It’s about 225 miles and typically takes a few weeks to complete.
Currently though, I have a two-year-old and a four-year-old, and we have another baby on the way, so my outdoor activities tend to be much shorter and closer to home. I got into road biking about 10 years ago and transitioned to mountain biking a few years back when my family moved to Marin. Being able to get out onto the local trails a couple times per week is an amazing opportunity to get a great workout in, and unplugging does wonders.
Finally, a ton of family time with my partner and kids. A big reason I decided to join Alto is because it provides a great balance of simultaneously being a high growth startup but it’s also a company that has an eye on culture and achieving work-life balance. At Alto, we're playing to win, and we’ve got a lot of things to get done, but there's a lot of support and representation for people with families with kids. It's nice to be able to work hard towards an incredible mission but also not have to sacrifice too much on the family front; so outside of work, I’m mostly focused on spending quality time with my family getting outdoors, getting to the beach, and things like that.
That's very exciting, having another child on the way. How has COVID-19 impacted your responsibilities of being a VP Engineering and a father?
Life is a lot harder during COVID, though I say that with a fair amount of awareness of the privilege my family and I have. On the home front, we are constantly trying to find that balance of keeping the kids entertained and learning but also doing it in a safe way that protects everyone. My wife and I are pretty fastidious about keeping the house organized and clean but that’s relaxed quite a bit during this time; there’s a lot of resetting of expectations, and I try to do as much as I can to support my wife.
Professionally, probably about half of our engineering team has interviewed and onboarded since the shift to remote work in March, and I’d say we are still iterating and adapting each month to work better in a fully remote environment. It’s been incredible to see our teams adapt to this new style of work, and while it’s not quite the same as our in-person environment was, it’s been really cool to see the team grow and have our organization make a bigger and bigger impact for our patients each month.
I'd love to talk about some of your past experiences. You went to the University of California, Berkeley (Go Bears!), then Expedia, then Uber, and now you're at Alto. What prompted each of those transitions?
Yeah, I’m kind of an outlier in the tech world in that I’ve only worked at 3 companies since graduating undergrad in 2004. I think I’ve been fortunate to find myself at companies that have had no shortage of growth opportunities and that led me to stay for considerable amounts of time at both Expedia and Uber.
Towards the tail end of my tenure at Expedia, I was managing the engineering team of a start-up that Expedia had acquired, and I knew in my heart that I wanted to move to a much smaller company. I spent a few months talking to a bunch of early stage start-ups but hadn’t found anything that felt right yet.
At the urging of my recruiter, I took a call with a company called Uber, which had seemed way too “big” for what I was looking for in that the engineering team was about forty people. Despite the role feeling different from what I was expecting, I was excited by the mission and the team, so I made the leap. Fast forward six years or so and it was an amazing ride, full of a lot of ups and definitely some learnings, but it was a truly formative experience for me.
Uber ultimately got to a point where I struggled a bit to pinpoint the impact I was making, and things overall at the company just felt slow. I wanted to work on something that was even more mission-driven, and one of my colleagues insisted that I chat with Alto. I was introduced to Jamie (Alto’s CTO). We talked over a number of months and found Alto’s needs and the challenges I was looking to solve aligned in a great way. So that's why I ended up joining.
Each of the companies that you’ve worked at have had large operational components. What are some of the key pieces to creating a strong partnership in a tech-enabled company?
What I would definitely say is that the tooling and the product that we built for ops at Uber was, at the time, world-class; it was just beautiful. Design was a first class citizen in our operational tooling because the workflow of our ops team was so critical to our company’s success.
This is something that Jamie and I bonded over about Alto; our internal platform (called Wunderbar) powers the functionality that allows us to process our patient’s prescriptions in an efficient and effective way. Getting this right is critical for our patients, and the fact that we put so much time and energy into getting the technology platform right goes a long way to build a great working relationship with our operations team.
Additionally, I’m passionate in general about operations since it’s often an area of the business that creates strategic advantages over competitors. And what I love about building software with operations is that it can’t be copied easily by competitors since there is no public surface area to observe. I view our task as an engineering team as getting to where we're crushing it as a business because we have nailed supporting operations with our product engineering work.
On that note, would you say Alto is an operations company, a pharmacy, or a tech company?
We aspire to a model of cross-functional leadership, whether it's between Engineering, Product, Ops, Growth, Marketing—whatever it is, the leads of areas and even the team members of each area need to be empowered to achieve the mission that they're setting out to do. If that's to enable, say, the flow of prescriptions coming through our system, maybe you could call that Ops-led, but at the end of the day, multiple functions have to come together to solve the problem. I almost want to call it vision-led.
There’s a time and a place where we need to be creating a faster horse, and there's a time and a place where we need to be thinking one to two years out about what the step up is from the faster horse: bringing the car into the situation, so to speak. Ultimately we need to be thinking on multiple time horizons at the company, and depending on the time and place and the strategy, you might see one function spiking up in terms of what we're rallying around versus another.
The engineering team at Alto has grown from eleven engineers and four managers when you started a year ago to more than fifty-five engineers with nine managers, directors, senior managers, and managers. What would you say has enabled that dramatic growth, and how do you plan on ensuring that that growth is well-managed?
For engineers, there are a lot of choices out there, and a big part of our hiring process is spent not only assessing technical skills, but also looking for signals that candidates align well with our patient-focused mission. From the beginning, we created an interview process that is fair and equitable, and that resonates strongly with our candidates. From there, we set out some really big goals that energized the team to push to make it happen.
I'm really proud that we've grown while maintaining a solid level-mix in terms of junior, mid-level, and senior engineers. Our engineering team is ~25% female, and while we only have single digit percentage points of representation of other underrepresented groups, representation is improving every quarter. Our goal over the next several years is for the team to achieve 50% gender representation and 30% from other underrepresented groups, so that our engineering team is representative of those we ultimately serve: our patients.
In order to make sure this growth is well managed, my philosophy is to hire or grow Engineering Managers well in advance of the acute need. On the manager side—and this was a big learning for everyone at Uber—we’d grow a team of fifteen to twenty engineers under a manager and not really have a great plan in place for how to bring in additional leadership and get the teams down to a right size of ten. When we approached that number, we'd battlefield promote someone and everything just felt strained. So I'm really proud of the fact that even at nearly seventy people now, we have a management team of nine that could actually support one hundred people pretty well. As the team continues to grow we’ll be making sure to stay ahead of the growth on the management side.
On that note, Uber has been reported to have an unhealthy culture. What have you learned from it to engender a more positive, inclusive culture at Alto?
Yeah, I’ve had a lot of reflection on this and a lot of learnings from my time at Uber. First, it’s that as a leadership team, we need to be vigilant about creating a team environment where team members feel they can do their best work. We need to always have great managers leading teams that are right-sized, and we need to have people-focused cultural values that help guide our behaviors and how we interact with one another.
At Alto, half of our cultural values are focused on skills that foster an environment where folks can do their best work. Yes, we're thinking constantly about impact, but we make sure to hold ourselves to a high interpersonal bar. This type of behavior has also been institutionalized at Alto in our engineering career ladder. Culture amplification is one of the five skills engineers are evaluated against, and I think it’s a very strong signal into what we hold dear and how we want to roll here.
Finally, I’ve put a strong emphasis on making sure that interviews at Alto assess behavioral skills in addition to technical ones. We didn’t do this well at Uber for too many years, and I believe it led to some of the cultural negatives that you’ve likely read about in the news. To me, it’s critical that we hire really talented folks who can work seamlessly with one another. Getting signal on this during our interview process is a big part of growing a healthy engineering organization.
You've gone from being a Software Engineer to Tech Lead, Engineering Manager, Director, and now, VP. What advice would you give someone at each of those stages? What advice do you wish you had back then?
The main piece of advice I’d relay is to make sure that you spend enough time in each role to get solid proficiency. I’ve come across a number of folks in my career who look to move through roles as quickly as possible, and I think that doesn't allow for solid bases of knowledge to be built up. The foundation I built up in my experience as an engineer I believe resonates with engineers; I’m not just a people manager that helps coordinate minutiae. Additionally, a lot of the skill-building in these roles happens as you encounter various real life situations; the only way to accumulate experience is over time. So my advice is to be patient.
I would definitely encourage everyone to work at a company where there are clear career paths for both ICs and managers. You should never feel like you need to move into management to “grow in your career.” One of the first things we put in place after I joined Alto was a career ladder so that folks could reason about how they wanted to grow over time and come up with a growth plan with their managers.
Finally, don’t go too long in a role or at a company where you don’t feel challenged and don’t feel like you are growing. To me, growth and challenge are proxies for job satisfaction. I would say I've achieved it about 80 to 90% of the time in my career. If you're not in a place where you're feeling like you're growing, you should go somewhere else.
What would you say to someone considering working in digital health? What are some challenges and benefits in this space?
It's not so fraught with red tape that you can’t get anything done. There is a process to work through with HIPAA (Health Insurance Portability and Accountability Act) to ensure patient privacy; there is a massive set of opportunities that support all of the activity in the space; and there are seams where startups can begin disrupting entrenched players.
There’s also a massive opportunity to solve hard technical problems while achieving these amazing, mission-driven ends. I think sometimes it seems that those can be separated to where it’s almost mutually exclusive. While we don't yet have the volume nor traffic that you might receive at companies like Uber or Google, there are still meaty technical challenges that haven’t been solved before.
What disruption is good in healthcare and what may not be?
The good disruption comes in places where companies can plug into an existing experience that patients go through to solve a problem and figure out new ways to address that problem. In the pharmacy space, we are disrupting the brick and mortar pharmacy experience that is effectively in the business of selling you Coca-Cola while you wait for your medication.
Bad disruption would be anything that goes against protecting a patient or their privacy. At Alto the engineering and security teams are tightly coupled so that we can best solve for the needs and privacy of our patients.
You mentioned technical challenges. What would engineers and other technical people get excited about in this space?
We don't yet have our architecture mapped out for scaling 100x on our business over the next couple of years, and it’s been really exciting to start to discuss our technical plans to enable that. At Uber, we went from a monolith to a full micro SOA (Service-Oriented Architecture)—both extremes that had quite a few problems as implemented. At Alto, we aim to find a better middle ground.
Additionally, we need to think about what the pharmacy experience will look like five to ten years from now and start building some of the pieces that will work us toward that future. Safety and accuracy are incredibly important to us now, but at one hundred times our scale, we’ll need to be constantly innovating our technology so that we can minimize / eliminate errors in our operational process.
We’re also bringing data silos together that have never been joined before. For example, as many as 50% of prescriptions are not picked up for retail pharmacies. Doctors have no idea which of their patients pick up medications or not. Insurers don't know what happens to patients after they take their medication. We are the interconnect between all of these customers.
As we grow, that data is going to grow inside of our systems. The information and the insights that we can derive from it is going to be incredibly powerful. But we're going to need a ton of awesome data analysis, products that allow us to collect the data while respecting patient privacy, etc. I'm really excited about that.
What are you most proud of from your time at Alto so far, and what are you most excited about in the next year?
What I'm most proud of is the team that's been hired. They are just amazing. Last year, we had a team of eleven engineers with such a large surface area: fulfillment, operations, customer app, customer website, our provider portal, etc. With so much to do across a team of that size, we were constantly making really hard prioritization decisions and were not able to tap into what we saw as our full potential.
Fast forward to today, we're now in a world where we have dedicated teams for surface areas, and we’re solidly parallelizing efforts. Seeing the bandwidth, the throughput that's going to be rolling out each quarter, is really cool. We're going to have orders of magnitude more output each quarter than we did a year ago. That's what I'm most proud of now.
What am I most excited about? There's the business aspect, expansion. We've really only covered six markets and are now looking at covering many, many more lives. The next couple of years are going to be a lot of fun.
Last question. Someone's considering working at Alto: Why should or shouldn't they join?
Alto’s at a stage where things are changing constantly. Folks who like dynamic environments will thrive here, as the work is challenging, and we are trying to solve problems that have not been solved before. Given that Alto operates within a multi-sided network, we have a lot of opportunity to create value, but it also means there are multiple players to think about when building a product. There's a richness to our patient, provider, and insurer base that makes it both challenging and exciting to make sure that we're finding the opportunities that deliver value to broad strokes of folks without leaving others behind.
Finally, engineers should join if they want to be part of a mission-driven company, enjoy working in an inclusive environment and diverse team, and like to be at the intersection of technology and the physical world, whether that's operations, delivery of things to humans, etc. If we succeed, the way society thinks about health, prescriptions, etc, ten to twenty years from now will look very different because of the work we’re doing here. If that's inspiring to you, and you want to be part of that, you should join.
Interested in joining the team? Reach out to us on LinkedIn.
