#14 - How to thrive as an Engineering Leader | Anant Gupta, SVP of Engineering & Data Science at Included Health
Anant's lessons to blossom
Hey friends,
This week, we’re welcoming Anant Gupta, SVP of Engineering at Included Health, and previously an Engineering Manager at LinkedIn and the Head of Engineering for New Mobility at Uber.
Anant Gupta is reflecting on his own experience to help you thrive as an engineering leader, in a long-form, insightful article. He won’t share an exact playbook though, because such a thing doesn’t exist: each individual has a different path but can get inspiration from others. If you want to ask yourself the right questions, read on. By the way, a surprise may await you at the end of this article ;-)
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This article all started from Anant’s talk at Elevate 2023:
You can follow Anant Gupta on LinkedIn.
How to Thrive as an Engineering Leader (in a Pre-IPO Company)
There’s no single playbook you can apply as an engineering leader — that’s part of what makes this career so thrilling.
But because there are so many variables, including the stage of the company you join, the maturity of your team, and the nature of the problems you’re solving, you could easily find yourself in a leadership position that’s not right for you.
I’m Anant Gupta, Senior Vice President of Engineering and Data Science at Included Health. Throughout my career, I’ve had the opportunity to take on leadership roles at several tech companies, both leading up to and after their IPO. I’d like to share my learnings and observations on how to thrive as an engineering leader.
In my role at Included Health, where I’ve been for about five years, I lead Engineering and Data Science—a team of about 200 people. And if you’re not familiar with Included Health, we’re a health tech startup with a mission of bringing data and technology to raise the standard of healthcare. Prior to Included Health, I was a manager at LinkedIn and an engineering leader at Uber, both pre- and post-IPO.
Throughout each phase of my career, I have encountered moments – both through direct experience and indirect observation – of what thriving can look like.
My definition of thriving
Thriving is a term that’s open to interpretation—it means different things for different people and it might even mean different things to the same person over the course of their life.
The way I look at it is that thriving is the alignment between your values, strengths, and areas of growth.
I believe you can thrive when you find the intersection of your values, strengths, and areas of growth in a role and company.
Your values are the things that matter to you, and you can use values as a way to filter the type of company you’d like to work for. This can include elements like the company’s mission, its stage of growth, the title or recognition you’d receive there, the technology you’d be working with, and the impact you’d be likely to have in the role.
Your strengths are the things that you are in the top 10% of. But it’s not just about being good at something—you need to find a place where you can use those skills in a way that benefits the business and where you feel good about using them.
And your areas of growth are the things you’ve decided you’d like to get better at. Consider how you’ll have the chance to develop these skills. Will you get to practice? Will you have access to a mentor or coach? Again, it’s important to look for ways your growth is aligned with the business’s, or else it could easily get put on the back burner.
4 tactics to help you thrive
Now that we’ve got a working definition of thriving, let’s consider a few strategies to help you make this a reality in your own career.
1. Be at the right place for you
If you’ve gone through the exercise of defining your values, strengths, and areas of growth that I outlined in the previous section, you’ll now have a blueprint to help you find a company that’s the right fit for you.
Here’s how I think about my values, strengths, and areas of growth.
My values mean I want to work at a mission-oriented company, a spot where I get to grow and be with people who are changing the world. I love working at startups that are disrupting an industry. That gives me personal happiness and satisfaction.
My top 10% strengths are building teams and organizations and making an impact at the pre-IPO to post-IPO stages.
My areas of growth are being the best leader I can be and creating excellent organizations.
Whenever I evaluate a new role or company, I try to find alignment in these three areas, and this is my advice to you. You first need to take the time to define what your ideal role and company would be and then try to find opportunities that are aligned with that.
Ideally, you’d define your values, strengths, and areas of growth and you’d find a company that’s a perfect match in every area — But the reality is often much more ambiguous.
Every role can teach you something, every role can leverage your skills, and every role could give you some of what you value. The clearer you are on what you want (e.g. learning AI or working at a post-IPO company), the more limited your choices will be.
The decision to choose a company will largely be a function of what you value. If you get the value part right, the other two will follow. If you value growth, then you might need to be willing to compromise on compensation. Or if you value cash compensation or title, you might need to be willing to forgo working on a more appealing mission or working with a great manager or team.
This means you have to get values right. Are you being honest about what you value? I have seen this all too often when manager candidates say they want to work at a small company (because they value growth and career upside) but they want to run large teams when they start (because that’s what they want to be doing).
They’ll need to make a decision: Do they value the growth they’d get from managing a small team that’s directly, causally changing the trajectory of the business? Or is it more important for them to have the title and clout they’d get from managing more people within a larger organization? There’s no judgment or right answer here—it’s something everyone needs to reflect on and answer for themselves.
If you’re facing this type of decision, one tactic that can help is to ask yourself, “What is the job after this one?” If you fast-forwarded a few years in the future, what would that role look like? How do you feel about the potential future state of that role and its alignment with your values?
Another framework I’ve used is to consider what will help you become the top 10% of the role you seek. We tend to get fixated on title, status, and role, and celebrate “success” as getting the role; not being great at the role. Honestly ask yourself if this role gives you what you need to get there and if it increases your probability of success.
Often applying these frameworks can help you narrow it down quite a bit. And if the answer is none of the roles, then it is better to wait if you can. I recognize that waiting is a privilege and not always possible. If you’re in a position where you can’t wait, it means that you value compensation or the job over the other items on the list. Again, there’s nothing wrong with this approach. The important part is that you do this consciously because doing so can accelerate your career and get you to where you want to be.
Finally, I’ll add that what “thriving” means to you will change throughout your career. As I’ve mentioned, what you value can fluctuate, your strengths will evolve, and of course, the areas where you want to grow will also change, too. I’d recommend taking time to re-evaluate your values, strengths, and areas of growth every three to five years. Doing it more frequently means you risk day-trading your career.
2. Lean into the challenges
When you join a startup, you’re making trade-offs.
You may choose a future reward (in the form of equity, career growth, or impact), which means losing out on certainty. Similarly, you may have greater autonomy, which comes with more ambiguity.
We may make these trade-offs consciously, or we may have done so without realizing it. I’ll often talk to managers who will tell me, “In my next role, I want to be able to have a strategic impact at my company.” And five minutes later, they’ll ask me what they need to do and to tell them exactly what the roadmap is for their team for the next 12-18 months. They don’t necessarily see that these two things might be at odds.
First, I’d recommend you consider some of the trade-offs you’re making when you join a startup. I’ve outlined several of them on the slide above. Do you feel comfortable with prioritizing the things on the left (growth, future reward, faster learning, etc.) over the things on the right (comfort, certainty, structured learning)? Great. A startup is probably the ideal setting for you.
Next, it’s helpful to look at the types of challenges companies are likely to encounter based on their stage of growth and how that lines up with your interests and strengths. Early-stage companies are trying to figure out how to ship a 0 to 1 product and find product/market fit. Mid-stage companies are focused on scaling the product. And late-stage companies are looking for how to scale the product across different verticals.
Once you’re aware of the challenges you’re likely to encounter, consider leaning into them rather than fighting them. Easier said than done, right?
If you join an early-stage company and it doesn’t have product/market fit, you can fight that, or lean into it and decide you’re going to solve it. You may also realize it’s not a challenge you want to solve and you’re not at the right place, in which case you’d be better off finding another company and role.
When I was at LinkedIn, we went through a process where we re-evaluated our technical architecture and stack during a multi-month pause. It was a big deal, but it propelled the company to be more successful.
We went through something similar at Uber—we had a project called Darwin that was trying to break up the monolith that Uber had and move faster.
And we’re undergoing a similar process at Included Health, where we’re refounding our technical systems that incorporate AI and product experiences at scale for millions of members.
I’m not saying that all startups are the same, but there are broad similarities that you can find in companies at various stages of growth (whether team size, product-market-fit stage, funding round, etc).
If you don’t like working in a company that’s optimizing to ship fast (and at times incurring tech debt), chances are working at an early-stage startup is going to be difficult for you because they generally start off working in a monolith in order to move fast and find product/market fit. If you want to work in a company where you get to break up that monolith, don’t join an early-stage startup because you’ll be fighting the business. Join a mid-stage or later-stage company and seek those experiences out.
Learn to recognize which trade-offs you’re making and which problems are to be expected at your company’s stage. Instead of being perpetually unhappy or blaming where you are, consider whether the pain or frustration you’re experiencing is the flipside of the trade-off you’ve made. This ties back to my previous point about really understanding what you’re looking for and making sure you’re at the right place.
Bringing it back to my personal experience—I’m a technologist, and love building products and experiences that make a user’s experience 10x better. Imagine trying to make search 10x better. Now imagine trying to make healthcare 10x better. For me, making healthcare 10x better is a more interesting problem, both technically and also around the dimensions of impact.
When I imagine my experience at a search company vs. a healthcare company, one is likely more known and is optimizing their software algorithms. The is other lesser known, with no less difficult technical problems to solve, but coupled with real-world messiness. I could be upset that working in healthcare means it has lesser brand recognition, or I can embrace it and work to change that and create a world where our healthcare experiences are 10x better and technology-driven.
As an anecdote, I remember doing a tech talk at Uber explaining the technical challenges at the company when I had first joined because I often had candidates mention they couldn’t understand what was difficult about Uber. In hindsight, that feels like an odd question, but this is the journey of disrupting and changing an industry through technology, and because I’ve been through it and seen the other side, I feel excitement for the opportunity and future ahead.
You need to have a point of view on where the world is going.
One final thing to note here: In order to choose the right company for you (especially if we’re talking about early-stage, pre-IPO companies), you need to have a belief about the future. You need to have a point of view on where the world is going. This can’t be a reactive decision.
In today’s landscape, for example, generative AI is already the next big thing. Having a long view allows you to focus on building your set of skills that give you a competitive advantage in the long run (as opposed to trying to shoehorn your skills to match a job description). So think long term, and pick the trade-offs you want.
Focusing on the areas where I wanted to have a competitive advantage, I chose to join LinkedIn, Uber, and Included Health because, at that time, it gave me exposure and experience at the size and scale I was looking for. Being at Uber or LinkedIn today is vastly different from where they were when I joined, and it was precisely that learning and growth that I was optimizing for.
3. Make the “and”
My next piece of advice is to make the “and.” What does this mean? At startups, you’re going to constantly find yourself facing choices. Here are just a few examples:
At LinkedIn, we acquired a company called Connected that was built entirely on Python/Django. LinkedIn’s entire tech stack was all in Java. What do you do in that situation? Do you rebuild it all in Java or ship it faster?
At Uber, we had to decide whether to build our own bikes and scooters or go with a partner. Building is capital-intensive, but partnering up could make our partner dominant in the space. There aren’t many companies that can operate at Uber’s scale.
At Included Health, the market and industry are moving faster and faster. How do we keep up? Do we press our technical advantage in the market or pause and work through our tech stack?
But what if we reframed our approach? What if we thought of these problems as AND rather than OR?
For example:
At LinkedIn, what if we rebuilt it in Java to integrate AND shipped faster?
At Uber, what if we built our own scooters AND partnered with a company?
At Included Health, what if we keep pressing the technical advantage AND investing in our tech stack for the future?
Now let me be clear – the idea is not just to do it all, but it’s to think about the AND so you create a different set of choices. Are two things mutually exclusive? They may not be unless you change a different set of variables.
Continuing on with the same examples:
At LinkedIn, we integrated the UI to learn sooner while building the data layer on LinkedIn’s stack. This allowed us to make progress toward integration while gaining useful learnings about the product.
At Uber, we jointly partnered to build Jump and Lime. This allowed us to prove a business model and have optionality in the future with Lime.
At Included Health, we’re prioritizing technology investments that unlock AI, Orchestration, and Total Care Platform. This means that while we may slow down in the short term, we plan to be considerably faster in the future.
Remember that making the “and” isn’t about dodging trade-offs.
Remember that making the “and” isn’t about dodging trade-offs—you’ll always have trade-offs. It’s about changing the “or” to an “and,” which produces a different set of choices. More often than not, the different set of choices ends up being a lot better.
Finding the “and” doesn’t eliminate the need for trade-offs, but it should help you end up with a better set of choices.
4. Invest in people
One of the challenges of a startup is you can’t hire people fast enough to keep up with what you want to do. Startups are trying to change the world and it’s hard to do that with a small number of people, but that’s the idea.
When I was at LinkedIn, we were trying to take on companies like Indeed or Monster.com. Uber was trying to take on the entire taxi industry. Included Health is aiming to raise the standard of healthcare for everyone and make an impact on the $4 trillion US healthcare industry. Engineering creates leverage for these types of businesses. We cannot make change at that scale unless we have the right people and have invested in those people.
Yes, it sounds obvious that you need to invest in your people. But you need to spend time defining what that means for you as a leader.
You might be thinking, “Of course, we need to invest in our people. No one’s going to argue with that!” While most people would agree that it’s important to invest in your people, if you press them to elaborate, you’ll find all kinds of different ways to interpret that phrase.
Since we’re focusing on technology leaders specifically, let’s consider some of the different styles of leadership you’re likely to come across: authoritarian leadership, servant leadership, and transformational leadership.
Authoritarian leadership allows a leader to impose their expectations and define outcomes. This style of leadership works when a leader is the most knowledgeable person on the team or when team members need clear guidelines.
Servant leadership involves leaders meeting others’ needs, helping them grow, and providing them with opportunities to be rewarded materially and emotionally. This style of leadership means the leader goes beyond self-interest and serves other people, organizations, and society.
Transformational leadership means the leader inspires their followers with a vision and then challenges, encourages, and empowers them to achieve it. The leader also serves as a role model for the vision.
Of course, there’s no single right or wrong way to do this. A leader's job is to create positive change and these are different styles that help.
Ask yourself, “Which style is the most effective in creating the change you are seeking to achieve?”
You can arrive at this answer by determining what your team needs, the ideal state of how they should work, and if there is a delta, what is the value of getting to the ideal.
All of those questions require judgment. If you get what the team needs wrong, or how it should work, then it’s not a leadership style problem, but a more fundamental problem on either problem-solving or critical reasoning.
While authoritarian leadership might sound bad and like it’s something to be avoided at all costs, the truth is there are some situations when it’s the best option, like at a very early-stage startup when you have a small team that just needs to execute.
In contrast, servant leadership sounds cool and I think it’s what a lot of individuals say they want from a leader. However, as I’ve gained more experience, I’ve come to the conclusion that servant leadership is not the most strategic style. It depends on the people in your team having a clear idea of what success looks like and you doing that to make them successful. Larger companies tend to embrace servant leadership and measure a leader’s success by the happiness of their team. These companies already have established processes and optimized their organizations to generate significant value for the business as long as they have happy contributing smart engineers.
However, that isn’t always the case in a pre-IPO hypergrowth company. There is often less process, higher ambiguity, and frankly a greater appetite for impact relative to the capacity of the organization. That requires a different leadership style.
Transformational leadership means you have a point of view on what the company needs to be successful and you inspire and motivate people against that vision. I now believe this is a more suitable style of leadership for me given the types of companies I seek out—fast-growing, pre-IPO companies.
One of the reasons I’m now drawn to the transformational leadership style is that I believe I’m here to create a step-function change in someone’s career. That step function change will take them from where they are to where they need to go.
Another critical piece of this puzzle is your role as a hiring manager. Just as I said you need to find the job that’s right for you, you also need to hire the right people for your team. This means finding people who are aligned with the values you hold true for the company, the strengths you will leverage, and the areas they want to grow in. If you find that, in my experience, the transformational leadership style will resonate with people.
To recap: Being a transformational leader starts with having a vision of where you are heading and what success looks like, followed by what would need to be true in order to achieve success. Finally, it involves finding the most efficient and high-probability path toward that.
To share an example from my own life, I believe healthcare can be a whole lot better and there are a lot of inefficiencies and waste in the system, where people, even with the best of intentions, don’t end up achieving the best results (outcomes, preference, cost). For a company to realistically change this you need:
Member trust/preference: If I’m going to change the way people interact with their healthcare, I need their trust.
Knowing what to do (the brain): I need the ability to figure out what is the optimal path for a member given their situation.
Integration and access into healthcare; access to data to best determine course
If so, then as I'm building the org, determining the technical architecture, hiring people, deciding to build vs. buy, defining processes, etc., I am always looking at what gets me closer to that goal, the probability of that being true, and if there are things I could do to improve the probability of success.
At Included Health, we’ve invested heavily in building consumer-grade healthcare experiences on top of a robust data and AI stack because we believe those will get us there and we’ve hired some amazing people toward that goal. We are also using a lot of open-source and supplementing where it is less necessary.
Final thoughts and takeaways
To sum up, I’ve shared the importance of being at the right place for you, leaning into the challenges, making the “and,” and investing in people.
Being in the right place for you—is the most important factor. People tend to base their decisions on things like comfort (I know someone who works there), competence (they use Java, I know Java), or extrinsics (the company will look great on my resume). Basing your decision on these factors is different from choosing a company based on principles.
Once you’ve taken a more thoughtful approach to finding the right company for you, it’s much easier to lean into the challenges you’re facing. If you’re focusing on pre-IPO startups, accept that it’s going to be chaotic and messy. That’s what you’re there for. You’re not there to spot problems; you’re there to solve them.
Make the “and.” Remember you’re always going to face choices, but they’re rarely either/or choices, even if they seem to be at first. Look for the “and” choices and you’ll find the better path.
Finally, invest in people by finding the leadership style that resonates with you. I introduced three styles here and talked a bit about the environments where they tend to be most successful, but this is your leadership journey, so spend some time exploring the topic more and find what works best for you.
Opening
I have a passion for my work and for helping people find a work environment where they can thrive. You can learn more about me and my initiatives at Included Health by checking out my interview on The Dream Team podcast and reading my Medium post about why I joined the company. Note that it was initially called Grand Rounds before it was renamed to Included Health.
If the challenges I've discussed at Included Health resonate with you and align with your values, strengths, and areas for growth, you'll be glad to know we're currently hiring for a broad range of technical roles. Discover more about our work culture and explore the current openings on our website and LinkedIn page.
And that’s a wrap!
If you're part of the brave ones and stayed with us till the very end, here’s a small gift for you: 40% off your ticket at Plato Elevate, the no-BS conference for Engineering Leaders, happening in San Francisco on June 5-6.
Use the code ELEVATE2024-ANANTISGREAT at checkout to get your discount!
Cheers,
Quang & the team at Plato