Startup Series: 3 Lessons From a World-Class Product Leader

Hiring your first product leader is no easy feat at an early-stage startup. But wouldn’t it be pure gold to learn a few secrets to better know what a great startup product leader looks like? Hernan Alvarez, VP Product at Great Expectations, has seen a lot during his 25+ year career. His career path was anything but linear, first working as a line cook, then sous chef while in art school for a career in the music business. He spent several years in the Seattle music scene as a touring sound engineer for grunge and heavy metal bands from around the world. It isn't possible to distill everything I covered with this “startup mechanic” in our wide-ranging conversation, but three noteworthy learnings for early founders stood out: Stay focused and don't do too much too early, mission clarity matters, and if you think all it takes is a fantastic job opportunity solving hard problems to land great leaders, Hernan may beg to differ. 

Hernan’s unorthodox path to product 

Hernan's early days working in the music business designing and building stadium sound systems literally set the stage for him to catch the tech itch in the early ‘90s, starting out in QA before making his way up the developer-track. Realizing he wasn't a fan of pure development, he made the leap to IT systems engineering and later to large scale Oracle database administration at Cotelligent. During his nearly 6-year stint there, he played a pivotal role in leading IT through a massive merger and acquisitions phase and then through the company's successful public offering, never looking back. As the tech world started to change, he saw an opportunity to build on top of his sound system engineering experience and pivoted to large scale infrastructure operations. From that, he’s built his tech career working for well-known companies like Mobliss, Whitepages, HP, Blue Box, Algorithmia, and DataRobot to name a few, as well as founding n2systems, Inc. in 2006.

Hernan said his shift to product was born out of change in the tech world — a time before cloud was even called cloud. What's now taken for granted didn't even exist. Infrastructure operations were becoming critical to a company’s success. The need for very specialized infrastructure and software implementations on top of that infrastructure was critical to build new technology businesses. In fact, we are seeing the same thing happen now with AI/ML and big data systems that we saw back then with software and early internet applications. Recognizing the transition then, led him on his product journey, where he's been in one shape or form ever since. Now he's applying his IT, big data, and large-scale infrastructure operator experience on enterprise AI/ML and data products.  

"I give a lot of credit to AWS and Amazon for really moving the idea of infrastructure and operations from just a cost-center to a strategic asset. As much as I hate competing against them," Hernan laughed. 

Stay focused, don't do too much too early. 

With a propensity for pinpointing chaos, Hernan knows startups often encounter unforeseen dysfunction during their initial growth spike. There's a lot of undefined space, everyone is moving fast, and people aren't necessarily on the same page. When an early team starts with 10 to 12 people, they're basically synchronous. Team growth leads to compounded assumptions due to the addition of new perspectives and experiences. Anything vague and only known by the core team doesn't always transcend this growth. People are flying by the seat of their pants and trying to do too much.  

"So many startups try to do way too much too early," Hernan said. "They have ten different initiatives going on, about nine of them are never getting completed, and the one that does may not be aligned with the mission."  

If not addressed quickly, this leads to team turnover, customer departure, or an engineering mess. Any one of or all these things combined brings a realization that product needs to be run as a discipline with compassion for the user and an understanding of the core basics. And this is exactly the socket that Hernan has become very savvy at finding and plugging into.  

"Leading product doesn't mean that I'm in charge of what we do in the company,” he said. “What it means is that I am there to ensure we are focused on mission, customers, and outcomes as our primary reason for what we're doing, who we are doing it for, and why we're doing it." 

When this clarity is reached, there's a natural synchronicity formed within the entire company. Product can serve to help create that clarity — the golden thread that allows the team to answer questions and continue to link the vision to the product being built. Then the team sees things, does things, and achieves things themselves, versus being told what to do.

Lead from the front. 

Hernan's experience with many early stage companies and as a founder shaped him as a leader and created a passion for bringing unification and alignment to teams. Hernan said that to do that, he had to learn how to lead from the front rather than push from behind. He has had many challenges and failures along the way, but that doesn't bother him.

"Failure itself is not virtuous, what you learn from it is. Failure is going to happen so be prepared to learn from it, grow from it as a team, as a leader, and as an individual," he shared.

In a startup, there's a ton of ambiguity. It's the job of founders to make values and the company's mission crystal clear, so in times when there's an absence of clear direction (which, let's face it, is often), teams can still anchor their work to something. This starts with getting the entire team aligned with the mission. Without that, the rest cannot exist. Hernan's passion for this is undeniable. He sees it as his biggest calling as a leader and the quickest way to drive meaningful team and customer outcomes. They know the "why" because you've kicked off every All-Hands with it. Keeping your values and mission in the spotlight is critical to keep teams in lockstep.  

"You can't just say something once and then never talk about it again. It doesn't sink in," Hernan said, stressing that many founders miss the opportunity to create the necessary fiber for people to work independently yet always connect to the mission. Adding, "Repeating the who, what, where, and why we exist as a company, and then aligning with clear goals creates that fiber." 

The money matters, but it's not the only thing.  

Early stage doesn't mean founders can seal the deal on the job opportunity alone, a point Hernan is transparent about during any gig he explores. For him, "show me the money" is a big part of the equation. Founders looking to hire top leaders for their business need to bring their competitive game and vet this as early as possible in the process to avoid unnecessary misalignments later. "You have to pay for experience," Hernan said, adding that the compensation must be there — something he firmly believes should be transparent from the beginning. "While we are all here to be compensated, and we get that money by building successful products with healthy organizations, those things can't exist separately from each other. I come to win together; otherwise, I could play with computers alone for free at home."

But to land the experience and talent, there has to be interesting problems to solve for real customers, strong culture, aligned team, and transparency. All startup leaders need to be aligned and thoughtful in how they frame their employee value prop (EVP) — especially for experienced leaders who have been through startup growth cycles before.

This clarity is critical for Hernan when he's committing his life to the next stage of a founder's story. Many leaders, including him, have shared that in-depth leadership working sessions, before joining the team, are critical in calibrating two-way fit. These sessions shed light on things like leadership philosophy, founder culture and working style, and give world-class talent like Hernan deeper understanding about the business challenges that lie ahead. These sessions can only be successful when the incoming leader and founder(s) are equally transparent. This allows each to see the future in a tangible way. Every startup has its challenges; those need to be on the table for all to see. Founders need to be as open as possible about the reality of what they have: The good, the bad, the ugly.  As a founder, you're betting your startup's future on great leaders who will take your business to the next level, and in return, they're making bets of their own.

"I'm betting my next couple of years on this, so I have to get the sense that we are all aligned — that this is a team I want to go to battle with. Startups are hard in every way and we only get through together."