Since joining the risk management and insights logistics platform Overhaul in 2016, Andy Fletcher has added two executive titles to his resume that he hadn’t held prior: VP of operations and chief technology officer.
Fletcher, a former engineer, initially signed on to oversee the startup’s operations, but following a reconfiguration of sorts, he made the strategic decision to temporarily consolidate engineering and product into a single group and took on the title of CTO.
“This allowed us to iterate and experiment faster, which helped us evolve our business model and form the identity that we know today,” Fletcher said.
The move helped the company grow substantially, including scaling the team to more than 130 employees and securing another $35 million in funding. It also deepened Fletcher’s understanding of the intricacies of working with and leading product teams.
“Product will always be caught in the middle of technical requirements, customer needs and strategic ambitions. It is impossible to satisfy everyone,” Fletcher said.
At mobile education platform Aceable, Senior Product Manager Josh Gilliland is still learning how to measure his success in management after advancing from an individual contributor to his first leadership position.
“There have been times with my new role where I have found myself feeling like I wasn’t being productive because the nature of my work changed,” Gilliland said.
Product professionals interested in following in their footsteps: Read on for industry intel that could help you in your future leadership positions.
What have you learned is imperative to leading product teams?
Tradeoffs must be made using established and agreed-upon methods. It is also essential to be a sympathetic communicator.
Still, even with processes and capabilities in place, one of the most common issues that I encountered was the need to document and circulate when and how those hard decisions should be made. For instance, it’s important to identify top priorities, and it’s just as important to list why something won’t receive resources to accommodate those top items.
The trick is to inform stakeholders about the decisions without getting to the point that it needs to be relitigated. For example, we recently completed the most viable product release of a tool for a specialized user on our platform. It passed customer acceptance and was in use. We didn't forget about our ambition for the project, but we did shift our focus from it after launch for perhaps too long.
We were OK, but it could’ve led to an assumption of progress from stakeholders. Had that happened, we likely would have had to make the decision between dedicating extra focus to catch up to stakeholder expectations or accruing product debt with the new feature.
Every department and team has their own structures and responsibilities, but we all have the shared goal to deliver a product that we are proud of.”
What advice do you have for product professionals looking to move into a leadership role?
Every problem is a people problem. Teamwork is the solution and leadership is responsible for putting people in positions to be successful. Software is a black box and can do anything we can imagine in the digital realm. Therefore, the main focus should be to engage team members through the problems you are attempting to solve and the value you deliver to customers.
Establishing clear responsibilities between departments helps build an organization. Effectively building a team, however, requires breaking down barriers between departments and fostering an environment of collaboration. Solving problems for a customer to deliver a positive user experience takes all of us working in unison. At Overhaul, every department and team has their own structures and responsibilities, but we all have the shared goal to deliver a product that we are proud of. This should be encouraged by creating opportunities for it to happen. Trust your coworkers and create goals that yield a shared sense of accomplishment.
Cross-functional collaboration and a one-team mentality will ensure every obstacle is met with energy and determination.
What has your career trajectory been at Aceable?
I began my career in product management at Aceable in 2015. At the time, I was focused on internal tools, primarily on a proprietary tool that we build and maintain to manage courses and users in our learning app. During the first few years, I gradually took on more customer-facing features in our learning app. This led to me owning more high-impact features across both our internal tool and learning app beginning in 2019, until I eventually became the primary product manager for our learning app, both back-end and front-end.
Last year, we decided that we needed to expand the product team to allow us to make more improvements to the student experience, and I was asked to manage a small team of two additional product managers. This has meant increased responsibility and moved me up a level in terms of where I operate day-to-day.
Look for opportunities to do the job before you have the job.”
What surprised you most about your new leadership role?
One of the biggest surprises is that I’m now not involved in all of the implementation decisions for our learning app. I had grown very used to being directly involved in all new features on our learning app, but with two additional product managers driving these features, and my additional responsibilities, that’s no longer possible. We began this year with a project to build new interactive elements for our courses. I helped run a short prototyping sprint, during which we created prototypes for the student experience of each interactivity—but not the internal tools for our learning experience team to create them. Then one of the product managers on my team ran with it.
A few sprints later, a new internal tool for one of the interactivities showed up for product manager review, and I realized that I hadn’t seen the designs before. They looked great, because our team is awesome, but it was an eye-opening experience for me in terms of my new role. I realized that I needed to shift at least part of my focus up a level to ensuring my team is aligned on the overall philosophy for our app and the process for how to get there.
What advice do you have for product professionals looking to move into a leadership role?
This is nothing new, but the biggest piece of advice I have is to look for opportunities to do the job before you have the job. Take ownership over what you are working on, and when projects come along that provide an opportunity for leadership, take them. As long as you do well, the opportunities should continue to present themselves, and should eventually be followed by the requisite new titles and promotions. If you do this, advocate for yourself with your lead. If you still don’t see the payout after a reasonable time frame, then it may be time to look elsewhere, in which case the leadership experience you gained will be very valuable, so it’s a win either way.
