My first year inside Insider
I joined Insider Inc. to head up its Engineering team on the 29th of May 2018. I was bright-eyed and looking forward to trying something new after three years at Time Inc. It’s been over a year now and what a ride it has been.
John Ore, our Chief Product Officer, and I first met early in 2018. Prior to my joining Insider, we would meet regularly to talk about the challenges of reshaping an engineering team.
When I arrived, I walked into a leadership vacuum. All of the senior tech leadership had been let go or resigned. The engineering team had been isolated from the rest of the organization and was in need of a complete overhaul.
An overarching symptom of an organization in trouble was projects typically took years to build and, when released, did not live up to expectations and already close to obsolete. This seemed to speak to a misalignment between the engineering and product teams, the root of which was a deep seated distrust which permeated throughout the culture of the organization and the teams.
One thing at a time
There were so many opportunities for improvement that it was immediately overwhelming.
Years ago, my good friend Ben Ronne gave me some good advice: “When in doubt, start where you stand.” So this is what I did. I would try to focus on one thing and fix it or get it on track. Of course you still need to balance this with departures, resource allocation, various fires and meetings — tons of meetings, team restructuring, title changes, salary level audit and adjustments, hiring, hiring, hiring, and more.
As soon as one thing was complete, I’d immediately move on to the next. There is no time to breathe at critical moments like this yet somehow you always need to remember to step back and take stock.
Weathering the storm
“You can please some of the people all of the time, you can please all of the people some of the time, but you can’t please all of the people all of the time”
— John Lydgate.
I was brought in to fix and make radical changes. Through this turbulent time we lost almost half of the engineering team. For some of those engineers that left, it was just time to move on, while others were disillusioned and already halfway out of the door. And some just didn’t like my leadership style.
In this type of situation, you have to make it work with those that stay. Times like this are often opportunities for those that remain to really shine. Out of the maelstrom arose a few stars who are continuing to excel and lead today.
While it’s difficult to focus on when a lot is happening, the only way to fix things is to set up a plan. As with all plans, it requires people to make it happen, but progress was frequently sidelined. Often, I’d assign an individual to take the lead on something only to have them depart, which would effectively hit the reset button on that initiative. Rinse. Repeat. Start over again. This happened way more often than I’d care to remember and was the biggest test of both the teams and my own morale.
Trust & no appetite for apathy
No team can be successful if they don’t know what’s expected of them. To make real changes, it was important to set my expectations clearly and early on. The most important thing that we needed to work on was “Trust.” I have worked in environments where there was little to no trust. It’s frustrating, demoralizing, and self-defeating. There was very little trust in our ability to execute on the work we committed to. It’s a simple word that is incredibly difficult to regain if you lose it.
In a series of team meetings, I reinforced the need for us to build trust with three guiding principles:
- Trust that you are giving your best, and that the engineer next to you is doing the same
- Trust that everyone is striving to make things better and have the best interests of the team and company at heart
- Build trust with stakeholders by delivering great products consistently and of high quality.
There was no place in our Engineering organization for apathy or waiting to see if things got better. Everyone had to contribute to make change happen. There was no tolerance for simply sitting back, hoping for this change. In the process, we had to be open and transparent with each other, acknowledge our problems, and work to fix them together.
Hiring and retention
In 2017, we had hired just 4 engineers and carried over 4 incremental open positions. Through the early part of 2018 we were losing engineers quickly because of the turmoil and uncertainty within the organization. My starting at Insider also prompted additional engineers to leave.
At the time, we had about 30 applicants in our hiring system for the one open position we had listed and 2 candidates in the process of interviewing. We were trying to hire the perfect senior candidates, which for those of you that have tried to hire engineers in NYC, it is not an easy feat.
We needed to change our approach to be more open minded and inclusive to give us a shot at getting great candidates. We also needed full time help on Talent side. Enter Anum Khan, our current talent acquisition manager. With her help and guidance, we created more general job postings for software engineers and started marketing them through LinkedIn, Twitter, and to anyone that would listen. Internally, we used any opportunity to promote our open positions and constantly asked for referrals. We started attending meet-ups and talking about what we were doing. We started posting on niche job boards.
On the screening side, we transformed our process to be as inclusive as possible in that we were interested in talented, bright engineers regardless of the languages they knew, their backgrounds, gender, or their level of experience. We opted to bring a broad range of engineers into the hiring process and relied on our initial screens to identify the candidates we would most want to hire. Our process went from taking months to bring in candidates to sometimes hiring candidates within a week of identifying them as potential hires. To help identify great, new engineers, we setup an internship program. The first cohort ended up being a huge success, with all 3 of our interns being placed in full time positions.
I was often asked the question, “I see we are hiring but what are we doing about employee retention?” My answer was always the same: “Everything we are doing right now is about retention.” I know this question really hinted at giving more money to people to stop them from leaving but this is a slippery slope and leads to leveling issues further down the line. Besides, this wouldn’t solve the underlying reasons surrounding why people were leaving. The only way to retain folks was to improve the underlying culture of the team, determine a challenging but achievable mission, and formulate a good technical plan for our platform. And we needed to do all that, together (repetitive I know, but it’s important).
No one achieves anything alone.
I needed help at the leadership level. I had a few incumbent leaders that had weathered the last year. Unfortunately, I also had a couple of leaders whose leadership styles involved abdicating all responsibilities in improving the current state of the team, while offering no real solutions for the situation at hand. I even received direct feedback that “You don’t understand how to manage engineers,” and “You are not here to change things.” It was a tense period but needless to say, we parted ways, which left the leadership team at half strength. It was time to rebuild.
On the Product side, I have been lucky enough to have been paired up with Tom Greaney, our SVP of Product. Tom had been in the unenviable position of basically saying “no” to everything from simple feature requests to longer term initiatives. Interestingly, he was still somehow optimistic for the road ahead.
Product and Engineering are two sides of the same coin — they fail together, but more importantly, they succeed together. Having a great working relationship between Tom and I, has been a key part of the success we’ve seen over the last year. We now see this level of partnership throughout the organization with shining examples of collaboration and teamwork throughout.
Team restructure & reorganization
We also needed to restructure the teams since they were matrix’ed with engineers reporting into one of two managers as well as operating in separate feature teams. Teams were both front-end and back-end whilst working on feature teams unrelated to their team managers. I go into more detail of this transition in “Why we got rid of our Front end and Back end Engineers” so please take a look if you’re curious.
It took about 3 evolutions to find the right fit but we landed on the following setup:
There are two types of teams — feature and central. Feature teams have a specific focus and work tends to get distributed to the team that is most likely to be able to complete the work. They are still expected to be able to take on work outside of their focus if there is a need.
All engineers are empowered to contribute to any code base if they have the skill, willingness to learn, and inclination. No code base is off limits. I’ll go into this more in a separate article to come discussing “Inner Sourcing.”
The Central teams primary stakeholders are the Product and Tech org. DevOps is focused on providing great tools and helping reduce developer friction. Test Engineering is focused on automation and testing quality for our platforms and tools.
No more QA
For at least 3 years prior to my arrival, the QA team’s primary focus was on manual testing. They were the largest team, made up of 7 testers with a director lead that departed shortly after my arrival. In order to scale with business, the team would need to continue to add headcount which wasn’t a viable option from a financial standpoint. The team needed to be rethought.
First, I had to address the leadership issue. Welcome Chai Rao! Chai had been working on the QA team for 3 years as a test engineer. When anyone sits down to talk with her, there is an innate sense of leadership that really comes across and leaves an impact. After talking it over together with Chai, I decided to move her into the leadership spot. Over a period of 3 months, Chai slowly stepped into the vacant management position and took charge of the team.
We also had several departures that brought the team down to about half of what it had been. While it’s always tough to lose people, the smaller team helped accelerate change. To address the scale issue related to manual testing we brought in Applause. I’d worked with them at Time Inc. previously and loved the service they provide. We replaced one of the open test engineer positions, which now gave us the ability to scale up to 10–15 testers and offload some of the manual testing responsibilities that were prohibiting the team from focusing on it’s true mission — Automation.
We decided to re-brand the team from ‘QA’ to ‘Test Engineering’ with the emphasis being on the engineering part of the role. This team has completely turned around and the results are evident. For example, time spent on QA for tickets in JIRA is 48% less compared to what is was prior to the team shifts. Now, we are releasing multiple times a day across our platform and seeing very few issues making it into production.
In conclusion
It was a turbulent, tough year but in the end, we came out on top. We lost 22 engineers but backfilled almost all of them. We lost half our leadership team but hired 2 great new leaders and promoted another person to a new leadership role. We faced enormous obstacles culturally and technically, both of which have completely turned around. We now have a culture of trust and accountability. On the technical side, we’ve removed or replaced most of the legacy systems with the rest on track to be deprecated by the end of this year. We’ve replaced our front end platform, built a Content API, improved our TTFB by 65%, built our Commerce product, unified our Subscriber product and so much more.
Of course, the work is never done and there is plenty more ahead of us. However, we have created an environment where people can grow, learn, and collaborate. An environment where its okay to speak up and voice your opinions and ideas. We’ve created an environment where we can ultimately succeed at anything we put our minds to.
The road ahead looks bright and I have no regrets!
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