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At These Companies, Any Engineer Can Be a Mentor

Below is an article originally written by Kelly O'Halloran and published on February 24th, 2021. This article is about PowerToFly Partner Teachers Pay Teachers. Go to Teachers Pay Teachers' company page on PowerToFly to see their open positions and learn more.

Mentorship programs may have once been intended to develop the skills of less experienced employees. But the engineering programs at the following companies aim to keep everyone in mind.

Squarespace, for instance, has set up an individualized specialization approach that helps ensure all engineers get the chance to sit in the teacher's chair.

"Teammates can then teach others, which provides everyone the opportunity to learn and practice mentorship," Josh Hixson, an engineering lead, said.

The result? Faster innovation, novel idea exchanges and a shared drive to gain expertise, Hixson said.

Meanwhile, Teachers Pay Teachers' VP of Engineering Kwame Thomison created learning and mentorship opportunities through one-on-one book clubs, project guilds and a weekly "Eng Learning Fridays" for engineers to pursue their own projects relevant to the business. All of which have helped engineers from all levels of seniority benefit, Thomison said.

For their programs' impacts, Built In NYC connected with Hixson, Thomison and CB Insights Senior Platform Engineer John Maguire.


At Squarespace, engineers of the website building platform each take on specializations, according to Hixson. Hixson, a lead on Squarespace's enterprise security team, said this model promotes cross-collaboration and mentorship between the engineers, regardless of seniority.

What's a practice your team follows that encourages a culture of mentorship and knowledge-sharing among your team members?

I like to make sure that every member on my team gets the opportunity to directly contribute to our projects. Everyone on my team has different skill sets, which is great because the work we do tends to be multi-disciplinary. The projects we take on can't be done in a silo. By making collaboration a necessity to success, our team naturally facilitates the knowledge-sharing process.

I like to make sure that every member on my team gets the opportunity to directly contribute to our projects."

How do you serve as a mentor to members of your team?

Practicing humility and sharing past failures allows me to support the team and help overcome imposter syndrome, which many security professionals experience, particularly those early in their careers. By sharing my own struggles with imposter syndrome, my team members are able to learn from my mistakes and gain the confidence in their knowledge and abilities, especially as our roles require us to work quickly and confidently under pressure.

How has a mentorship culture helped your team grow?

The mentorship culture we foster on our team has levelled up the skills and competencies of everyone on the team, myself included. Constant collaboration and sharing of information between team members elicits novel ideas, allows us to innovate faster and encourages everyone to gain expertise in certain areas. By growing their specializations, teammates can then teach others which provides everyone the opportunity to learn and practice mentorship.


A mentor to his direct reports as well as other engineers at Teachers Pay Teachers, Kwame Thomison has implemented key initiatives to drive learning and engagement within his organization. The VP of Engineering called out a program rolled out in 2019 named "Eng Learning Fridays."

What's a practice your team follows that encourages a culture of mentorship and knowledge-sharing among your team members?

We strive to provide a best-in-class learning and development program for our engineering team. Two years ago, we began experimenting with a novel approach to learning and development called "Eng Learning Fridays," which has since spread to other companies. We also rely heavily on learning guilds and project guilds to facilitate social learning.

With learning guilds, engineers choose a learning objective they're excited about, like web architecture or leadership, and work with other engineers to break down their learning goals into sprints. After each sprint, the guild meets to discuss what they've learned. Learning guilds have been highly effective for helping engineers level up on a specific set of skills or behaviors.

Project guilds then encourage engineers to explore a technology or problem they're interested in, like service mesh or blog redesign, that's relevant to our business. Every Friday, engineers meet to review progress on their projects and continue hacking. The primary goal is learning but if people choose to finish these projects, we actually ship them, which is a nice bonus. Project guilds are an effective way for engineers to follow their curiosities and increase their impact.

Internal experts have a natural forum to spread their expertise, which is really important."

How do you serve as a mentor to members of your team?

I use several different approaches to mentorship. With my reports, my favorite approach is organizing one-on-one book clubs. It's a great way to explore a subject together in addition to understanding each other more deeply. I choose a book we're both excited about and that is oftentimes one I've already read and internalized. We read a little bit of the book each week, and most importantly reserve ample time for discussion. By the end of the book, at worst you have a common language for a given domain and at best you walk away with a shared set of values.

I also mentor several members of the engineering team who don't report to me. We focus on career growth and challenges with day-to-day work. Mentees find this valuable because they get to hear an additional perspective and learn more about what's happening outside of their team. I've also found this to be a great use of time since it gives me a chance to form deeper connections with more people, identify emerging leaders and learn more about challenges engineers on the team face.

How has a mentorship culture helped your team grow?

We have a much better understanding of how to use learning as a tool to solve problems and increase our collective impact. People are forming more connections with people outside of their team, which is important in a hyper-distributed setup. Internal experts have a natural forum to spread their expertise, which is really important, especially for emerging leaders. Ultimately, engineers at all levels of seniority have benefited from "Eng Learning Fridays."


At the tech market intelligence platform CB Insights, the engineering organization hosts learning events that anyone from the company can attend despite being engineering-related in nature. John Maguire, a senior platform engineer who runs these initiatives, explained how their book club, video club and code dojo help foster a culture of mentorship companywide.

What's a practice your team follows that encourages a culture of mentorship and knowledge-sharing among your team members?

Our team runs a few programs that are focused on sharing knowledge across the entire organization. Our video club invites colleagues to join us every week in watching a conference talk that is followed by a discussion on what we learned. We also have a book club that involves reading a book on software development or a related topic together. We read at a sustainable pace and meet once a week to discuss what we've read.

Another program that we're in the process of building is a weekly code dojo to solve practice problems and engage in deliberate practice. These all have the effect of getting not just engineers, but anyone in the company.

Through the mentorship relationships we've built, the entire team has been able to level up their development skills."

How do you serve as a mentor to members of your team?

I'm able to serve as a mentor to the rest of the team through our continuous learning program, which includes the video club, book club, code dojo, and more to come. From the different elements of the program, I'm able to interact with many members of our teams which has led to more direct mentorship relationships. The programs have also opened up the door for other senior engineers in our organization to form mentorship relationships.

How has a mentorship culture helped your team grow?

I think the culture of mentorship that we've grown at CB Insights has helped our team mature into a symmathesy, an entity composed of contextual mutual learning through interaction. Through the mentorship relationships we've built, the entire team has been able to level up their development skills while also being able to bridge some of the gaps that can arise from operating remotely. For example, in a recent book club meeting we covered the Circuit Breaker pattern. Afterward, members of the club were able to identify areas of our code that could benefit from that additional stability provided by that pattern and refactor them.


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