Jack McDermott, Manager, Growth @ Chegg

Jack McDermott is an athlete. Or at least that’s how he saw himself earlier in life. It was a lot easier to self identify that way on the football or lacrosse field where he confidently performed instead of the classroom. You see, Jack had a stutter. Growing up, he kept getting pulled out of class to go to his speech therapy sessions. And from an early age he noticed that classrooms and our education system weren’t always designed for a kid like him. He had a problem he needed to solve.

Jack grew up locally in Medfield before heading to Tufts to play lacrosse. But not before he started mentoring other younger students who had the same speech challenges. Over his years of practice he felt like he understood what it took to practice effectively and began to help teach others the same insights and exercises he’d learned.

He entered undergrad as an offensive Attackman and graduated as a defensive Midfielder. There was a need, so Jack filled it. Did I mention he helped Tufts win the 2014 national championship his senior year? This is a decorated athlete! He happens to be running his first Boston Marathon this spring too. Here is his donation page benefitting the American Red Cross (my plug, not his).

While at Tufts, Jack saw the emergence of Apple’s app store as a perfect way to help other students with their speech. A bigger megaphone, if I may. He founded a company before he even knew what startups were called Balbus Speech. They had two apps – Speech4Good and Fluently. Speech4Good was an app with an audio graph that visually tracked people’s speech patterns with a delayed audio feedback tool. Fluently was a more technical product that detected moments of stuttering and provided real-time speech analysis. His apps generated >25k users and thousands in revenue highlighted here in an article by Inc magazine from 2013. The company even raised some venture capital from General Catalyst’s student run fund, Rough Draft Ventures. 

Balbus Speech ultimately didn’t turn into a full time thing for a variety of reasons – changing app store guidelines, shifting monetization strategies, and not to mention Jack was only 21 years old juggling a startup, his studies and NCAA athletics. Long story short, he knew he had a lot more to learn to build an enduring tech platform. But let’s not gloss over the accomplishments. From Jack’s own words, Balbus Speech “was an incredible experience to see an idea I had transformed into a product for people I’d never met. It was so impactful to know I could build learning experiences and products of my own that other people would use.” 

Jack had the startup itch.

The 2010-2014 timeframe was a special time for Boston startups and a formative experience for Jack. The Greenhorn Connect newsletter. The UnConference. Hubspot was still a smaller growth stage company! SCVNGR was funded and became Level Up. There was disruption in higher education from companies like Boundless Learning. Investors serving students like Peter Boyce and Zach Hamed from Rough Draft Ventures. Other fellow local university students like Delian Asparahouv, Emma Tangoren, and Jack’s good friends John Brennan & John Capecelatro from this time have gone on to do interesting things in tech & investing over the years across the U.S. Maybe come back to Boston friends?

So Jack left Tufts and wound down Balbus Speech, trophy in hand. He knew that he wanted to work in tech and get deeper experience in the education space. Jack relayed to me that for the entirety of his career he’s been working on the same problem: “how can you make education work better for students?” 

He put feelers out in the Bay Area but settled locally. Sam & Zack Dunn @ Robin were nice enough to grant him some office space to work on his speech apps where he met the Panorama Education team through a co-worker, fresh off their graduation from Y Combinator.

Panorama Education built a data platform to improve outcomes for K-12 schools & their students. He was drawn to their mission “to radically improve education for every student” and joined the company as one of the first 10 employees. They had a marketing need, so Jack filled it as their first marketing hire. The company & role were a bullseye for what Jack was looking to accomplish.

Jack got to learn from a great founding team – Aaron Feuer & Xan Tanner – backed by top investors with a team of former teachers and a Harvard Ed School professor. A truly fantastic environment to launch a career in EdTech. Jack got to work on surveys for school districts helping them measure student outcomes beyond standardized test scores. The company grew from 10 > 140 employees over his 5 years there. He even moved to San Francisco in 2017 to help them build out their west coast office. His role transitioned from a marketing generalist to demand generation building their inbound motion and refining the product story. He helped launch new products and eventually moved over to Product Marketing, specializing on honing their messaging to break into larger school districts and serve those school systems.

Jack kept inching toward his goal of learning how to be a great Founder / Operator who can bring things to scale. He learned a ton at Panorama and then it was time to sharpen his cross functional skills in Finance, Operations, Management, Strategy and up level his credentials so off he went to The University of Virginia Darden School of Business. 

While at Darden he completed an internship at Thinkful via a Darden alum. Thinkful was a skills based learning platform which had been acquired by learning giant Chegg. Is it a coincidence that both of their logos are orange? Can’t be sure. Upon graduation, Jack moved back to Boston to start his post MBA career with Chegg.

Jack loves to run on the Esplanade as he gears up for the Boston Marathon. He loves Curio coffee in East Cambridge. Another fun factoid is that Jack’s great grandfather was Mayor John Hynes. A member of the Lost Generation, John Hynes was anything but. He was responsible for opening The Freedom Trail and brought Prudential Insurance to town, helping lay the groundwork figuratively and literally for Boston’s new era of “The Hub”.

Today, great grandson Jack blazes his own path developing a new digital education system upskilling American youth. How about that symmetry?? Chegg strives to improve the overall return on investment in education by helping students learn more in less time and at a lower cost. 

Jack is responsible for Chegg’s growth initiatives centered around reskilling and upskilling. A broader mandate but one still very much focused on improving educational outcomes for those slightly displaced outside of the core system. Or more directly give them the skills needed to succeed in the modern, high tech workplace.

Here are three insights he shared with me that has informed his work and trends from his career:

Emergence of the Growth Field: Growth has taken on a whole new meaning these past few years. Jack has seen up close at Chegg the value of carving out a custom role built to deliver on a specific growth goal. His insight is that teams “don’t always maximize growth opportunities by having functional teams in sales, marketing, product, etc. Building toward top line growth with a specific role that owns the north star business objective has been hugely exciting for me and impactful for the business”. Or said another way, when teams keep things siloed at the functional level, the overall experience (and growth) is likely to suffer. Missed synergies and communication across functions are going to eventually be felt by the consumer. Brian Balfour, former Head of Growth at Hubspot currently building Reforge, has been a huge driver in this space Jack made sure to add!

Shift to Skills Based Hiring: Jack has started to recruit his own remote team based upon hiring criteria derived from the Chegg skills platform. He’s been able to recruit teammates from NYC, Grand Rapids, Bloomington, and beyond. Witnessing the interplay between platform work his team is executing on then actually hiring based on those qualified skills is “walking the talk”. Building teams outside of the core tech hubs and proving that people can be re-skilled and upskilled to do jobs from basically…anywhere. Tip of the cap to Chegg in supporting recruiting talent from anywhere based on the requisite skills.

Having a Personal Mission: Jack feels fortunate that he’s gone into roles & industries that are traditionally hard to solve for. Building products in K-12 education is not easy and falls much closer to the “hard tech” side of the scale when you think about the red tape, need to prove efficacy, and institutional rigidity. Jack shared a great ancient quote with me – “Fear not work that has no end” – that has driven him for a long time. He followed that up with sharing how much he’s learned from being in roles and at companies for multiple years in this era of job hopping. He’s been fortunate enough to witness the arc of how things get built and scaled amidst industry shifts: “you get an intimate understanding of problems that can be solved & approaches for how to solve them. There’s nuance involved and solving for education is hard to do. It takes detail & depth of understanding”. In an era where we overestimate the work we can do in a year and underestimate what we can do in 10, Jack keeps plugging away at the same problem set: “how can we make education work better for students?”

And then he hit me with it: “You need to ask yourself what you’re passionate about – what big change in the world do you want to play a part in? I felt it as a kid growing up that school could be better. I’ve been trying to solve that same problem in a variety of ways in a variety of roles through different strategies. That’s been the core driver for me.”

That hit me like a ton of bricks. Isn’t that what it’s all about?? For more of Jack’s career & project work and for getting in touch with him directly you can check out his personal website here. Thanks for sharing Jack. See you at the top!