From High School Teaching to Corporate Learning: Klaviyo’s L&D Leader Talks Developing Job Architecture - Senior Executive

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9 min

From High School Teaching to Corporate Learning: Klaviyo’s L&D Leader Talks Developing Job Architecture

Jim Page shares the skills teachers bring to corporate L&D and how he’s envisioning job architecture at Klaviyo.

by Kimberly Valentine on June 15, 2023

Jim Page

Jim Page

Director of Learning and Talent Development


  • Nearly a decade in corporate L&D leadership after a career transition from high school teaching.

  • Served as a judge for Chief Learning Officer’s LearningElite Awards (2020, 2021, 2022).

  • Worked as the director of people development at cybersecurity solutions company Rapid7 in 2018 when it won an ATD BEST Award.

If you can navigate a classroom with 25 teenagers who all woke up on the wrong side of the bed, you can navigate any personality in the learning environment. At least that’s what Jim Page says he realized when he transitioned from a career as a high school teacher into corporate learning and development. 

While teaching entrepreneurship at the high school level, Page says he most enjoyed building a program from scratch and then scaling it. He started with about 40 students per year and grew the program to nearly 250 students per year by the end of his 12 years as a teacher. “I realized at that point, when your program is connected to taxpayer dollars, despite program success, the growth of the program is kind of capped there,” he says. “I started getting an itch to explore elsewhere.” 

Corporate L&D allowed him to build programs at a greater scale, and he found similarities in the type of work. “The common thread that I think high school students appreciate as much as adult learners is that applicability in real time,” Page explains. “If you’re able to ensure learners can walk out of your classroom or walk out of the program…and apply [the lessons] in real-life settings immediately, you build a fan club following really, really quickly.” 

In his new role as the director of learning and talent development at Klaviyo, Page says he’s building L&D programs within a company where learning is embraced by leadership. The technology company demonstrates their ‘always learning’ culture through the following employee benefits:

  1. A $3,000 annual stipend for every employee to spend on learning and development, such as American Sign Language classes and leadership and DEI certifications.
  2. Unlimited free books to employees — as of mid-May, 58% of employees had taken advantage of the perk this year.

During a discussion with Senior Executive L&D, Page shared the skills that transfer from the academic classroom to the corporate learning space and how he’s updating the job architecture at Klaviyo. Read on for an edited excerpt from that interview. 

Senior Executive Media: You mentioned you hired several former teachers onto past L&D teams and coached others to make the career transition. What skills do you find teachers most often have that benefit them in corporate L&D?

Jim Page: Listening. Full stop. I noticed that oftentimes in corporate settings when you think of a typical corporate trainer, the approach is one of stand and deliver a lecture. And even during my time in the classroom, I learned quickly, we have to flip that model where the teacher or the instructor or facilitator should be doing less of the talking and really pulling the learning out of the students… That listening skill set that I picked up on interacting with folks time and time again in the public classroom — what a great skill set to bring into corporate. 

But also, I’ll call out some other skill sets, like project management or program management… As a teacher, you are planning to the minute to ensure that you are providing your students with the most learning in a really fixed amount of time. Fast forward to corporate, that time almost becomes even more precious there so your ability to plan and navigate plenty of curveballs that are thrown your way [is] extraordinarily helpful. 

One thing I’ve realized [is that] any teacher that I brought onto the team [at previous companies] so quickly can transfer their skill sets in a really immediate manner to all things L&D. I remember my first leap into corporate: ‘Who is this teacher guy? Can he hack it in corporate?’ And then as I continued to build my team in that first role, quickly our CLO said, ‘Hey, Jim, do you know any other teachers?’

The approach that I bring to corporate today is anchored so heavily on my learning from the 12 years in the classroom space, and I think it’s a differentiator. I think it’s what creates a learning environment where learning is not something that people have to do but learning is something that people want to do.

Senior Executive Media: You’ve been at Klaviyo since February. What’s your approach to joining a new company as an L&D leader? 

Jim Page: Walk into any organization, regardless of if it’s L&D or any other function, I think so often folks are eager — ‘Hey, I’m just gonna start doing things!’ While doing impactful work is incredibly important, I think it’s important that you go slow at the onset to go fast later on. My first month or two was anchored on needs analysis and discovery conversations. Having interactions and conversations [with] folks up, down, across the org, from ICs (independent contributors) to members of the C-level suite, across geographies, time zones, the works, to find out what is going extraordinarily well, what is perhaps going less well, and where do opportunities exist… As we look to the year ahead, there’s a lot of things that folks are eager to have learning and talent development dig into.

Senior Executive Media: What does your role oversee and how do you work with other departments to achieve learning and development objectives? 

Jim Page: My purview focuses on learning and talent development, and so that includes all things learning and development, all things talent management, employee engagement, and our onboarding program as well… One of the things that appealed to me so much about the role and the team setup here at Klaviyo was that intersection between those functions. So for example, on the talent management side, to be able to leverage performance management data… What do we do with that data? How can we transition that to learning opportunities? Ta-da, there’s learning and development… Performance review and engagement data help drive content curation and creation for the team… It’s like a huge opportunity to turn that partnership into a real superpower. 

What I love is that third element of looking at employee engagement — realizing that an employee’s desire and ability to learn, grow, and develop at an organization really puts rocket boosters on any individual’s intent to stay at an organization. So the fact that we’re able to kind of bring that engagement piece in as well makes it a really cool trifecta of teams to do amazing things going forward.

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Senior Executive Media: Can you share a project that you and your team are currently working on? 

Jim Page: I think in the past, there used to be this eagerness to be a Netflix-of-learning… ‘Look at everything we have for you to take advantage of.’ Fast forward, I think L&D has quickly realized the Netflix approach to learning is not what’s necessary, but rather a really carefully curated list of learning opportunities and programs that help get you to where you need to be. If nothing else that I’ve learned over the last few years, [through] COVID in particular, it can just be overwhelming if there’s not guidance and curation. Where L&D’s role used to be one of ‘create, build lots of stuff,’ we realized over time that while creation is important to some extent, curation of the right resources at the right time for the right learner is extraordinarily important.

We realized over time that while creation is important to some extent, curation of the right resources at the right time for the right learner is extraordinarily important.

– Jim Page, Director of Learning and Talent Development at Klaviyo

So a biggie here at Klaviyo is something called career architecture… In short, we are connecting for every single role at Klaviyo the skills required for that role, and then follow up: What does that actually mean?… If we’re looking at skill A, that translates to this behavior… Everyone in the company now has clarity around, ‘Hey, I want to be awesome in my role. Here are the skills and behaviors that I need to demonstrate and model and exemplify here.’ 

What really excites me [is] to take that one step further and connect that to learning opportunities. We’re spending a lot of our efforts in the coming six months really focused on our career architecture model to ensure that everyone has clarity around their role, our people leaders have clarity around what and how to deliver feedback on specific skills, and then ultimately tie all of those skills to all things learning development. Do you want to develop skill A? Fantastic! Here are the learning opportunities for you. 

Senior Executive Media: That sounds like a big endeavor. Where are you in the process of building an organizational framework for jobs at Klaviyo and what do you envision it looking like on the user side? 

Jim Page: We have the current architecture. We’re off the ground and running with that. We’re eager to start overhauling our learning technology stack the back half of the year to start leveraging, for example, AI-powered skills engines so that, as your role evolves, the skills required for your role evolve. We’re able to pivot in a real-time basis to ensure those learning opportunities exist so that we can either upskill or reskill talent in an extraordinarily fast manner.

[The end deliverable is not designed yet, but the intention is for it to be interactive and personalized on the user side. The vision is that…] You log on in the morning, your role is ABC. ‘Here are the skills required for your role, would you like to take learning A? Would you like to take learning B? Would you like to take learning C?… You already have all of these skills, have you considered these other career opportunities at Klaviyo?’ Realizing that career mobility is not just about moving upward, but it’s also kind of like a career lattice. How can you move up, down, across the org to ensure that you’re continuing to learn and grow and we’re driving business impact?

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