A Year in Life as Head of PLG

The Journey of a Product-Led Growth Leader: A Year in Review

Congratulations if you've made it this far in your PLG (Product-Led Growth) journey! The fact that your company has invested in a year-worth of PLG strategy is truly something to celebrate. Reflecting on passing our one-year mark, I want to share the rollercoaster journey that transformed our approach to product-led growth.

The Exciting Beginning 😁

The journey starts with optimism. We assumed launching would lead to traction immediately. The year began with a bang – our company had invested in a PLG strategy (thanks to OpenView Partners' belief in product-led growth), and we were ready to launch. There was an air of excitement and anticipation, rah rah fun stuff, team chants and getting the internal team excited. 🎉🎉🎉 We created countdown videos, wrote fun meme messages, and even used the Amazon reverse press release technique to educate the company about our plans. Everyone felt the excitement, and we were eager to see the results.

The Reality Check 😰

However, reality hit hard when the initial results fell short of expectations. The early metrics were humbling:

• First quarter: 2 sales

• Second quarter: 5 sales

In the six months, we had less than 10 total sales. With significant investment and a large team, these numbers felt disappointing. That feels like, "Are we doing something wrong?" 😥 Doubts crept in. In the first six months, we didn't figure it out. It felt like such an imposter moment - always having to keep saying, "It's going to work, it's going to work," and it didn't work. This is all a failure and feeling like an imposter.

Leading Through Uncertainty 🤔

The challenges weren't just about metrics. Let me tell you what was keeping me up at night 😨:

• How long would the company continue investing in PLG?

• What about team morale?

• Were we wasting people's careers?

• How do we maintain team alignment with conflicting personalities?

• How do I keep up my confidence while also encouraging my team?

Alignment and team morale are so important for the Head of PLG. And I think a big part of the Head of PLG role is setting those expectations and continuing to communicate the changes that the team is making, communicating the trends and the analysis and the things that we're constantly learning to showcase that, yes, there are opportunities here we're working towards every nook and cranny.

Finding Our Way ☝🏼

It wasn't until Q3 that pieces started falling into place. We stripped down investments. We had to do more things that didn't scale; I began to do more sales outreach myself, trying to figure out the front line and learn as we went. This experience taught me that in PLG, you need to be multifaceted:

• A product person

• A customer success person

• A salesperson

• An experimenter

You learned that growth in PLG is about constant experimentation, data-informed tactics, and weekly iterations of messaging, sales pitches, and packaging. 🧑🏽‍🔬

The Turning Point 👍🏼

Eventually, you figure it out by doing things that don't scale, by brute forcing it. Eventually, it worked. In Q3 and Q4, we started to see glimmers of hope. First, just some signals, then more signals. Two-quarters of a trend? Hey, that's a fantastic signal. That's really powerful stuff!

Not all people are cut out for it. We started with a large group of people, a significant investment because OpenView Partners invested in my company, and they believe product-led will work.

But in actuality, thinking back, it's about:

• Starting small and not going all out

• Starting small and scrappy

• Trying to figure out what works

• Trying to figure out the signals

• Being very experimental

By Q4, we started to see the light and opportunities. If we continue the trajectory from the previous quarter, we will reach X success quota - not the initial goal we imagined, but we are making traction. Also, I gained perspective from other PLG experts by asking, "How long does it take to get traction?" 🎯

You realized that PLG isn't about going all-in from day one. It's about starting small, staying scrappy, and running experiments until you find what works.

The Importance of Communication & Setting Realistic Expectations 🗣️

Throughout this journey, communication was a significant skill to learn and apply. It wasn't just about external communication with potential customers but also internal communication with stakeholders, team members, and the broader company. Transparent communication about progress, challenges, and learnings helped manage expectations and leave no stone unturned — was what maintained organizational support and backing on PLG efforts. 

And only until a year out, you say, hey, it's become a solid foundation for our company strategy. We have another strategy in our sales, marketing, and product arsenal. So, product-led growth in a year was tremendous. 🙌🏼

Maintaining Sanity During the PLG Journey 😵‍💫

Throughout the year, I managed my emotions.

So, if you're reading this, how should you manage your emotions?

Being in front of the computer all day doesn't solve these problems... I learned that quickly. I needed to step away. Here's what I did to keep my sanity and health:

Finding My Reset Button: The Power of Swimming 🏊‍♂️

So, during that time, I started to go swimming. It was my quiet meditation. My community had a local pool, and I went swimming three or four times a week. It was just during lunch and just a time to reset. Whatever you're feeling - challenges, troubling personalities, you know, reflecting on what to talk about - I used that time to quiet my mind, swim, and reset. 🧘🏽‍♀️

When I returned to my desk in the afternoon, I had a clearer sense of what needed to be done and my action items.

Getting Perspective: The Value of Professional Coaching 🎯

Another thing that helped me was hiring a coach. So I hired Andrew Capland as my coach, and we met about once every two months or so, and he just gave me perspective.

A lot of it is just perspective, and I asked for very specific tactical things - and it was not anything tactical around product-led growth. We know all the tactics. We know what needs to be done. We know we needed onboarding, lifecycle marketing, activations, and self-served documentation. So that's not the challenge.

The tactical issues are:

• How do I communicate when it's not successful?

• How do I communicate with a personality that has been challenging on my team?

• How do we communicate with the rest of the company as a team?

• How do you better influence others in your team horizontally and diagonally in the organization?

• How do you manage upward and skip-level communication?

• How to be very transparent and open?

• How do we communicate downward, be encouraging, and have a coaching mindset?

It's a whole communicating 360 and managing all these types of folks in the company, the stakeholders.

Setting Clear Goals: My North Star ⭐

Another thing that helped me keep my sanity was my clear view of what I wanted to accomplish throughout the year. I'm talking about my, the team's, and our organizational success. I have a clear understanding of what I am here to accomplish. What would achieving this look like for me? 📝

I paired it down to what I was trying to learn from this experience. What am I trying to pinpoint and figure out? It was getting back into B2B SaaS territory after six or seven years of working in social network growth and consumer growth. Being in the B2B space, I was learning:

• Sales

• Revenue

• Customer Success

• Building those relationships with the customers

Having ownership of an operation budget and recording some of the wins and losses from a business and revenue standpoint - were things I didn't have much previous exposure to.

Throughout this one-year experience, I set the foundations for me to achieve those goals. I asked the questions to get on top of those types of things. Whether I did it right or wrong, it was a mental exercise to put those documents together, be in those job functions and responsibilities, and take on those tasks. Understanding where that leads me because those types of skills are what I needed and what I recognized I needed to become a founding entrepreneur myself.

Finding Balance at Home 🏠

And lastly, having support at home. One year might feel short, but you can consider it very long. I felt like one year and two years flew by at work, but one year and two years in life were so important. I was moving through cities and dealing with family health challenges. It was more like, hey, yes, it was a year of learning at work but also a year of learning out in life.

Managing that at home was important, and having outlets like:

• My partner

• My family

• A support group

• A therapist

• Friends

• Personal ways to cope

• Meditation

• Swimming

When things are not so successful, and when things are successful - both not doing well and doing good - don't bring it home. Be very conscious about bringing it home. Even though it's such a journey, such a ride, it's important to maintain some of that line of having balance at home.

That was one of the things that Hiten Shah told me about a long, long time ago - if you have that peace at home, you can go to work with clarity.

Looking Back: A Year of Growth and Learning 📈

And so life as head of PLG in four quarters, in one year, was such a lot of lows and highs, and there was a lot of learning. The year was filled with challenges that tested my resilience. It's a lot of self-reflection on what I have accomplished. What have I learned, where am I going with all the people around me, and what is my interaction with them? Those are very important aspects to self-reflect in a year.

To those on a similar journey, success in PLG is rarely immediate. It requires patience, adaptability, and a willingness to learn from successes and failures. Most importantly, it demands effective communication within your team and the organization. Maintaining a balance with yourself when you are navigating PLG is also important.

Read about Product-led Growth

1. Day in life as Head of PLG 🧢

2. Week in Life as Head of PLG 🎓

3. Month in Life as Head of PLG ⛑️

4. Quarter in Life as Head of PLG 🪖

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I am Gary Yau Chan. 3x Head of Growth. Product Growth specialist. 26x hackathon winner. I write about #PLG and #BuildInPublic. Please follow me on LinkedIn, or read about what you can hire me for on my Notion page.