🎂 My One Year Anniversary at Guild

Reflections and gratitude

👋🏻 Helen here with the latest Mind the Beet Sunday newsletter.

This month, it’s been a year since I left mega-corp and joined a mid-stage growth company (read my initial post on Mega-corp to growth stage company transition). Guild.

As I reflect on the past 12 months, I have asked myself these questions:

🏆 What have I achieved?

🎼 What have I learned that surprised me?

🔥 Compare workload/burnout at a start-up vs. mega-corp

💪🏻 What I wish I could tell myself as I was debating this opportunity

☝️ It all comes down to…

🏆 What have I achieved in a year?

Vision and roadmap, set up a team, established communication processes and a cake slack channel

A year is a long time in most tech jobs but it’s longer at startups in comparison. The ever-changing priorities, shifting landscape and higher people turnover make it a harder place to make sustainable progress and stick to your roadmap. At the same time, it takes less time to make an impact - in comparison to a huge matrixed company.

The work: So in retrospect, I am proud of the fact that within a year, I was able to build out my team - hire and onboard three awesome leads, set up good communication practices and transparency while setting out the vision for the domain I own for the next 18-24 months. The teams now have a backlog they can work against and when new things come up, they are able to discuss trade-offs.

The fun: The most notable “small” company thing that I did that seems unfathomable at a large one is I started a company-wide slack channel focused on cake. I’m so glad that I am able to bring my whole self to work and celebrate both professional achievements as well as the latest cake that I have baked (you can follow the latest and greatest @mindthebeet on Instagram as well).

🎼 What have I learned that surprised me?

How to help people find new opportunities, love of teaching and coaching

A fast-growing company means that the company’s needs are changing. So one of the hardest things I’ve had to do was to have honest conversations with people in our organization on whether or not they are in the right role or the right place. When you go from 20 people to 1400 people in ~5ish years, the skills required are meaningfully different. So I’ve helped team members find a new job internally as well as see that this is no longer the right place for them because the needs are now different.

Additionally, I’ve been also able to support other Guilders’ career mobility by hiring from different disciplines into product management and building out tools to help them succeed. In an effort to support talent development and career-switchers, under my leadership, we created a Boot Camp for Associate Product Managers (combining reading, classes from Product School/LinkedIn Learning and regular “lessons” and check-ins) that we are going to scale for the entire Product organization.

As a result, I learned that I not only love coaching people, but I also enjoy teaching and actively supporting people through their growth.

🔥 Do people burn out the same way at a growth company as they do at a large company?

Most people I know across industries, companies, and disciplines leave their job for two reasons: it is too hard to do their job (processes, resources, red tape, etc.) or they have a bad manager. At a start-up, the first reason becomes acute quicker than at an already large company. Many people remember a time when there were fewer teams, fewer processes, you can just ship stuff/do stuff/try stuff and not worry about the right “how.” As the company grows, there are more stakeholders to manage, more change management to do, and the ability to move quickly slows down. So people yearn for the “simpler” days and leave oftentimes to go to a smaller, younger start-up where they get to be less tied down.

In my time at Guild, most people who I’ve seen leave by choice, have departed for a start-up of fewer than 100 people vs. going to big tech or something of similar size.

To the question of do people work harder/longer/more intensely at a start-up vs. at a large company - it really depends. For me, I have really intense working hours, but no meetings at night (as opposed to working at a Global company when I needed to have meetings across time zones in the evenings or early mornings).

Also, there are things that smaller companies can do, for example close the office for an entire week, to support employees’ wellbeing. Guild does this on a regular basis, which is really helpful to manage burnout.

💪🏻 What do I wish I could tell myself a year ago as I was contemplating leaving Microsoft?

I would tell myself that there is a whole big world out there outside of big tech and I will learn more in a year at a startup than I could possibly imagine.

The things you’ll learn are also not as predictable and clear cut so it’s hard to fathom it ahead of time.

In my scenario, I ended up with more seniority and scope so therefore I carried a lot more responsibility and weight on my shoulders. So I needed to learn how to thrive under more pressure, how to be more accountable, and responsible for the output that I and my team produce.

At the outset, I was not clear how I would grow and what mentorship would look like. at a smaller company. I ended up finding all of that in spades at Guild (both inside the company and through outside resources such as Better Up coaching) and I have now met and built out a new network of people.

Having said all that, I continue to encourage people I mentor to never make a leap out of an existing role or job just for the sake of a leap. I recommend not running away from a bad job if you can avoid it but instead running toward something new and exciting. For me, specifically, this was the right time in my career to make a leap to something smaller, but it wasn’t an escape valve.

☝️It all comes down to…

People. As Brene Brown says, “People, people people.” It is interesting to observe that people matter even more at a smaller company as they do at a large one. After all, in a big company, it is easier to move jobs and “start over” vs at a small company where you know a higher percentage of people.

At the end of the day, I love my job for many reasons but the main one is that I have a great set of peers I work with who support me, joke with me, and are committed to what we are trying to do. I also have an awesome manager who sees me and what I bring to the table. He does this by meeting me where I am, advocating for, and supporting me. Finally, the team I have built - my direct reports - makes my job easier and more fulfilling because we are in sync and work well together. It’s the small and the big things that make getting out of bed and showing up to work fun. For example, on my birthday this year, my team showed up to a meeting with happy birthday banners to support me as organized by the leads on my team.

The culture of retrospection and openness to feedback is also notable at Guild. For example, a very senior person in the organization pulled me aside and shared with me how my demeanor in meetings can be misinterpreted, and asked me if I’m aware of that. There was no ask to change but a flag that I may want to be more intentional. No one has ever in my past paused to coach me quite like that. I felt kindness and care, not judgment and indictment.

The additional cool thing about people at a mission-driven company is the deep sense of purpose that people have across departments, teams, and disciplines. So that creates an additional common ground that in previous teams took time to establish.

🙏🏻 Summing it up and gratitude

All and all, it’s been a great year. I have gotten to grow as a product and a cross-functional leader, as a product thinker, and as a teammate. I’ve been able to mentor and coach as well as be coached. I can’t wait to see what next year at Guild brings! Onwards!

How I am supporting Ukraine 🇺🇦

Not a day goes by when I don’t think about the unjustified attack on Ukraine that is going on. I am so grateful that my parents got us out of Russia in the early 1990s and have enabled my sister and me to build a life in the democratic world.

I have found myself looking for additional ways to give from what I wrote about two weeks so, so here are the organizations Adam and I have been supporting lately:

1KProject.org - Matching sponsors and families, this organization is using wise.com to wire $1000 at a time to families in Ukraine in need. You can give less as well. I am also now volunteering with this organization.