I’ve worked with Automattic, makers of WordPress.com, for three and a half amazing years. The company, and its faith in me, have transformed me. A leadership coach recently encouraged me to start a learning journal to jot down all the things I’ve learned the past few years. I was astonished by the list, which included successfully leading a distributed team that spans hemispheres, speaking in front of large audiences, organizing events, and, along with 14 of my co-leads, helping scale the processes and operations of a globally distributed support team of more than 120 Happiness Engineers.
An opportunity fell into my lap a few weeks ago: an opportunity to join Support Driven, a small company that exists to serve a growing community of Customer Support professionals. At first I didn’t consider it. I had everything I wanted at Automattic: smart and funny coworkers, freedom to learn and grow, a decent work-life balance, the ability to work from home, acknowledgement and recognition from my peers, great salary and benefits. I was safe, content, and doing well in my work. I wasn’t looking for a new job.
When the Support Driven founder, Scott Tran, presented me with a Director of Operations job proposal, I told him it looked pretty exciting for the right person. They’d get to help design the company structure from the beginning, make strategic decisions for the business, play a key role in shaping company culture, and bring value to the entire Customer Support industry. I got a nervous thrill about it, even though I wasn’t looking for a career change. Scott probed, asking what concerns I had about taking the job myself. Aside from the fact that I wasn’t looking to leave my current job, I had really big apprehensions: security, stability, time with my family.
Going from a company of 650+ — with a stable salary and benefits, plenty of backup if I’m out sick or on vacation, where I know what I’m doing and have found a good rhythm — to a company of fewer than five people, where my efforts would be intimately tied to the success of the business (and therefore my job security) felt like a huge risk. Making a move like this wasn’t just about me and my career. The three most important people in my life — my husband and two kids — would be impacted by whatever decision I made. We eat dinner together, around the table, every night, even during sports seasons. Evenings are sacred. Our time with our kids at home is shrinking: our son will move out in four short years, and our daughter two years after that. Being absent to my family now for a job that might pay off later was not a risk I was willing to take. I’d gotten my work week down to a reasonable number of hours. Moving to a position where I might need to work 60 or 70 hours a week, potentially during evening family time and frequent weekends, in order to ensure the company’s success was not palatable to me.
I was frank with Scott about all of this. I told him my family is more important to me than any job. And for every concern I had, Scott eased my mind. He also has a family. He also wants down time and doesn’t want to work 60-70 hours per week. He is also motivated by stability and security. He intends to grow the business slowly and sustainably, and assured me that we are in control of the amount of work we do, and when, such that we can focus on the projects that work for the community and for us, and back off of projects that don’t.
In other words, he leveled the playing field for many of the external reasons for not taking a new job. I found myself in the position of making a decision based on the work itself, and the outcome of the work I’d do.
By providence, I had recently listened to an Unstoppable Women podcast interview with Anne Raimondi, SVP of Operations at Zendesk. The host, Archana Ravichandran, asked “How do you know when it’s time to leave a company?” Anne flipped that and answered instead, “How do I evaluate a new opportunity?” Her answer guided me through what would have otherwise seemed an impossible decision:
- Do I believe in the mission? Can I get up for work every day eager to solve the problem the company is looking to solve?
- Who will I be working with? The people around us shape us.
- What will I learn, and what impact will I have?
I believe in the missions of both Automattic and Support Driven. As a writer and blogger, I am a proponent of democratizing publishing. As a support professional, and especially as one who has both craved and created resources for improving in the craft of support and developing in my profession, I am also a proponent of advancing Customer Support as a career. I could wake up every day and be equally motivated to work towards both of these missions.
I love my colleagues at Automattic. They are like family to me. They are smart, kind, generous, and I laugh all day at work. From my interactions with Support Driven — in the community Slack, volunteering as an organizer, and at conferences — I know the Support Driven community are also smart, kind, generous, and funny. If I took the new job, I’d still get to engage with and help my Automattic colleagues who are part of Support Driven, and I’d be part of an amazing broader community as well.
At Support Driven, in addition to being part of the community, I would also be part of the company-level decision-making structure. This is a pretty huge opportunity that also requires a good look at who I’d be working alongside. Based on previous experience organizing conferences together, I know I respect, appreciate, and work well with the founder and owner, Scott. He is motivated by many of the same things I am: a rewarding job that aligns with his values, supports him and his family, brings good to the world, and does not consume him. I also like how he thinks things through: he plans ahead, gathers intel from the community, researches before acting, and is open to iteration without being attached to certain outcomes if they’re not what the community wants. These are important qualities if I’m considering taking a leap.
In terms of mission and people, both jobs are excellent choices. And so we come to learning and impact. These, ultimately, were the key. Where will I be five or ten years from now depending on the choice I make today?
In terms of learning, there aren’t many opportunities more ripe for learning than getting in on the ground floor of a small startup. Support Driven would allow me to stretch and grow in new-to-me ways, through phases that Automattic has already gone through as a larger organization, and that I’d not have a chance to learn or influence if I stayed. With Support Driven, I would have an opportunity to make decisions at the organization level, including budgets, recruiting, hiring (and firing), compensation and benefits, allocating resources, designing company structure, making decisions on what projects we will take on, managing those projects, and ultimately helping shape the company culture that, as Scott said, will ripple into the future.
In terms of impact, at Automattic I would continue to have an impact as a team lead, and somewhat more if at some point in the future I had the opportunity to lead leads or lead a support division, but the impact would stay mostly within the organization. With Support Driven, I’d be able to help not just the company, but the whole industry. At the business level, I’d have an opportunity to plan, organize, and set expectations from the start so that we are moving forward thoughtfully and with a plan. This is very attractive to me, as this is the way I operate: organize, figure out the how, name milestones, assign a responsible individual, and carry out the plan.
But even bigger than the company-level impact, I am driven by the industry-level impact. Customer Support in the way that companies involved in the Support Driven community approach support — as an integral part of a business, as an asset, as a respected and reputable career choice — is an emerging industry. Resources, products, and services for support professionals are scanty, support professionals are hungry for what Support Driven is offering, and there is huge potential for us to help a large number of people and careers, and ultimately to encourage more companies to recognize the value of excellent customer support.
So, starting March 19 Support Driven will grow by one person — me — to get to work on the projects already in progress, and to direct operations so we can continue to do awesome things for the community.
I am so grateful for everything I learned at Automattic, for my wonderful Automattic colleagues, and for the career theme park Happiness at Automattic provides to hungry learners like me. I am excited to explore a new land soon, to ride the monorail over to Support Driven, where I’ll have a chance to engage with professionals throughout Support. I can’t wait to help even more people, to provide the professional-development resources the community is looking for, and transform the way companies think about support.