Storyteller, writer, marketer. Founder of the Master Slam, a poetry slam-style debate about startups and tech. Former Director of Content at Help Scout. Former Executive Director of Boston Content, the largest community and career development resource for marketers in Boston. TEDx organizer and speaker trainer. Instructor at General Assembly and Startup Institute. Writing at medium.com/@devinemily.
How did you break into leadership?
I broke into leadership by saying no to a job offer. I was working at a startup doing community management and product marketing when I received an inbound job offer from another startup that wanted to hire me for a customer support role. I politely declined, as I had changed careers from support to marketing. The president of the company pressed me for a call, which I accepted. He was a good salesman, so he pitched me again on the support role, saying I could build my own team, etc. I said no, and to that, he asked, “What do you want to do?” I told him, and I ended up building and managing the support and marketing teams. They were both small teams, because it was a startup, but it was a great opportunity to grow my management skills.
I took a slight step back at my next job, which some people worry about—but it’s not career suicide. In my spare time, I ran my own TEDx event and managed a team of over 20 volunteers. I also took over leadership of a content marketing group with over 2K members and a 6-person board. Those extracurricular activities helped me land my last job as Director of Content at Help Scout.
What unique obstacles or challenges have you faced as a woman in a tech leadership role?
Until recently, I’ve never had a budget, while my male peers always have. I’ve worked that to my advantage by simply not asking for permission anymore. Oddly, that has worked quite well; I’ve never had to explain myself when I just do what I want. It’s when I ask permission that the microscope comes out.
My new hires have been either co-opted or micro-managed by my boss, to the extent that my entire leadership team fought over a potential hire that they were not going manage. I’ve been told not to fire people before, simply because the CEO liked the person. I’ve also had a VP of Marketing role offered to me, then rescinded weeks later, while at the same time being told the role I currently occupied was being removed and I would be fired if I couldn’t make VP—all without giving me a job description or expected timeline for leveling up to VP. A few weeks later, on the day I thought I would be fired, my boss told me he was going to “go easy on me” and hire a VP of Marketing, and that I could keep my job.
How do you negotiate a higher salary?
Salary is an important challenge for me, and one that I have taken head-on since the beginning. I always go into a salary or raise conversation knowing what I want, and I say no to a job when they lowball me. Typically that leads to them coming back to the table with a middle ground that I negotiate up with things like options, bonuses, and services (like insurance, travel expenses, etc.).
When asking for a raise, I talk about accomplishments that can be pointed to, quantifiable professional development, numbers improved, etc. Basically, I never feel or want anything—I have a practical discussion that is centered around tangible accomplishments, growth, and corresponding role and compensation, both of which have industry standard minimums you can use as a baseline.
The biggest thing that has helped me, though, is saying no and walking away. There is no job that is so great that you deserve to be paid less for.
If you could do it all again, what would you do differently?
I would give a lot less f*cks a lot sooner in my career. I would realize how much more talented I am than my bosses ever paid me or recognized me for, and leave those companies for one that actually challenged me and gave me the trust, support, and respect to spread my wings. So much of my career has been fighting bad behavior and finding ways to grow outside of work. If I could do it all over again, I would quit companies faster, worry less about career history, and go after my dreams a whole lot sooner.
I would also question leadership as a path a lot earlier. You can make a great career as a contributor—management isn’t the only way to grow. I wish I had known that sooner, because management is a lot of spreadsheets and repeating the same things over and over to your boss or CEO. It’s also dealing with a lot of team challenges that you’ll never get recognition for. It can be rewarding, and some people love it, but I would have had a more serious heart-to-heart with myself earlier on to see if I cared more about being creative or business organization and numbers.
What’s been the highlight of your career thus far?
Helping other women through these challenges and having a tribe of successful, talented, kind, generous, and powerful women who help me, too. No tangible accomplishment measures up to the community I have, because it is what has kept me going through all the BS.
To be honest, the older I get, the less I give a sh*t about work and being successful at someone else’s company. I care about being happy and doing what I love. If that happens to be at a company, cool—but that’s not the point. The point is, the highlight that lasts and lifts even the darkest times is doing what you love.
Share something valuable or interesting with the community.
Failure is a ghost that haunted me for a while, and it ended up materializing in a way I never expected. So I wrote this story about it, which helped me get through a particularly harsh failure: You Failed…Or Did You?
I also highly recommend The 5 Dysfunctions of a Team and The Tao of Leadership.
Thanks to Jes Kirkwood who conducted this interview in January 2018.