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HERstory: Margaret Kelsey

Director of Marketing, OpenView

Margaret Kelsey is a B2B SaaS marketing leader with a background in Product-Led Growth companies. She’s a builder of strategic brand and content programs, and currently is the Director of Marketing at OpenView.

Before OpenView, Margaret was Director of Brand & Creative at Appcues. Previously, she built content programs for InVision’s design community for 3.5 years and has roots in painting and PR.

How did you break into leadership?

I had a strange start to my career that included a circuitous route through education, photography, and hospitality PR.

About 4.5 years into my career, I found myself in a role and industry I loved as a content marketer for InVision. There, I had my first taste of leading a team as an interim manager for a short period of time. I found myself energized by thinking of ways to inspire and connect the fully remote team.

But it wasn’t until another 3.5 years later at Appcues where I was offered the opportunity to not only lead a team, but build one from the ground up.

What unique obstacles or challenges have you faced as a woman in a tech leadership role?

I’m aware that I’ve been very privileged. I’ve been taken seriously in both companies where I’ve had positions of leadership.

That’s not to say I haven’t seen or faced gender-based obstacles and challenges. But they were more inherent to how women in tech are perceived and treated overall, rather than specific to being a woman leader. It’s been the typical stuff: inappropriate comments, seeing male counterparts rise faster with seemingly less tangible results or knowledge of a space, etc, etc.

But one very unique obstacle I’m facing right now is returning to (now remote) work as a new mom with limited access to childcare in the midst of this global pandemic.

The Motherhood Penalty is a real thing—and was so long before this crisis. So, I’m trying to balance showing my team that I’m indeed a mom with an infant at home with showing them that I’m capable of doing the work needed for the role.

That means sometimes I join a zoom meeting with my son strapped to my chest, using his changing table as a standing desk. And then immediately doubt myself and wonder how it was perceived by others on the line.

So, I’m working on that balance, which I think will come from giving myself a lot of grace during this time, too.

When’s the best time to change where you work?

The biggest leaps in my career—leaps in responsibilities, title, and salary—have been from when I’ve changed companies. That being said, I also think it takes longer than 12 months to truly make a difference and solve a problem at a company, and that jumping around just to increase your title or salary can backfire.

So the question is, how do you know that it is time to change where you work?

I’d recommend asking yourself a few questions:

  • Are you still inspired by the problem your role solves for the company?
  • Are you still inspired by the problem the company solves for its users/customers?
  • If you’re ready for more challenges, is there space/support for you to take those on at your current company?
  • Are you paid fairly?

If you answer yes to those questions, I’d stay. Being able to go deep and solve real problems is vital to both your skillset and your resume.

But if the answer is no—to even one of those questions—it’s imperative that you make a real effort to find somewhere you want to be.

Life is too short to be uninspired at work.

If you could do it all again, what would you do differently?

I would have read Radical Candorthe moment the ink was printed on the page. That book changed my life and career.

What’s been the highlight of your career thus far?

Probably creating The Product Led Growth Collective at Appcues with my brand and creative team.

The site is a careful balance of types of content that each serve a critical purpose:

  • Foundational content (long-form articles) optimized for organic traffic
  • Tactical articles from folks in the community to inspire sharing/forwarding through networks and social media
  • A video series that highlights strategic (VP and above) PLG leaders, lending credibility to the entire site

The creation of the site was a labor of love—emphasis on the labor part. But the result is something that is not only great because of its value to the company, but for the community, too.

Share something interesting or valuable with our community.

I had a drink with Guy Fieri once (humble brag from when I used to be cool) and, since then, have loved to use his reaction GIFsin Slack convos. They are really exceptional, and I find them very useful.

Thanks to Jes Kirkwood who conducted this interview in September 2020.

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