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Product Marketing Spotlight Series: Jessica Webb

jesswebbCrayon's Product Marketing Spotlight is an interview series where we chat with product marketers to get a glimpse into their careers and gain unique insight into product marketing strategy. In this edition of Product Marketing Spotlight Series, we shine the light on Jessica Webb, Senior Product Marketing Manager at Trello.

ED: What is your role?

JW: I’m a Senior Product Marketing Manager @ Trello (Atlassian). I have worked with many teams throughout my almost 3 years here, but currently, I lead our Growth Marketing team. We are focused on experimentation at the top of the funnel and at the activation level to try to get more users signed up and actively using Trello.

ED: What does the company do?

JW: Trello is a tool for teams (and individuals) to collaborate on projects and be more productive. The premise is simple and visual. Think of it as sticky notes on a board - the web and mobile apps are based on the concept of cards on lists and boards to organize any type of project, from planning a conference to going on vacation with your friends. For example, once you create a card or task, you can tag your teammates on it, set due dates, and - once it’s done - move it from your To-do List to the Done List. You can also view your cards in calendar format. We’ve seen users use Trello to work on group projects from wedding planning to marketing campaign management. We were acquired by Atlassian about 2 years ago and it’s been a really natural fit, as both companies are focused on unleashing the power and potential of all teams. We create software to help people do their jobs in a way that is also enjoyable.

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ED: Tell me a little bit about your career path. What was your first job, and what else happened along the way to bring you to where you are now?

JW: When you enjoy what you do or the company you work for, you naturally exude an energy,  and I think that’s what helped me connect with so many people who have shaped the next step in my career.

My first real job out of college was working at the Apple Store in downtown Boston. I was a “workshop specialist,”  teaching people how to use the different types of Apple products and software. It was a ton of fun and the training was incredible. Apple has a really thorough onboarding that all new employees go through and I can say from experience that it works and it applies to much more than working at the store.

After Apple, I was referred to HubSpot by a friend I’d met at Apple. Many of my former colleagues had joined the HubSpot support team and it felt like the right opportunity for me. I worked in HubSpot support helping users get their sites up and running, working through marketing concepts with them, and learning the ins and outs of what it HubSpot had to offer. I knew from the moment I got there that my goal was to join the HubSpot marketing team, in my mind, it was the pinnacle of #goals. To be on the marketing team for one of the premier marketing software companies in the world? Yes, please!

So after about a year in customer support, I started working on side projects for the HubSpot marketing team and eventually interviewed for a position on the team that handled top of the funnel lead generation - big thanks to Ellie Mirman for taking a chance on me! :) I joined the team and specialized in email, then took a personal interest in growing our Instagram account. Here are some articles I was featured in during my time at HubSpot:


In April 2016, I met my now current boss, the illustrious Stella Garber, at the Collision Conference in New Orleans, where we discussed opportunities for co-marketing between HubSpot & Trello. The result was this ebook about How to Master a Successful Marketing Campaign in Trello, and we haven’t stopped working together since. I soon joined the Trello marketing team as a content marketer, working specifically on long-form content like customer stories and doing research about our users to develop personas.

Throughout my time at Trello, I’ve shifted from more of a content marketing focus to a product marketing and growth marketing specialization. I’ve sat with multiple product teams from Growth to Activation and Acquisition and on each one, I’ve loved getting closer to the product and closer to our users to understand what they need most and how we can help them be more productive with Trello.

ED: How much of your day-to-day involves competitive intelligence?

JW: We’re getting more data-driven each day. Having access to the right information at the right time is integral to getting my job done. Whether it’s understanding the customer segments that we’re focusing on or diving deeper into existing user trends, competitive intelligence drives the strategic decisions we’re making as a company. The biggest thing I think product marketing often struggles with is getting the full picture - sometimes it’s necessary to pull from disparate sources to get a clear indicator of what may be going on across tools, customer segments, and the industry at large.

ED: What is your advice for someone who is planning a product launch for the first time?

JW: First, define your target market and develop the value proposition. How is this helping our users? Bonus: write the PR brief before writing the GTM strategy: Why should people care about this thing that you are launching? How will it improve their lives? How would you explain it to a non-technical audience?

Second, craft your messaging and choose the right channels to deliver it (email, social, PR)

Third, Make sure all internal stakeholders are aligned and on a schedule. Use Slack? Get them into a channel, stat!

Finally, make sure everyone stays on the same page! Trello is great for GTM Launches - as it makes it super easy to for everyone to see progress and updates (and you can copy that board again the next time you have a launch -yay templates!)

ED: What advice do you have for someone who wants to start a job in product marketing?

JW: Get your hands dirty with the product and talk to users all the time.

ED: What skills have you learned from past roles that helped prepare you for your current role?

JW: You can always ask the user what they need/want/like (this should be paired with proper user research as well because sometimes people don’t know what they need!)

It’s important to feel your users’ pain, get into the product and break things, try out different scenarios.

Your biggest allies are in other departments. Understanding their jobs will help you do your job better. You also won’t fall into the trap of “that’s not my job

ED: What programs or resources have you found to be most impactful throughout your career?


  • Reforge Growth Series: Masterclasses for experienced growth practitioners to continue leveling up their skills.
  • BU Alumni network: Proud Terrier here! I’ve loved getting to network at events with local alums and to help mentor current students.
  • Traveling: Seeing more of the world expands your mind and your perspective. It’s amazing how feeling so small can give you such big ideas.
  • Industry events and conferences: Rubbing elbows with the leaders in your field is awesome. Who doesn’t love to geek out about SEO, experimentation and GTMs?

ED: What’s the best career advice you’ve ever received?

JW: Think deeply before committing to a project or task. You should be at 80% capacity as much as you possibly can, meaning you keep 20% of your time available for ad hoc projects that will inevitably come up. Think about what committing to something new means for other projects you’re working on and learn when to say no!

ED: When you’re not hard at work, what’s your favorite thing to do?

JW: Do all the crossword puzzles, eat unique cuisines, visit interesting places, and take portraits of people.

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Emily Dumas
Emily Dumas is a product marketer who leads content strategy at ZoomInfo, a global leader in modern go-to-market software, data, and intelligence. Prior to joining ZoomInfo, she spent several years on the Crayon marketing team.