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Jessica Webb Kennedy

Head Of Marketing, Tailscale

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If product marketing is a relatively new function at your company (relative to product), what advice do you have on becoming a strategic partner and more involved earlier in the product roadmap development process?

Tailscale Head Of Marketing • December 9

This happens a lot, PMMs are brought in quite frantically once a team already has a very specific way of working and it's on the PMM to figure out how to slot themselves in. I think the first thing that needs to happen is to clearly delineate and articulate team members' roles and responsibilitie......Read More

1878 Views

How do you advocate for adding a new feature to the roadmap when it's something competitors have launched and customers are asking for, but internally it isn't seen as a priority?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

This is always tough, for Trello this was trello.com/templates, it's something we had thought about doing for a long time but we didn't want to be overly prescriptive about how people should use our product. That being said, we got a lot of inquiries about templates - and a LOT of other tools pro......Read More

1742 Views

How do you think about your first 30/60/90 day goals when coming in as the Head of Product Marketing in a startup that didn't have product marketing before?

Jessica Webb Kennedy

Tailscale Head Of Marketing • June 17

PMM wears so many hats it's important to recognize what is needed at any stage of a company. When first coming into an organization as the first PMM I think the most important thing to do is establish what does and doesn't exist - and where the biggest holes that can be plugged are. This can be a......Read More

1411 Views

If you have to improve the adoption rate of a SaaS product, where would you start?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

I'd start with the data! This may mean tapping your data analysts, marketing analysts, basically anybody who is knee-deep in the metrics. What I would do first is attempt to map out the funnel for the product in question (if this doesn't already exist) - figuring out how people get to your websit......Read More

1376 Views

What's the best template for process organisation that you have used as a PMM bridging different company circles?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

I definitely think the process when it comes to PMM life is very important. Especially for things like GTMs. One of my team's go-to resources is the Confluence Messaging House Template - I like this one because it really is essential for getting everyone on the same page about a product or featur......Read More

1301 Views

What made you decide to choose Product Marketing over Product Management?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

Great question and I've thought about this a lot, I LOVE watching Product Managers work and think that the problems they tackle are super fascinating, that being said, I'm a marketer at heart. I think PMMs are lucky to be in a position where we get to work super closely with PMs but our jobs are ......Read More

1112 Views

As a product marketer, how do you prioritize the features that you are requesting in the roadmap?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

Some of the best prioritization I've seen and been a part of is based on the ICE framework: * Impact: what do we think this feature will do for our user-base, our metrics, our bottom-line. This is also a place to consider the size of the opportunity, is it going to impact your whole userb......Read More

1031 Views

What are short and sweet messaging templates or frameworks that you and your team use?

Jessica Webb Kennedy

Tailscale Head Of Marketing • November 19

A great way to think about framing your messaging is by starting out with a short paragraph outlining who you are talking to and why they should care or need your solution/product. At Atlassian, we often start with these questions: Is this how you want your product or service to be represented? A......Read More

1014 Views

What specific areas of roadmap influence do you think product marketing can help the most with?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

Bringing in information about trends in the market, what competitors are doing, and the most important thing - USER FEEDBACK! I have learned over the years that the best way to get any sort of buy-in for roadmap planning is to come armed with real evidence. This includes existing user anecdotes b......Read More

901 Views

As a product marketer, when and how do you communicate your product roadmap to both active and prospective customers?

Jessica Webb Kennedy

Tailscale Head Of Marketing • December 9

This is always a bit of a dance, I'd say we've fluctuated over time with being better at sharing things in advance vs. more so communicating a changelog of features we've added over time. In my eyes, this often comes back to who owns this type of communication, and it can sometimes be a bit of a ......Read More

896 Views

Credentials & Highlights

Head Of Marketing at Tailscale

Formerly Atlassian (Trello), HubSpot, Lyft