Jenna Crane

Jenna CraneShare

Senior Director of Product Marketing, Klaviyo
Jenna Crane is the Head of Product Marketing at Klaviyo. She has more than a decade of experience marketing B2B technology, at companies like Dropbox, Upwork, and Drift. As an early employee at Dro...more
Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

My favorite question is "What would be your positioning statement for yourself as a product marketer?" 

I love that question because it shows me how comfortable they are with the basics of positioning, and it tells me a lot about the aspects of product marketing that they care most about. For example, they may highlight their strength in messaging and positioning, or their customer-centricity, or their ability to partner with teams across the company. It's also another opportunity to see how they communciate complex concepts in a clear, concise, and compelling way.

I've heard a lot of great responses, and there is no right answer. But I always come away with a deeper understanding of how they view their strengths, as well as the type of work they like to do.

Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

I'd recommend having on hand:

  • Your story. Be prepared to give a brief walkthrough of your background and experience. I always like to see when someone has a strong narrative about their career — why they made each move, the highlights of their experience and what they learned, and what they're looking for next. 
  • An example of a product launch or major project you led that you were particularly proud of. Be prepared to talk about the process of putting it together, any difficulties you faced and how you overcame them, and what the impact was (with actual metrics like revenue, product adoption, or awareness / engagment lift if you can!). 
  • Examples of how you've worked with each of the functions represented on the interview panel. If you're speaking with a PM, a sales director, and a performance marketer, for example, prep stories about how you've worked with product, sales, and performance marketing. 
  • A few companies that you think are doing product marketing well. The first time I got asked this question in an interview, I didn't have an answer prepared, and it was super tough to think of a few on the spot. You may not get asked this question, but you'll be grateful to have an answer in your back pocket if you do. 
  • Questions for each of the panelists. Even if they're basic ones like 'how do you envision the person in this role will work with your team?' or 'what are the characteristics of people who are really successful at this company?' you don't want to be left without any questions for the interviewer. 
Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

1. They didn't prepare. It's really hard to justify moving a candidate forward if they don't know basic details about our company, their answers lack details and depth, and/or they don't have questions for the interviewer.

2. They are too long-winded or rambling, and/or their answers are mostly jargon. Of course we want to hear candidates reference terms we use in our day-to-day work. But if all their answers are more buzzwords than substance, or if they struggle to communicate in a concise and clear way, we have to pass. So much of product marketing success is about effective communication — with customers and prospects, as well as people across the company — so I give this a lot of weight.

3. They can't effectively connect with cross-functional partners on the panel. We make sure our panels have key partners from the cross-functional teams they'd work closely with. Sometimes we see candidates struggle to build rapport or have productive conversations with those interviewers, which can indicate they may not have enough experience working with those teams. (It also doesn't make those key stakeholders super excited to partner with that person.) Less common but even more concerning: we sometimes see people who, in trying to talk about their experience working with that function, inadvertently disparage that function. (For example, throwing their current product team under the bus is always concerning, but especially when talking to a PM.) That's a big red flag.

Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkJuly 15

I find that it depends on the scale of what I’m messaging. If it’s for a small project (a landing page, a video, etc.) I like to go with:

  • Key message
  • 3 supporting value propositions, with taglines and descriptions
  • Supporting points for each of those value props — whether those are unique differentiators, supporting features, and/or reasons to believe/proof points

I like to use the following table structure: 

If it’s for something slightly larger — a launch or a campaign, for example — I add on to the above with:

  • Overall
    - Target headlines
    - Key message per target persona, and/or guidance for how to adapt the messaging to serve different audiences
  • For each value prop:
    - Key benefits / value delivered
    - Key use cases
    - Success metrics — what are the key outcomes someone can expect to see? (e.g. higher customer lifetime value)

And if it’s for an entire product line or company, I typically compile messaging frameworks for 3 different stages of the customer journey:

  • Awareness: Why should customers should evaluate your type of solution? This doesn’t mention your company or product at all, and is designed to inform really top-of-funnel activities or conversations. For example, the messaging framework for Klaviyo’s SMS product talks about why text message marketing is so valuable, and why companies should consider it, but never mentions Klaviyo.
  • Consideration: Why should your company earn a place in the consideration set? This pays off the awareness messaging above it, explaining how your company/product delivers on the value propositions established in the awareness-level messaging. In the Klaviyo example, the 3 awareness-level value props are ‘deliver a better customer experience,’ ‘double your ROI’ and ‘build direct relationships with your customers.' The consideration-level messaging uses those same value props, but talks about how Klaviyo delivers on them — knowing that those are the criteria that people will use to build their consideration set. It’s like you're giving the prospect permission to say "ok, this company checks those boxes, I’ll learn more."
  • Decision: Once you’re in the consideration set, this is where you set yourself apart from competitors and define the purchase decision criteria. This messaging should live at the intersection in the Venn Diagram of: what customers value, what your product/company does uniquely well, and what is competitively differentiated. This is usually the most extensive framework I build out, because it shapes the majority of what goes out into market: website language, sales assets, paid ads, etc.
Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

Getting on my soapbox here for a second (though I suppose I've been on it this whole time) — make sure your resume is concise and clear. It should be 2 pages MAX, ideally 1 page. I don't care if you've been in the industry for 30 years, you should be able to distill down your experience into 1 or 2 pages. 

I've passed on candidates who technically have strong experience because their resume is a long rambling mess that I tried to read and couldn't get through. 

This sounds like a ridiculous and arbitrary practice, but it's not. Here's why. Your resume is the first work sample you submit. It's an example of how you position yourself as a candidate. Think of it like a one-pager you'd make for sales, but about yourself. 

If a candidate struggles to convey their experience (and value) in a clear, concise, and compelling way, the same will be true for how they market our company and our products. 

Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkJune 27

Cross-functional work is Product Marketing's middle name! 

PMM <> Sales

  • Key deliverables: Pitch decks, enablement assets (internal resources like battlecards and personas, external resources like one-pagers and case studies), and trainings 
  • Key goals: Improve win rates, improve competitive win rates, increase ASP, shorten sales cycles, improve demo request to demo held rates, generate pipeline, improve sales team confidence 


  • Key deliverables: Same as sales, but with an existing customer upgrade / health / cross-sell / retention angle. Add in enablement on new features and important changes (like pricing), and resources like maturity models or crawl/walk/run decks. 
  • Key goals: Average customer health score, net retention or churn rates, NPS, CS-driven expansion, lifetime value [though be careful about signing up for these, as seen in one of my other answers!]

PMM <> Marketing

  • Key deliverables: Messaging and positioning, launch moments and/or campaigns, website pages, case studies, personas and customer insights, demo and/or explainer videos, competitive intelligence, and more
  • Key goals: Website traffic, share of voice, engagement metrics for external moments like launches or campaigns, website conversion rate / bounce rate, and (whenever possible) revenue-focused metrics like leads/demo requests, MQLs, opportunities/pipeline, and self-serve ARR

PMM <> Product

  • Key deliverables: Product positioning, roadmap feedback, market/customer research, competitive intelligence, launches, GTM strategy for new products, support with onboarding experiences and product-led growth/virality
  • Key goals: Feature adoption, adoption and/or revenue generated from new product lines, self-serve revenue, NPS, net retention rate, specific virality metrics
Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkOctober 17

I know this situation well; it's the same here at Klaviyo! 

First, you need to understand the composition of both audiences. Are the self-serve customers smaller businesses that don't need to talk to sales to feel comfortable using the product? Are at least some of them actually enterprise customers poking around in the product before they talk to sales? Is this a product-led company that makes it easy for end users at enterprise companies to self-serve? Maybe a combination of the above? 

With that in mind, there are some core differences and some potential differences. 

The core differences:

  •  The buyer journey. Self-serve customers usually don't have long and complex evaluation processes with lots of different stakeholders. Enterprise customers usually have long sales cycles involving multiple different stakeholders. Serving both audiences means you need to invest in both self-serve content (mostly via your website) and sales enablement (pitch decks, one-pagers, training on personas and competitors and objection-handling, etc.).
  •  The onboarding and value-realization process. Self-serve customers need an intuitive, self-driven onboarding flow that helps them not only learn how to use the product, but also realize value very quickly. There's no one holding their hand as they get up to speed, so they can easily drop off (and it's hard to win them back). Don't forget that the onboarding experience is both inside and outside of the product. Meanwhile, enterprise customers generally have more complex and resource-intensive onboarding and implementation journeys, usually led by Customer Success and/or Solutions Architect teams. There's still the potential for failure, but human-driven experiences are generally more forgiving than self-serve experiences. 
  •  The upsell/cross-sell motion. Similar to the buyer journey, driving expansion among self-serve customers looks very different than doing so with enterprise customers. In the former you need to use the channels available to you (in product, email, etc.) and ideally surface these prompts at precisely timed moments in the customer journey. Pricing & packaging can also be a powerful lever here. For enterprise customers, upsell and cross-sell happens via the Customer Success team (or sometimes specialized sales teams focusing on the existing customer base), so you need to give them the resources — assets, training, etc. — to effectively have those conversations. 

The potential differences: 

  •  The positioning, messaging, and proof points. Enterprise customers are trying to solve different problems — or at least at different scale — than smaller customers. That means your positioning and messaging, the language you use, the customer proof points, the use cases, and sometimes even the features you emphasize should be different across the two audiences. For each audience, you want prospects to have the same takeaway — "this product was made for companies like mine / people like me." 
  •  The product & success needs. Enterprise customers tend to have more complex product requirements than smaller customers, and almost always have more rigorous support needs. This has implications on the product roadmap, your pricing & packaging, and your Customer Success model/staffing. 
Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

Absolutely writing samples! I always ask for those. (As you can tell from my other answers, communication is something I care deeply about!) 

Case studies, landing pages, pitch decks / other enablement assets, and messaging frameworks can also be great additions to a portfolio. Just make sure you can speak to the process of building those, because it's impossible to know just from looking at them how much was built by the candidate vs. a collaborator. 

What really makes a candidate stand out, I've found, is a short 'about me' deck. I've seen some great decks that include: 

  • Work samples (including some commentary about the process of developing that work)
  • Some thoughts about their approach to product marketing 
  • A slide or two about their career and the highlights of their experience
  • Bonus: Something that tells me a little bit about who they are as a person outside of work (hobbies, things they're passionate about, etc.)

Not only is this full of great insight into the candidate, but it's also a great example of how they position themselves. It's essentially a sales enablement asset, which should hopefully translate into how well they can do that for our company and products. 

Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

As you can probably tell, I am a big fan of focusing on process, not just outcomes. I like to ask people to walk me through a project they led, and I ask them plenty of questions — things like 'why did you decide to position it that way?' or 'what was the most difficult part of the process, and how did you handle it?'

Usually when you dig into the details it becomes apparent whether they led the work autonomously or just played a small part. 

I'm also a big fan of hypotheticals. I give someone a scenario that is well within the scope of what they would be doing in the role, give them plenty of background context (and make sure they know they can ask me for more information), and then ask them to walk me through how they would approach it. 

Jenna Crane
Jenna Crane
Senior Director of Product Marketing, Klaviyo | Formerly Drift, Dropbox, UpworkNovember 17

Prep and practice! 

Prep your answers beforehand, have them on hand for reference if you need them. 

Practice by getting in more reps. Talking about yourself and your experience gets easier every time, and you get more insight into the types of questions that come up (so you can improve your prep). 

Credentials & Highlights
Senior Director of Product Marketing at Klaviyo
Formerly Drift, Dropbox, Upwork
Top Product Marketing Mentor List
Lives In Boston, MA
Knows About Category Creation, Competitive Positioning, Developer Product Marketing, Product Laun...more