AMA: Calendly Head of Product Marketing, Jeff Hardison on Enterprise vs PLG Product Marketing

What's defined as "enterprise" and "mid-market" differs in many companies. Generally, sales leadership works with the executive team to segment which size customers they go after such as small businesses (say, under 150 employees), medium-sized (say, 150 to 2,500), and enterprise (say, 2,500 and up). As you know if you've worked in differently sized companies, how those companies operate — from 150 employees to 10,000 employees — really evolves. For example, in a medium-sized, 700-person company an SDR might still have the freedom to sign up for a scheduling-automation tool as along as it's free. Yet, in a 10,000 person company, that SDR might be blocked by IT from using non-approved tools because larger companies often think more about security and software sprawl. Therefore, how you do product marketing must evolve, whether you're working for a vendor targeting 150-person company SDRs or 10,000-person company IT people. One key, day-to-day difference in doing Enterprise PMM work over mid-market is that you have more internal stakeholders to consider (not just the SDRs, but also their bosses and IT) and you need to spend more time educating and arming your sales and CS teams to work with all of these stakeholders.

Stepping back, let's differentiate the enterprise sales motion from the product-led growth motion: Smaller companies have less employees and, therefore, can often easily buy from you with a credit card. Some SDR in a sales dept. can purchase your self-serve plans with their boss' credit card. Some recruiter coordinator can do the same with their own and maybe expense it. In these situations, it's often less about the PMM trying to train or support the sales team in hand-holding a customer to enter their credit card information. Instead, it's about doing things that help customers buy on their own: writing in-app conversion copy about a paid feature, conducting self-serve pricing research, or launching a new feature that's on a paid self-serve tier. Enterprise customers have more employees, which (often) begets more bureaucracy: legal teams who want to go back and forth on a contract, purchasing departments that want to haggle over the price, and multiple stakehholders in different departments who want to weigh in and ask questions. Salespeople — humans! — are much better at working with other humans on the above than products are (at least, today, that is). With bigger customers, your job as a PMM is to help Sales and Customer Success do that hand-holding with customers. This means training Sales/CS on features that are more expensive (they work on commission!), advocating for more differentiation in the Enterprise plan with research, and copywriting for them (sales emails, PDFs, etc.). If you want to "provide more lift in the Enterprise motion," help Sales and CS close more enterprise deals. Start by trying the above, and ask your Sales/CS colleagues what they need as well.

My favorite product marketing OKRs are the ones that clearly support the company's OKRs. And the second-best OKRs are ones that are shared with other departments because you can always do better, together, with other departments — when you work in PMM. Let's say that your company's OKRs are the following: - Increase self-serve, credit card growth. - Increase sales-led growth with large enterprise customers. Now, let's take one of those: "increase self-serve, credit card growth." Well, then your OKRs could be: - Launch new X feature on the self-serve pricing plan with Y customers upgrading by Z date (co-owned with Product Management) - Overhaul email and in-app communications with small and mid-sized customers to drive X upgrades in 90 days (co-owned with Lifecycle Team and Growth Product Management) See how your OKRs ladder up into the company ones? And how they're shared?

I like to measure all marketing in terms of: Outputs: What you did marketing-wise such as sent X emails to whom, created Y social posts, made Z video, etc. Outcomes: How did people engage with your marketing such as clicks on the email CTAs, customers' tweets about your launch, Product Hunt results, etc.? Outtakes: What happened downstream for the business as a result of your launch/campaign? This is often the most difficult to measure quickly, yet the most important for execs. How much pipeline did your launch/campaign create for the sales team? Within a reasonable amount of time (e.g., two weeks), how many people upgraded to a paid credit-card plan as a result of your email? How many existing customers used the feature and rated it highly in a survey? While so many experts focus on outtakes, I believe measuring all three — outputs, outcomes, and outtakes — is important because you're a) evaluating each step of the marketing journey (making the thing, observing how the thing performed in real-time, and measuring how the thing impacted the business), and b) like you suggested, sometimes it takes months to measure the business impact and you want to report on something now. Specific to your situation (i.e., two months or longer sales cycle), I recommend aligning with your leadership that you'll publish a few different reports at different moments in the sales cycle: - In the first couple of days, just report on outputs and outtakes. And, if you can, report on increase in demo requests (for sales). - After two weeks, report on any credit-card upgrades to paid plans (for self-serve/PLG) among people who engaged with your marketing. Also report on how Sales is engaging with the demo requests (e.g., sales says 10 of the 20 demo requests are sales accepted opportunities by them). - After a couple months, report on pipeline or closed deals related to the launch/campaign, credit-card sales, and usage by existing customers. Also, share happy customer quotes from Customer Success, social, etc.

Many career climbers recommend being very choosy about where you work. You'll hear advice like "work at a hot/big company first because the reputation will carry you," "choose an amazing product if it's a startup so that the marketing work will be less difficult," "pick a trendy category because it's more interesting," and so forth. While I've repeatedly worked in some categories multiple times — customer data/analytics, meeting software, e-commerce, productivity, deep tech — it's often been on accident. Someone such as a recruiter or hiring manager sees that you work in the space, they believe you'll be able to quickly ramp up at their employer, and so they recruit you. Therefore, I guess that's the main advantage: domain knowledge is an easy way to get recruited. Personally, though, I often choose to move around in the industry based on what I think will be fun or interesting. Perhaps I used the product before (Clearbit), maybe I liked how the founder ran the business in a PLG + Sales fashion (Calendly), maybe I'd been studying the space on a personal level (location-aware mobile: Meridian), or I wanted a hard challenge (helping a small startup earn its first millions: Lytics). In summary, there are all kinds of moves you can make that are strategic for your career but, for me, I just enjoy liking my employer.

1. Ensure you're writing the correct case studies for your business. Align with your executive team — particularly sales and CS — on the types of customer stories they need. Enterprise or mid-market? Certain products or use cases? Which industries or job roles? Then, try to check off each with a "gold-standard" case study. 2. Work with your customer success and sales teams to create a shared OKR around delivering the biggest names associated with these targets. If you can't get big names, work to compromise with execs to deliver the next best logos they approve of. 3. If you don't have a customer-reference manager, be prepared to help sell the customer on participating. Get them excited to tell their story for their own glory and career. And, bonus points, work with sales on delivering customers' discounts or other incentives in return. 4. Most executives controlling budget don't just want a good story; they also want to see return on investment (ROI). Challenge is, perhaps the customer doesn't know their ROI. Offer to help them think through metrics they care about and do the math for them. These ROI calculations are obviously the most difficult thing to learn how to do, but it's what takes case studies from silver to gold. Here are some examples of Calendly case studies where we try to do the above.

If I had a dollar for every time someone didn't want to help PMM update videos because it's too time-consuming, I'd have enough money to pay a video agency to do it! 😃 Personally, I recommend having the PMMs and PMs create quick, rough screenshare videos using something such as Loom. That way it requires no outside video editing help — and it looks more authentic. In addition, for our monthly product-update newsletter, sometimes I just create a Quicktime screenshare — with no voiceover with something such as Loom — and then turn it into a .gif. Takes about 10 minutes.

In the last couple of companies, what I've done is create a slide that shows the academic definition and jobs to be done in product marketing: research, positioning/messaging, etc. Then, I host meetings with stakeholders, and show them the slide, ask them what they have experience with product marketing handling, what they liked, didn't like, and so on. Then, I ask them what they need help with going forward in our company. That input helps inform how I prioritize the team. It's important to have these alignment meetings each quarter, as needs change, new leaders join, and the company's objectives/strategies shift.

The No. 1 way you can build trust with cross-functional partners is by listening to them. Try meeting with them at least quarterly and asking: - What have you liked that product marketers have done for you in the distant past? - What are some things my team/I have done for you that's been helpful this past quarter? - What are some things my team/I have done that aren't as helpful? - What's changing in your department that you think might affect product marketing? - How are you feeling pressure in new ways from your managers, teammates, etc.? (Perhaps you can take this into account as a PMM when you're developing empathy for them.) And then meet with them again one month or a quarter later and report back on how you addressed these issues and needs. Then, ask them the questions all over again, as work dynamics change for cross-functional partners quarter to quarter.

Each quarter, we survey our salespeople and ask them how we did. You can ask questions like: - How would you rate our help from 1-10? - What's something that was very helpful in closing deals? - Do you have any examples of deals we helped close? - What's something we should work on to improve? Then, report on how well you move the needle in improvement each quarter.

I like people who stretch themselves and try, despite all of the challenges others may perceive against them. So, I'd ask myself how has this junior candidate tried to become a product marketer? 1. Have they read some books on product marketing and taking some courses (or gotten certifications)? 2. For me, writing is critical. Has this person studied writing in college, worked in journalism/blogging, or even written short stories? 3. If no one has given them an opportunity to do product marketing, have they volunteered to do product marketing for free for a small startup to get some experience? (I did volunteer marketing work when I was starting out with no savings — it was difficult and stressful but helped me land my first job in marketing.)

There are a few things I look for when recruiting enterprise PMMs in a product-led growth company going upmarket (with a sales team): - Have they done enterprise PMM work before? This usually means both have: 1) owned the product marketing work for the enterprise pricing plan (in a PLG company this plan often includes security/privacy features like SCIM, SSO etc.), and 2) gained experience targeting enterprise-sized companies (what's "enterprise" varies at every company but let's say 10,000 employees or greater for discussion sake). - Do they have positive experiences working with internal sales and customer-success coworkers? And do they enjoy it? I can't tell you how many PMMs have worked with sales and customer-success teams on enablement and more, yet don't enjoy it. I like people to enjoy their jobs, so this question is critical for me. - Do I think they'd be successful in working with our particular sales and customer success teams? Every culture is different. Who will impress our sales and CS team may not work well at another company. For example, at one company the sales team might have its own sales enablement team — and not need much help with training. Yet, at another company, the sales team might not have their own enablement team and need a lot of help. Are you willing to adjust as a PMM to our particular situation? - Do you have a growth mindset? In some PLG companies, being an enterprise PMM is more difficult from a personal resilience perspective than a non-enterprise PMM — particularly in a PLG company — because you have more stakeholders to deal with. Not only do you have to work with Product, Marketing, and Support, but you also have have customer-success managers (with important large accounts) and salespeople (trying to close bigger deals than your average deal size for self-serve credit-card sales). Therefore, you need to have a thick skin and be proactive.

Account-based marketing started because, for decades, sales did account-based selling. Instead of a salesperson just opening up a list of, say, every financial services company in the world (thousands) with no focus, they work with their sales leadership to identify a target account list to focus on (perhaps it's the top 10 financial services companies, or a certain size financial services company they could be successful with). Then, often times, that salesperson could only reach out to those target accounts in their list. It might be only 10 target accounts, but they might have to build relationships with 20 people at each target account (IT, VPs, etc.) to get buy-in across the company. Why would they have to get buy-in across the company with so many people? The bigger the company, the more people who want to weigh in on what products the company buys. (Think about when a coworker has bought a tool that you've not liked from a previous job, and how you wished you could have given your input; that's the political dynamic at work.) Account-based marketing is the practice of helping these salespeople go after these short lists of target accounts by doing more targeted marketing to just those companies (say, the top 10 financial services companies) and their stakeholders. Account-based marketing involves emailing those stakeholders in those target accounts, serving ads to just employees in those accounts (when possible, because it's difficult), inviting those stakeholders to private events, observing intent signals (some software shows you what those accounts are researching) and more. Generally, there's an account-based marketer — often in the demand generation team — who leads the operations efforts around ABM. Yet, like most things demand gen, they need your help in PMM to help craft messaging for these communications.

There are different types of competitive product research. Therefore, it's important to ask execs who this research is for. Doing extensive competitive product research to train sales and customer-success is one thing. They're often satisfied with a one- to two-page "battle card" that will help them beat the competition. They rarely need an exhaustive list of every feature (and, if you did create that exhaustive comparison list, it would likely overwhelm them anyway). If the research is for product management — because, say, they want to create complete feature parity with the competitor — I recommend asking to partner with the product manager on a shared OKR around competitive research. For the latter, you'd likely need access to the competitor's software (if they have a freemium offering that makes it easier than something you have to talk to their sales team about), their help-center documentation, and interviews with your customers (be sure to check with your customers to ensure they're not violating any contractual NDAs by giving you information).

There are two main ways tech companies make money: - sales-led: a salesperson works with a customer and closes the deal (which was the norm for decades) - self-serve: a customer can manually enter their credit-card information into the product to purchase something, bypassing a human. Self-serve/credit-card sales is only one aspect of product-led growth (PLG), which also includes using the product to sign up customers (which humans used to own), activate them (which humans used to own), upgrade them (see above), and renew them (which humans used to own). At its most basic level, PLG marketing is more about helping the product itself — and the humans who work on it — do the heavy lifting of attracting customers, getting them to sign up, trying various features, upgrading, and then renewing. Sales-led marketing is more about helping your human coworkers (salespeople, customer success managers, etc.) do more of that marketing/sales/customer-success work. A hybrid company (PLG + Sales like we have at Calendly) is about doing a mix of both.