AMA: Calendly Head of Product Marketing, Jeff Hardison on Messaging

One of the biggest category creation mistakes is trying to create your own category — when there's already a category you could join and dominate as the leader. Many of the "category creation" companies people often trumpet didn't really create the categories from scratch. They took emerging categories, and explained the category and their concomitant leadership in the category better than anyone else.

The best ways I've found to ensure your messaging lives for more than a few weeks: 1) Collaborating with your company leaders to not just review, but also develop the messaging 2) Testing the messaging with real customers (and sharing their responses with your coworkers) 2) Training — and sometimes testing — your coworkers on the messaging so they know how to use it 3) Spreading the messaging everywhere — website, video, emails, etc. — you can and measuring the effectiveness (and sharing that measurement with coworkers) When I haven't done at least two of the above, someone often steps in and starts tweaking the messaging. As Netscape's CEO once said, "Show me the data. If all we have are opinions, we'll go with mine." That said, if you work in a fast-moving company, the messaging will evolve as you get new data from customers, the competition, and so forth. Being flexible and riding the waves is something we all have to learn as product marketers.

For me, there are few types of "Why's." There's the lowercase "why." And the uppercase "Why." Lowercase "why" gets at communicating why a prospect should choose your offering over the competition. For that, I recommend the popular value pillars/differentiation method I mention in another question about corporate positioning/messaging. The uppercase "Why" gets at why should this company exist in the world? How are you making a dent in the universe? How are you improving the world for the better? What gets you up in the morning to work on these opportunities versus a different company's? To me, this is a company's "Mission." The uppercase "Why" is one of the most difficult jobs of a marketer because not every executive team (or even founder) thinks about work that way. So, you can't just ask them. However, sometimes, your CEO (particularly a founder) already has this Why set and on repeat on stages, in investor presentations, with the media, etc. Just ask them! To get around the tendency for some exec teams to not think about a Why, I try to lead a workshop in which we start writing down some potential ways we're improving the world for the better. We also look at other famous company's Why's including masters of the craft such as Apple, Patagonia, etc.

Good product marketing helps build the brand. Good brand marketing helps drive usage of the products. To me, they're like cousins in marketing. Perhaps more so than any other marketing disciplines. Take Apple, a master of marrying their brand marketing and product marketing. Here's an old ad for the iPod. There's the logo, and an engaging illustration of someone dancing, sure. Some people's idea of brand advertising might stop there. But Apple doesn't. Then they add: 10,000 songs in your pocket. Mac or PC. That's Product Marketing meets Brand Marketing. 10,000 songs (feature) in your pocket (benefit plus differentiation — other MP3 players were big and/or didn't hold many songs). Mac or PC (audience targeting). Makes you want to dance — and look fun to others (brand).

If you frequently find yourself in a "messaging by committee" situation, I'd recommend working directly with your boss (e.g, the CMO) and the CEO to create a DACI document (Driver, Approver, Contributor, Informed). Let's take company messaging. You might be the Driver. Your boss might be the first Approver, but the final Approver is the CEO. Contributor could be the other C-level executives. Informed could be the other people who typically weigh in, as well as other who need to use your messaging, but your CEO and CMO don't think should be Contributors. When people try to weigh in later, you can show the DACI document, yet let them know that you're happy to ask the DACI committee if they should be included in future exercises. All of that said, messaging is better when passionate coworkers weigh in. You might not change the words because of each person's opinion, but "voice of the coworker" should be second to "voice of the customer" when it comes to your research.

One of the biggest mistakes I see marketers make when talking about Artificial Intelligence (AI) or Machine Learning (ML) is they just throw the terms around. Like their employer can just sprinkle some AI salt on something to give it extra marketing zest. Think like a journalist for a small-town news site, instead, and try to explain why AI/ML is important and how it works for the use case at hand. Interviewing a software developer working on the AI/ML aspect of your product is one of my favorite shortcuts. They're used to explaining complex stuff to all kinds of people! Less helpful example: Our customer data platform uses machine learning to target customers who are "likely to convert." Perhaps a more helpful example: Say you're a marketer for a health and wellness website and you want to send a "paid subscription" email promotion to a set of free subscribers. You could use our customer data platform to find a small group of free subscribers that the software thinks are likely to engage with your promotion and renew their subscriptions. The way we do that is by using an approach called "machine learning" that combs through thousands of interactions of readers who have already subscribed and looks for common (they've visited your website's subscription-renewal page) behaviors as well as seemingly odd ones (they use a Chrome browser). We then find the free subscribers who have done similar things (visited the renewal page plus use a Chrome browser) — yet not subscribed — and allow you to target them. Our customers say that using this approach to target "likely to convert" customers doubles the effectiveness of their paid-subscription promotions. If you look at my writing for Calendly, I'm always using either real customer examples or making up hypothetical ones to explain stuff. I recommend trying it.

It's never too early to first write down some words about either the problem you're trying to solve (pre-product market fit) or are solving (post-product market fit) — and then running those words by potential customers, investors, employees, and more. For hundreds of years, humans have explained ourselves, and been moved by others, through narratives. Embrace it every day.

Repeat, repeat, repeat. As our CMO Jessica says, once you start getting tired of sharing the messaging, then you're just getting started. Of course you need to email, share on Slack, host on Asana, and so on. But that's just the beginning. Speak publicly about the messaging. Present on the messaging in not just one-to-many meetings but also small meetings with demand gen, content, different sales teams, etc. Get their feedback in small, "safe" situations. Record Looms of you presenting the messaging too, for those async communications fans. Get people using the messaging. Don't just hand the messaging off to people, but also create shared OKRs with different teams to use the messaging. For example, we have new Enterprise Messaging at Calendly. We agreed on a shared OKR with product marketing, program management, lifecycle marketing, content, and more teams to use the messaging together and test the results with customers. People understood the messaging so much more by using it together. Watch Gong calls to see if people are using the messaging in Sales and CS calls. If they're not, ask them why and if you can help better explain or support them. Promoting new messaging is a daily exercise. Never stop!

One thing I've seen work is positioning "positioning" as business strategy or a business plan versus marketing "words" we want people to think about and use. Positioning is the company's strategy — based on research and expertise — for who we're going after (e.g., sales teams) with what category of product (scheduling automation) to solve what problems or address what jobs to be done (qualify, route, and schedule meetings via the marketing website) to achieve a business outcomes (shorten the sales cycle, improve the customer experience in the buying process, generate more eager leads, etc.). Unlike the competition, you can self-serve and launch our product for this in 30 minutes — versus weeks with technical help. The positioning is the company's strategy for winning. It's not just marketing stuff on a page. Sure, marketing will do things to tell this story, but the whole company will also rally around the strategy. Product will continue to differentiate us from the competition with better UX, new features, and integrations. Sales will prioritize sales-team buyers. CS will help support and track the business outcomes our customers got excited about. Messaging, on the other hand, are the words we will all use to talk about the offering, benefits, differentiation, etc. when engaging with customers, creating ads, writing emails, drafting sales scripts, and so on.

If the product's audience includes a handful of large Enterprise customers, I'd ask for approval from Sales and Customer Success to reach out to the customers and run the messaging by them on a video or phone call. "Hey, Big Customer. We value your opinion, and would love just 15 minutes to run by you some words we're using to explain this new product. We thought you could give us your honest opinion — we won't be offended! — on what's working and what's not working with our messaging." One of our solutions marketers — with the help of our customer marketing manager — just did this at Calendly, and the results were invaluable. Who doesn't love giving their honest opinions to people who say they won't be offended? If they don't love it, try offering an incentive (gift card, discount, free trial, etc.). When I'm working in other environments where Sales and CS aren't as comfortable with employees talking to customers about non-Sales/CS motion stuff, we in Marketing volunteer to help the Sales and CS team close deals by playing Sales Engineer. We did this at Clearbit for a new product line that we understood very well in Marketing, and not only did Sales and CS get help with closing deals, but we were able to test our messaging via a slide deck used in the beginning of the calls. After every call, I tweaked something in the deck — or I realized I needed more than one deck depending on who I was talking with.

One thing I've seen work is positioning "positioning" as business strategy or a business plan versus marketing "words" we want people to think about and use. Positioning is the company's strategy — based on research and expertise — for who we're going after (e.g., sales teams) with what category of product (scheduling automation) to solve what problems or address what jobs to be done (qualify, route, and schedule meetings via the marketing website) to achieve a business outcomes (shorten the sales cycle, improve the customer experience in the buying process, generate more eager leads, etc.). Unlike the competition (name them), you can self-serve and launch our product for this in 30 minutes — versus weeks with technical help. The positioning is the company's strategy for winning. It's not just marketing stuff on a page. Sure, marketing will do things to tell this story, but the whole company will also rally around the strategy. Product will continue to differentiate us from the competition with better UX, new features, and integrations. Sales will prioritize sales-team buyers. CS will help support and track the business outcomes our customers got excited about. Messaging, on the other hand, are the words we will all use to talk about the offering, benefits, differentiation, etc. when engaging with customers, creating ads, writing emails, drafting sales scripts, and so on.

We've all seen this and cringed, right? Over-reliance on benefits: "Our scheduling automation platform help you shorten your sales cycle! Want a demo for something that you don't understand at all but somehow magically shortens your sales cycle?" Over-reliance on features: "Our scheduling automation software allows your customers to book meetings with you on your website. Want to pay a bunch of money for something that sounds like something you could hack together yourself?" Instead, I like to tell a story that includes a mix of Features, Tech, Benefits, Differentiation, and a Customer Quote/Mention or Hypothetical Customer Example. For example, here's a LinkedIn post I wrote for the launch of Calendly Routing. It's 2023 and a weird economy where you can't afford to give a prospect a bad experience. Countless studies — from even back when the economy was amazing! — say the companies that win in sales respond the quickest to leads. Trouble is, a sales rep might be on vacation when a lead comes in. Or asleep. Or sending auto-replies that go into a prospect's spam folder. How about just removing the need for a sales rep to respond right away? Let the prospect schedule a demo meeting right when they're visiting your website. And the system integrates with your Marketo or HubSpot signup forms. And takes advantage of your Salesforce data such as who is the account owner on your sales team. You get all of this with the new Calendly Routing. "Y'all the Calendly Routing tool is pretty rad." - Deven Pearson It's a little longer than I'd like, but it's got features, tech, benefits, customer quote, and hypothetical customer example. What it's sorely missing is how our offering differs from the competition's. If I could do it over, I'd add something a customer told me yesterday: "'And it only took 30 minutes to set up,' says Bryce from Smith.ai." Always be talking to customers to bring your features+benefits to life!

There are so many ways to test messaging, but here are some of my favorites: 1. Work with your Sales and Customer Success teams to reach out to your customers with an offer to give you feedback on your messaging via a phone or video call. This works better than you'd expect, but if they don't engage for some reason, offer an incentive (gift card, discount, etc.). This is even easier if you're Customer Marketing team has already pre-qualified customers who want to give feedback on messaging, product betas, etc. 2. Offer to join prospect calls with your Sales Team as a product expert. For example, if you're the PMM for your new AI product, and the salesperson is new to the subject matter, offer to run the demo. While on the call, test your new slide deck with the customer to offer context before the demo. This is by far my favorite way to test messaging, as so few PMMs do it, and your sales teams will love you if you can help close a deal. Plus, you'll developer greater empathy for how hard sales is. 3. Use a service such as Respondent, Wynter, or Usertesting to reach non-customers who are getting paid to give you feedback. This costs money, but not that much for what you're getting — and it's so easy. 4. A/B test different messaging on your website, in the product, etc. This is more difficult to do in small startups, as the busy engineering team will often roll their eyes because they're just trying to get the MVP out the door. So, in smaller companies, I recommend testing via channels you control such as email and social media. Testing via social media — something recommended by Dave Gerhardt — is probably what I'm using most frequently before I test somewhere riskier that I can't take back (e.g., email). Of course, as you get bigger you'll want to consider testing software such as Optimizely. 5. The good ol' survey. With an incentive, you can create a short survey in Google Forms or Typeform that will get you lots of results at scale — in minutes.

First off, I recommend reading my friend Adam DuVander's book Developer Marketing Does Not Exist. He is the master of teaching people about how to work with developers. In the past, when I've done developer marketing, these were some of my most successful initiatives (but please read Adam's book as he's much more comprehensive): 1. Create a solid developer portal that not only provides access to your developer tools and technical documentation, but also includes examples of what other developers have created. Developers learn from other developers. 2. Ask developers — either your own or partner/customer developers — to speak at developer events. Back in the day, pre-Covid, some of my biggest developer relations wins were at in-person events like this. I haven't had as much luck with online developer conferences, but short webinars and videos have performed well in this remote-work environment. 3. Working with your CTO or a developer to blog about developer topics, and then sharing those on Hacker News, etc. is daunting for some marketers, but it can outperform anything in terms of one-off tactics. At Meridian, an indoor mapping software company acquired by HP/Aruba, we drove heaps of interest in our software development kit (SDK) by working with our CTO to write about topics such as "An iOS Developer Takes on Android" or "GIT is Simpler Than You Think." We didn't directly promote Meridian or even the SDK, but instead talked about what it's like to tackle developer problems while an employee of the company. The association drove interest in the company, which in turn drove usage of the SDK.

One of my first jobs in tech marketing was promoting Amazon's software development kits (SDK) to developers. What I learned from everyone at Amazon is the power of using "plain English" when talking about anything. If you look at Amazon's site, you'll notice they use very simple language to talk about everything from shoes (on the retail site) to highly complicated software tools (in Amazon Web Services). The idea, I think, is that everyone can benefit from the writer working really hard to understand a subject well enough that they can explain it in simple terms. I, myself, don't always succeed at using "plain English" to describe my employer's products to people. Sometimes, I get pulled into hanging out with the Cool Jargon Kids. But I recommend always trying to use simple words and sentence structure if you can.

I recommend collaborating with your executive team to first create "umbrella" positioning/messaging that covers your entire product line. Then, the product-line product marketers + product managers can create their own positioning/messaging for each new feature/product that aligns with the umbrella messaging. For the umbrella corporate messaging at Calendly, we use the popular Value Pillars / Differentiators method, but we tweak how the inventor might have envisioned it to sound natural in our culture or not awkward in a call with a big customer (one place I like to test positioning/messaging). Value Pillars: When your biggest customers are considering the category of product you offer — competitors, your company, or sticking with the status quo — what four things are they generally looking for? "When we've spoken to our customers, they've told us they look for": Value Pillar 1 - Increase Efficiency Value Pillar 2 - Increase Revenue Value Pillar 3 - Reduce Costs Value Pillar 4 - Be Secure Differentiation or "Why Your Company Instead of the Competition": When your biggest customers choose you over the competition to meet the needs associated with those value pillars, what are the distinct reasons they choose you (that your competitors can't address in total)? Differentiation Point 1 - Artificial Intelligence Diff. Point 2 - Artificial Intelligence Diff. Point 3 - Artificial Intelligence Diff. Point 4 - Just joking :) You absolutely need executive involvement in the above exercise, and you need to test the experiment with customers. Or it won't stick. And don't be surprised if it evolves and morphs every year (or more!).