"Let's kill the story!"

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I have been trying to better understand functions outside of design, product, and engineering at startups. While I haven’t worked outside of product and partnerships in my jobs, I have worked with teams across accounting, legal, and communications to do my job. I think I know enough to get interested enough to dive deeper into most of the “soft” functions.

One of them is communications. It feels like the most misunderstood and underappreciated function. That sentiment was echoed to me by Ceci Stallsmith, the Cofounder of the consulting firm Calyx, and Cristin Culver, VP of Communications at Notarize, in my recent chats with them. While those chats explored communications through a strategic lens, today’s chat has a more tactical lens.

I talked to Jack, the 12th employee and ex-head of communications at Robinhood, one of the last decade's most talked about consumer companies.

I got to ask him if comms people are ever in Olivia Pope style crisis communication war rooms. 

Sar: When we think about engineering, design, and sales, most people have a good grasp of what those functions do and why they matter. They are concrete and more quantifiable. When you think about comms, they are often like these touchy, feely functions that are much harder to appreciate. At the highest level, it's like comms tell the story of a company, right? I think everyone gets that. And in the most reductive sense, their job is to email journalists daily pitching stories. What's the right framework for, let's say, engineers, to think about what comms people do?

Jack: The communications team is responsible for distilling why your company exists to external audiences. What does your product do for me, and why is it superior to what is out there now? What does the world or specific industry look like if your company succeeds enormously? So distilling all of that down to the simplest parts and sharing those messages externally.

Sar: Isn’t this the founder’s job in the earliest days? Realistically, not many companies prioritize making a comms hire in their first 10-20 hires when they are still figuring out the product. There are exceptions when companies hit escape velocity very early on, and the founders would rather have someone else do comms. That doesn’t seem common, though.

Jack: Yes, the founder is ultimately the chief spokesperson. It’s their company, their baby. They are the most passionate about what they’ve set out to build, and harnessing that energy as a spokesperson can be super powerful. It can convince top talent to join their company, help them land a bigger valuation, and excite consumers about their products.

Of course, founders wear all hats, especially in the early stages. They’re the HR department, on every candidate “sell” call, and answer customer support tickets at 10:00 pm. Developing and executing a comms strategy is not a good use of a founder’s time. Most companies in the seed to series A stage don’t have someone squarely focused on comms. Depending on their space and exact business goals, I’d make the case they probably should invest in comms early and consider hiring a mid-level comms person in-house. They don’t need to hire a VP or a “head of,” but someone with five to seven years of experience to own external and internal comms until it makes sense to hire dedicated people for some of these areas.

Sar: If we just look at storytelling in an abstract sense, there are multiple functions at a company that tell the story to a different audience. Investor Relations are talking to shareholders, who roll up into the CFO, not the comms head. Then there's marketing, which is storytelling to your prospects and customers. There are internal comms that you mentioned. Is communication, as a function, just like a catchall for all of these things to grow into distinct areas as the company grows?

Jack: Right. “Communications” is a broad term. Startups need to tell a compelling story to so many different audiences. Your customers, employees, investors, regulators, partners, media, and potential candidates. And the comms team isn’t the only department talking to these audiences. Your recruiters talk to candidates, your managers meet with their direct reports, and your policy team is over in Washington. The comms team is uniquely positioned to help all of these internal stakeholders consistently communicate your company’s purpose, products, value, and business opportunity. Everyone should sing from the same song sheet.

Sar: Talk about this ongoing debate, Marketing versus Communications. Who should report to whom? How do those two functions interact with each other? It’s more common to see Marketing in the C-Suite.

Jack: Yep. There’s always been little tension between marketing and comms, which is silly. Historically, communications have reported into marketing in organizations with marketing and comms. I think this is changing though. Founders realize what a weapon comms can be and how important historically overlooked areas of comms like internal or employee communications are to a company’s productivity and cohesiveness. I always point to what are some of the biggest businesses and or best brands in the world, like Apple, Airbnb, and Meta, where they recognize comms as a critical function and have separated comms from marketing and appointed a Chief Communications Officer or SVP of Comms reporting into the CEO.

Sar: This brings me to the interactions between media and comms. It is common to see stories where the spokesperson refused to speak on the record. Can you talk about like on the record versus off the record? Being off the record doesn’t necessarily mean the comms people are not influencing the journalist. How does that work?

Jack: There are reasons why you may not want to or legally cannot comment on something publicly. Maybe there’s a complex and ongoing legal matter or a financial transaction. When that’s not the case, and you still see “X company declined to comment” in an article, it doesn’t mean that the comms person didn’t share information, context, or point to an external data source to help present their side of the story. It only means they didn’t provide an on-record statement attributed to the company or an exec.

Sar: I’m still wondering about the downsides to being on the record. You are still repping the company. How do you approach engagement on vs off the record during a bad news cycle? What are the incentives at play?

Jack: Every situation is different, especially when it comes to a sensitive issue, so it’s hard to generalize, but I’ll try. I think it’s always better to be front-footed and as transparent as possible. Sometimes that means making your CEO or another executive with subject matter expertise available for an interview or maybe sharing a company statement. There are various levels of engagement when you choose to go on the record. In terms of downsides, engaging on the record on a sensitive story could open the company or executive to further exposure and also, frankly, give the negative news cycle more credibility or airtime.

Sar: Walk me through what steps you take when you first hear a negative story is being written about your company.

Jack: Sure. Let’s say you receive an email from The Wall Street Journal, and they’re about to publish something negative like losing your biggest customer to a competitor. The first step is talking to internal stakeholders and wrapping your arms around the facts. What’s true, what’s not true? If something is true, is there any context, and is there anything that could position the company in a more positive light? What are some good facts that are relevant? Maybe you’re keeping some of the business, maybe you signed with two other impressive customers. So figuring out how to “cushion” the bad facts to help soften the blow is important.

And once your fact-finding mission is over, you have to determine if you will respond, and if so, what does that look like? Do we put our CEO or an exec forward for an interview? Do we email a statement over? Suppose the story in question is super damaging. In that case, you may want to take a more comprehensive approach and consider directly communicating with your customers through your channels, tapping any 3rd-party supporters, or briefing reporters at key outlets, among many other tactics. Oh, all of this happens within a few hours, and if you’re lucky, a few days.

Sar: What does the comms team do internally to prepare for any blowback internally or externally?

Jack: Once you’ve done everything you can to mitigate the story, you’ll want to give a heads up to key internal stakeholders, notifying them of the looming negative story or news cycle. Typically, this would be the rest of the executive team, if they aren’t already aware, and recruiting, legal and policy, marketing, sales, and if you’re a larger company or public, IR. It’s also incumbent on comms to arm each of these important teams with a messaging guide or fact sheet if needed, so there’s consistency in the response different audiences receive. I’m also a big proponent of telling your employees things - both good and bad - before they read about them online. It goes a long way in building trust with your team.

Sar: And is it internally considered a failure when you know something is coming and you can’t stop it?

Jack: No. We all watch movies and shows like Scandal, where people run around barking at their PR person to “kill the story” before it is published. This is only possible in the earliest stages of a story being worked on. For example, if Bloomberg comes to you and says, “Hey, we heard from one source that you’re partnering with Uber on something,” and your partnerships team has legitimately never met with them, then you can “kill” that story pretty quickly. On the other hand, if a damaging, well-sourced story comes out and you’ve already done everything you can to show your side, explain the steps you’re taking to remedy the situation, and so forth, then that story will probably still run. Hopefully, the work you did upfront to soften the blow and present your side will be highlighted in the article.

Sar: To what extent do comms teams play a role in generating glowing profiles on companies? Is it more like a journalist who likes what you do and decides to do a story, and all you can do is influence it?

Jack: It can be either. If a certain writer has been covering your company for a while, maybe they come to you with an idea for a larger feature where they can dive in more. Sometimes it’s the comms person who has a strong pulse on what’s coming down the pike and reaches out to a writer, offering them an exclusive look at a new product line you’re launching in five months and what it means for the industry.

Sar: There’s a principle in your world that comms people should be mindful about becoming a story themselves. They have to work behind the scenes. We are seeing some comms leaders break that norm these days, whether intentionally or unintentionally. Substack comes to mind. Do you have any takes on that trend?

Jack: Yeah. Lulu’s great. And in her role at Substack, she was a great example of a high-ranking communications leader being a strong champion and ardent defender of their offering and values in the media — and on Twitter, where most of the debates around Substack take place.

Traditionally, comms execs have worked behind the scenes. They help shine a light on the products, the business opportunity, the visionary founder, and the talent at the company. Now, we’re seeing faster news cycles, misinformation spreading across the internet like wildfire, and more critical looks at companies. I think this all calls for a different approach and one where companies have to be more front-footed, aggressive, and active in places where the news and sentiment change the fastest.

For some companies - not saying everyone should do this - it makes sense to have their top comms person be a visible face of the company. They are sort of perfectly positioned…they are media savvy and know what to say and what not to say because they created the messaging. Facebook PR did this well years ago with a few product comms people around the election integrity issues. Amazon’s former top comms guy Jay Carney was pretty outspoken during his tenure, and now we’re seeing people like Meta’s Nick Clegg as probably the most extreme example. I’m more likely to read and internalize a tweetstorm from Nick Clegg than I would one from a faceless @MetaNewsroom account.

Sar: This reminds me of many of the founders of DTC brands over the past decade. Their reputations and brands were effectively the company's reputation and brands. What are your thoughts on the company and founder brands getting deeply linked? What are some pros and cons?

Jack: I avoided reading those…I’ve read too many takedowns. Founders are powerful in that they can inspire consumers, candidates, and investors, but it’s bad business to make them the sole face of the company. Take Elon Musk, who people would probably cite as an example against my argument. Even unconfirmed news reports of him getting closer to buying Twitter sent Tesla’s stock down. Over the last year, we’ve seen high-profile founders running huge companies like Amazon, and Pinterest step down to pursue other endeavors. So whether a founder is stepping down after a great run or a scandal, you don’t want Wall Street or your employees thinking your best days are behind you.

Sar: Ultimately, it all boils down to people, correct? Like the spinning, how much a journalist trusts you, how much you trust the journalists, your read of specific people working at specific outlets on specific beats. All of these things boil down to judgment calls and trust, right?

Jack: Totally. Reporters are talking to people every day with different agendas and incentives. They can quickly suss out who is feeding them bullshit, a pissed-off former employee, an exec at a competing startup, an agency PR rep promoting their client, but it goes both ways. So if you’re the comms person, especially because your allegiances are as clear as day, you want to establish yourself as a credible and highly-informed person. And that pays dividends when shit hits the fan and certain facts are not on your side.

I’d also add that this goes both ways, though. Comms people are also trying to understand the writer’s goal with their story or if they have any preconceived notions. This can be derived from the writers’ initial inbound and line of questioning, their prior coverage of the space or your startup, and even what they’ve tweeted about your startup or competitors. You can glean a whole lot from tech media on Twitter. This plays into the calculus of whether you engage, who engages, and what is said.

Sar: You have been making angel investments. What do you wish early-stage founders asked you to do more in terms of help? What do you find yourself doing or saying too much?

Jack: Most founders I’ve helped back bring me in to help with launch moments, but in some cases where they don’t, I see missed opportunities, lackluster announcements, or confusing messaging. I’ve recently told founders to get on Twitter more often. It can be daunting if you’re introverted or don’t have any followers - but it’s where the tech conversations take place.

Sar: Let’s end our chat with a fun question. Let’s give shout-outs! Who are the up-and-coming comms leaders in our world of startups that we should pay attention to?

Jack: Alex Modiano (Strange Brew), Sarah Dresdow (Six Eastern), and Mo Osborne (Acorns)

Sar: Who are some must-reads for you?

Jack: Maureen Dowd (NYT Opinion), Matt Levine (Bloomberg Opinion), and Zoë Bernard (Freelance)

Sar: Which startups at Series A or B stage are doing communications really well?

Jack: Royal, Cann, and Incredible Health

I have also talked with a few journalists in the past :

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