Why Communications Deserves a Seat on the Exec Team: Hard‑Won Lessons from Square

Sunlit modern boardroom with a long conference table, leather executive chairs, and a wall display labeled COMMS with strategy icons, prepared for a communications meeting with microphones and notepads.

Communications isn’t a PR afterthought — it’s a strategic lever that shapes product perception, credibility, and go-to-market outcomes. When I look at the companies that out-execute their peers, they elevate comms to the executive level, align it tightly with product strategy, and treat it as a system — internal and external — not a series of press moments. That’s the lens I brought to a deep dive on startup communications with one of the sharpest operators in the field.

After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley’s School of Law, Aaron now runs Background Partners, a communications consulting firm.

In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on:

Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. I’ve seen comms drive strategic clarity across product, GTM, and people operations — and when it reports into the CEO alongside product and revenue, you get tighter narratives and faster decisions. Early-stage founders often think an agency will manufacture momentum; in reality, founder-led storytelling, disciplined messaging, and consistent execution are far more effective (and cost-efficient) than outsourcing too early.

The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. In the zero-to-one phase, comms should align the company around a sharp narrative, build trust with early users and talent, and reduce confusion in the market. Media coverage can be a credibility accelerant, but it’s rarely a dependable pipeline channel. Treat it like air cover for your product-led or founder-led GTM, not a replacement for it.

A 3-question framework for simplifying your company message early on. The most resilient narratives fit on a single slide and answer three things crisply: What problem do we solve? Why now? Why us? I map this directly to product positioning and roadmap priorities so every launch, customer story, and executive communication reinforces the same core promise.

How to prep for interviews and deal with difficult lines of questioning. Great media training looks a lot like great product reviews: anticipate the hard questions, practice concise answers, and bridge back to your core message without dodging. I keep a living Q&A doc, run red-team drills with my staff, and record mock interviews to tighten delivery, tone, and body language. When challenged, acknowledge, answer, and anchor — it earns credibility.

How to think about commenting on events in the news, or message layoffs to the team. Not every headline requires your voice; when you do comment, ensure it’s authentic, relevant to your mission, and aligned with your stakeholders. For sensitive internal communications — especially layoffs — specificity, empathy, and accountability matter most. Explain the why, the what, and the what’s next, and ensure managers are equipped to support their teams in real time.

Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen. The explosion of owned channels, the speed of social, and the blurring of internal and external narratives mean your messaging framework must be simple, repeatable, and durable across audiences — customers, candidates, investors, and employees.

We also recommend checking out his two excellent Medium posts:

What’s Your Hour in ‘Silicon Valley Time’?

No, you don’t need to hire an agency

You can follow Aaron on Twitter at @zamosta.


Inspired by this post on First Round.


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Why should communications be elevated to the executive level?

Communications is a strategic lever that shapes product perception, credibility, and go-to-market outcomes. The most successful companies treat comms as a system aligned with product strategy rather than a series of press moments.

Why shouldn’t early-stage founders rush to hire PR agencies?

Founders shouldn’t rush to hire PR agencies. Founder-led storytelling, disciplined messaging, and consistent execution are more effective and cost-efficient than outsourcing too early.

What are the jobs-to-be-done of the comms function in the early days?

The jobs-to-be-done of the comms function in the early days are to align the company around a sharp narrative, build trust with early users and talent, and reduce confusion in the market. Media coverage can be a credibility accelerant, but it’s rarely a dependable pipeline channel.

What is the 3-question framework for simplifying your company message?

The three questions are: What problem do we solve? Why now? Why us? The framework maps to product positioning and roadmap priorities so every launch reinforces the same core promise.

How should you prep for interviews and handle difficult lines of questioning?

Great media training resembles great product reviews: anticipate the hard questions, practice concise answers, and bridge back to your core message without dodging. I keep a living Q&A doc, run red-team drills with my staff, and record mock interviews to tighten delivery, tone, and body language.

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