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Three emails every founder should send

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Three emails every founder should send
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As fledgling startups struggle to find their footing, tackling high visibility metrics becomes the main focus. But in Collin’s experience, simply pursuing progress isn’t enough — an extra dose of discipline around communication provides the accountability that makes those goals more likely to materialize.

For Collin, that discipline lies in the three carefully constructed emails she has sent with an almost frightening regularity since Front’s earliest days: a weekly update to the entire company, a note to her direct reports and a monthly update to her investors. Read on for a closer look at how she crafts them and why they’ve been critical to Front’s results.

TO: All users SUBJECT: Revenue update

As with most startups, Front’s early days were marked by an obsession with revenue. “We had no excuse if those numbers weren’t trending upwards. So I started sending a daily email to the team to bring that metric front and center. It explained how much revenue we added yesterday, what we did well and what didn't go so well,” says Collin.

“I soon changed it to a weekly email as that was a better cadence, but ever since I’ve sent this email every single week to our entire company. It always has the same structure and is sent around the same time. And I haven’t missed a single one in the past four years,” she says.

“In the first few years, I wrote this completely on my own and it probably took me about an hour,” says Collin. “This may seem like a lot of time for an early-stage founder to spend on an internal note every single week, but it was vital. Amid all the growing pains, people knew exactly what success meant and evaluated everything they did through the lens of ‘How can we make that number go up?’”

SENT FOLDER: Below you'll find an early example of the weekly emails Collin sends to the Front team.

SENT FOLDER: Here’s a more recent, real-world (and lightly scrubbed) example of how Collin's weekly email template has evolved over time as Front has scaled.

Collin's weekly email as Front scaled

For Collin, there’s power — and pressure — from this kind of transparency. “Sharing the good, the bad and the ugly provides accountability and a forcing function. If you see numbers that are less than great, you’ll be tempted to make an excuse, point to another bright spot, or hold off on sharing until things improve,” she says. “Or you might shift gears and work on another project as a distraction. But you can’t afford to do that.”

Concentrate on a single metric. If it’s not improving, resist the easy comfort of letting up and focusing on something else. Stay the course.

TO: Direct reports SUBJECT: Goals for the week

As another exercise in accountability, a different email flies out of Collin’s inbox at 10am sharp every Monday morning: a note to her direct reports.

“I quickly run through all of my goals for the week. It’s not about telling your reports every single thing you’re going to do. Rather it's a chance to share what’s top-of-mind for you, which of course should be top-of-mind for them. More generally, it’s helpful to know how managers spend their time — often it’s a more of a black box instead. That’s also why I’ve made my calendar public and shared a deck that explains what I do all day as CEO of Front,” she says. This email habit also sets an example. “If I start to slip or if my weeks don’t ladder up to those big goals we’re focusing on, that sends the wrong message,” says Collin.

SENT FOLDER: Below is an example of Collin’s direct report email in action.

TO: Investors SUBJECT: Monthly update

Another one of Collin’s favorite tricks for bringing discipline to her communication is the update email she sends to Front’s investors. “I sent the same note every month for years, and only changed to quarterly after our Series B,” she says.

SENT FOLDER: Below you'll find an example of what Collin’s note to investors looks like in practice.

Collin’s faith in the power of demonstrating your focus to investors has only increased now that she’s on the other side of the table.