Why monday.com's upsell email works | Email Teardown with Kirsten Ebey
I had the absolute pleasure of sitting down with project management pro Kirsten Ebey, founder of Path to Summit LLC, to unpack a beautifully structured email from monday.com, and talk about why it works so well.
Clean, calm, clear design
Because so Kirsten and many of her clients use monday.com she keeps a close eye on their emails. When this particular message hit her inbox, she immediately shared it with her team.
The first thing you notice is the white space. Generous spacing gives the content room to breathe - you literally feel the calm before you even process the headline. There’s no clutter, no heavy graphics, no colour overload.
Kirsten summed it up perfectly: “I can consume this in 10 seconds.” And that’s exactly what strong email design should do.
A powerful, emotionally intelligent header
The headline reads: “Lead with confidence, scale with control.”
It hits two key notes. First, it taps into emotion - confidence and control are universal motivators for founders, executives, and project leaders. Second, it speaks directly to decision-makers. This email promotes monday.com’s Enterprise plan, the highest-tier product. That audience isn’t looking for friendly chit-chat; they want reliability, capability, and authority.
Even the personalisation is confident. Instead of a “Hi Kirsten,” the email simply begins: “Kirsten.” Direct, clean, authoritative (without feeling cold).
Intentional product features
Further down, the email showcases four key feature blocks, each with an image, subheading, and a short description. The top feature? Permissions and control. According to Kirsten, this is the number-one source of confusion for monday.com users - and something her team is constantly asked about.
Then comes the security block. With organisations wrapping up strategic plans for the year, including cybersecurity initiatives, it’s a smart, timely reminder: “Did you finish this project? If not, we’ve got enterprise-grade security ready to go.”
This is product marketing done with awareness of customers’ real, current priorities.
The offer…
Here’s where it gets interesting! monday.com offered a sizeable discount, but only if you commit to a 24- or 36-month plan. Two- to three-year contracts are a big decision in a world where tech evolves at lightning speed. AI is transforming tools monthly - sometimes weekly.
So while the discount feels generous, it also locks the customer into a long-term relationship that benefits monday.com. Smart for them, potentially valuable for the right buyer, but definitely a commitment.
Rounded corners!
During our conversation, Kirsten and I ended up chatting about something that might seem small at first: rounded corners in email design. It’s easy to dismiss as “just aesthetics,” but there’s actually a little psychology behind it. Rounded shapes are easier for our brains to process than sharp-cornered rectangles, so content feels softer, more approachable, and less visually taxing. In other words, those subtle curves can make your emails feel a touch friendlier without shouting for attention.
I’ve been noticing this trend in inboxes for a while, and it’s even been highlighted in email design trend reports over the last couple of years. Kirsten and I agreed it’s fascinating to see how different teams weigh these little choices, from aesthetic appeal to readability to user comfort.
Bookmark emails you love. Start a folder and save anything that makes you think, “Ooh, that’s good.” It’s one of the fastest ways to develop your own email style.
Want your own (private!) email review? I can SHOW you what works, what doesn’t, and how you can make sure YOUR emails convert. I teardown your emails, so that you can build them up bigger and better - CLICK HERE!
