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From: review@...
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Date: Tue, 23 Sep 2025 15:45:45 GMT
Subject: Why Sierra built a design partnership program on “hard mode”
To: [email protected]
Date: Tue, 23 Sep 2025 15:45:45 GMT
Subject: Why Sierra built a design partnership program on “hard mode”
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This week, Sierra's first go-to-market hire shares his playbook for building a truly impactful design partnership program from scratch.
The Hard Way Pays Off: Inside Sierra’s Design Partner Strategy [https://review.firstround.com/r/9f4efdc5?m=3bf082c0-d1c6-4f48-923f-fc779193d705]
https://review.firstround.com/r/57edf7a2?m=3bf082c0-d1c6-4f48-923f-fc779193d705
Most design partnerships are set up to be easy — friendlies giving feedback in an unstructured format on a product that’s nearly complete.
Logan Randolph, the first GTM hire at customer experience AI company Sierra, intentionally built the company’s design partnership to be hard. The approach was worth it: 100% of its design partners would convert to paying customers. “Completely orient your company around your partners’ success, because ultimately their success creates your success,” he says.
He took a contrarian approach to just about every aspect of the design partnership:
Instead of working with friendlies, he targeted strangers.
Sierra was founded by Bret Taylor (co-creator of Google Maps, Chairman of OpenAI and former co-CEO of Salesforce) and Clay Bavor (a product leader at Google for 18 years). It would’ve been easy to rely on their networks to find design partners. “It’s one thing to have close friends tell you it’s a great idea. But the views of strangers are not clouded by your existing relationship. So they hold you to a different standard,” says Randolph.
Instead of targeting smaller companies, he went after enterprises who weren’t “AI tourists” from day one.
Even though it’s more difficult to work with large companies, Randolph partnered with enterprises because there was a direct correlation between the size of the company and their problem. “If you have two CX managers and you ramp up to four during the holidays, that’s not a huge deal. But if you have a call center of 5,000 employees and have to ramp to 7,000, that’s really tough to manage,” he says. And no matter the size of the company, Randolph wanted partners who had real problems to solve that would meaningfully impact their businesses — not partners who were interested in “playing with AI.”
Instead of free feedback, he made it a paid, structured engagement.
“Both the timeboxed partnership window and the payment were commitments for the partner. They had skin in the game,” says Randolph. A significant-enough financial commitment — “10-20% total contract value feels right,” he says — helped disqualify AI tourists. He also established a strong timeline and clear expectations around what the partnership would require: strict launch deadlines, access to partner systems, weekly meetings, shared Slack channels and defined swimlanes. "We told partners upfront: ‘We'll give you dedicated engineers, direct access to our founders, and our cell phone numbers. But in return, we need real investment from you,’” he says.
In this essay, Randolph breaks down the exact steps he took to build Sierra’s design partnership program from scratch. Its impact can be felt in more than just the company’s 100% partner-to-customer conversion: “A true design partner program is not about early selling, it’s about building with your customers for the long term,” he says.
Thanks, as always, for reading and sharing,
-The Review Editors
Take me to The Review [https://review.firstround.com/r/153d910d?m=3bf082c0-d1c6-4f48-923f-fc779193d705]
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<span class="preheader" style="color: transparent; display: none; height: 0; max-height: 0; max-width: 0; opacity: 0; overflow: hidden; mso-hide: all; visibility: hidden; width: 0;">Sierra’s first GTM hire, breaks down every step of their playbook.</span>
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<p style="margin: 0 0 1.5em 0; line-height: 1.6em;"><em>This week, Sierra's first go-to-market hire shares his playbook for building a truly impactful design partnership program from scratch. </em></p><h2 id="the-hard-way-pays-off-inside-sierra%E2%80%99s-design-partner-strategy" style="margin-top: 0; font-family: -apple-system, BlinkMacSystemFont, Roboto, Helvetica, Arial, sans-serif; line-height: 1.11em; font-weight: 700; text-rendering: optimizeLegibility; margin: 1.5em 0 0.5em 0; font-size: 32px;"><a href="https://review.firstround.com/r/9f4efdc5?m=3bf082c0-d1c6-4f48-923f-fc779193d705" rel="noreferrer" style="overflow-wrap: anywhere; color: #62DCAD; text-decoration: underline;" target="_blank">The Hard Way Pays Off: Inside Sierra’s Design Partner Strategy</a></h2><div class="kg-card kg-image-card" style="margin: 0 0 1.5em; padding: 0;"><a href="https://review.firstround.com/r/57edf7a2?m=3bf082c0-d1c6-4f48-923f-fc779193d705" style="overflow-wrap: anywhere; color: #62DCAD; text-decoration: underline;" target="_blank"><img src="https://review.firstround.com/content/images/size/w1600/2025/09/Header-1.png" class="kg-image" alt loading="lazy" width="600" height="400" style="border: none; -ms-interpolation-mode: bicubic; max-width: 100%; display: block; margin: 0 auto; height: auto; width: auto;"></a></div><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">Most design partnerships are set up to be easy — friendlies giving feedback in an unstructured format on a product that’s nearly complete.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">Logan Randolph, the first GTM hire at customer experience AI company Sierra, intentionally built the company’s design partnership to be hard. The approach was worth it: 100% of its design partners would convert to paying customers. “Completely orient your company around your partners’ success, because ultimately their success creates your success,” he says.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">He took a contrarian approach to just about every aspect of the design partnership:</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;"><strong style="font-weight: 700;">Instead of working with friendlies, he targeted strangers.</strong></p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">Sierra was founded by Bret Taylor (co-creator of Google Maps, Chairman of OpenAI and former co-CEO of Salesforce) and Clay Bavor (a product leader at Google for 18 years). It would’ve been easy to rely on their networks to find design partners. “It’s one thing to have close friends tell you it’s a great idea. But the views of strangers are not clouded by your existing relationship. So they hold you to a different standard,” says Randolph.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;"><strong style="font-weight: 700;">Instead of targeting smaller companies, he went after enterprises who weren’t “AI tourists” from day one.</strong></p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">Even though it’s more difficult to work with large companies, Randolph partnered with enterprises because there was a direct correlation between the size of the company and their problem. “If you have two CX managers and you ramp up to four during the holidays, that’s not a huge deal. But if you have a call center of 5,000 employees and have to ramp to 7,000, that’s really tough to manage,” he says. And no matter the size of the company, Randolph wanted partners who had real problems to solve that would meaningfully impact their businesses — not partners who were interested in “playing with AI.”</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;"><strong style="font-weight: 700;">Instead of free feedback, he made it a paid, structured engagement.</strong></p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">“Both the timeboxed partnership window and the payment were commitments for the partner. They had skin in the game,” says Randolph. A significant-enough financial commitment — “10-20% total contract value feels right,” he says — helped disqualify AI tourists. He also established a strong timeline and clear expectations around what the partnership would require: strict launch deadlines, access to partner systems, weekly meetings, shared Slack channels and defined swimlanes. "We told partners upfront: ‘We'll give you dedicated engineers, direct access to our founders, and our cell phone numbers. But in return, we need real investment from you,’” he says.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">In this essay, Randolph breaks down the exact steps he took to build Sierra’s design partnership program from scratch. Its impact can be felt in more than just the company’s 100% partner-to-customer conversion: “A true design partner program is not about early selling, it’s about building with your customers for the long term,” he says.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;">Thanks, as always, for reading and sharing,<br><br><em>-The Review Editors</em></p><p style="margin: 0 0 1.5em 0; line-height: 1.6em;"></p><div class="btn btn-accent" style="box-sizing: border-box; width: 100%; display: table;"><table border="0" cellspacing="0" cellpadding="0" align="center" style="border-collapse: separate; mso-table-lspace: 0pt; mso-table-rspace: 0pt; width: auto;" width="auto"><tr><td align="center" style="font-size: 18px; vertical-align: top; color: #15212A; border-radius: 5px; text-align: center; font-family: -apple-system, BlinkMacSystemFont, Roboto, Helvetica, Arial, sans-serif; background-color: #2CC58A;" valign="top" bgcolor="#2CC58A"><a href="https://review.firstround.com/r/153d910d?m=3bf082c0-d1c6-4f48-923f-fc779193d705" style="overflow-wrap: anywhere; border: solid 1px #3498db; border-radius: 5px; box-sizing: border-box; cursor: pointer; display: inline-block; font-size: 14px; font-weight: bold; margin: 0; padding: 12px 25px; text-decoration: none; background-color: #2CC58A; border-color: #2CC58A; color: #FFFFFF;" target="_blank">Take me to The Review</a></td></tr></table></div><p style="margin: 0 0 1.5em 0; line-height: 1.6em;"></p><hr style="position: relative; display: block; width: 100%; margin: 3em 0; padding: 0; height: 1px; background-color: transparent; border: 0; border-top: 1px solid #e0e7eb;">
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