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Stop asking “What’s your biggest pain point? ” in customer discovery
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From: review@...
To: [email protected]
Date: Tue, 10 Mar 2026 15:53:38 GMT
Subject: Stop asking “What’s your biggest pain point?” in customer discovery
To: [email protected]
Date: Tue, 10 Mar 2026 15:53:38 GMT
Subject: Stop asking “What’s your biggest pain point?” in customer discovery
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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;">The discovery question that uncovered a billion-dollar startup idea</span>
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<p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;"><em>This week, we’re back with another installment of our Paths to Product-Market Fit series with Serval, an AI startup taking a swing at a hundred-billion dollar ITSM incumbent.</em></p><h2 id="servals-path-to-product-market-fit-%E2%80%94-win-enterprise-buyers-by-treating-them-like-consumers" 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; color: #15212A;"><a href="https://email2.firstround.com/c/eJxUj0tq7DAQRVcjzdSUqvQpDTR48PA-9I1F7Haw1R3I6kOaTDK8lwOHU2PO2hnZovaetGXQVrY9jU2NGl3IQLUGTpC5A4Bu2bfg5Bo5l86JKbnSNAaDLnXoWfdUuQSLckQEdEAatLVEeKPUgklcS2FrE1VhoI_zmufxuNdbOXa5xXXOj0vQP4GLwOVsz9E-b3-pn1_gkotvrnEQtOyC_lPuwFhAVV2cMt2wCkhd9eJ90IGqByvP-DVPYWAbaT_uL-WMb-txTfVKljPmx_b-O54RvwMAAP__KghVfA" rel="noreferrer" style="overflow-wrap: anywhere; color: #62DCAD; text-decoration: underline;" target="_blank">Serval's Path to Product-Market Fit — Win Enterprise Buyers by Treating Them Like Consumers</a></h2><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">When hunting for startup ideas, <strong style="font-weight: 700;">Jake Stauch</strong> opened with the textbook discovery question: “What’s your biggest pain point?” It got him nowhere.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">He’d had dozens of conversations with IT buyers, a persona he’d spent a lot of time with as a product leader at security platform <strong style="font-weight: 700;">Verkada</strong> and wanted to build for at his new startup.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">“Nowadays people have mostly solved the problems they're aware of. They've already got some tool in place,” says Stauch. “I did a lot of interviews where I’d ask, ‘What keeps you up at night?’ And I just didn’t hear anything very interesting.”</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">So he swapped in a new question: “<strong style="font-weight: 700;">If you could hire somebody today to sit next to you and do your work for you, what would you have them do</strong>?”</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">“When you frame the question as, ‘Hey, if you had somebody else here to help you, what’s the work that you'd give them?’ That's a nonjudgmental way of asking for pain points because you're saying, ‘What would you push over to this new person?’” says Stauch. “That way, they can be much more free to say, ‘I don't like to do these things or I am doing a lot of this and I think somebody else could do it for me instead.’”</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">The answers to that question sparked the idea for <strong style="font-weight: 700;">Serval</strong>, an AI platform that automates help desk requests and other IT workflows.</p><p style="margin: 0 0 1.5em 0; line-height: 1.6em; color: #15212A;">Stauch had these discovery conversations in April 2024, while still at his day job at Verkada. Serval’s now a billion-dollar startup that nabbed a $75M Series B just one month after announcing its Series A, with customers like Notion, Clay and Vercel.</p><div class="kg-card kg-image-card" style="margin: 0 0 1.5em; padding: 0;"><a href="https://email2.firstround.com/c/eJxUj81qLCEQRp9Gdw5Vlr8LFxcu_R5qaVrSPR26nQnk6UOGbLL8Pg4cDqdS0BnZEnpPaAOglW3PY1ODk4sFiDmGDCV0AMBWfItOrqk6wuydcw5CRofsCzXmgroHY7nJkTRoB4SA1hLpG-UWTQ5ca7A2EwsDfZzXPI_HnW_12OWW1jk_LkH_hF6EXs72HO3z9pf6-YVeAEiX2KugZRf0n0qHoCsoxuqU6SaoqKmrXr2PGIk9WHmmr3kKA9vI-3F_KWd6W49rqleynKk8tvff8Uz6OwAA__-JfVSk" style="overflow-wrap: anywhere; color: #62DCAD; text-decoration: underline;" target="_blank"><img src="https://review.firstround.com/content/images/size/w1600/2026/03/Serval-PMF-Timeline-1.jpg" class="kg-image" alt loading="lazy" width="600" height="362" 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; color: #15212A;">On The Review, Stauch shares his biggest PMF lessons two years into building, before the early decisions blur into a glossy timeline.</p><table class="kg-card kg-button-card" border="0" cellpadding="0" cellspacing="0" style="border-collapse: separate; mso-table-lspace: 0pt; mso-table-rspace: 0pt; width: 100%;" width="100%"><tbody><tr><td class="kg-card-spacing" style="font-family: -apple-system, BlinkMacSystemFont, Roboto, Helvetica, Arial, sans-serif; font-size: 18px; vertical-align: top; color: #15212A; padding: 0 0 1.5em 0;" valign="top"><table class="btn" border="0" cellspacing="0" cellpadding="0" align="center" style="border-collapse: separate; mso-table-lspace: 0pt; mso-table-rspace: 0pt; box-sizing: border-box; width: auto;" width="auto"><tbody><tr><td align="center" style="font-size: 18px; vertical-align: top; color: #15212A; padding: 8px 20px 9px; background-color: #62DCAD; border-radius: 6px; text-align: center; font-family: -apple-system, BlinkMacSystemFont, Roboto, Helvetica, Arial, sans-serif;" valign="top" bgcolor="#62DCAD"><a href="https://email2.firstround.com/c/eJxUj81qLCEQRp9Gdw6l5e_CxYVLv4dlaVrSPR26nQnk6UOGbLL8Pg4cDmci7a1sWYeA2kXQTra9jE0Nzj4RIHOKBSh2ANCNQkterjk0SiUE4mqg12opRpt0xEal9lC9HNmA8YAatHOI5oalJVsi1xqdK8jCQh_nNc_jcedbPXa55XXOj0vgP2EWYZazPUf7vP2lfn5hlsaGbAIvcNkF_kfqEE0Fxbp6ZbuNKhnsqtcQkk7IAZw889c8hYVtlP24v5Qzv63HNdUrWc5Mj-39dzyz-Q4AAP__QTJVeA" style="overflow-wrap: anywhere; box-sizing: border-box; color: #FFFFFF; cursor: pointer; display: inline-block; font-size: 15px; font-weight: 600; margin: 0; text-decoration: none;" target="_blank">Continue reading on The Review</a></td></tr></tbody></table></td></tr></tbody></table>
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This week, we’re back with another installment of our Paths to Product-Market Fit series with Serval, an AI startup taking a swing at a hundred-billion dollar ITSM incumbent.
Serval's Path to Product-Market Fit — Win Enterprise Buyers by Treating Them Like Consumers [https://email2.firstround.com/c/eJxUj0tq7DAQRVcjzdSUqvQpDTR48PA-9I1F7Haw1R3I6kOaTDK8lwOHU2PO2hnZovaetGXQVrY9jU2NGl3IQLUGTpC5A4Bu2bfg5Bo5l86JKbnSNAaDLnXoWfdUuQSLckQEdEAatLVEeKPUgklcS2FrE1VhoI_zmufxuNdbOXa5xXXOj0vQP4GLwOVsz9E-b3-pn1_gkotvrnEQtOyC_lPuwFhAVV2cMt2wCkhd9eJ90IGqByvP-DVPYWAbaT_uL-WMb-txTfVKljPmx_b-O54RvwMAAP__KghVfA]
When hunting for startup ideas, Jake Stauch opened with the textbook discovery question: “What’s your biggest pain point?” It got him nowhere.
He’d had dozens of conversations with IT buyers, a persona he’d spent a lot of time with as a product leader at security platform Verkada and wanted to build for at his new startup.
“Nowadays people have mostly solved the problems they're aware of. They've already got some tool in place,” says Stauch. “I did a lot of interviews where I’d ask, ‘What keeps you up at night?’ And I just didn’t hear anything very interesting.”
So he swapped in a new question: “If you could hire somebody today to sit next to you and do your work for you, what would you have them do?”
“When you frame the question as, ‘Hey, if you had somebody else here to help you, what’s the work that you'd give them?’ That's a nonjudgmental way of asking for pain points because you're saying, ‘What would you push over to this new person?’” says Stauch. “That way, they can be much more free to say, ‘I don't like to do these things or I am doing a lot of this and I think somebody else could do it for me instead.’”
The answers to that question sparked the idea for Serval, an AI platform that automates help desk requests and other IT workflows.
Stauch had these discovery conversations in April 2024, while still at his day job at Verkada. Serval’s now a billion-dollar startup that nabbed a $75M Series B just one month after announcing its Series A, with customers like Notion, Clay and Vercel.
https://email2.firstround.com/c/eJxUj81qLCEQRp9Gdw5Vlr8LFxcu_R5qaVrSPR26nQnk6UOGbLL8Pg4cDqdS0BnZEnpPaAOglW3PY1ODk4sFiDmGDCV0AMBWfItOrqk6wuydcw5CRofsCzXmgroHY7nJkTRoB4SA1hLpG-UWTQ5ca7A2EwsDfZzXPI_HnW_12OWW1jk_LkH_hF6EXs72HO3z9pf6-YVeAEiX2KugZRf0n0qHoCsoxuqU6SaoqKmrXr2PGIk9WHmmr3kKA9vI-3F_KWd6W49rqleynKk8tvff8Uz6OwAA__-JfVSk
On The Review, Stauch shares his biggest PMF lessons two years into building, before the early decisions blur into a glossy timeline.
Continue reading on The Review [https://email2.firstround.com/c/eJxUj81qLCEQRp9Gdw6l5e_CxYVLv4dlaVrSPR26nQnk6UOGbLL8Pg4cDmci7a1sWYeA2kXQTra9jE0Nzj4RIHOKBSh2ANCNQkterjk0SiUE4mqg12opRpt0xEal9lC9HNmA8YAatHOI5oalJVsi1xqdK8jCQh_nNc_jcedbPXa55XXOj0vgP2EWYZazPUf7vP2lfn5hlsaGbAIvcNkF_kfqEE0Fxbp6ZbuNKhnsqtcQkk7IAZw889c8hYVtlP24v5Qzv63HNdUrWc5Mj-39dzyz-Q4AAP__QTJVeA]
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Warning
Almost all the messages that arrive here are garbage! Resist the urge to click on any unexpected or questionable links.
It may happen that e-mail will claim to come from liamon.com, perhaps from some administrative role or process. There are no users with liamon.com addresses that should be sending anyone e-mail. There are no accounts to expire. There are no passwords to leak. These are certainly garbage messages. These are certainly phishing attempts in some messages.
Absolutely ignore those links!