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Taylor Britton is an enterprise account executive at UiPath, where he hunts new logos in the Fortune 500 and Global 2000 and finished last year at 495% of his number. His patch runs through retail, consumer goods and discrete manufacturing, and the year was anchored by a deal worth 3.1 million in total contract value, paid three years up front, that he and his team closed in ten months rather than the two years it could have taken. He came to sales sideways. He was pre-med at Georgia Southern until a junior-year rethink, added a business minor in a semester and a half, and started in renewals at Veeam Software before moving into an outbound seat back when the job was still called an ISA. He reports to Thom Wright, a regional vice president at UiPath, a long-time listener of this show who has recruited off it.
Taylor opens with the three things he credits most, tenacity and grit, resourcefulness and authenticity, and accountability, then gets specific about the mechanics underneath them. He reads pain as a wave measured in frequency and magnitude, explains what made him put the chips in the middle of the table in a one-on-one last May, and walks through the one-line email that looked like the end of the deal. He is blunt about what has stopped working, including a buyer he met who takes 2,200 emails a day, and specific about what replaced it: warm paths, executive to executive and customer to customer. He makes the case for day 2 ready, the idea that contract signature is roughly the halfway mark and value does not begin until adoption does. Along the way there is the Birmingham meeting that went off the rails three sentences in, why customer knowledge beats product knowledge, why champions turn up in procurement, and a closing challenge to go find three customer stories you can tell as your own.
What We Covered:
[00:42] The top three things he credits for his success
[00:52] Tenacity and grit, resourcefulness and authenticity, accountability
[01:29] Walking through all three, and why people resist the change you are there to create
[06:45] Context: the role, UiPath, and a shout out to Thom Wright
[07:49] New logo hunter: Fortune 500s, Global 2000s, retail, CPG and discrete manufacturing
[09:32] What actually made up a 495% year
[10:06] The components of a good deal, and pain measured as a wave
[10:34] Chips in the middle of the table, and the one-on-one where he called it
[14:01] Every meaningful deal nearly dies two or three times
[14:27] The one-line email: no longer a priority for the business
[16:08] Origin story: pre-med at Georgia Southern, and the junior-year rethink
[16:18] Renewals at Veeam Software, an ISA seat, then owning the cycle
[18:41] Finding his sea legs, and controlling outputs through inputs
[20:25] What he would do differently: arm in arm, not kicking and screaming
[21:24] Walk through open doors, and why forcing it is quicksand
[22:58] It is software, and if they could have solved it they already would have
[23:40] The Birmingham meeting: expecting the CIO, meeting his generals
[27:57] Sales as leadership, between order taker and your baby is ugly
[30:07] What he is most proud of, and the player coach answer
[33:16] Selling past the close, and what it would take to be on your stage
[34:45] If the last item on your mutual plan is contract signature, stop
[34:46] Day 2 ready, and where value actually starts
[36:59] The hard part: a people game in a crowded market
[38:19] Why outbound is categorically different than it was eight months ago
[41:07] The buyer taking 2,200 emails a day
[41:56] What is working right now: warm paths, executive to executive
[43:59] Information diet, and reading his buyers rather than business books
[48:30] The one psychology book: Predictably Irrational
[50:02] The whole day, alarm to pillow, with the gym as the anchor
[52:41] Two roast chickens, and cooking things he has never cooked
[53:46] The stack he cannot work without
[55:54] An amalgamation of Challenger, Sandler and solution selling
[58:41] How he sources customer stories, and why renewal matters more than the sale
[1:02:52] Getting past the marketing slide and the two-page case study
[1:03:52] Motivation, and what changed once there was a family in the picture
[1:06:21] The show is not called Sales Shortcut Stories
[1:06:51] Ed Viesturs, and No Shortcuts to the Top
[1:08:59] The thing most enterprise sellers would think is crazy
[1:09:16] Why a rigid sales cycle guarantees nothing, and the power of no
[1:11:15] Deals go backwards, and most systems will not let them
[1:12:09] There is no such thing as a product that sells itself
[1:13:03] Advice for someone starting out: find the scar tissue
[1:15:22] Product knowledge or customer knowledge
[1:16:21] For anyone stuck: ask for help, and get an outside-in read
[1:18:52] The Sales Success Summit, October 12 and 13 in Austin
[1:20:12] Connecting the connectors, and who opens the door for you
[1:23:37] Nos are great, yes is even better
[1:24:13] Inheriting a territory, and talking to whoever held it before
[1:26:30] Katie Jane Bailey: discovery is a lifestyle, not a stage
[1:27:21] What he would want to learn from top sellers elsewhere
[1:29:54] Titles mean nothing, and champions come from anywhere, including procurement
[1:31:57] Internal referrals, and surfing the org
[1:33:05] Coach or champion, and knowing which one you have
[1:34:19] The challenge: three customer stories you can make your own
Quotes:
“You can do everything right, air quotes, everything right, and still, still lose.” (00:02:39)
“Pain is measured. It’s like a wave. It’s measured in both frequency and magnitude.” (00:10:18)
“It’s software. There’s nobody bleeding out in front of us. We’re not ER doctors.” (00:23:05)
“Never ever underestimate the human element of this job.” (00:26:17)
“Catching lightning in a bottle is not a strategy.” (00:32:21)
“Signing a contract just formally allows us to begin working together.” (00:35:01)
“A good customer story will beat any and every fact sheet.” (00:57:31)
“There is no such thing as the product sells itself.” (01:12:31)
“Nos are great.” (01:23:35)
“Yes is even better.” (01:23:38)
“In the enterprise game, like titles don’t mean anything. Like champions, influence, and authority come from anywhere.” (01:30:26)
Resources Mentioned:
Extreme Ownership by Jocko Willink and Leif Babin
Predictably Irrational by Dan Ariely
No Shortcuts to the Top by Ed Viesturs
Into Thin Air by Jon Krakauer
Episode 111: Katie Jane Bailey on a World Class Sales Team at Figma
2026 Sales Success Summit, October 12 and 13 in Austin
Connect with Taylor Britton on LinkedIn
Sales Success Stories is part of the Sales Success Media family hosted by Scott Ingram