This episode’s guest is Patrick Donnelly, the top strategic enterprise AE at Nook. Patrick brings a founder’s mindset to the field, he originally wanted to be a rock star or a startup founder, but found his creative calling in enterprise sales instead.
Now three years in at Nooks, he has built the process, led the upmarket charge, and stayed at the top by doing the same things that got him there. Patrick shares a candid, practical playbook built on curiosity, humility, and the conviction that discovery is not a stage it is a lifestyle.
What We Covered
[00:00:32] — Patrick’s top 3 contributors to sales success: be a partner to the bigger picture, have humility, hate to lose
[00:04:00] — The painful loss that taught Patrick never to move too fast: “I was trying to run the show when I was also every cast member in the show”
[00:08:02] — Why sales is a team sport at the highest level and how Patrick builds internal relationships that actually deliver
[00:10:30] — What Nooks does and who Patrick serves: AI platform for revenue teams, parallel dialing, AI coaching, sequencing, and agent workflows
[00:12:37] — How Patrick got to number one and what it takes to stay there in a fast-changing market
[00:15:00] — The origin story: from wanting to be a rock star and founder to becoming an intentional individual contributor — and why he keeps choosing the field over management
[00:18:58] — Curiosity as a lifelong superpower: “I just kept asking questions and I think that is a big part of why I’m where I’m at today”
[00:28:12] — Favorite win: how Patrick flipped a prospect who had already signed with a competitor using nothing but great discovery questions and genuine curiosity
[00:31:34] — “Discovery is a lifestyle, not a stage” — the quote that still holds up and why Patrick lives it
[00:33:20] — The early career loss: the CMO call that went sideways and what it taught him about over-preparation vs. presence
[00:46:04] — The K-shaped future of sales in the age of AI: why transactional sellers are in trouble and consultative ones will command a premium
[00:47:00] — What it is like to sell an AI product while working alongside AI thought leaders building the product in real time
[00:49:33] — Daily habits, morning routine, and how Patrick structures his day to stay sane in a fast-moving environment
[01:02:36] — What actually motivates Patrick: it is not the money — it is scaling revenue as a team and waking up every day for the person next to him
[01:07:18] — Soapbox moment: why money is not the best motivator and what Patrick would rather have than a spiff
[01:23:58] — Final advice: sit down, take quiet inventory, write down where you are and where you want to be, and start one intentional action a day
[01:25:19] — Silver bullet and favorite discovery question: “Where are we at and where are we trying to get to?” — and why starting with “we” changes everything
Quotes:
“Be a partner to the bigger picture. I don’t think anybody wants you to look at things super single-minded.” (00:00:50)
“No tasks are below you. You need to do what needs to be done to get the deal done.” (00:02:19)
“Hating to lose is probably the most powerful motivator. I haven’t found a better characteristic that creates more grit.” (00:03:10)
“I just kept asking questions and I think that is a big part of why I am where I am today.” (00:19:42)
“Discovery is a lifestyle, not a stage.” (00:31:52)
“If you are transactional and just doing the stuff that AI can do, you are in a whole lot of trouble. But if you are building trust and connecting all the complicated dots between two organizations, your value is so much higher.” (00:46:04)
“Money is not the best motivator. When you focus on money, you start to get away from the core of why you are actually in the role.” (01:07:37)
“I wake up every day to go and accomplish the goal with the person next to me. That is my strongest motivator.” (01:04:42)
“Where are we at and where are we trying to get to? That is the backbone of our partnership.” (01:27:12)
Resources Mentioned
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Nooks: AI platform for revenue teams (nooks.ai)
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Winning by Design: SPICED methodology (Situation, Pain, Impact, Critical Event, Decision)
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The Social Network: Patrick’s founding inspiration
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Sales Success Summit