Diary of a Sales Engineer

How to Win Million Dollar Deals as a Sales Engineer

42 min · 11. maj 2026
episode How to Win Million Dollar Deals as a Sales Engineer cover

Description

Ryan Krueger and Sameer Sahay-Kausar are back with a deep dive on how sales engineers actually win the biggest deals of their careers. Whether you're working a $100K opportunity that's the largest your team has ever seen or a million dollar enterprise deal, the framework is the same and it starts with people, not technology. In this conversation, we get into how to identify who really has the power inside a buying committee, how to build a champion who sells for you when you're not in the room, and why pushing back on prospects can be the move that earns you the deal. Ryan shares why every big deal will give you "blisters" and what to do when your champion goes dark for three months. We also unpack the difference between hard savings and soft savings, and why the way most sales teams pitch ROI makes CFOs roll their eyes. If you're a sales engineer, AE, or anyone working complex enterprise deals and trying to figure out how to navigate the politics, the timing, and the approval gates that come with seven-figure contracts, this one is for you. Diary of a Sales Engineer is available on Spotify, YouTube, and Apple Podcasts. www.diaryofasalesengineer.com

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All episodes

37 episodes

episode RIP Traditional Presales artwork

RIP Traditional Presales

RIP traditional presales. Ryan Krueger and Sameer Sahay-Kausar sit down to map what is actually replacing it, and what the shift means for your career as a sales engineer. We get into why "pre-sales" is a label that no longer fits, the new roles taking shape (we coin a couple live, the account engineer and the forward deploy solution engineer), and how consumption-based pricing quietly rewires everything about how solutions engineers create value. We also dig into why SEs are already writing and shipping code to fix product gaps, the three dials every SE has to balance, and how leaders should be thinking about team building in this chaos. There is also a simple, freeing takeaway about switching industries and why saying "I don't know" makes you more credible, not less. If you are a sales engineer, solutions consultant, forward deployed engineer, or an SE leader trying to stay ahead of where the role is going, this one is for you. Diary of a Sales Engineer is available on Spotify, YouTube, and Apple Podcasts. www.diaryofasalesengineer.com

7. juli 202642 min
episode How to Win Million Dollar Deals as a Sales Engineer artwork

How to Win Million Dollar Deals as a Sales Engineer

Ryan Krueger and Sameer Sahay-Kausar are back with a deep dive on how sales engineers actually win the biggest deals of their careers. Whether you're working a $100K opportunity that's the largest your team has ever seen or a million dollar enterprise deal, the framework is the same and it starts with people, not technology. In this conversation, we get into how to identify who really has the power inside a buying committee, how to build a champion who sells for you when you're not in the room, and why pushing back on prospects can be the move that earns you the deal. Ryan shares why every big deal will give you "blisters" and what to do when your champion goes dark for three months. We also unpack the difference between hard savings and soft savings, and why the way most sales teams pitch ROI makes CFOs roll their eyes. If you're a sales engineer, AE, or anyone working complex enterprise deals and trying to figure out how to navigate the politics, the timing, and the approval gates that come with seven-figure contracts, this one is for you. Diary of a Sales Engineer is available on Spotify, YouTube, and Apple Podcasts. www.diaryofasalesengineer.com

11. maj 202642 min
episode From Sales Engineer to CEO | Jeff Wang, CEO of Windsurf artwork

From Sales Engineer to CEO | Jeff Wang, CEO of Windsurf

Jeff Wang is the CEO of Windsurf (now part of Cognition) and a former solutions engineer who rode the SE skill set all the way to the top of one of the most high-profile AI startups in the industry. He sits down with Ryan and Sameer to talk about what that journey actually looked like. You'll hear how Jeff built automation bots that saved his teams hundreds of hours, why he started blogging about AI to land his first role in the space, and how Windsurf structured an entirely new set of engineering roles that are reshaping how companies think about presales and post-sales. We also get into what it takes to close enterprise deals when nobody knows your name, what product market fit really feels like versus what people assume, and Jeff's advice for SEs who want to build something of their own. If you're thinking about your next career move in presales, or you're curious about how the sales engineering role is evolving in the age of AI agents and forward deployed teams, this one's for you. Diary of a Sales Engineer is available on Spotify, YouTube, and Apple Podcasts.www.diaryofasalesengineer.com [http://www.diaryofasalesengineer.com]

18. mar. 202657 min