Eps 31: 2025 Wrapped

How Sales Engineers Handle Difficult Prospects Without Losing the Deal

In Episode 36 of Diary of a Sales Engineer, Ryan and Sameer discuss how sales engineers can handle difficult prospects, skeptical buyers, technical roadblocks, and prickly internal stakeholders. They break down the difference between buyers who have been burned before, people who create roadblocks, and stakeholders who simply show up in a bad mood. The episode covers audience management, technical objections, InfoSec and architecture conversations, follow-up discipline, internal relationships with product and engineering, and how SEs can stay calm while protecting deal momentum.

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

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]

If Your SE Never Says No, You Don't Have a Partner

Ryan's LinkedIn post went viral: "If your SE has never told you no, you don't have a partner. You have an order taker." In Episode 33, Ryan and Sameer turn that into a full playbook for saying no with confidence. They cover how to shift your identity from technical resource to strategic partner, how to negotiate with your AE rather than just blocking ideas, how to use curiosity to give hard feedback without creating conflict, and why knowing when to kill a deal is just as important as knowing how to close one. Packed with tactical, real-world advice for SEs at every stage of their career. Don't let your ego get in the way of success.

Eps 32: GTMshift with James Kaikis

Sales engineering career advice and go-to-market strategy with James Kaikis, co-founder of Pre-Sales Collective, founder of GTM Shift, and co-founder of Solution Exec and AI Sales Studio. The predictable revenue model that defined B2B SaaS for the last decade is breaking down. AI-first companies are collapsing the traditional sales cycle. Roles are merging. Swim lanes are blurring. And sales engineers are sitting in the best position to capitalize on all of it. James shares the full story behind his exit from Pre-Sales Collective, what he learned running revenue as a CRO at Testbox, and why he came back to entrepreneurship to build three businesses: GTM Shift (consulting and events for go-to-market leaders), AI Sales Studio (AI proficiency training for GTM teams), and Solution Exec (a private network for senior solutions executives). He also announces that he and Jeff Margolese are writing a book on solutions engineering. We get into the tactical stuff too. How to build a career roadmap from SE to CRO. Why lateral moves to account management or sales matter more than people realize. How to prepare for the convergence of SE, AE, CS, and professional services roles. And why the SEs who treat themselves as students of the game will be the ones who thrive in the next era of B2B. Ryan also shares his prediction on the emergence of the "account engineer" role, and we talk openly about work-life balance, setting boundaries, and being present at home while building a career in tech sales. This one is personal for us. James and the Pre-Sales Collective are the reason Ryan broke into sales engineering. 32 episodes later, here we are. If this episode hits home, send us a message. Those notes from listeners are the reason we do this.