OpenAI's Oliver Hedborg: Take on post-sales without doing it all

Many SEs prefer pre-sales to post-sales. But with AI and usage-based pricing, revenue needs adoption, so more SEs are asked to do both. Is this the end of the pre-sales-only SE?Oliver Hedborg has worked on both sides of the fence. He did pure pre-sales at Slack, and roles that blended both at Microsoft and Figma.Today he's an Applied AI Architect at OpenAI. He's the technical lead across a focused set of digital-native customers, covering everything from discovery and pilots through to success plans and adoption.In our conversation, we get into:Why proactivity, rather than technical depth, is the biggest change going from pre-sales to post-salesWhy knowing when to bring in experts beats knowing everything, and the early-career mistake that taught himHow to start building post-sales skills in your current role, and use them to stand out in interviewsIf you're wondering how much post-sales work is in your future, this one's for you.Lastly, the pre-sales landscape is changing fast but you don't need to navigate it alone. My free Field Guide brings together insights from over 20 guests at companies like Anthropic, OpenAI and Microsoft to answer some of the biggest career questions being asked right now.Get your free copy here: https://chrisjamesclark.co.uk/insights?utm_source=podcast&utm_medium=description&utm_campaign=field-guide

FDE is the hottest job in tech, and lots of SEs are thinking about a move. But the role varies a lot between companies, and there are other roles SEs might be overlooking, particularly the Deployment Strategist.Rosemary has worked in incident management, technical account management and solutions engineering. She’s since made the jump to FDE at Lorikeet, a Series A start-up building an AI concierge for customer support.There she covers the full customer lifecycle, from discovery and scoped pilots through to taking customers live and shipping production code.In our conversation, we get into:Why you should stress-test what the FDE role looks like day to day before making the moveWhy the Forward Deployed Product Manager (or Deployment Strategist) role deserves a look tooAnd last, but not least, how to decide which role is right for your next moveIf you’re deciding whether FDE is your next move, this one’s for you.Lastly, the pre-sales landscape is changing fast but you don't need to navigate it alone. My free Field Guide brings together insights from over 20 guests at companies like Anthropic, OpenAI and Microsoft to answer some of the biggest career questions being asked right now.Get your free copy here: https://chrisjamesclark.co.uk/insights?utm_source=podcast&utm_medium=description&utm_campaign=field-guide

Most SEs will happily spend hours building a demo. Ask them to build a personal brand, and they cringe. But in today’s crowded job market, it can be one of the most rewarding things you invest in.Ryan and Sameer, hosts of the Diary of a Sales Engineer podcast, are testament to that. Their work on the show, as well as on LinkedIn, helped them both land roles, at Glean and Homerun Presales.Today they have thousands of followers and a top 10% podcast on Spotify, but it all came from humble beginnings, with a batch of memes made at an airport and months of Sameer nudging Ryan to get started.In our conversation, we get into topics like:Why building your brand inside your company is a great place to startHow to use AI without losing your authenticityHow keeping a bank of ideas makes it easier to post consistentlyIf you’re looking for practical advice on how to build your personal brand, this one’s for you.

Lots of SEs are considering a move into sales. Chapman Swaine did the reverse, twice.At Slack, he went from enterprise sales to building out the value consulting team.Then he joined Ashby as its second sales hire, before building out the SE function from scratch.Today, he works on special projects across Ashby’s GTM org, reporting directly into the VP of Sales.Every move in his zig-zag career has been intentional, rooted in his values and what he wanted from his career.In our conversation, we get into:Why time spent selling builds skills you can’t fakeHow to handle your ego when you step from leadership back into an IC roleHow he earned the right to shape his current role, and why company stage mattersIf you're weighing up a lateral move in GTM, this one's for you.

Do you like the sound of new tech, a bigger scope and more equity upside? If so, you’ll want to hear how to land an SE role at a start-up.Arvi Carkanji, CEO and Founder of Elite Talent Recruiting, has spent the last three years helping candidates do exactly that, at start-ups ranging from seed through to Series C.She has a great read on the market, including what hiring managers look for and what disqualifies candidates at different stages.In our conversation, we get into:The number one reason candidates get rejectedHow to prove you’re start-up ready from a big companyThe outreach step fewer than 10% of candidates takeIf you’ve been eyeing a move to a start-up, this one’s for you.

What if you could turn a side project you love into your full-time role? Hee Jin’s done it not once, but twice, most recently as an SE at OpenAI.It all started with a holiday in Korea, where she offered to meet local customers. That led to helping US colleagues with their Korean accounts and, eventually, a formal rotation.Since then, Hee Jin's helped OpenAI launch in Korea, Australia, India and Brazil, in a role that has kept her customer-facing throughout.In our conversation, we get into:How to avoid ending up with two jobs, by being honest with your manager about what needs to come off your plateWhy you can't be precious about your work when building something new, as much of it will end up being thrown awayAnd last, but not least, why demos matter more than ever at AI-native companies, where so many of the use cases are still being definedIf you've got a side project you'd love to turn into your day job, this one's for you.

The move from pre-sales to sales doesn’t have to be a one-way door, and Eric’s career path is a great example of that.He got his start in go-to-market as a Solutions Architect, after being headhunted by the vendor of a product he'd implemented internally.Since then, he's moved back and forth between the two sides. He tried his hand as an AE, returned to pre-sales at Slack, then led the SE team at Coda before becoming its Head of Sales.What surprised Eric about carrying a quota, and why having his leader's backing mattered when he moved into salesHow Sierra's outcome-based pricing changes the way customers evaluate the product, and why a great demo still mattersAnd last, but not least, how Sierra's SEs work with its Agent Software Engineers, effectively FDEs, and why that team adds to the SE role rather than replacing itIf you're an SE weighing up a move into sales, this one's for you.

Deciding how much to specialise, and when, is one of the biggest choices in an SE's career. I think Richard Barrett’s approach is spot on.Richard has spent almost 17 years working with Microsoft's productivity and collaboration technologies, so you might think he's the archetypal specialist.And yet, alongside that consistency, he's done a real range of roles, from implementation to sales to pre-sales, across very different companies: a boutique SI, a global SI, and now a hyperscaler.In our conversation, we get into:Why it’s important to try different things out, particularly early on in your careerWhat carrying a number taught Richard and why he’d recommend it to other SEsHow a specialist SE role is different to being the only SE on an accountIf you're weighing up how deep to go versus how broad to stay, this one's for you.

After almost 12 years at Salesforce, Gavin Guinane felt disconnected from the tech, so he left leadership to become an IC again at Glean.Since then, he’s worked on some of the company’s largest and most complex deals, and has built out a local SE team which he now leads.In our conversation, we get into:Why prospects are increasingly demanding production-grade solutions in pre-salesWhat that means demoing, and the type of SE that Glean now hires forHow the whole account team is “shifting to the right” on technical skills and AI fluencyIf you’re looking to make the move from an established SaaS company to an AI-native start-up or scale-up, this one’s for you.

Few people know pre-sales better than Chris. He’s been an IC, a leader, the GM of PreSales Collective and is now Head of Community at Iris.Chris's current role combines evangelism, partnerships, voice of the customer and more. It’s not one you’ll find advertised, Chris crafted it himself.His advice to others looking to do the same? Focus on a problem to solve rather than a specific company or title.In our conversation, we get into:Why ICs can have more power to change things than managers doWhy buyers now arrive as prepared as you are (and what that means for demos)Why relationships and in-person matter more than everIf you like the sound of crafting a role based on a problem space that interests you, you'll want to hear how Chris has done it.