"What makes B2B thought leadership worth reading — and why does most of it get ignored?"

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is the gap between what we produce and what actually gets read. We publish a fair amount — white papers, reports, point-of-view pieces — and the engagement metrics are fine on paper, but I'm not confident the content is actually shaping how our target accounts think about us. The pressure I feel from the board is very short-cycle: what did this drive in pipeline? And that framing makes it genuinely hard to invest in content that's meant to build positioning over time. So we end up in this middle ground where pieces aren't pure demand gen but they're also not distinctive enough to actually move someone's thinking. The other thing I'm wrestling with is voice. A lot of what we put out sounds like it came from a committee — because it did. And I know from my agency years that the content that actually gets passed around, that someone forwards to a colleague, tends to have a specific person's perspective behind it. We haven't fully cracked how to do that at scale without it feeling forced.

What's the most important thing you need to understand or solve here?

For us, the core problem is that a lot of what gets labeled thought leadership is really just content marketing with a fancier name. We publish, our vendors publish, everyone publishes — and most of it sounds like it came from a committee, because it did. What I'm actually trying to solve is credibility at scale. We're in a space where our buyers — retail technology buyers, store ops leaders, finance — they're skeptical of vendor-produced content by default. So the question I'm wrestling with is how do you produce something that reads like it came from a real point of view, not a brand safety review, without putting so much on individual executives that it's not sustainable.

What does 'good' look like to you — and how far are you from that today?

Good thought leadership, to me, means content that actually changes how I think about a problem — or gives me a framework I can bring into a conversation with my board or my CEO. It's not just confirmation of what I already know dressed up with data. Where we are today? Probably 60% of the way there on what we produce internally. We've gotten better at grounding content in real customer language — pulling from sales calls, from NPS verbatims — but the honest gap is that a lot of what goes out still sounds like it came from a committee. The voice gets smoothed over in the approval process and by the time it publishes, it's lost whatever edge it started with.

What would change your perspective on this entirely?

That's a hard question to answer cleanly. I think what would genuinely shift my view is if I started seeing thought leadership that was built around a real point of view — not just "here are five trends" packaging, but an actual stance that a vendor or peer was willing to defend even if it cost them an audience. Right now most of what crosses my desk sounds like it came from a committee, and it probably did. The other thing that would move me is better proof that it connects to something downstream. I'm not asking for a direct attribution model — that's not realistic — but if I could see clearer signals that the content was actually shaping how buyers think before they enter a sales process, that would change how seriously I take it as a channel. Right now I'm largely taking it on faith.

What question are you not being asked that you wish someone would ask?

That's a fair question. I'd probably want someone to ask about the relationship between thought leadership and internal alignment — meaning, how much of what gets published externally is actually believed internally. In my experience, a lot of B2B content gets watered down because it has to survive legal, compliance, the CEO's office, sometimes the board. By the time it's approved, whatever edge it had is gone. So the real question isn't "why is thought leadership boring" — it's "whose job is it to protect the point of view through the approval process." That's a real organizational problem that doesn't get discussed enough.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is the gap between content that sounds credible and content that's actually useful when you're in the middle of a real decision. We're evaluating a couple of infrastructure vendors right now, and I've been going through their published material — white papers, blog posts, whatever — and most of it reads like it was written to win a Google ranking, not to actually help someone in my position think through a tradeoff. What I'm wrestling with is how to identify the signal faster. There's a lot of executive thought leadership that's technically competent-sounding but has no actual operational specificity. I want to know what the failure modes are, what the integration surface looks like, what other CTOs actually ran into — not a sanitized case study where everything worked out. The other piece is on our own side. We publish content too, and I'm genuinely uncertain whether what we put out clears that bar for our buyers. That's an open question for me.

What's the most important thing you need to understand or solve here?

The core thing I'm trying to figure out is what actually makes technical content worth the time to read versus what's just filling a content calendar. For us, the signal I care about is whether something changes how I think about a problem or gives me a concrete approach I hadn't considered — architecture decisions, vendor evaluation frameworks, security tradeoffs. If it doesn't do one of those things, it's background noise. The harder part is that most thought leadership in our space is written to reassure rather than to inform. It's optimized for the author's credibility, not the reader's problem. I'd rather have one piece that addresses a real tradeoff honestly than five that tell me cloud-native is the future.

What does 'good' look like to you — and how far are you from that today?

For us, "good" means content that actually changes how I think about a problem or gives me a framework I can take back to my team. Not "here are five trends to watch" — something with enough specificity that I can tell the author has actually been in the weeds on this. How far are we from that? Pretty far, in my experience of what's out there. The stuff that clears the bar tends to come from practitioners — engineers who became founders, CTOs who write about real architectural decisions they made — not from marketing teams trying to produce a certain volume of pieces per month. There's a quality-volume tension that most companies resolve the wrong way.

What would change your perspective on this entirely?

If I started seeing content that actually influenced a decision we made — where someone on my team forwarded something and said "hey, read this before we finalize the architecture call" — and it traced back to a vendor's thought leadership, that would shift my view pretty significantly. Right now I can't point to a single example of that happening. The other thing would be if a publication or author consistently got the technical specifics right. Not just the framing, but the actual tradeoffs — like "here's why you'd choose X over Y in a multi-tenant environment at your scale." That level of specificity would earn real attention from me. Most of what I see is written at a level that could apply to any company in any industry, which means it's not really useful to anyone in particular.

What question are you not being asked that you wish someone would ask?

What makes thought leadership actually useful in the context of a specific technical decision you're mid-process on? Not general "trends" content, but something that lands when you're actively evaluating, say, whether to build an internal auth layer or buy an identity provider. That's when I actually want to hear from someone who's been through that exact tradeoff — and that content is genuinely hard to find.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the main thing I'm wrestling with is the build-versus-buy question on content production. We're at a stage where leadership wants more thought leadership output — more bylines, more POVs, more presence in the conversations our buyers are having — but the quality bar is inconsistent when you scale it up fast. So you end up with a lot of material that sounds like it came from a committee, not from someone who actually has a perspective. The other piece is attribution. I can see engagement metrics, I can see someone read a piece or attended a webinar, but connecting that to pipeline in a way that holds up to scrutiny from our CFO is still genuinely hard. So there's always this tension between investing in content that builds credibility over time and showing near-term return on the spend.

What's the most important thing you need to understand or solve here?

The core problem for us is that we're producing content to support pipeline, and if the content doesn't actually move buyers through a decision, it's overhead. So the question I keep coming back to is: what does our audience actually read versus what do they skim or ignore entirely? We're a Series B, so we have real buying committees to address — not just a single champion — and most thought leadership I see doesn't account for that. It's written for a generic "VP of X" persona when the actual decision involves finance, security, ops, sometimes a board member. Getting content to land across that committee is genuinely hard to solve.

What does 'good' look like to you — and how far are you from that today?

For us, good thought leadership passes a pretty simple test: does it change how someone on my team or in our prospect base thinks about a problem? Not just validates what they already believe, but actually shifts something. That's a high bar and most content doesn't clear it. Where we are today — we produce a decent volume of content, some of it is genuinely useful, but I'd say maybe 20-30% of it meets that standard. The rest is table-stakes stuff that checks a box. Part of that is bandwidth, part of it is that we're still too internally focused — writing about what we think is interesting rather than what our buyers are actually wrestling with. I've been pushing us to do more customer call mining, using their actual language as the starting point, but we're not fully there yet.

What would change your perspective on this entirely?

That's a hard question to answer cleanly because I'd need to see evidence that thought leadership actually moves pipeline in a measurable way — not just engagement metrics or "brand lift" surveys. If I consistently saw content tied to shortened sales cycles or higher win rates against specific competitors, that would shift how I allocate resources toward it. Right now I treat most of it as a supporting signal, not a primary driver. The data in our environment doesn't justify treating it otherwise. The other thing that would change my view is if the category started producing content that actually reflected how practitioners talk — using the words buyers use in sales calls, not the words a content team invented. That gap is real, and when someone closes it, the content reads completely differently.

What question are you not being asked that you wish someone would ask?

That's a good question to end on. I'd probably want someone to ask about the internal dynamics that actually determine whether thought leadership gets resourced or killed. We spend a lot of time in this conversation talking about what makes content good or bad. But in most orgs, the real friction isn't the content quality — it's whether leadership will give marketing enough runway to build something that doesn't show immediate pipeline attribution. Brand equity and positioning take time, and if every content initiative is being measured on a 90-day lead gen cycle, you're going to get lowest-common-denominator stuff. Nobody asks about that tradeoff explicitly, but it's probably the biggest driver of why so much B2B thought leadership is mediocre.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is that there's so much content landing in my inbox and my feed, and I genuinely can't tell what's worth my time until I've already spent ten minutes on it. From a sales leadership perspective, what I actually want is something that helps me think about a real problem — pipeline coverage, comp plan design, how buyers are making decisions right now. But most of what gets labeled thought leadership is just someone positioning themselves or their company. The other thing I'm wrestling with is on my own team's behalf. We're trying to figure out what content actually moves deals forward versus what just gets LinkedIn likes from other vendors and our own employees. Those are very different outcomes and I'm not sure the content we're producing — or consuming — is optimized for the right one.

What's the most important thing you need to understand or solve here?

For me, the core question is whether the content actually helps my team close deals or move opportunities forward — or whether it's just something we're producing to say we're producing it. That's the filter I apply. Right now, marketing sends over a lot of content and I honestly don't know how much of it my reps are even using in active conversations. If thought leadership isn't showing up in the buying process — like a prospect referencing it, or a rep sharing it at the right stage — it's basically decorative. That's the problem I'd want to solve.

What does 'good' look like to you — and how far are you from that today?

Good thought leadership, for me, is content that answers something my team or I are actually wrestling with right now — pricing strategy shifts, how to structure comp plans when you're moving upmarket, how other sales orgs are handling longer buying cycles. Stuff that's specific enough to be actionable. Where we are today? Pretty far from that, honestly. Most of what lands in my inbox or feed is either too generic to do anything with, or it's clearly just a vendor trying to get me into a pipeline. The ratio of genuinely useful to "this is dressed-up marketing" is not great.

What would change your perspective on this entirely?

If someone could consistently show me a direct line between a specific piece of content and a deal closing — not just "this prospect engaged with our whitepaper at some point in a six-month sales cycle" — that would genuinely shift how I think about it. Right now the attribution story is always muddy, and that makes it hard to prioritize. The other thing that would move me is seeing a competitor win a deal partly because their thought leadership shaped how the buyer framed the problem before we even got in the room. That's happened once or twice where we found out late in the process that the prospect was already using someone else's framework. That stings, and it makes the ROI argument a lot more concrete.

What question are you not being asked that you wish someone would ask?

That's a good one. I think the question that doesn't come up enough is: "Who specifically is this piece of content actually written for?" Not the persona, not the ICP category — the actual person sitting in the chair making the decision or influencing it. Because so much thought leadership gets written for a general audience that doesn't really exist, and then everyone wonders why nobody engages with it. When I read something that clearly understands my specific situation — managing a sales team, defending my pipeline numbers, dealing with a comp plan change — I notice it immediately. That's the content that actually makes me forward something to a colleague.