Technical leaders aren’t interested in your feature checklist. They have real problems to solve, budgets to protect, and teams to keep productive. Yet most vendors approach them with the same tired playbook: endless feature demos, AI buzzwords, and generic value propositions.
We recently sat down with Neal Bey, a fractional CTO with 25 years of engineering leadership experience across companies ranging from startups to multi-billion dollar enterprises like Paramount, HBO, and Gartner. His insights reveal a significant disconnect between how vendors think they should sell to technical buyers and what actually influences purchasing decisions.
The Feature Trap That Kills Deals
“I think the part that a lot of marketers might get wrong is that I might be focused on how many features you have in your toolset and whether you have AI or not,” Neal explains. “It’s really about understanding what are the problems that your customer has and trying to identify with those and seeing how your product correlates with that need.”
This disconnect isn’t limited to initial outreach. It extends throughout the entire sales process, creating friction that could easily be avoided with better preparation and targeting.
The reality: CTOs evaluate solutions based on outcomes, not capabilities. They want to understand how your product will solve their specific operational challenges, reduce risk, and deliver measurable results.
The Questions CTOs Actually Ask (That Sales Reps Can’t Answer)
When Neal evaluates vendors, he’s transparent about his priorities from the first meeting. But many sales teams aren’t prepared for the technical and strategic questions that matter most to buyers in this role.
“I will be asking, you know, what happens afterwards, once this deal ends? What would an exit—what would that look like?” Neal shares. “I definitely feel I’m very transparent about what my needs are. So I will ask those questions upfront.”
Key evaluation criteria technical buyers prioritize:
- Implementation complexity and timeline
- Vendor lock-in and exit strategies
- Total cost of ownership (not just licensing)
- Operational overhead for their teams
- Security and compliance implications
- Integration requirements with existing systems
These aren’t questions for the technical sales engineer later in the process. CTOs expect the initial sales conversation to address these concerns meaningfully.
Why Gated Content Fails with Technical Buyers
The traditional B2B playbook of gating everything behind lead capture forms creates immediate friction with technical buyers who are in research mode.
“If it’s a cold website visit, I would probably bounce,” Neal admits. “I need some level of confidence before I go through a gated channel.”
Technical buyers will engage with gated content only when they’ve already built confidence in your solution through other channels—peer recommendations, third-party reviews, or educational content that demonstrates genuine expertise.
What works instead:
- Technical documentation that’s freely accessible
- Case studies that detail implementation challenges and solutions
- Thought leadership that addresses industry-specific technical problems
- Tools, calculators, or assessments that provide immediate value
The AI Hype Problem
Every vendor claims to be “AI-powered” or “AI-first,” but this messaging often backfires with technical buyers who understand the technology’s current limitations.
“Stop selling me on how AI will solve everything,” Neal advises. “I think every solution out there right now is an AI-powered this, an AI-powered that. I personally think AI in certain cases will deliver, and in certain cases it’s a lot of hype.”
Technical leaders have been burned by overpromised technology before. They’re looking for vendors who can articulate specific use cases where AI adds measurable value, acknowledge current limitations, and provide clear implementation pathways.
How Technical Buyers Really Research Solutions
Neal’s research process reveals why traditional account-based marketing often misses the mark:
- Internal problem identification: The process starts with understanding what they’re trying to solve
- Peer consultation: Networking groups, Slack communities, and former colleagues provide initial recommendations
- Third-party validation: YouTube reviews, podcasts, and industry publications build confidence
- Vendor evaluation: Only after building initial confidence do they engage directly with vendors
“I’ve been leveraging more peer-centric networking groups, be it ones that are on Slack channels, in-person networking, things like that, to actually get secondary opinions, or actually primary opinions on what they recommend as a product,” Neal explains.
This means your content strategy should focus heavily on third-party channels where technical buyers are already gathering information, not just your owned channels.
The Multi-Stakeholder Challenge
Technical leaders rarely make purchasing decisions in isolation, but they’re often frustrated by vendors who treat all stakeholders the same way.
“Having a multi-stakeholder narrative is really important when you go into any meeting,” Neal emphasizes. “I think within each department, or operationally, if you’re not speaking to your customers’ problems and tailoring your answer to what everyone’s needs are, I think you are going to dig yourself into a hole.”
What this means for your sales approach:
- Technical buyers want implementation details, security implications, and operational impact
- Business stakeholders want ROI, competitive advantage, and strategic alignment
- Financial stakeholders want the total cost of ownership, pricing models, and budget predictability
Your sales team needs different conversation tracks for different stakeholder groups, not a one-size-fits-all presentation.
Building Confidence Before the First Meeting
Technical buyers expect vendors to do their homework before requesting a meeting. Neal looks for “advanced preparation” that demonstrates understanding of his specific challenges and evaluation criteria.
“I think showing that you’ve done your homework on what I’m looking for and correlating that, I think that is probably going to be a big driver for that initial meeting,” he explains.
Pre-meeting preparation should include:
- Research into their current technology stack and potential integration points
- Understanding of industry-specific challenges and regulatory requirements
- Preparation for technical questions about security, scalability, and performance
- Clear connection between their stated problems and your solution capabilities
The Personal Connection Factor
Despite the technical nature of these purchases, relationships are still significant. Neal emphasizes the importance of personal connections and face-to-face interactions.
“I think personal connection matters a lot. So like I said, I go through my peers to get recommendations. I think going to these networking events and presenting yourself, tech people are at a lot of these startup engagements, so I think there’s a lot you can do from in-person engagement to kind of get your foot in the door.”
This reinforces the importance of field marketing, industry events, and relationship-building activities that many B2B companies have deprioritized in favor of digital-only approaches.
Practical Steps for Marketing to Technical Buyers
Based on Neal’s insights, here’s how to adjust your approach:
Content strategy:
- Create freely accessible technical documentation
- Develop case studies that detail implementation challenges
- Produce educational content addressing specific technical problems
- Build thought leadership around industry-specific operational challenges
Sales enablement:
- Train sales teams on technical implementation questions
- Prepare stakeholder-specific conversation tracks
- Develop pre-meeting research templates
- Create technical validation tools and assessments
Channel strategy:
- Invest in peer-to-peer marketing channels
- Prioritize industry events and networking opportunities
- Build relationships with technical influencers and practitioners
- Develop partner and customer advocacy programs
Messaging framework:
- Lead with problem identification, not feature lists
- Address operational impact and implementation reality
- Acknowledge technology limitations honestly
- Focus on outcomes and measurable results
The Bottom Line
Technical buyers like CTOs are sophisticated evaluators who appreciate vendors that understand their challenges and speak to their priorities. The companies that win their business are those that move beyond feature-driven marketing to outcome-focused conversations that acknowledge the complexity of technical decisions.
Instead of trying to sell features, position yourself as problem solvers.
This article draws insights from our B2B In Flux podcast, where we interview real buyers about how they research, evaluate, and purchase B2B solutions. Listen to the full interview with Neal Bey for additional insights into technical buyer behavior.
Want to understand how other members of the buying committee make decisions? Subscribe to B2B In Flux for conversations with real buyers across different roles and industries.
