Going upmarket: Chase results, not tactics

If you believe life is about the journey, not the destination, you might struggle with business outcomes too.

Philosophical quips aside, there’s wisdom in being results-oriented, especially when you’re trying to reach a new audience. Many SaaS companies run into this: after saturating the mid-management market, they look upmarket to sell to executives.

The first move? Update the website. Write blogs with more sophisticated language.

The result: Crickets. 😴

Why? Because reaching execs takes more than dressing up your existing content. You need to rethink where you show up and what you’re saying.

The marketing trap of momentum and familiarity

Mid-level managers care about hands-on tools and incremental improvements. They’re solving day-to-day problems: faster workflows, better processes, improved team performance. That’s why your messaging probably focuses on features — “make OAuth 25% faster,” “simplify cloud migration,” or “reduce dashboard build times by half.”

Executives care about large-scale, strategic outcomes. They’re not trying to “make OAuth faster.” They’re trying to reduce security risks company-wide. They’re not thinking about dashboards; they’re thinking about how to drive data-driven decision making at scale.

The problem is momentum. What worked to win mid-level buyers is familiar and comfortable, so you keep doing it, but with fancier language. That might look like:

• Swapping out “teams” for “enterprises.”

• Talking about “strategy” while still focusing on tactical improvements.

It’s a common trap that’s easy to fall into. But I’m here to help you not fall for it.

Solution: Talk to and learn about executives to find out what they want to hear from you. Leverage your customer relationships and ask them directly. Ask to speak to the higher-ups. Build relationships. Take them out to dinner and spend the whole night listening. Then start delivering personalized content directly via email to an audience of one. It’s not scalable, but you’re still listening and learning.

Executives don’t consume content the way their teams do

If you want to reach executives, you have to meet them where they are — and it’s probably not your blog.

They’re not searching for solutions on Google or skimming SEO articles. They consume content differently:

• LinkedIn: Scrolling for thought leadership and insights from their peers.

• Business publications: Reading outlets like Forbes, Harvard Business Review, and The Wall Street Journal.

• Consulting firms: Looking to Gartner, McKinsey, or Deloitte for reports and frameworks.

• Conferences: Listening to other leaders share their experiences and lessons learned.

If you’re not showing up in these places, you’re invisible to them.

Solution: Challenge yourself to reach execs through channels they use, and only via those channels. Don’t send them to your blog or your website. Stay on those channels and see how far you can develop that relationship. Keep them in their comfort zone while you get out of yours.

Speak to execs’ problems, not their teams’

Business leaders think big. They oversee massive programs with massive stakes. Instead of tactical questions like “how can we move data to the cloud faster?” they’re asking:

• “How do we modernize our infrastructure to support growth?”

• “How do we implement data governance to reduce compliance risks?”

• “How do we align our AI strategy with company priorities?”

They don’t care about features. They care about outcomes. If you’re not framing your solution as an answer to a business-level challenge, they won’t see its value.

Solution: Develop an entire content strategy solely around what you’ve learned so far. If it looks and smells like what you’re doing to reach mid-level managers, don’t do it. This is an exercise of constraints and developing new muscles. Don’t rely on success outside of the channels where you find execs. “Well, the piece resonated with directors who saw it” is not success.

Earn trust with real thought leadership

Executives don’t “Google it” when they have a problem. They turn to trusted sources — other executives, industry analysts, and business thought leaders.

They’re looking for:

• Case studies of similarly-sized companies that navigated the same challenges.

• Change management insights to ensure company-wide initiatives succeed.

• Strategic thought leadership that helps them connect the dots between problems and solutions.

This isn’t content you can squeeze into a 1,400-word SEO blog. It’s long-form, high-value material with real depth. It’s stories from other leaders, actionable advice from trusted experts, and data that backs up your claims.

If you’re trying to reach executives, that’s the kind of content you need to create.

Solution: Assuming you have some interesting thoughts about your industry, the broader market, or the tech you use, start writing about it. Make videos. Send personalized videos to people to start a conversation.

Sacrifice revenue for future opportunity

Reaching executives isn’t about dressing up what you already have. It’s about stepping into their world. You might have to actually stop what you were doing so you can start doing something new that will work for this new executive persona. This might *gasp* cost you money.

Show up on LinkedIn, business publications, and at conferences. Speak to their priorities: strategic outcomes, not tactical wins. Build trust with thought leadership that answers their biggest questions while showing how your solution fits into the bigger picture.

Executives are out there, looking for answers. But they won’t come to you if they haven’t already. You have to go to them.