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One-Off Sales Plays Every CTO (& Sales Team) Should Be Running

People assume that because I’m the CTO, I’m removed from sales.

It’s true that most of my day-to-day is spent on product development, systems, and building out AiSDR.

But sales pipeline isn’t a “sales problem”. It’s a company problem.

And there are specific moments where the technical cofounder or CTO is uniquely positioned to step in and run high-impact GTM plays.

However, these plays aren’t scalable: They can’t run forever. And they’re not meant to.

But they are timely, relevant, and extremely effective in short bursts. And every team should be running several of these one-off plays over the year.

Bad press targeting competitors

This is one of the easiest and highest leverage plays a person can run.

When a competitor hits the news for the wrong reasons (e.g. Rippling/Deel, Boeing), the market pays attention:

Customers get nervous
Prospects re-evaluate
Employees talk
Investors watch

That’s when your voice matters the most.

At AiSDR, we’ve done this a few times. I’ve stepped in during competitive drama to publish calm, factual breakdowns of what happened and what we stand for.

When the 11x situation happened, I was able to speak credibly about AiSDR’s product philosophy and technical standards without a word of badmouthing our competitor.

For instance, if I publish a LinkedIn post breaking down what happened, sharing context, and explaining our philosophy, we use AiSDR to automate outreach to anyone who engages with my post.

It’s the perfect combination of:

Founder-led thought leadership
Social proof
Real-time intent
Timely targeting
Competitive momentum

Every company in every industry can do this. All you need is someone willing to speak publicly and a GTM engine to follow up with people who engage.

Sports events (March Madness & beyond)

Major sports events create moments of universal attention where people who normally ignore messages may suddenly respond thanks to the message striking a cultural nerve.

The best example I’ve ever seen?

March Madness

I’ve seen and talked with teams who book huge pipeline with March Madness-themed campaigns. It’s the perfect blend of competitive spirit, nationwide relevance, school pride, and mass participation.

Not everyone loves team sports like baseball, basketball, or football.

But most support their university (or hate their rival).

Other good sports events are the Super Bowl, Stanley Cup, World Series, and College Football bowl season.

Summer 2026 presents another huge opportunity: the FIFA World Cup – a global event that takes place only once every four years.

If your messaging can successfully tap into the emotion, excitement, and rivalry of the moment, you have a chance of standing out. Plus, sports gives you permission to be fun and creative in your outreach.

Holiday seasons

Holiday campaigns work for one reason: People are ready for humor, creativity, and seasonal themes.

But most companies do this poorly. They slap a pumpkin on a template, make a generic “spook-tacular discount” joke, and call it a day.

The right way to do holiday plays is to actually anchor the message to the context of the holiday.

Santa cameos. Easter egg-style memes. Holiday-specific patterns tied to the product.

As CTO and cofounder, I can lean one of two ways:

Cofounder angle	Technical angle
Thoughtful commentary on the market, AI, or our philosophy, wrapped in the holiday’s theme. Like for Thanksgiving, I can share why I’m grateful to AI.	Product insights, roadmap previews, or engineering lessons, tied into the moment. For New Year’s, I might give a detailed glimpse into our direction for next year.

Here are some of the best opportunities in the next few months:

Halloween
Thanksgiving
Black Friday
Christmas
New Year

The trick (no pun intended) is to avoid going overboard and leaning too heavily into cliches that your messaging becomes cringe over creative.

Big news events

Reaching to major events around the world of one of a CTO’s most powerful outreach plays.

This is the moment where technical leadership becomes mission critical.

When something major happens in the industry, especially something technical in nature, a CTO’s voice can carry even more weight than the CEO’s.

Here are a few moments that come to mind:

Major security breach (if you sell security or compliance software)
Well-known outage like AWS or Cloudflare
Global-impact incident like the Crowdstrike outage
Regulatory shifts affecting data, AI, or cloud infrastructure
Breakthroughs in LLMs or AI models

As the CTO, I’m often the best person in the company to break down what happened, why it matters, and how you can protect yourself.

And this type of content performs well because it builds your authority while signaling your expertise. With the right angle and timing, you can generate plenty of qualified inbound.

Then you hand the leads to sales and let them run with it.

Because nothing builds pipeline like stepping into the conversation when it matters most.