Jim Cyb: Scaling Go-to-Market in Hypergrowth

Jim distills decades of experience into lessons on scaling sales, finding clarity in crowded markets, and thriving as a leader in hypergrowth environments.

How can companies break away from industry playbooks?

• Being different starts with listening to customers, not following industry playbooks.
• Duo Security broke away from fear-based security marketing by offering a simple and reassuring message: “You’re going to be okay.”
• Sales and marketing reinforced the brand by thinking outside the box in moments that mattered, like sending pizza and Red Bull to teams working through security breaches.
• Disruption worked because it happened across product, marketing, and sales, not just in one area.

“If companies are going to disrupt something, you have to be disruptive on many different factors. You can’t just do one thing different.”

How do you differentiate your company in a crowded market?
Differentiation is hardest when thousands of vendors are competing for attention.

• Jim implemented a “help, help, ask” approach, meaning you had to provide value twice before requesting a meeting.
• Go-to-market success came from consistently launching new “startup initiatives” across markets, geographies, and product lines.
• New initiatives only work when the entire company rallies behind them, not when they are side projects for one or two people

“The most important thing was to consistently launch startup initiatives inside the organization – new experiments in product, sales, or marketing that pushed the boundaries of how we went to market.”

What mindset helps companies succeed when entering new markets?

• Humility is essential when entering new markets. What works in one segment rarely carries over unchanged into another.
• Companies often fail by assuming success in SMB will translate directly to mid-market or enterprise.
• The right approach is to start fresh in each market, applying first-principles thinking to understand customers, buying processes, and personas.
• Relearning every market helps leaders avoid overconfidence and uncover the differences that really matter.

“Approach every new initiative with the same startup lens and vigor that got you there in the first place. Don’t underestimate how different new markets can be.”

How do leaders thrive personally during hypergrowth?

• In hypergrowth, every quarter feels like a new job. Leaders must constantly reset priorities.
• The best leaders stay self-aware, ask for feedback, and realign with company strategy regularly.
• Scaling requires hiring great people who know more than you in key areas and enabling them to succeed.
• Not every employee will thrive in scale mode; some will choose to return to startup mode, and great leaders help them land where they fit best.

“In startup land, every quarter it’s a new job. You have to reset, get alignment, and surround yourself with people smarter than you in key areas.”