How Cybersmart grew to $5M ARR with $20M in funding.
How Cybersmart grew to $5M ARR with $20M in funding With Jamie Akhtar

How Cybersmart grew to $5M ARR with $20M in funding.

Jamie, CEO of Cybersmart, shares invaluable insights and strategies for B2B SaaS founders navigating the journey from startup to scale-up. From effective time management to fostering a supportive company culture, Jamie offers practical advice from his own experiences.

He has been transitioning from a hands-on founder to a visionary leader, which requires a shift in focus toward strategic initiatives and personal growth. Founders can steer their companies toward sustainable success by stepping back from day-to-day operations and honing in on high-level goals and vision-setting.

Embracing change, fostering a robust company culture, and focusing on personal development is essential for navigating the complexities of scaling a SaaS business. The evolution from being deeply involved in every aspect of the company to empowering the team and driving organizational success is a crucial phase in the founder’s journey.

Listen to the full episode here:

Key takeaways

  1. Clarity with OKRs: Establishing clear objectives and key results (OKRs) provides direction for both individuals and teams, guiding them towards common goals.
  2. Time Management: Effective time blocking, supported by an excellent assistant or chief of staff, enhances productivity and ensures focus on tasks that matter most for a SaaS founder.
  3. Identifying Unique Contributions: As a founder, determining what tasks only you can do is crucial. Delegating other responsibilities allows for a more strategic focus on driving the company forward.
  4. The “Deep Zone”: Setting aside dedicated time, like a “deep zone” day, facilitates focused thinking and ideation, leading to more impactful outcomes.
  5. Embracing Creativity: Recognizing when you’re in a creative zone and aligning tasks accordingly optimizes productivity and idea generation.
  6. Value of Idea Banks: Recording ideas as they arise, then revisiting them during dedicated time blocks, helps prioritize and refine concepts effectively.
  7. Importance of Information Flow: Streamlining how information is communicated and decisions are made within teams enhances efficiency and fosters collaboration.
  8. Culture Investment: Overinvesting in company culture is key to attracting and retaining talent, driving change management, and maintaining a shared sense of purpose.
  9. Personal Focus: Founders must resist the temptation to be involved in every detail and instead focus on strategic planning and decision-making to propel the company forward.
  10. Perseverance: Success in entrepreneurship requires resilience and determination. Embracing setbacks as opportunities for growth and staying committed to the journey is paramount.

Full recording:

Key Timecodes

  • Jamie’s Background and Entrepreneurial Journey (00:37)
  • Goals and Motivation (01:46)?
  • Company Overview and Metrics (02:28)?
  • Funding and Investor Relationships (03:18)?
  • Product Market Fit and Customer Feedback (05:11)
  • Go-to-Market Strategy and Channel Partnerships (12:27)
  • Company Challenges and People Management (16:37)
  • Personal Development and Time Management (30:26)
  • Advice for SaaS Founders at Different Stages (35:41)
  • Jamie’s Advice on Leadership and Planning (39:38)
  • Encouragement for SaaS Founders (40:06)
  • Stay Quivered – Perseverance and Adaptability (40:57)




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