Cybersecurity Sales Mastery | My Success Strategist
Cybersecurity Sales Training

Close More Cybersecurity Deals by Selling the Way Business Owners Actually Buy

Learn from 20 years of real-world experience — Fortune 500 to Main Street — taught by an industry veteran who's closed deals with FedEx, Target, American Express, and small businesses alike.

Enroll Now — $399 See What's Included

Katherine's cybersecurity sales experience includes deals with

FedEx · Best Buy · Target · CVS · American Express · Wayfair · HECO · SRP · SDGE

You know cybersecurity inside and out. But when it comes to closing that dental practice, law firm, or manufacturing company, prospects say "let me think about it," stall on budget, or go with someone else entirely.

Most cyber sales reps are brilliant technicians who never learned how business owners actually make buying decisions.

The good news: that's a learnable skill, not a personality trait. Small business owners buy peace of mind — this training teaches you how to offer it honestly.
Meet Your Instructor

Katherine "Kat" — 20 Years Selling Cybersecurity at Every Level

I ran two cybersecurity consulting and reseller firms for 20 years, personally closing deals with companies like FedEx, Target, and American Express. I've also sold to five-person shops and local family businesses.

Here's what that range taught me: the fundamentals of trust-based selling don't change based on company size — but how you apply them does. A Fortune 500 buyer has a procurement team and months to evaluate you. A small business owner is making a gut call, often alone, with no security background.

That's a different conversation. It requires more patience and more translation — not more pressure. This training teaches you how to have that conversation well.

  • 20 years running cybersecurity consulting & reseller firms
  • Sold into FedEx, Target, Best Buy, CVS
  • Closed enterprise security deals with American Express & Wayfair
  • Sold into major utilities: HECO, SRP, SDGE
  • Also sold directly to small businesses across every industry
  • Now teaching SMB-focused cybersecurity sales through My Success Strategist
The Curriculum

Three Trainings. One Sales Transformation.

Real-world sales experience, translated for the SMB market.

Training 01

30-Day SMB Sales Transformation

From tech talk to trust builder
  • Daily strategic lessons that rewire your sales approach
  • SMB-specific scripts that work on business owners, not IT managers
  • A trust-building sequence that turns skeptics into buyers
  • Conversation starters that make prospects lean in
Training 02

SMB Discovery Call Mastery

Uncover real pain in 30 minutes
  • A 20-minute vulnerability assessment framework
  • How to identify the true decision-maker
  • A risk-translation method — technical threats into business impact
  • How to justify premium rates with clarity, not pressure
BONUS
Training 03

AI-Enhanced SMB Sales Toolkit

Modern tools for traditional buyers
  • AI objection handling for "we're too small" scenarios
  • Automated follow-up sequences for SMB decision cycles
  • Faster, more thorough prospect research tools
  • Positioning yourself for the future of SMB cybersecurity

This Training Is Perfect If You...

  • Sell cybersecurity to small/mid-sized businesses (10–500 employees)
  • Own an MSP/MSSP serving the SMB market
  • Work for a VAR or reseller targeting local businesses
  • Want to feel confident charging fairly for real expertise
  • Know SMB owners need security but struggle to make the case clearly
  • Want practical, repeatable scripts — not vague advice

What You'll Walk Away With

Why This Is Different

Real Range, Not a Single Playbook

Most cybersecurity sales training comes from people who've only ever sold in one context. This training draws on experience selling at the highest levels of enterprise and directly to the smallest local businesses — and what that range teaches is that good selling, at any size, comes down to the same thing: understanding what the person across from you actually needs, and being honest about how you can help.

Results

What Students Are Saying

"Katherine taught me how to speak executive language. I went from $45K to $95K in eight months applying these frameworks to mid-market accounts."

Sarah M.
Cybersecurity Sales Rep

"The discovery call framework alone was worth the entire program. I used this approach with a retail client and closed our biggest deal ever."

Mike R.
MSP Owner
Enroll Today

Get Instant Access to All Three Trainings

Complete Sales System
$399 one-time
  • All 3 comprehensive training modules
  • Bonus AI-Enhanced Sales Toolkit
  • Industry certification upon completion
  • Optional 1:1 coaching session
  • Lifetime access to all materials
  • 30-day money-back guarantee
Enroll Now — Full Access
Help Shape What's Next

Tell Us What You Want to Learn Next

New training programs launch every quarter, built around what the cybersecurity sales community tells us it needs most.

Don't see exactly what you need? Submit a topic request below and join the mailing list to be first in line when new trainings release.

New training programs launch every quarter based on real feedback from the cybersecurity sales community. Join the mailing list above to stay informed on the release cycle — and help decide what gets built next.

Beyond Training

Custom Go-to-Market & Sales Coaching

Need more than a course? Through My Success Strategist, Katherine provides hands-on go-to-market strategy and sales coaching for independent cybersecurity companies ready to scale.

Go-to-Market Strategy

  • Market positioning & competitive analysis
  • Sales process optimization
  • Revenue growth planning
  • Team structure & hiring guidance

Sales Team Training & Coaching

  • Custom training built for your market
  • Individual & group coaching sessions
  • Sales process audits
  • Performance coaching for underperformers

Executive Coaching

  • Leadership development for technical founders
  • Sales leadership coaching
  • Strategic planning & execution
  • Sustainable growth & work-life balance