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“There’s a 5% chance of a $5 million loss. Is it exactly right? No. But it’s way better than saying medium, because medium means nothing.”
Kenny sits down with Rob Black, Founder and CEO of Fractional CISO, to break down how to translate cyber risk into language executives actually act on: probability, dollars, tradeoffs, and clear acceptance instead of vague labels that disappear into a slide deck.
We also get into the “magic genie” myth of GRC tools, what vCISO looked like back in 2017, and the origin story behind Rob’s legendary wig videos.
Key takeaways:
Learn more about Rob Black here:
Learn more about FractionalCISO:
Learn more about Kenny:
Learn more about Paramify:
Federal compliance is having a moment. FedRAMP, FedRAMP 20x, CMMC, the whole alphabet soup is going mainstream, fast.
In this episode of The Paramify Podcast, we sit down with Justin Rende, Founder and CEO of Rhymetec, to talk about what’s actually changing, what’s still painfully hard, and why “compliance automation” only works if you stay obsessed with real risk.
Justin also shares his origin story (tech ➝ film festivals ➝ tech), how Rhymetec grew from early penetration tests into full vCISO and compliance programs, and the most New York lead gen strategy ever: biking around the city delivering Google Homes and handwritten notes to prospects.
If you’ve ever been promised an “easy button” for SOC 2, ISO, or FedRAMP, this one’s for you.
In this episode:
Why federal compliance is exploding (and why it’s not slowing down)
FedRAMP 20x and the pace of government innovation (yes, really)
The risk of “checkbox compliance” in a world of automation
How to set expectations with customers when security is never just one toggle
Bootstrapping, building recurring revenue, and staying flexible
Customer experience as the real differentiator (care scales better than you think)
Where to find Justin and Rhymetec:
Learn more about Paramify:
Chapters
0:00 Federal compliance is exploding (and getting mainstream)
“There’s this misconception in the marketplace that you need to be a coder to do GRC Engineering. You don’t. I don’t want people to be bogged down in scripting. I want them to be systems thinkers focusing on architecture and orchestration.”
Kenny and Mike sit down with the GOATed pioneer of GRC Engineering, Ayoub Fandi. In case you’ve been living under a rock, Ayoub is the Security Assurance Automation Team Lead at GitLab and the Founder of GRC Engineer.
This episode covers Ayoub’s wild pivot from middle school English teacher to sending 500 cold LinkedIn DMs to break into security. We dive into his first trip to Utah (discovery of "sugarcane fillets" and life-changing butter cake), why APIs are the “landlines” of the past, and how he sparked the movement behind the GRC Engineering Manifesto to give practitioners their own “Phoenix Project” moment for compliance.
Key Takeaways:
Learn more about Ayoub:
Learn more about Paramify:
Chapters
00:00 Intro — Utah, butter cake, and Ayoub's first time in the U.S.
Kenny and Mike sit down with Dixon Wright, Head of Delivery at Eden Data, for a grounded and insightful conversation on security, compliance, and building smarter systems.
They cover:
- Dixon’s journey from college football to leading security at Eden Data
- What it takes to actually deliver cybersecurity — not just sell it
- Why Eden Data joined the FedRAMP 20x pilot
- How compliance is evolving across commercial and federal sectors
- Why trust, transparency, and execution matter more than buzzwords
It’s one of the most real conversations we’ve had about what delivery actually looks like in the compliance world.
Chapters
Learn more about Eden Data:
Learn more about Dixon Wright:
Learn more about Paramify:
Learn more about Kenny:
"The AI age we're in is going to force startups to compete in the higher upper echelon of risk assurance."
Jack Rumsey Head of GRC at Swimlane explains why startups will no longer have the luxury of maturing later and how the AI era is pushing even early-stage teams into enterprise-grade security.
This episode covers why assurance needs to evolve, how 20X can level the playing field, why automation is changing everything about how companies prove trust, and Jack's brief era as "the richest fifth-year college student of all time."
Key Takeaways:
Chapters
Learn more about Jack Rumsey:
Chapters
Learn more about Jack Rumsey:
Security isn’t sexy. It’s laundry. You know you need to do it, but you’d rather have a tool do it for you.
Kenny Scott and Mike Schreiner from Paramify sit down with George Manuelian from RapidFort to talk about freeing the captives — the engineers buried in spreadsheets, patch tickets, and compliance chaos.
They cover:
Why security always seems at odds with progress
How automation can fix what boredom created
The giant washing machine for open source
Starting clean, staying clean, and why “7 million vulnerabilities” isn’t a vibe
FedRAMP, CMMC, and the art of not losing your mind in compliance
It’s the least boring conversation you’ll ever hear about vulnerabilities.
FedRAMP as we know it is changing. In this episode, Mike and Kenny sit down with Mike “Waffle” Craig, founder and CEO of Vanaheim Security and longtime cloud and cybersecurity leader, to unpack what FedRAMP 20x means for agencies and vendors across FedCiv and DoD. We get into compliance philosophy, how to define your boundary the right way, why sponsorship strategies matter, and where scalability will make or break 20x.
Mike Craig shares hard-won lessons from incident response, multi-cloud ATOs, and advising startups so they don’t burn six or seven figures chasing the wrong path.
What we cover:
• Why FedRAMP 20x signals the future of federal compliance
• Sponsorship realities, Ready pitfalls, and how small vendors survive
• Boundary, data flows, and “if you can’t draw it, you can’t secure it”
• Zero trust in practice and multi-zone risk profiles across stacks
• AI and LLM/RAG inside a FedRAMP world and change approval at scale
• JAB is gone, human variance is not, and how to navigate the psychology of yes
• CSFC as a model for defined stacks and what that could mean for AI patterns
• Practical diagramming tips and the surprising power of PowerPoint
• The “Waffle” origin story and a DoD “Beta Blocks” style experiment
Guest:
Learn more about Paramify:
Exploring FedRAMP 20x, GovRAMP, FISMA, or CMMC and want a faster path to audit-ready deliverables and ConMon at scale? Talk to Paramify. We help teams get compliant and stay compliant 90% faster at a quarter of the cost.
Timestamps / Chapters
“Once you’re in Hotel FedRAMP, you can’t leave.”
Jason Oksenhendler, Cybersecurity Director of FedRAMP®/GovRAMP at Baker Tilly x Moss Adams, sits down with Kenny and Isaac to talk about FedRAMP’s past, how 20x is shaping the future, and why nobody ever really checks out of Hotel FedRAMP.
👉 Key Takeaways:
• FedRAMP 20x was a “hand grenade” for everyone’s roadmap, and it’s already transforming compliance speed and evidence collection.
• Risk-first programs survive change — smart architecture and design decisions matter more than chasing checklists.
• Flexibility vs. rigor — 20X offers new freedom, but assessors must still enforce strong security.
• Collaboration wins — assessors and CSPs working together can turn impossible timelines into success.
Learn more about Jason:
https://www.linkedin.com/in/jason-oksenhendler/
Learn more about Baker Tilly x Moss Adams:
https://www.bakertilly.com/
https://www.mossadams.com/
Learn more about Kenny:
https://www.linkedin.com/in/kenny-g-scott/
Learn more about Isaac:
https://www.linkedin.com/in/isaacteuscher/
Learn more about Paramify:
https://www.paramify.com/
Timestamps:
00:00 – Moss Adams x Paramify team-up
01:00 – Less than two-week deadline
01:44 – Submitting against moving targets
02:24 – Nature of FedRAMP change
02:56 – Success despite chaos
03:07 – The reality check
03:13 – Official podcast kickoff
04:01 – Jason’s career origin story
05:40 – First FedRAMP assignment
11:43 – Co-creating the FedRAMP High Baseline
13:00 – Early FedRAMP pain
15:32 – “You could do a Seinfeld routine on this crap.”
17:30 – Culture shock of change
20:00 – Continuous monitoring reality
22:50 – FedRAMP rigor vs. other frameworks
25:00 – 20X blows up the roadmap
29:00 – Cross-team collaboration
34:00 – 20X flexibility vs. rigor
38:00 – Scaling 20X & future baselines
46:00 – Tools then vs. now
49:30 – Lifelong learning
55:00 – “Get over it. This is the future.”
59:02 – Career lesson from a mentor
1:02:04 – Closing
In this episode of the Paramify Podcast, Karen Laughton, EVP of Advisory at Coalfire, joins Kenny Scott (CEO of Paramify) and Mike Schreiner to unpack the future of government cybersecurity and compliance modernization. From the hard realities of FedRAMP 20X to lessons learned from the early days of FSMA and CMMC confusion, this conversation pulls no punches.
Karen shares how she broke into cybersecurity via HR (and a saltine-fueled CISSP exam), why automation without strategy won’t scale, and what it's going to take to make 20X work at moderate and high baselines. If you're curious where compliance, automation, AI, and public sector modernization are headed—you’ll want to tune in.
⏱️ Timestamps:
02:44 – Meet Karen Laughton: Coalfire EVP, community leader, and accidental cyber exec.
03:35 – Saltines, pregnancy, and passing the CISSP: Karen’s origin story in cyber.
08:01 – AC-7 and the mouse jiggler: when coarse-grained controls meet real-world demos.
10:03 – FedRAMP in the early days: the “marathon in flip-flops” era of inconsistent TR feedback.
13:01 – The worst documentation nitpicks Karen’s ever seen (IP addresses and diagram chaos).
14:46 – FedRAMP then vs. now: why decentralization could hurt even as risk-focus improves.
17:28 – What scaling 20X to moderate and high will actually require.
20:03 – Are we solving the right problem with KSIs? Recapping Coalfire's “automation of arrested development” blog.
23:08 – Why automation isn’t a silver bullet (and why it still needs humans).
24:57 – 3PAOs aren't going anywhere — and that’s not just job security talk.
26:15 – Andrej Karpathy, robot soccer, and the early innings of AI assurance.
29:30 – Why agencies aren’t lining up to sponsor FedRAMP 20X.
31:08 – How Coalfire responded to 20X: culture, planning, and Compliance Essentials.
33:41 – Leveraging Paramify to accelerate automation where it makes sense.
36:42 – Politics, acquisitions, and why automation hits limits in complex orgs.
37:27 – DoD, CMMC, and 20X: where things stand and why there’s still confusion.
41:01 – The case for CMMC enclaves (and why most orgs want to isolate the mess).
42:00 – Mentorship, career pivots, and embracing “knowing nothing” as a superpower.
47:58 – Why questions make you smarter — and why cybersecurity people love answering them.
50:00 – Why cybersecurity never gets boring (and feels like a family reunion at every conference).
50:59 – Wrap-up & future part two tease.
Learn more about Paramify: https://www.paramify.com/
It’s not only about faster authorizations—it’s about unlocking the full potential of modern cloud for government.
FedRAMP 20X is how we get there.
In this exclusive roundtable, Pete Waterman (FedRAMP Director), Karen Laughton (EVP of Advisory, CoalFire), Rob Otten (Sr. Director, Risk & Compliance, Flock Safety), Kenny Scott (Founder & CEO, Paramify), and Mike Schreiner (COO, Paramify) break down:
- The mission, process & real impact of the 20X pilot
- How Key Security Indicators (KSIs) make compliance faster & smarter
- What Continuous ATO looks like in practice
- Why agencies are holding the line—and what they actually want
- The bold vision to transform FedRAMP from 50 authorizations a year… to 50 a week
Timestamps:
1:56 – Welcome & Introductions
2:53 – Pilot Progress Update
5:17 – Industry Perspective: CoalFire
8:40 – CSP Perspective: Flock Safety + Paramify
12:03 – Why It Worked
14:22 – The Risk-Based Shift
17:06 – ATO vs Authorization
19:02 – The Good, The Bad, and the Fast
24:04 – Rob's Advice to CSPs
25:48 – Breaking Outdated Rules
27:07 – Agency Buy-In: Will They Accept 20X?
36:40 – Continuous ATO in Practice
42:00 – The Integration Trap
44:55 – End User Risk Responsibilities
47:00 – Monitoring What Actually Matters
50:00 – Change Processes & CI/CD
56:00 – Driving Innovation Through Standards
1:00:00 – Final Advice to CSPs
1:06:04 – Reframing the Goal
Learn more about our guests:
Pete Waterman: https://www.linkedin.com/in/petewaterman/
Karen Laughton: https://www.linkedin.com/in/karen-laughton-6484115/
Rob Otten: https://www.linkedin.com/in/robertotten/
Looking into FedRAMP or FedRAMP 20X? Lets' talk: https://www.paramify.com/frameworks/fedramp
From the publisher's feed
The Paramify Podcast is a practical, occasionally chaotic show about GRC, risk management, and staying audit-ready without losing your mind. It’s part talking security strategy, and part group therapy.
We talk with cybersecurity and GRC leaders, including CISOs, auditors, founders, and security engineers, about FedRAMP and FedRAMP 20x, SOC 2, CMMC, NIST RMF, the shift toward continuous evidence, and everything in between.
Learn about what we do at Paramify here: www.paramify.com