The Paramify Podcast

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:https://rhymetec.com  / justin-rende  
Learn more about Paramify: Paramify website: https://www.paramify.com/Mike Schreiner (LinkedIn):   / mikecschreiner  Kenny Scott (LinkedIn):   / kenny-g-scott  
Chapters
0:00 Federal compliance is exploding (and getting mainstream)0:30 Welcome to The Paramify Podcast + Justin Rende intro1:34 Justin’s origin story: tech ➝ film ➝ tech2:53 Starting Rhymetec with pentesting (and betting on SaaS early)4:25 Tribeca and Doha: running VIP experiences and meeting “heroes”5:33 The real lesson from film: make the customer have a good time7:01 Mess-ups happen, recovery is the job8:15 “Don’t meet your heroes” (Rudy story)9:24 Leaving film, chasing stability, spotting outdated consulting10:43 Bootstrapping vs taking investment and why flexibility wins13:53 From big pentest checks to recurring revenue and vCISO programs15:24 Employee experience: quality of life, culture, and remote done right18:10 SOC 2 and ISO automation: the pros, the cons, and the risk gap20:25 The “easy button” myth (MFA is never just one button)21:38 Sales overpromising, complexity, and doing right by the customer25:36 Biking NYC: Google Homes, handwritten notes, and standing out27:13 “Magic” in packaging, Alchemy, and why it works31:28 Why Rhymetec leaned into federal compliance32:24 SOC 2 race to the bottom vs doing it the right way39:15 What’s improving in federal compliance (and what still hurts)40:11 FedRAMP 20x innovation and building in public42:52 FedRAMP scale, CMMC scale, and why it’s all accelerating44:29 Legacy environments and why DoD adoption takes longer46:24 Where to find Rhymetec + closing thoughts

“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:* Systems Over Scripts: GRC Engineering isn't about being a "coder." It’s about systems thinking and moving away from the "crawl space" of manual scripting.* The "Cell Phone" Moment: Why GRC is skipping the "landline" era of APIs and jumping straight to agentic workflows with MCP (Model Context Protocol).* FedRAMP® 20x: How Key Security Indicators (KSIs) move the burden of proof from 4,000-page narratives to 80%+ automated validation.* The 7-Minute Threat: AI-powered adversaries can pop a machine in 7 minutes. If your compliance isn't "threat-driven," it's irrelevant.
Learn more about Ayoub:Gitlab: https://about.gitlab.com/ GRC Engineer: https://grcengineer.com/GRC Engineer Podcast: https://www.youtube.com/channel/UC8cvmIXoEEBs0dryLh2p2cAAyoub's LinkedIn: https://www.linkedin.com/in/ayoubfandi/
Learn more about Paramify:Website: https://www.paramify.com/Kenny's LinkedIn: https://www.linkedin.com/in/kenny-g-scott/Mike's LinkedIn: https://www.linkedin.com/in/mikecschreiner/
Chapters
00:00 Intro — Utah, butter cake, and Ayoub's first time in the U.S.02:00 How Ayoub got into GRC (500 cold DMs and ISO cramming)09:00 Struggling to commit to GRC — until Adobe's program changed everything13:00 What GRC Engineering actually means15:00 Why evidence collection is plumbing, not strategy20:00 Why AI won’t kill GRC — it’ll force it to grow up25:00 Architecting assurance: the new role of GRC30:00 Why APIs are losing ground to agentic protocols like MCP35:00 Landlines vs. Cell Phones: How automation skipped a generation38:00 Platformization, assurance, and the SaaS vendor dilemma43:00 Can platforms fix SOC 2 quality?48:00 Sticker fatigue and the case for continuous assurance52:00 Why threat-driven compliance is the only way forward56:00 Advice for early-career GRC professionals in an AI-native world

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.
Chapters00:00 Intro: From field goals to FedRAMP02:00 Dixon’s career in security consulting05:00 What Eden Data does and who they serve09:00 Joining the FedRAMP 20x pilot14:00 Building credibility through execution18:00 Security in practice vs. theory23:00 Why delivery teams need flexibility27:00 Shifts in federal and commercial compliance32:00 Trust, tools, and transparent reporting36:00 The future of cybersecurity delivery41:00 Final thoughts
Learn more about Eden Data: https://www.edendata.com
Learn more about Dixon Wright:  / dixon-wright-aab68321  
Learn more about Paramify: https://www.paramify.com/
Learn more about Kenny:  / kenny-g-scott  Learn more about Mike:  / mikecschreiner  

"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:• Automation is reshaping how companies prove trust and security• Startups will need enterprise-grade security earlier than ever• Continuous monitoring is becoming the new foundation for real assurance
Chapters00:00 Security teams are drowning02:40 Scaling trust in public sector06:10 Check-the-box isn’t cutting it10:00 The promise of low-code automation13:40 Swimlane’s mission and momentum17:00 How to reduce alert fatigue21:30 Integrating detection with compliance26:15 CMMC and automation opportunities30:00 Why orchestration needs flexibility34:00 Future of GRC tooling36:50 Final thoughts on doing more with less
Learn more about Jack Rumsey: https://www.linkedin.com/in/jack-rumsey-83303469/Learn more about GRC Destroyer: https://grcdestroyer.substack.comLearn more abou Swimlane: https://swimlane.com
Learn more about Kenny: https://www.linkedin.com/in/kenny-g-scott/Learn more about Mike: https://www.linkedin.com/in/mikecschreiner/Learn more about Paramify: https://www.paramify.com/
Chapters00:00 Security teams are drowning02:40 Scaling trust in public sector06:10 Check-the-box isn’t cutting it10:00 The promise of low-code automation13:40 Swimlane’s mission and momentum17:00 How to reduce alert fatigue21:30 Integrating detection with compliance26:15 CMMC and automation opportunities30:00 Why orchestration needs flexibility34:00 Future of GRC tooling36:50 Final thoughts on doing more with less
Learn more about Jack Rumsey: https://www.linkedin.com/in/jack-rumsey-83303469/Learn more about GRC Destroyer: https://grcdestroyer.substack.comLearn more abou Swimlane: https://swimlane.com
Learn more about Kenny: https://www.linkedin.com/in/kenny-g-scott/Learn more about Mike: https://www.linkedin.com/in/mikecschreiner/Learn more about Paramify: https://www.paramify.com/

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 Mike Craig: https://www.linkedin.com/in/michaelcraig26/Learn more about Vanaheim Security: www.vanaheimsecurity.com
Learn more about Paramify: https://www.paramify.com/?utm_source=MikeCraig&utm_medium=Podcast&utm_campaign=Mikecraig&utm_id=Podcast&utm_term=podcast&utm_content=Mikecraig
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 / Chapters0:00 — “FedRAMP as we know it” and the 20x future1:42 — Welcome back to The Paramify Podcast (Mike & Kenny)3:01 — Meet Mike “Waffle” Craig (Vanaheim Security)4:04 — Hero’s journey: Air Force → cyber → IR → compliance5:04 — “Cyber warfare” era and being the translator across teams6:02 — Global regs, midnight IR, and burnout7:04 — From IR to compliance architecture & multi-cloud ATOs8:05 — Protecting small vendors from six–seven figure mistakes9:11 — When compliance runway kills a program (DoD case)11:03 — Waffle’s 0% abandonment rate and why it matters11:14 — DoD “defense combine” experiment (Beta Blocks vibe)13:41 — Operators, COs, entrepreneurs: fixing feedback loops16:26 — Federal sponsorship 101 (pre-20x) and targeting wisely18:16 — Two bad options for first-timers: sponsor vs. Ready gamble21:02 — FedRAMP Ready pitfalls and the 12-month clock22:08 — Cost realities (150k+ assessments) for small teams22:44 — Why 20x changes the game (starting low, scaling up)27:04 — Compliance philosophy: scope, boundaries, and frameworks30:00 — “If you can’t draw it, you can’t secure it” (data flows)31:04 — Hot take: PowerPoint is the best diagramming tool33:39 — Prototype confession: Excel/Sheets and millennial ops37:39 — 20x at scale: staffing, humans-in-the-loop, and risk39:07 — Post-JAB reality: more variance, harder prediction40:05 — LLM/RAG in FedRAMP: data sources & significant change42:05 — Boundaries got harder—how to think about them43:08 — Paramify’s CIA risk profile approach across stacks47:01 — Corporate, dev, infosec, tech-ops: multi-zone modeling49:05 — Knowing your data (AI makes the gap bigger, faster)50:06 — Control weighting & psychology of “yes”50:47 — NSA CSFC as a model for defined stacks52:02 — Could FedRAMP define AI patterns? (playbook potential)54:46 — Where to find Mike / Vanaheim Security55:31 — Name jokes and close

“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-upJason recounts how a shared client pushed both teams into the deep end of 20X, asking to include the auditors before Paramify even had an assessment portal built.
01:00 – Less than two-week deadlineThe group describes the chaos of spinning up a 20X package in record time, with Rob (the auditor) agreeing to figure things out alongside them.
01:44 – Submitting against moving targetsJust as the package was ready to go, the final low 20X KSIs dropped — forcing last-minute changes and stress.
02:24 – Nature of FedRAMP changeJason compares FedRAMP shifts to “big boulders” coming at you, not “mousy” tweaks — change is always disruptive and massive.
02:56 – Success despite chaosTeams (Paramify, Flock, Baker Tilly) pulled it together, got the package in on time, and landed among the first four 20X submissions posted publicly.
03:07 – The reality checkJason: not everything in FedRAMP is “dillydallying” — clients, deadlines, and bills make delivery non-negotiable.
03:13 – Official podcast kickoffKenny introduces the episode: Jason Oksenhendler (Baker Tilly, formerly Moss Adams), and Paramify’s “rising star” Isaac Teuscher.
04:01 – Jason’s career origin storyFrom news anchor ➝ IT tech writer ➝ into FedRAMP (starting around NIST 800-53 Rev 2).
05:40 – First FedRAMP assignmentJason recalls his boss handing him a paper: “Go do FedRAMP.” He walks through early JAB/ISSO processes, feedback loops, and working with Matt Goodrich and Ashley Mahan.
11:43 – Co-creating the FedRAMP High BaselineJason describes working with DoD’s Ron Rice to build the High Baseline from scratch.
13:00 – Early FedRAMP painMicrosoft Word & Excel “hell,” endless regurgitated control statements, and why some CSPs made assessors want to “bang their heads on the desk.”
15:32 – “You could do a Seinfeld routine on this crap.”Jason on version control disasters and 600-page SSP reviews without track changes.
17:30 – Culture shock of changeReactions to FedRAMP 20X mirror the same resistance to earlier shifts — but it’s always been “do once, use many.”
20:00 – Continuous monitoring realityJason emphasizes executive buy-in as essential, recalling how ConMon and POA&Ms separate prepared orgs from overwhelmed ones.
22:50 – FedRAMP rigor vs. other frameworksJason argues FedRAMP is among the toughest frameworks, on par with DoD IL4-6.
25:00 – 20X blows up the roadmapKenny calls 20X a “hand grenade” for Paramify’s product plans.
29:00 – Cross-team collaborationJason highlights how six strangers in a Slack channel worked seamlessly under pressure — “like a chocolate fountain.”
34:00 – 20X flexibility vs. rigorJason explains the challenge of balancing new freedoms with maintaining strong security.
38:00 – Scaling 20X & future baselinesSpeculation about moderate and high 20X baselines and how CSPs will adapt.
46:00 – Tools then vs. nowFrom CSAM, RSAM, and E-MASS to Paramify — Jason praises ease-of-use as critical to speed and quality.
49:30 – Lifelong learningFedRAMP’s ever-changing landscape keeps security careers fresh, like his days in broadcasting.
55:00 – “Get over it. This is the future.”Jason’s blunt advice on 20X: stop resisting change, go where the work is, and be all-in.
59:02 – Career lesson from a mentorJason shares the Navy SEAL “my way, the right way, or the wrong way?” story — the moment that launched his assessment career.
1:02:04 – ClosingRelationships last longer than frameworks; Kenny, Jason, and Isaac wrap up the episode.

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:00:00 – "Dang, we need to modernize our government" — Karen's IRS nightmare becomes a metaphor for digital transformation.
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 Coalfire: https://coalfire.com/Learn more about Karen Laughton: https://www.linkedin.com/in/karen-laughton-6484115/
Learn more about Paramify: https://www.paramify.com/Learn more about Kenny: https://www.linkedin.com/in/kenny-g-scott/Learn more about Mike: https://www.linkedin.com/in/mikecschreiner/

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:0:00 – The Big QuestionPete Waterman shares the spark: “What if we did 50 FedRAMP authorizations a week?”
1:56 – Welcome & IntroductionsMeet the panel: Pete Waterman, Karen Laughton, Rob Upton, Kenny Scott.
2:53 – Pilot Progress UpdatePete dives into pilot metrics, early submissions, and success stories.
5:17 – Industry Perspective: CoalFireKaren Laughton shares lessons learned from advising CSPs and 3PAOs.
8:40 – CSP Perspective: Flock Safety + ParamifyRob & Kenny reveal how they rapidly pivoted into the pilot and delivered results in 2 weeks.
12:03 – Why It WorkedWhy KSIs resonated and how automation made it achievable.
14:22 – The Risk-Based ShiftSecurity is about risk, not checklists. Kenny, Rob, and Pete riff on the deeper mindset change.
17:06 – ATO vs AuthorizationPete clarifies the difference and why 20X is fixing the current barriers.
19:02 – The Good, The Bad, and the FastKaren details what’s working well—and what’s still a mess (agency sponsorship, complex systems, DoD holdouts).
24:04 – Rob's Advice to CSPsRob advocates a risk-first approach and common sense improvements.
25:48 – Breaking Outdated RulesKenny rants about FIPS encryption requirements and why 20X could fix it.
27:07 – Agency Buy-In: Will They Accept 20X?Pete confirms: Yes. OMB and formal policy will mandate adoption.
36:40 – Continuous ATO in PracticeWhat’s working, what’s confusing, and what the FedRAMP team is learning.
42:00 – The Integration TrapKenny explains why black-box integrations don’t cut it—and what CSPs must do instead.
44:55 – End User Risk ResponsibilitiesA critical callout: security breaches are often misconfigurations by users—not tech failures.
47:00 – Monitoring What Actually MattersForget CVEs. Pete & Karen emphasize real-time config validation (e.g., MFA being disabled).
50:00 – Change Processes & CI/CDHow continuous snapshots and CICD can coexist with security—without slowing innovation.
56:00 – Driving Innovation Through StandardsWhy 20X exists: to force the ecosystem to build what’s long been talked about but never delivered.
1:00:00 – Final Advice to CSPsShould you jump into 20X? Panelists give concrete guidance for startups, hyperscalers, and advisors.
1:06:04 – Reframing the GoalPete closes with a powerful vision: delivering equal access to secure cloud tech for federal workers—faster, better, and at scale.
Learn more about our guests: 
Pete Waterman: https://www.linkedin.com/in/petewaterman/FedRAMP: https://www.fedramp.gov/
Karen Laughton: https://www.linkedin.com/in/karen-laughton-6484115/Coalfire: https://coalfire.com/
Rob Otten: https://www.linkedin.com/in/robertotten/ Flock Safety: https://www.flocksafety.com/
Learn more about Paramify: Kenny Scott: https://www.linkedin.com/in/kenny-g-scott/Mike Schreiner: https://www.linkedin.com/in/mikecschreiner/Paramify: www.paramify.com
Looking into FedRAMP or FedRAMP 20X? Lets' talk:  https://www.paramify.com/frameworks/fedramp

Today, we’re sitting down with StackArmor’s Martin Rieger — a FedRAMP veteran with over 300 engagements under his belt — for an unfiltered deep dive into the origin, evolution, and future of FedRAMP compliance.
We cover everything from the early days of DIACAP and gold images to today’s world of automation, OSCAL, and AI-powered documentation. Martin shares war stories, explains why so many companies fail audits even with AI, and gives his take on where FedRAMP 20x is headed.
Key takeaways- AI can't replace expertise: Using ChatGPT (or any AI) to generate FedRAMP documentation without human validation leads to failure—AI is a tool, not a replacement for expertise.
- Right tools + right people = success: AI and automation can massively accelerate compliance work if handled by professionals who understand the frameworks deeply.
- FedRAMP’s evolution: FedRAMP has matured from infrastructure-heavy beginnings to a focus on SaaS and cloud-native tools, with an increasing push toward automation and standards like OSCAL.
- Common ATO pitfalls: Many companies underestimate the effort required for continuous monitoring (ConMon) and maintaining their ATO, mistakenly thinking the hardest part is getting authorized.
- Martin: FedRAMP may move toward sponsor-less paths (like StateRAMP) for Low/Moderate baselines, and AI + OSCAL will likely reshape how security packages are created, validated, and shared.
This episode is loaded with insights for anyone serious about federal cloud compliance.
⏱️ Timestamps:04:10 – Martin’s early FedRAMP journey & Navy background10:00 – DIACAP, early tools, and Excel-era compliance16:35 – How Kenny and Martin met (NIST OSCAL event story)25:00 – StackArmor’s shift from golden images to modern cloud35:00 – The problem with AI-generated SSPs43:30 – POAMs, audit problems, and compliance documentation49:45 – FISMA vs. FedRAMP, ‘FISRamp’, and ATO inefficiencies56:40 – Predictions: FedRAMP 20x, agency sponsorship & PMO1:02:20 – The future of FedRAMP automation & OSCAL + AI
🔗 Learn more about StackArmor: https://stackarmor.com/👤Learn more about Martin Rieger: https://www.linkedin.com/in/martinrieger/
🔗 Learn more about Paramify: https://www.paramify.com/?utm_medium=social👤 Connect with Kenny: Kenny G. Scott: / https://www.linkedin.com/in/kenny-g-scott/👤 Connect with Mike: Mike Schreiner:  / https://www.linkedin.com/in/mikecschreiner/