PODCAST · business
Drafting Compliance
by Hyperproof
To lighten the dark corners of compliance, hosts Kayne and Tom as share with you Hyperproof's journey to becoming FedRAMP moderate, an overall roadmap to achieve FedRAMP compliance in a year, and the tips and tricks they learn along the way. As if compliance isn't fun enough, the hosts also try out a new beer each episode and rate it on a scale from 1-10.
Episodes
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FedRAMP Readiness: Lessons for SaaS & Growing Enterprises
FedRAMP compliance is one of the toughest challenges facing SaaS companies working with the federal government, and in this episode we explore the most common readiness gaps, misconceptions, and cultural shifts organizations must overcome to succeed. Drawing from extensive experience advising...
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CCPA live from HyperConnect 2025
Join Kayne and Tom live from San Diego, CA, home of the CCPA, as they sit down with Rob Carson, Founder and CEO of Semper Sec, to unpack what the California Consumer Privacy Act (CCPA) really means for businesses, even outside the Golden State. From Article 9's evolving cybersecurity audit...
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Auditing: AI and the Future
Kayne and Tom talk about an article on the future of auditing with consideration for AI and it’s uses. Along the way, they uncover where organizations should be considering strategic shifts around AI and where they need to exercise caution. Of course we all get to enjoy another face of disgust…
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How to handle Data Privacy for AI with Dustin Wilcox
Kayne and Tom talk about AI and regulatory consequences with a Special guest, and Tom’s brother, Dustin Wilcox, a Fortune 20 CISO with a Global Healthcare company. They knock back a delicious Porter beer and uncover the secrets of AI and regulatory management. A blockbuster of a good time. ▬...
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Risk Assessment with Adam Brennick
Kayne and Tom talk with Adam Brennick, Director of Security, Risk, and Compliance at Cockroach Labs. Adam dives into the risk assessment process and some of the best practices for building and maturing the risk management lifecycle. Kayne has a surprising score for the beer today and it is marked...
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All About DORA
Kayne and Tom talk about DORA and its applicability. Learn where DORA applies, how you may need to be concerned about DORA even if you think you don’t and why DORA is causing confusion in US companies. Kayne and Tom try an unusual option to drink and we come close on the scoring.Reference...
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Controls, Questionnaires, and Risks with Eric Hammersley
On this episode, we're expanding the show to talk about more than FedRAMP. But before we get to that, I want to mention: we're sitting in the same room in San Diego, in front of a live audience at HyperConnect 2024 , with our special guest Eric Hammersley of Nutanix, and we have some beers. ▬...
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Frameworks and Auditors with Lisa Hall
Kayne and Tom talk with Lisa Hall, CISO at Safebase. Recorded from Austin, Texas, they try a flight of local beer! They also take time to discuss Lisa's FedRAMP journey, talking with auditors, and the implications of the CrowdStrike disaster. ▬ Contents of this episode ▬▬▬▬▬▬▬▬▬▬ 0:00 - Intro…
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FedRAMP Moderate with Alexander Neff
Kayne and Tom talk with Alexander Neff, Lecturer at ASU and Senior Director of InfoSec at Faro Health. Great conversation was had on both Alexander’s FedRAMP experience and his beer choice. Come see Kayne’s highest rated beer! Beer: Lindemans Framboise Reference documents:...
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Victoria Southall on FedRAMP Compliance and ATO
Kayne and Tom talk with Victoria Southall, the Director of Cybersecurity, Governance, Risk, and Compliance (GRC) at Everfox. Kayne learns the art of double fisting… or should I say triple fisting, as we try 3 beers in this episode. Results vary, but as always, the tasting brings out the best in...
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FedRAMP with Eric Holtzclaw
Kayne and Tom talk with Eric Holtzclaw, Field CISO, with Blackcat Security. Eric shepherded the first company through FedRAMP Tailored Li-SaaS. We learn how the very first effort went, and what Eric learned along the way. Dare we say, Eric was a Guinea Pig for the FedRAMP. Of course, we subject...
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3PAOs and FedRAMP with James Leach
Kayne and Tom talk with James Leach, A Principal with Fortreum, a 3PAO. James pulls the covers back on the role 3PAOs plays in the FedRAMP journey. From advice, then assessment and working with the larger FedRAMP ecosystem, James helps us understand where 3PAOs provide value. We try New Belgium,...
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FedRAMP with Matthew Feldman
Special Guest Matthew Feldman joins Kayne and Tom to pull the curtain back on his FedRAMP experiences. Matthew has a wealth of experience and understands the nuances of FedRAMP. Mathew helps understand the importance of best practice when looking through the lens of compliance. Of course, as...
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FedRAMP Project Update
Tom provides an update on the status of the Hyperproof FedRAMP project. Along the way, Kayne uncovers some of the challenges associated with the project and suggests solutions for others going through the same process. And straight out of left field, Kayne actually likes a beer more than Tom.…
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Planning
Tom and Kayne uncover the intricacies of the Planning family of requirements in FedRAMP Moderate. Learn about the SSP, Rules of Behavior and Architecture in the planning process. Also, of course, learn about Cigar City Brewing’s Jai Alai IPA, one of Tom’s favorites and Kayne’s… well Kayne is Kayne.
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Audit and Accountability
Come and see how Boulevard Brewing rebounds after a poor showing and shines with its Tank 7 American Saison beer. Kayne and Tom talk about the Audit and Accountability family of controls in FedRAMP Moderate. Learn the challenges and technologies leveraged to cope with the many requirements. Maybe...
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Risk Assessment
Kayne and Tom choke down the very sweet and sticky Boulevard Brewing Co.’s Cinnamon Bun Ale. Along the way they discuss the intricacies of the Risk Assessment family of FedRAMP controls and what challenges it might present. The episode ends with a surprising agreement on the beer and equally...
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System and Services Acquisition
Kayne and Tom uncover the nuance of the System and Services Acquisition family of FedRAMP controls. Tune in to hear how FedRAMP has matured how organizations should think about supply chain providers. Tom has a definitive belief on how this family of controls will evolve over time. Of course, a...
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System and Information Integrity
Kayne and Tom dive into the System and Information Integrity family of FedRAMP Moderate controls. Find out what challenges Hyperproof has faced with this family of controls and learn some tips to help you in your own FedRAMP journey. A clear outlier shows up in this show’s beer reviews, tune in…
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ATO Process with Michael Chaoui
Kayne and Tom are joined by special guest Michael Chaoui, the Founder of Atlas One Security. Michael pulls the covers back on some of the challenges of companies going through the ATO process. We also discuss recent legislation and draft memos intended to modernize the FedRAMP process, all while...
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System and Communications Protection
Kayne and Tom talk about the System and Communications Protection family of FedRAMP Rev5 controls. Learn about the “catch all” approach to this control family and some challenges faced to implementation. Tom and Kayne try a stout for the first time on the show, and Kayne seems to group it with…
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Special Guest Steve Gentry
Kayne and Tom talk with Steve Gentry about his FedRAMP experience and the lessons learned. Costs to consider, how to build controls thoughtfully and where you should consider FedRAMP control initiatives in the context of a business discussion. Of course we threw another drink in Kayne’s hands for...
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Live from HyperConnect 2023
Live from Austin, Texas, Kayne and Tom discuss supply chain risk under FedRAMP. They also try a local beer, live on stage, from HyperConnect 2023.
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Special Guest Matt Fryer of Infoblox
Kayne and Tom talk with Matt Fryer about the cost structures and strategies associated with a Cloud Service Provider (CSP) FedRAMP project. Matt brings a well established perspective and helps understand the challenges of the increased controls focus apparent with FedRAMP. Plus, they try Modelo...
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Moving to FedRAMP Rev5
Kayne and Tom talk about the FedRAMP Rev4 to Rev5 transition. Learn about key control changes, the shell game that is Rev5 and obviously, the unique flavor profile of a new beer.
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3PAO Accreditation Loss with CISO Joe Evangelisto
Kayne and Tom talk with Joe Evangelisto from Tango Analytics about an interesting and stressful scenario where his 3PAO lost its accreditation. Of course, Kayne tackles yet another beer that elicited a memorable response.
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How to do Personnel Security for FedRAMP
Kayne and Tom talk about personnel security, background checks, what FedRAMP requires for onboarding and terminating employees as well as a host of tips and tricks for meeting this control family. Of course, they also try a new beer and maybe, just maybe, agree on the score.
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How to do Media Protection for FedRAMP
Kayne and Tom talk about Media Protection while sipping a new pale ale. Learn the challenges of removable media, both digital and non-digital, along with a few tips and tricks for getting started with your Media Protection journey.
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FedRAMP Costs with Guest Jacob Berry
Kayne, Tom, and special guest Jacob Berry (Field CISO at Clumio) talk about the challenges in pursuing FedRAMP. Costs, hidden challenges and go-to market are rounded out with two drinkable, but not memorable, non-alchoholic beers. Listen for the knowledge, stay for the beer ratings.
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FedRAMP Authorization with CISO Mark Houpt
Kayne, Tom, and special guest CISO Mark Houpt talk about a GSA rules change that affected Mark’s prior FedRAMP certification, the consequences, and his ultimate solutions and lessons learned from the experience.
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Identification and Authentication for FedRAMP
Kayne and Tom talk about the domain under FedRAMP moderate, providing both an overview of the domain as well as specific examples of controls, and real-world scenarios for the use of those controls. They also come close to agreeing about “Color Cloud Pink”, a Berliner Weisse with “Pink Guava,...
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How to do Contingency Planning for FedRAMP
Kayne and Tom talk about the Contingency Planning domain under FedRAMP moderate, comparing it against the best practice of Business Continuity Planning, and providing specific guidance for key elements of a successful contingency plan. They also find what amounts to near common ground on this...
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What about the Maintenance Domain Under FedRAMP?
Kayne and Tom talk about the Maintenance domain under FedRAMP moderate, including how it is related to the Configuration Management domain. They also nearly agree on Rogue’s Hazelnut Brown Nectar, although Kayne still likens it to old hotel coffee while Tom will drink a free one.
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How to do a FedRAMP Security Assessment and Authorization
Kayne and Tom talk about the requirements of continuous compliance under the Security Assessment and Authorization family of controls, including key considerations for continuous monitoring and reauthorization. During the episode, they explore yet another fruit-forward beer, Deschutes’ Farmstand...
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FedRAMP Supply Chain Challenges
Kayne and Tom talk about recent challenges caused by two vendors in our software supply chain not achieving FedRAMP Moderate in 2023. While discussing their path forward, they sample the New Belgium Voodoo Ranger Juice Force IPA.
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How to do Configuration Management in FedRAMP
Kayne and Tom talk about the major pillars of Configuration Management. While digging into inventory management, baseline configurations, configuration drift, and risk, they tackle Bell’s Two Hearted American IPA.
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Physical and Environmental Protection under FedRAMP
Kayne and Tom uncover the different approach to the Physical and Environmental controls, with a discussion of all-cloud, on prem and hybrid scenarios. Of course, they tackle a new beer as well, maybe Kayne will like this one, and maybe Tom will not… I think you already know!
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Security Awareness Training Deserves a Good Beer!
Kayne and Tom talk about the joys of security awareness training, managing training, and the different types of security and privacy training you should consider, and as always, beer. This episode’s beer is Sierra Nevada Hazy Little Thing IPA.
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FedRAMP and Beer: April First Special
Kayne and Tom tackle the interesting nuances of both beer and FedRAMP. Does a beer consumed by CISOs need to also be FedRAMP compliant? Come find out.
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What Is the FedRAMP Incident Response Control Family?
In this episode, Kayne and Tom talk about the nuances of the Incident Response family of FedRAMP controls, some of the required documentation, testing, and beer. This episode’s beer is Woods Boss Brewing Company’s Pulaski Pecan Brown Ale.
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The FedRAMP Access Control Family
Kayne and Tom discuss FedRAMP's access control family, language that must be in the access control policy, wireless access control for SaaS companies, and how to prevent creating a paper tiger. Includes beer tasting notes for Epic Brewery's Hopulent.
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How to do a FedRAMP Gap Analysis
Kayne and Tom dive into where to begin in your FedRAMP gap analysis. They discuss the efficiencies that Hyperproof found in order to save time, and suggest other approaches. Includes beer tasting notes for Oliphant's Super Squishy.
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How to Define the FedRAMP Authorization Boundary
Hosts Kayne and Tom talk about how to create the Authorization Boundary, a cornerstone of the System Security Plan (SSP) as part of FedRAMP certification. Includes beer tasting notes for Black Butte Porter.
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What IS FedRAMP?
Join Hyperproof hosts Kayne McGladrey, CISSP, Field CISO, and Thomas Wilcox, CISSP, Sr. Director of Security and Compliance, as they discuss the intent and overall roadmap to achieve FedRAMP compliance in a year. Includes beer tasting notes for Anchor Steam.
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ABOUT THIS SHOW
To lighten the dark corners of compliance, hosts Kayne and Tom as share with you Hyperproof's journey to becoming FedRAMP moderate, an overall roadmap to achieve FedRAMP compliance in a year, and the tips and tricks they learn along the way. As if compliance isn't fun enough, the hosts also try out a new beer each episode and rate it on a scale from 1-10.
HOSTED BY
Hyperproof
CATEGORIES
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Frequently Asked Questions
How many episodes does Drafting Compliance have?
Drafting Compliance currently has 44 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Drafting Compliance about?
To lighten the dark corners of compliance, hosts Kayne and Tom as share with you Hyperproof's journey to becoming FedRAMP moderate, an overall roadmap to achieve FedRAMP compliance in a year, and the tips and tricks they learn along the way. As if compliance isn't fun enough, the hosts also try out...
How often does Drafting Compliance release new episodes?
Drafting Compliance has 44 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Drafting Compliance?
You can listen to Drafting Compliance on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Drafting Compliance?
Drafting Compliance is created and hosted by Hyperproof.
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