Best Andrew Monaghan Podcasts (2025)

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The Art of Timing Your First Sales Hire in a Cybersecurity Startup – Tony Surak, Partner, DataTribe 40:55

Play Pause

11d ago40:55

40:55

Send me a text (I will personally respond) Are you wrestling with the decision of when to bring on your first sales leader? Wondering if your startup has achieved enough product-market fit before scaling the sales team? Curious about common pitfalls and best practices in building a sales function that can take you from zero to millions in ARR? This…

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Helpdesk Scars & PowerShell Wins with Andrew Taylor 55:52

12d ago55:52

55:52

Andrew Taylor shares his journey from studying business to becoming a seasoned IT professional with over 20 years of experience. He discusses his early days in help desk support, his transition to end user computing, and the challenges he faced in various IT roles, including managing multiple tenants in the MSP world. Andrew emphasizes the importan…

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The Unconventional Growth Playbook: Europe, SMBs, and Cyber Insurance – Christian Werling, CRO, Eye Security 40:27

18d ago40:27

40:27

Send me a text (I will personally respond) Are you wondering how to leverage unconventional go-to-market strategies to accelerate growth in cybersecurity? Curious about integrating cyber insurance into your offer to stand out in a crowded landscape? This episode provides answers by spotlighting a company bucking the traditional playbook—and winning…

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Writing, Teaching, and Defending: Ru Campbell’s IT Adventures 58:00

16d ago58:00

58:00

Ru Campbell shares his journey from starting in IT in 2012 to becoming a Microsoft 365 consultant and security expert. He discusses the importance of help desk experience, betting on oneself in career progression, and the transition to specializing in Microsoft Defender. Ru emphasizes the value of understanding security practices, the challenges of…

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From 8 to 500: Scaling Hypergrowth in Cybersecurity GTM – Ryan Carlson, President of GTM, Chainguard 42:23

25d ago42:23

42:23

Send me a text (I will personally respond) Are you wrestling with how to scale your sales team without losing focus on what truly matters? Do you wonder how to maintain a customer-centric approach as your company experiences hypergrowth? Or maybe you’re trying to figure out the right time and way to segment your go-to-market organization. This epis…

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From Packaging Apps to Podcasting with Rory Monaghan 53:04

23d ago53:04

53:04

Rory Monaghan shares his extensive journey in the IT field, starting from his early days in application packaging to his current role in end user computing. He discusses the evolution of application virtualization, particularly App-V, and its impact on organizations. Rory emphasizes the importance of community through user groups and the value of p…

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Building Better Reporting with Garth Jones 1:08:14

1M ago1:08:14

1:08:14

Garth Jones shares his extensive journey in the IT field, starting from his early days running a BBS to becoming a pivotal figure in endpoint management with SMS. He discusses the evolution of IT roles, the importance of proactive management, and the challenges he faced while building Enhansoft. Garth also reflects on his experiences with blogging,…

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Networking, Fundamentals, and the Future of IT with Mattias Melkersen 47:10

1M ago47:10

47:10

In this conversation, Mattias Melkersen shares his journey from dropping out of school to becoming a successful IT consultant. He discusses the importance of mentorship, continuous learning, and the impact of AI on IT management. Mattias emphasizes the need for networking and community building in the IT field, as well as the significance of unders…

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Pedaling Through IT Careers with Paul Winstanley 1:02:44

1M ago1:02:44

1:02:44

In this conversation, Paul Winstanley shares his journey in the IT industry, starting from his early days in retail IT support to specializing in endpoint management and becoming a community leader through blogging and speaking engagements. He discusses the importance of mentorship, the evolution of his career into consulting, and the impact of AI …

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From Dismantling a PC at 14 to Co-Founding a Tech Company with Jose Schenardie 1:07:03

2M ago1:07:03

1:07:03

In this conversation, Jose Schenardie shares his journey from starting his IT career in Brazil to becoming a co-founder of a cybersecurity company in Australia. He discusses the importance of niche conferences like MMS, the evolution of endpoint management with Intune and SCCM, and the role of AI in shaping the future of IT. Jose emphasizes the val…

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Cloud Skills, Content Creation & Cardio – Andy Jones IT Journey 1:01:02

2M ago1:01:02

1:01:02

In this conversation, Andy Jones shares his extensive journey in the IT field, starting from his early days in web development to his current role focusing on cloud technologies and Intune. He discusses the importance of continuous learning, mentorship, and the evolution of technology, particularly AI and its implications for IT professionals. Andy…

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Helpdesk to Consulting with Chris Cavazos on Shaping Tech Careers 51:19

2M ago51:19

51:19

In this conversation, Chris Cavazos shares his journey in the IT field, starting from his early experiences in the 90s to his current role as a principal consultant. He discusses the importance of mentorship, the transition from in-house IT to consulting, and the impact of Azure Virtual Desktop during the pandemic. Chris also touches on his persona…

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From Construction Sites to Configuration Profiles with Jóhannes Geir Kristjánsson 55:41

3M ago55:41

55:41

Johannes Geir Kristiansson shares his unique journey from a construction background to a successful career in IT, particularly in endpoint management and Intune. He discusses the challenges and rewards of transitioning from a hands-on trade to a more abstract field, emphasizing the importance of community and knowledge sharing. Johannes also reflec…

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How Dustin Gullett Went from Mowing Lawns to Microsoft MVP 56:30

3M ago56:30

56:30

Dustin Gullit shares his journey from mowing lawns for a school district to becoming an IT consultant with a wealth of experience in military network security, healthcare IT, and MDM solutions. He discusses the evolution of Intune, the impact of AI on technology and daily life, and his passion for photography and blogging. Dustin emphasizes the imp…

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Scaling the Fastest-Growing Data Security Startup 38:33

3M ago38:33

38:33

Send me a text (I will personally respond) Are you struggling to keep up with the rapid pace of growth in cybersecurity sales? Wondering how to build a high-performing go-to-market team without sacrificing consistency or culture? Curious about what it takes to lead and enable teams through hypergrowth while navigating constant change? If so, you’ll…

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How Nearly Becoming a Doctor Led to a Career in Cyber Security with Spencer Alessi 53:23

3M ago53:23

53:23

Spencer Alessi shares his journey from almost becoming a doctor to pivoting to IT, emphasizing the importance of help desk experience, mentorship, and continuous learning. He discusses his passion for systems administration, the significance of disaster recovery testing, and his transition into security. Spencer also reflects on his experiences in …

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Unlocking Business Value In Cybersecurity From a 25+ Year Cyber Sales Veteran 49:09

3M ago49:09

49:09

Send me a text (I will personally respond) Are you struggling to turn small niche security products into strategic, high-value revenue streams? Curious how to elevate your sales approach from feature dumping to genuine value conversations? Ever wonder why comp plans always seem so complicated—or how real sales leaders attract and keep A-players? Th…

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Naming OUs and Racing Bikes: The Balanced Life of Michael Escamilla 56:32

3M ago56:32

56:32

Michael Escamilla shares his journey in the IT field, discussing his experiences at conferences, his involvement with OSD Cloud, and the importance of community engagement. He reflects on his career path, the challenges faced in IT, and the significance of automation. Michael emphasizes the need for continuous learning and offers advice for aspirin…

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How to Build a Cyber Sales Machine From Nothing That Delivers 30X ARR Growth and 166% NRR 39:56

3M ago39:56

39:56

Send me a text (I will personally respond) Are you leading a cybersecurity sales team aiming for responsible, accelerated growth—but unsure how to scale without just adding headcount? Do you struggle to shift your messaging above the noise and communicate true business outcomes? Are you balancing highly technical sales cycles with the need to engag…

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Imposter Syndrome, Authorship, and Entrepreneurship with David Brook 57:09

3M ago57:09

57:09

David Brook shares his journey in the IT field, discussing his early experiences, the importance of apprenticeships, and the challenges of starting his own business. He emphasizes the value of community, public speaking, and the need for continuous learning in the fast-paced world of technology. David also opens up about his struggles with imposter…

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Partnerships That Scale: How Valence Security Empowers Resellers 19:33

4M ago19:33

19:33

Send me a text (I will personally respond) Are you struggling to build a high-velocity partner program that actually drives revenue? Wondering how to structure channel margins and opportunity registrations to attract—and keep—great cybersecurity resellers? Curious about how emerging technologies and evolving needs are shaping the next generation of…

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From Paramedic to Redmond, Sean Bulger’s tech journey 1:12:07

4M ago1:12:07

1:12:07

In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous lear…

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Regulation, Revenue, and Reluctance: Selling to OEMs in Cyber 19:55

4M ago19:55

19:55

Send me a text (I will personally respond) Are you struggling to identify the most lucrative customer segments for your cybersecurity solution? Wondering how new regulations are shaping buying behavior among OEMs and enterprises? Curious about how innovative technologies and partnerships can accelerate your go-to-market and revenue growth? This epi…

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Breaking Out of Stealth: The Story Behind Spektion’s New Approach to Software Vulnerability 27:12

4M ago27:12

27:12

Send me a text (I will personally respond) Are you a cybersecurity sales or marketing leader seeking new ways to stand out in a crowded market? Do you struggle with demonstrating real value to CISOs who have “seen it all” and are wary of generic pitches? Wondering how to engage technical buyers who know the ins and outs of your product’s shortcomin…

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Steve Weiner’s Unexpected Tech Journey: Music, Youtube, and Modern Management 59:22

4M ago59:22

59:22

In this engaging conversation, Steve Weiner, co-founder of Get Rubix, shares his unique journey from a music career to the tech industry, detailing his experiences at Apple and as a tech consultant. He discusses the evolution of his YouTube channel, the impact of pandemic on IT practices, and the importance of community engagement through open-sour…

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EMEA Expansion, AI Experiments & Channel Secrets: Inside Legit Security’s 2025 Strategy 20:52

4M ago20:52

20:52

Send me a text (I will personally respond) Are you struggling to differentiate your cybersecurity company in a sea of similar-sounding competitors? Wondering how to effectively position your solution in a market flooded with acronyms and overlapping technologies? Or are you trying to scale growth while navigating the complexities of partnership-dri…

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Turning Customers Into Your Best Sales Team: Real-World CS Strategies 22:56

4M ago22:56

22:56

Send me a text (I will personally respond) Are you struggling to build a customer success function in an early-stage cybersecurity startup? Wondering how to prove real value and drive renewals in a crowded threat intelligence market? Or are you curious about innovative approaches to proactive cyber defense that could give your GTM strategy an edge?…

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Code, Cloud & Confidence with Hailey Phillips 1:06:47

4M ago1:06:47

1:06:47

In this episode, Hailey Phillips shares her journey from an HR internship to becoming a prominent figure in the IT industry. She discusses her passion for technology, the importance of automation and cloud computing, and the role of soft skills in tech. Hailey also reflects on her experiences in the gaming industry, her travels to Japan, and the si…

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Accelerating Cybersecurity Deals: Channel-First Go-to-Market in Cybersecurity 35:37

4M ago35:37

35:37

Send me a text (I will personally respond) Are you struggling to differentiate your channel program in a crowded cybersecurity market? Wondering how to speed up your sales cycle and create more value for partners? Curious about what it takes to scale globally with varying partner expectations? If these questions hit home, this episode offers field-…

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From Startup to Rocket Ship: Building Doppel’s Hyper-Growth Sales Team 34:33

4M ago34:33

34:33

Send me a text (I will personally respond) Are you struggling to scale your cybersecurity sales from mid-market to enterprise? Wondering how to build a high-performance sales team that consistently generates pipeline? Curious about what it really takes to win enterprise clients—and keep them? This episode of the Cybersecurity Go-To-Market Podcast d…

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Steve Jesok’s Journey - From Rockstar to IT Rockstar 53:25

4M ago53:25

53:25

In this conversation, Steve Jesok shares his journey into the IT field, his involvement with user groups, and the evolution of community engagement in technology. He reflects on his early career, transitioning from a professional musician to an IT professional, and highlights the importance of user groups as resources for learning and networking. 0…

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Making “Channel First” Work (And Pay!) in Cybersecurity 24:29

5M ago24:29

24:29

Send me a text (I will personally respond) Are you struggling to scale your cybersecurity sales team effectively while launching a disruptive new product? Wondering how to build a winning go-to-market culture, especially when working channel-first? Trying to figure out how to attract and enable the right channel partners to drive real revenue growt…

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The New Era of Sales Enablement: Content When Reps Need It Most 46:29

5M ago46:29

46:29

Send me a text (I will personally respond) Are your sales reps struggling to implement the playbook you’ve invested so much in? Do you wish you could drive higher conversion rates without simply adding more headcount? Wondering how to use modern sales enablement to make your team smarter, faster, and more adaptive in every single call? This episode…

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Dean Ellerby on IT, AI, and Launching His YouTube Journey 58:16

5M ago58:16

58:16

In this engaging conversation with Dean Ellerby, he shares his journey through the tech industry, starting from his early experiences in a gaming company to becoming a consultant specializing in SCCM and Intune. He discusses the challenges and learning moments throughout his career, including his transition to content creation on YouTube during the…

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Community, AI, and the Future of IT with Mike Terrill 56:18

5M ago56:18

56:18

Fabian and Mike Terrill discuss a variety of topics ranging from the extreme weather in Phoenix to the intricacies of community engagement through user groups like azsmug. They delve into the challenges faced by user groups post-COVID, the evolution of systems management, and the future of device management in the context of AI. Mike shares valuabl…

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From Portraits to PowerShell: David Segura on Building OSDCloud 47:50

5M ago47:50

47:50

In this conversation, David Segura discusses the birth of OSDCloud, highlighting its popularity and the significant impact of automation in IT management. He also touches on future trends in system administration, emphasizing the importance of adapting to new technologies and I learn how down to earth he is! Chapters 00:00 Introduction to David Seg…

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Bryan Dam – Onesies, Sysadmin Life & Sneakernet Solutions 1:11:21

5M ago1:11:21

1:11:21

In this conversation, Bryan discusses his early experiences in IT management, particularly focusing on the unconventional methods he employed, such as the 'sneaker net' approach, to manage devices and install software. He reflects on the challenges and best practices he learned along the way. Chapters 00:00 Introduction and Background 03:47 Career …

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Matt Zaske’s Mustache Origin + Task Sequences in 2025 1:14:19

5M ago1:14:19

1:14:19

Matt Zaske, a seasoned sysadmin in higher ed, dives into device management, Windows 11 migration, and how his theater background shapes his IT communication. He shares his path into tech speaking, explores home automation, and showcases his passion for 3D printing and custom conference collectibles. We also learn the fun origin story of his iconic …

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Smallstep’s Groundbreaking Device Security: Lessons in Standards, Scale, and Startup Wins 17:00

5M ago17:00

17:00

Send me a text (I will personally respond) Are you struggling to convince enterprise buyers to trust your early-stage cybersecurity startup? Wondering how to differentiate technical innovation in a crowded market? Curious about how device identity and hardware-bound credentials can change the sales conversation? In this exciting episode, we dive de…

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The Most Significant Bottleneck for Security Operations? With Innovation Sandbox finalist Dov Yoran CEO at Command Zero. 18:35

5M ago18:35

18:35

Send me a text (I will personally respond) Are you struggling to help SOC teams move beyond alert fatigue and scale investigations effectively? Curious how innovative startups are transforming security operations by empowering analysts, not just automating them? Wondering what truly sets apart the next wave of cybersecurity platforms—and what you c…

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Securing AI in the Enterprise with Aurascape, RSA Innovation Sandbox Finalist 29:35

5M ago29:35

29:35

Send me a text (I will personally respond) Are you confident your organization’s data is secure as employees rapidly adopt new AI tools? Are current security gateways truly enough to protect sensitive information in the age of AI? How can visibility into AI app usage transform your go-to-market efforts in cybersecurity sales? If these questions hit…

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Crafting Precise ICPs for Better Cybersecurity Marketing Outcomes with Sri Sundaralingam 41:19

5M ago41:19

41:19

Send me a text (I will personally respond) Are you struggling with defining your ideal customer profile (ICP) while ensuring successful pipeline generation? How can you effectively balance investments in brand and pipeline to maximize ROI? Curious about strategies to differentiate your product in a crowded cybersecurity market? Dive into this episo…

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Big Rocks First: Prioritizing What Matters in Sales Onboarding 28:19

7M ago28:19

28:19

Send me a text (I will personally respond) 🤔 How can you ramp up new sales hires to deliver revenue within six months when your sales cycle is approximately the same length? 🤔 What are the essential components of an effective new hire onboarding program in the cybersecurity industry? 🤔 How does focusing on prospects and their challenges create cont…

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Role Plays vs. Real-Life Practice: Making Sales Training Work 47:46

8M ago47:46

47:46

Send me a text (I will personally respond) Are your seasoned sales reps struggling to adapt to new strategies? Have you ever invested heavily in sales training only to see minimal changes? How can you ensure training leads to real behavior change and improved sales performance? In this conversation we discuss: 👉 Why traditional sales training often…

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The Road to $10 Million ARR: Cyber Donut’s 2025 Sales and Marketing Playbook 25:39

8M ago25:39

25:39

Send me a text (I will personally respond) Are you struggling to increase your ASP and conversion rates? Does your sales team lack a unified approach to handling prospect questions? Are you eager to scale your ARR significantly in 2025? In this conversation, we discuss: 👉 How Cyber Donut achieved significant ARR growth from 2023 to 2024. 👉 The impo…

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Get PR like the well known companies get 48:38

8M ago48:38

48:38

Send me a text (I will personally respond) Are you struggling to get media attention for your cybersecurity startup? Wondering how to make your PR strategy stand out in a crowded market? Curious about the secrets behind successful media campaigns in cybersecurity? In this conversation we discuss: 👉 Original analysis and data vs. product promotion i…

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How to run a world-class POV with Alexei Rubenstein, VP of Sales, Engineering, and Customer Success at Morphisec 39:44

9M ago39:44

39:44

Send me a text (I will personally respond) Are you struggling to convert your Proof of Value (POV) to sales? Do your POV periods often extend beyond reasonable timelines? How can you involve multiple evaluators while keeping the process efficient and engaging? In this episode of Cybersecurity Go-To-Market Podcast, Alexei Rubinstein joins Andrew Mon…

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Rebranding vs. Distribution: What's Really Holding Cybr Donut Back? - Rob Sobers, CMO at Varonis 34:46

10M ago34:46

34:46

Send me a text (I will personally respond) Are you struggling to expand your cybersecurity company's market reach? Finding it challenging to get potential customers to notice your brand? Wondering if rebranding could be the silver bullet to boost your company's awareness? In this episode, Robert Sobers, CMO at Varonis, shares his expert advice on g…

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Interactive demos and demo experiences: Helping Cybr Donut sell more with better demos - Damian Tommasino, Founder at Cyber Informants 50:36

11M ago50:36

50:36

Send me a text (I will personally respond) Are you struggling to boost engagement during demos? Facing challenges in customizing sales conversations to resonate with prospects? Wondering how to improve your conversion rates from initial discussions to closed deals? In this episode of the Cybersecurity Go-To-Market Podcast, Damian Tommasino shares i…

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How to Hire Cybr Donut's GTM Leaders - Josh White, SVP of North America, Intaso 52:52

11M ago52:52

52:52

Send me a text (I will personally respond) Are you curious about the ideal timing for bringing in a senior sales or marketing leader? Not sure the right profile to hire? Need insights on avoiding decision paralysis in hiring? Have you ever faced the dilemma of hiring in industry or someone from another one? In this conversation we discuss: 👉 The be…