In this episode of Remote First Innovators, Jake sit down with Cameron Bolinger of CytraCom — a leader in unified communications built for modern, distributed teams. From overnight phone-system migrations to the evolution of VoIP, AI, compliance, remote-work connectivity, and what it really takes to keep teams running smoothly, Cameron reveals how companies can stay connected without complication.

Whether you're scaling a distributed workforce, modernizing legacy phone systems, or navigating compliance and security in a digital world, this conversation offers valuable, real-world insight from someone who has lived it for over a decade.

⏱ Timestamps

00:00 — Welcome to Remote First Innovators

00:27 — Show introduction

00:45 — Guest intro: Cameron Bolinger

01:11 — The origins of CytraCom

01:35 — How CytraCom evolved from PBX to full unified communications

02:05 — Remote work adoption during COVID

03:13 — Voice, text, fax & collaboration under one platform

04:09 — Supporting remote and hybrid teams

04:31 — The role of hardware in remote connectivity

05:22 — 24/7 US-based support

06:08 — Work-life balance through smart routing

07:10 — Separating work and personal calls

08:12 — Texting vs calling: meeting modern preferences

09:02 — Shared inbox explained

09:53 — Industries that benefit most

10:20 — The overnight onboarding story

11:48 — Handling complex phone migrations

12:15 — Challenges with legacy phone systems

12:57 — Making cloud communication feel seamless

13:22 — How shared inbox was created

14:21 — Customer feedback shaping product roadmap

15:07 — Partner-driven support model

16:01 — VoIP vs UCaaS explained

16:27 — Will desk phones disappear?

17:43 — Deciding which tech innovations matter

18:11 — Why simplicity wins

18:34 — AI expectations vs practical value

19:38 — Where AI could truly help

20:01 — AI and the future of call centers

21:09 — Limitations of AI today

21:34 — Compliance and security in communication

22:01 — SOC2, HIPAA, PCI — how CytraCom handles sensitive data

22:29 — FOIA request success story

23:13 — Why fast response matters

23:33 — Spam calls & FCC texting rules

24:26 — Blocking spam across devices

25:02 — The 10DLC registration challenges

26:10 — Making compliance easier during onboarding

26:39 — What phone system switching feels like for users

27:35 — Adding users for seasonal or fast-growing teams

28:18 — Provisioning new users in hours

28:47 — Consistency across devices

29:23 — Desk phone call quality

29:41 — Ease of use

30:31 — Why CytraCom stands out for IT directors

31:15 — Month-to-month flexibility

31:39 — Hardware included at no additional cost

32:00 — US-based support

32:20 — Phone upgrade cycle

32:43 — Expanding beyond phones

33:07 — Control One: network management & SASE

33:52 — Telivy: vulnerability & AI usage scans

34:45 — Endorsements from partners

35:38 — Redundant data centers

36:10 — How calls stay online during outages

36:35 — Staying connected worldwide

37:00 — Cameron’s career arc: Dish → Gartner → CytraCom

38:36 — Discovering the tech industry

39:04 — Working in the channel

39:32 — Mentors who shaped Cameron’s career

40:19 — Lessons from early role models

41:34 — “We’re all just figuring it out.”

42:21 — Final reflections

43:12 — Closing thoughts and appreciation

44:12 — Outro and reminders

📣 Call to Action

If you found this episode helpful:

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When remote work exploded overnight, most leaders scrambled to adapt. Liam Martin helped shape the playbook.

In this conversation, we dig into the realities of scaling distributed teams, what compliance really costs you, why trust is breaking inside hybrid workplaces, how AI is rewriting the rules of work, and the uncomfortable truths leaders need to confront in 2025.

No fluff—just honest stories, clear frameworks, and battle-tested lessons you can put to work immediately.

Key Discussion Points

00:00 – Intro and why remote work isn’t going anywhere

05:12 – The G20 “half a million seats overnight” story

10:48 – What COVID taught leaders about scale and chaos

14:20 – Black swan thinking: how to stay adaptable

18:33 – The 2025 Remote Stack: security, documentation, async

25:10 – The three tools every remote team should start with

30:34 – How Time Doctor is using AI (and what’s coming next)

36:50 – Productivity benchmarks and what leaders really want

41:55 – The truth about SOC 2, compliance, and million-dollar deals

50:02 – Why “secure” and “compliant” are not the same thing

56:28 – Mouse jigglers, overemployment, and the trust crisis

1:05:40 – How accountability should work in remote teams

1:10:30 – Entrepreneurship, failure, and doing hard things

1:18:20 – A challenge for leaders: run an asynchronous week

1:22:05 – Where to find Liam + Running Remote resources

If this conversation gave you something to think about, don’t forget to:

👍 Give this episode a like

🔔 Subscribe so you never miss these deep-dive conversations

💬 Drop a comment sharing your biggest insight about remote work or AI

🔗 Share this with another leader who’s navigating distributed teams

#RemoteWork #FutureOfWork #AIProductivity #Leadership #SaaS #Compliance #TimeDoctor #RunningRemote #AsyncWork #RemoteTeams #Entrepreneurship #DigitalTransformation

In this episode, host Jake Gump sits down with John Moffa, Head of Customer Experience at Roam, to explore how virtual offices are revolutionizing remote work culture. John shares his journey from 8 years at Yext leading IT operations to building something groundbreaking at Roam - a platform that's replacing entire tech stacks with one comprehensive solution.

Discover how Roam's "Super Bundle" replaces 8 different tools (Slack, Zoom, Calendly, Loom, and more) for just $18/month, while creating the digital office culture that remote teams have been missing. From Magic Minutes AI note-taking to drop-in availability features that recreate spontaneous office interactions, John breaks down how Roam is solving the biggest challenges in remote work.

Whether you're a startup founder, remote team leader, or just curious about the future of work, this conversation reveals practical insights on building culture, managing global teams, and leveraging AI to enhance productivity.

🔔 Don't forget to SUBSCRIBE to Remote First Innovators for more insights on building successful remote companies and scaling distributed teams!

Key Takeaways:

Roam replaces 8 different software tools with one platform for $18/month

The visual office map creates transparency, accountability, and culture

Magic Minutes provides AI-powered meeting summaries with ChatGPT integration

Drop-in availability recreates spontaneous office interactions

Global hiring becomes seamless with visual presence indicators

Virtual assistants democratize AI access across entire organizations

Resources Mentioned

Roam Website: roam.co

Free Trial: Available with both self-serve and white-glove onboarding

Connect with John Moffa

Company: Roam (roam.co)

Role: Head of Customer Experience

Background: 8 years at Yext, MBA from Baruch College, BA from James Madison University

Timestamps

00:00 - Welcome & Introduction

01:05 - Meet John Moffa: From Yext to Roam

02:11 - The transition story: Why John joined Roam

03:25 - The virtual office vision: Recreating Yext's amazing culture digitally

05:16 - The problem with Slack + Zoom combinations

07:04 - Building with a trusted team: The family aspect

08:33 - The visual magic: How Joe Woodward brings Roam to life

10:07 - The Super Bundle: 8 products for the price of one

12:20 - Audio/visual quality: 99%+ satisfaction scores

13:27 - Magic Minutes: AI note-taking that lives in your inbox

16:19 - Breaking down the $18/month value proposition

17:26 - The AI revolution: Virtual assistants for everyone

19:28 - Real-world case study: Hiring talent in Dubai

21:20 - The "meeting after the meeting" problem solved

23:31 - Fun features: Emojis, game rooms, and personality shelves

26:18 - AI Inbox: The Slack killer explained

27:47 - Lobby feature: Virtual salesroom for prospects

30:42 - The future of remote business in 2025

31:26 - John's origin story: Long Island roots

32:05 - The fourth-grade robot that started it all

34:15 - Mentors who shaped the journey

37:45 - How to get started with Roam

38:48 - Final thoughts and wrap-up

Ready to transform your remote team's culture and productivity? Try Roam's free trial at roam.co and experience the future of virtual offices today!

The Remote First Innovators podcast is produced by Creative IT. Subscribe wherever you get your podcasts for insights on building thriving remote organizations with practical solutions you can implement immediately.

Welcome to Remote First Innovators, the podcast for leaders and operators scaling remote-first companies.

In our debut episode, host Jake Gump sits down with Robert Phelps, President of Creative IT, to explore the real operational challenges of building and scaling distributed teams. From filmmaking to Apple to leading one of the Southeast's most trusted IT firms, Robert brings unique insights from supporting over 130 remote-first companies.

CHAPTER TIMESTAMPS:

0:00 - Welcome & Why This Podcast Exists

3:09 - Why 2025 is Different for Remote Work

6:18 - The Moment Remote Became More Than a Trend

9:12 - Data Security Risks Remote Companies Miss

12:01 - The Compliance Wake-Up Call (SOC2, CMMC, HIPAA)

16:33 - Must-Have Policies for Remote Teams

18:17 - Incident Response & IT Hygiene Basics

23:22 - Culture Over Technology: The Real Compliance Secret

26:16 - AI Training Done Right

30:01 - Essential Tools for Remote-First Companies

32:07 - AI Security Risks You Need to Know

36:04 - Robert's Journey: From Filmmaking to Creative IT

40:51 - Leadership Lessons & Mistakes Made

43:33 - What's Next: Remote Operating System & Book Launch

What We Cover:

• Why remote work in 2025 is fundamentally different than 2020
• The compliance frameworks that now have real teeth
• Security blind spots that could sink your company
• Device management and data protection across time zones
• Building security culture from the top down
• AI governance and the tools you should (and shouldn't) allow
• The Remote Operating System launching in 2026

SUBSCRIBE NOW for bi-weekly conversations with founders, ops leaders, and innovators doing remote work right.

Remote First Innovators Podcast is for leaders scaling companies operating outside the normal office convention. The show breaks down the operational engines, tools, workflows, and decisions that drive distributed work at scale. It’s built for those tackling trust, communication and operations across time zones.

Conversations feature founders and operators shaping high output remote organizations. Topics range from async workflows and automation to scaling work from home teams and decision-making. Listeners gain a advantage by learning from those leaders who have been there, and overcome remote-first challenges