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

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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:

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