Remote First Innovators

Building with Intention in High-Growth Environments | Josh Oliver | EP 107

In this episode, Josh Oliver joins the show for a candid conversation about leadership, entrepreneurship, and building companies with intention rather than ego.Josh shares his journey through startups, acquisitions, and high-growth environments, offering honest reflections on what it takes to scale responsibly while staying grounded. He speaks openly about decision-making, learning through failure, and why clarity of values matters more than speed when building something that lasts.Throughout the conversation, Josh emphasizes the importance of self-awareness, surrounding yourself with the right people, and resisting the pressure to chase every opportunity. His perspective offers a practical and human look at leadership in environments where momentum, risk, and ambition collide.This episode is especially valuable for founders, operators, and leaders navigating growth without losing alignment.⏱ Timestamps00:00 — Welcome and episode intro 00:49 — Introducing Josh Oliver 01:38 — Early career path and entrepreneurship 03:21 — Learning through building and selling companies 05:04 — Leadership lessons from growth stages 07:12 — Decision-making under pressure 09:44 — Knowing when to say no 12:16 — The cost of chasing everything 14:05 — Building teams you trust 16:37 — Ego, humility, and leadership maturity 18:58 — Learning from failure 21:31 — Values-based leadership 24:09 — Staying grounded as momentum grows 26:47 — Advice for founders and operators 29:14 — Final reflections and close📣 CALL TO ACTIONIf this episode resonated with you: 👍 Like the video 💬 Comment with your biggest takeaway 🔔 Subscribe for more leadership and founder conversations 📤 Share this episode with someone building something meaningful

Selling Without Pitching in a Remote-First World | Brian K. McNeill | EP 106

In this episode of Remote First Innovators, host Jake Gump sits down with Brian K. McNeill, sales coach, keynote speaker, and author of nine books including Timid Entrepreneurs Have Skinny Kids and Mastering Sales Language.With over 30 years of experience teaching entrepreneurs how to sell without pitching, Brian breaks down why traditional sales tactics no longer work — especially in a remote-first world. This conversation dives deep into storytelling over pitching, why being “likable” isn’t enough, and how sales today is really about helping people move forward with confidence.From mastering virtual presence on Zoom to understanding why people actually say yes, Brian shares practical frameworks, mindset shifts, and language changes that help sales leaders, founders, and remote teams sell more effectively — without pressure, manipulation, or gimmicks.If you’re building trust, selling services remotely, or leading distributed teams, this episode will fundamentally change how you think about sales.⏱️ TIMESTAMPS00:00 – Welcome to Remote First Innovators 00:27 – Introducing Brian K. McNeill 01:22 – Selling without pitching 01:50 – The shift from in-person to remote selling 02:56 – Scaling impact through virtual workshops 03:38 – Why remote selling increased reach and revenue 04:48 – Building trust fast on Zoom 05:25 – Letting prospects realize what they don’t know 06:41 – Why people don’t buy (even when they like you) 07:53 – Time and money as buying motivators 08:35 – Daily habits that elevate sales performance 09:46 – Champions practice before the game 10:46 – The four questions that reveal sales clarity 11:52 – Why elevator pitches fail 13:32 – Storytelling instead of pitching 14:23 – Defining who should buy from you 15:23 – What you call your clients reveals your business 16:49 – Identifying the real problem you solve 17:11 – Turning agreement into momentum 18:58 – Introducing yourself as the solution 21:46 – Why benefits matter more than features 23:14 – “Lucky them” mindset in sales 25:22 – How to avoid sounding pitchy 26:26 – Giving value before asking 28:27 – Why offering help is not selfish 29:17 – Why “know, like, trust” is incomplete 31:31 – The danger of being too likable 32:26 – Asking for business confidently 33:46 – The psychology of asking 35:42 – “Will you give us a try?” 37:08 – Eliminating negative sales thoughts 38:27 – High-probability vs low-probability selling 40:16 – Why logic must support the yes 42:33 – Letting clients articulate the value 44:12 – Failing forward and building systems 46:17 – Systems outperform personality 48:29 – No pitches, no deals — only offers 49:40 – Mastering sales language 52:04 – Helping vs selling 54:08 – Mentors and lifelong learning 56:23 – Where to find Brian 58:16 – Final advice for entrepreneurs 59:02 – Subscribe, rate & share🎧 CALL TO ACTION👉 Subscribe to Remote First Innovators for real-world insights on scaling distributed teams. 👍 Like the episode and drop your biggest takeaway in the comments. 🔔 Turn on notifications so you don’t miss future episodes. 📩 Share this with a founder or sales leader navigating remote selling.

Voice That Scales for Remote Teams | Cameron Bolinger | EP 105

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.⏱ Timestamps00:00 — Welcome to Remote First Innovators00:27 — Show introduction00:45 — Guest intro: Cameron Bolinger01:11 — The origins of CytraCom01:35 — How CytraCom evolved from PBX to full unified communications02:05 — Remote work adoption during COVID03:13 — Voice, text, fax & collaboration under one platform04:09 — Supporting remote and hybrid teams04:31 — The role of hardware in remote connectivity05:22 — 24/7 US-based support06:08 — Work-life balance through smart routing07:10 — Separating work and personal calls08:12 — Texting vs calling: meeting modern preferences09:02 — Shared inbox explained09:53 — Industries that benefit most10:20 — The overnight onboarding story11:48 — Handling complex phone migrations12:15 — Challenges with legacy phone systems12:57 — Making cloud communication feel seamless13:22 — How shared inbox was created14:21 — Customer feedback shaping product roadmap15:07 — Partner-driven support model16:01 — VoIP vs UCaaS explained16:27 — Will desk phones disappear?17:43 — Deciding which tech innovations matter18:11 — Why simplicity wins18:34 — AI expectations vs practical value19:38 — Where AI could truly help20:01 — AI and the future of call centers21:09 — Limitations of AI today21:34 — Compliance and security in communication22:01 — SOC2, HIPAA, PCI — how CytraCom handles sensitive data22:29 — FOIA request success story23:13 — Why fast response matters23:33 — Spam calls & FCC texting rules24:26 — Blocking spam across devices25:02 — The 10DLC registration challenges26:10 — Making compliance easier during onboarding26:39 — What phone system switching feels like for users27:35 — Adding users for seasonal or fast-growing teams28:18 — Provisioning new users in hours28:47 — Consistency across devices29:23 — Desk phone call quality29:41 — Ease of use30:31 — Why CytraCom stands out for IT directors31:15 — Month-to-month flexibility31:39 — Hardware included at no additional cost32:00 — US-based support32:20 — Phone upgrade cycle32:43 — Expanding beyond phones33:07 — Control One: network management & SASE33:52 — Telivy: vulnerability & AI usage scans34:45 — Endorsements from partners35:38 — Redundant data centers36:10 — How calls stay online during outages36:35 — Staying connected worldwide37:00 — Cameron’s career arc: Dish → Gartner → CytraCom38:36 — Discovering the tech industry39:04 — Working in the channel39:32 — Mentors who shaped Cameron’s career40:19 — Lessons from early role models41:34 — “We’re all just figuring it out.”42:21 — Final reflections43:12 — Closing thoughts and appreciation44:12 — Outro and reminders📣 Call to ActionIf you found this episode helpful:👍 Like the video💬 Comment with your biggest takeaway🔔 Subscribe for more interviews with leaders shaping the future of remote work📤 Share this episode with your team or network

Preparedness, Compliance & the Future of Remote Work | Liam Martin | EP 104

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 Points00:00 – Intro and why remote work isn’t going anywhere05:12 – The G20 “half a million seats overnight” story10:48 – What COVID taught leaders about scale and chaos14:20 – Black swan thinking: how to stay adaptable18:33 – The 2025 Remote Stack: security, documentation, async25:10 – The three tools every remote team should start with30:34 – How Time Doctor is using AI (and what’s coming next)36:50 – Productivity benchmarks and what leaders really want41:55 – The truth about SOC 2, compliance, and million-dollar deals50:02 – Why “secure” and “compliant” are not the same thing56:28 – Mouse jigglers, overemployment, and the trust crisis1:05:40 – How accountability should work in remote teams1:10:30 – Entrepreneurship, failure, and doing hard things1:18:20 – A challenge for leaders: run an asynchronous week1:22:05 – Where to find Liam + Running Remote resourcesIf 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

Why South Africa is the Secret Weapon for Building World-Class Remote Teams | Michael Bassin | EP103

8 Tools in 1: John Moffa Shows How Roam Creates Real Office Culture in Remote Team | John Moffa | Remote First Innovators | EP 102

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/monthThe visual office map creates transparency, accountability, and cultureMagic Minutes provides AI-powered meeting summaries with ChatGPT integrationDrop-in availability recreates spontaneous office interactionsGlobal hiring becomes seamless with visual presence indicatorsVirtual assistants democratize AI access across entire organizationsResources MentionedRoam Website: roam.coFree Trial: Available with both self-serve and white-glove onboardingConnect with John MoffaCompany: Roam (roam.co)Role: Head of Customer ExperienceBackground: 8 years at Yext, MBA from Baruch College, BA from James Madison UniversityTimestamps00:00 - Welcome & Introduction01:05 - Meet John Moffa: From Yext to Roam02:11 - The transition story: Why John joined Roam03:25 - The virtual office vision: Recreating Yext's amazing culture digitally05:16 - The problem with Slack + Zoom combinations07:04 - Building with a trusted team: The family aspect08:33 - The visual magic: How Joe Woodward brings Roam to life10:07 - The Super Bundle: 8 products for the price of one12:20 - Audio/visual quality: 99%+ satisfaction scores13:27 - Magic Minutes: AI note-taking that lives in your inbox16:19 - Breaking down the $18/month value proposition17:26 - The AI revolution: Virtual assistants for everyone19:28 - Real-world case study: Hiring talent in Dubai21:20 - The "meeting after the meeting" problem solved23:31 - Fun features: Emojis, game rooms, and personality shelves26:18 - AI Inbox: The Slack killer explained27:47 - Lobby feature: Virtual salesroom for prospects30:42 - The future of remote business in 202531:26 - John's origin story: Long Island roots32:05 - The fourth-grade robot that started it all34:15 - Mentors who shaped the journey37:45 - How to get started with Roam38:48 - Final thoughts and wrap-upReady 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.

The Future of Remote Work: Insights for 2025 and Beyond | Remote First Innovators | EP 101

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 LaunchWhat We Cover:Why remote work in 2025 is fundamentally different than 2020The compliance frameworks that now have real teethSecurity blind spots that could sink your companyDevice management and data protection across time zonesBuilding security culture from the top downAI governance and the tools you should (and shouldn't) allowThe Remote Operating System launching in 2026SUBSCRIBE NOW for bi-weekly conversations with founders, ops leaders, and innovators doing remote work right.

Remote First Innovators Podcast

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