Remote First Innovators

Robert Phelps and Jake Gump
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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

Episodes

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

    JAN 13

    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. ⏱ Timestamps 00:00 — 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 ACTION If 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

    1h 6m
  2. Selling Without Pitching in a Remote-First World | Brian K. McNeill | EP 106

    12/24/2025

    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. ⏱️ TIMESTAMPS 00:00 – 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.

    1 hr
  3. Voice That Scales for Remote Teams | Cameron Bolinger | EP 105

    12/03/2025

    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. ⏱ 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: 👍 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

    45 min
  4. Preparedness, Compliance & the Future of Remote Work | Liam Martin | EP 104

    11/18/2025

    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 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

    1h 14m
  5. Why South Africa is the Secret Weapon for Building World-Class Remote Teams | Michael Bassin | EP103

    11/04/2025

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

    Remote First Innovators

    1h 20m
  6. 8 Tools in 1: John Moffa Shows How Roam Creates Real Office Culture in Remote Team | John Moffa | Remote First Innovators | EP 102

    10/21/2025

    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/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.

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

    10/07/2025

    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 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.

    47 min
  8. Remote First Innovators Podcast

    09/24/2025

    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

    1 min

Trailer

About

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

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