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Remote First Innovators

Remote First Innovators

Written by: Robert Phelps and Jake Gump
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About this listen

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

Economics Leadership Management Management & Leadership
Episodes
  • Building with Intention in High-Growth Environments | Josh Oliver | EP 107
    Jan 13 2026

    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

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    1 hr and 6 mins
  • Selling Without Pitching in a Remote-First World | Brian K. McNeill | EP 106
    Dec 24 2025

    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.

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    1 hr
  • Voice That Scales for Remote Teams | Cameron Bolinger | EP 105
    Dec 3 2025

    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

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    45 mins
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