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

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📤 Share this episode with someone building something meaningful

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.

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

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🔔 Subscribe for more interviews with leaders shaping the future of remote work

📤 Share this episode with your team or network