Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-josh-og-sales

Episode Summary:

In this episode of the Next Gen Sales Leaders Podcast, Ben Reed sits down with Josh Gillespie, former Enterprise Sales Director at PandaDoc and former Head of Growth at Aomni. Josh shares his journey into enterprise sales and breaks down why disqualification, deep ICP research, and human intelligence still outperform AI-driven outbound in today’s noisy market.

What You’ll Learn:

- How Josh entered sales through a non-traditional career path

- What enterprise sales actually looks like behind the scenes

- Why most RFPs should be disqualified early

- How the Zero Interest Rate Period (ZIRP) reshaped SaaS sales

- Why AI has saturated outbound channels and reduced effectiveness

- How top sellers gather insight humans, not bots, can uncover

- Why close-lost deals are critical to long-term growth

Episode Highlights:

[00:01:32] From philosophy major to first sales role at Yelp

[00:03:58] Building PandaDoc from $0 in revenue

[00:13:07] Equity vs. cash tradeoffs in venture-backed startups

[00:17:10] Why unqualified RFPs are usually a trap

[00:21:00] Enterprise sales as detective work, not pitching

[00:40:53] How AI has hurt email, phone, and LinkedIn outreach

[01:02:00] Learning more from lost deals than won deals

Featured Guest:

Josh Gillespie - Head of Growth at Aomni, Sales Coach & Mentor at AlwaysHired, Founding AE at PandaDoc

Connect with Josh:

LinkedIn: https://www.linkedin.com/in/ogsalesjosh/

Host:

Ben Reed - Host of the Next Gen Sales Leaders Podcast

Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/

Love this episode? Subscribe to the Next Gen Sales Leaders Podcast for expert insights on B2B sales, GTM strategy, growth, and RevOps. If you found value in today’s episode, please leave us a review.

Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-josh-og-sales

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-teodora-v

Episode Summary:

In this episode of the Next Gen Sales Leaders Podcast, Ben Reed sits down with Teodora Vukasinovic, a B2B growth strategist and LinkedIn expert, to explore why there is no such thing as a perfect strategy. Teodora breaks down how over-reliance on AI, templates, and “guru frameworks” is hurting modern GTM efforts, and why deep ICP understanding, active listening, and authentic messaging are the real levers of sustainable growth. The conversation dives into market research, copywriting psychology, multichannel outreach, and why many founders get stuck scaling past the $1-5M revenue range.

What You’ll Learn:

- Why “perfect strategies” don’t exist in B2B growth

- How AI and templated outreach are eroding trust and credibility

- Why deep ICP research beats automation at every stage

- How to conduct meaningful customer interviews using the Mom Test

- Why messaging is psychology, not just words on a screen

- How to structure multichannel outreach that actually converts

- Why generic ghostwriting damages brand reputation

- How self-awareness and authenticity drive better GTM decisions

Featured Guest:

Teodora - B2B Growth Strategist, founder of HotTake.ly

Host:

Ben Reed, Host of the Next Gen Sales Leaders Podcast

Episode Highlights:

[00:01:11] Why LinkedIn gurus, templates, and frameworks fail across markets

[00:06:10] How founders accidentally scale the wrong ICP

[00:12:12] The danger of falling in love with your solution instead of the problem

[00:28:00] Structuring effective multichannel outreach and follow-ups

[00:38:37] Why AI-generated messaging kills differentiation

[00:41:05] Why ghostwriting is often a waste of money and reputation

Connect with Teo:

LinkedIn: https://www.linkedin.com/in/teodoravukasinovic/

YouTube: https://www.youtube.com/channel/UCOZuemv4x3MFoJhSXwzXV5Q

Follow Ben on Social:

LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/

Love this episode? Subscribe to the Next Gen Sales Leaders Podcast for expert insights on B2B sales, GTM strategy, growth, and RevOps. If you found value in today’s episode, please leave us a review.

Join our B2B GTM & RevOps Entrepreneur Community:

https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-teodora-v

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-justin-kroeger

Episode Summary:

In this episode of the Next Gen Sales Leaders Podcast, Ben Reed sits down with Justin Kroeger, Founder of HiveSight, to unpack why outbound is breaking in the age of AI. Justin shares why trust, not scale is the real GTM bottleneck, how fake personalization has eroded buyer confidence, and why familiarity and third-party credibility outperform automation. Together, they explore when LinkedIn content actually works, why early-stage founders should avoid scaling too early, and how doing things that don’t scale still drives real B2B traction.

What You’ll Learn:

- Why outbound reply rates are declining despite better AI tools

- Why trust and believability matter more than personalization

- How familiarity and third-party credibility accelerate sales

- When LinkedIn content helps and when it hurts GTM efforts

- Why early-stage founders should avoid automation and scale manually

- How to validate offers through design partnerships

- Why niche credibility beats virality in B2B markets

- The hidden risks of scaling the wrong message

Featured Guest:

Justin Kroeger - Founder, HiveSight

Host:

Ben Reed, Host of the Next Gen Sales Leaders Podcast

Episode Highlights:

[00:01:00] Why AI-driven outbound is increasing noise and modern buyer skepticism

[00:04:36] Founder bias and the power of third-party credibility

[00:14:17] Why viral LinkedIn content doesn’t convert in B2B

[36:00:00] When founders should not invest in content marketing

[47:05:00] Doing things that don’t scale to reach first revenue

[59:40:00] Design partnerships and early GTM validation

[01:04:22] The cost of scaling unproven messaging

[01:06:00] Justin’s final advice on trust and GTM discipline

Connect with Justin:

LinkedIn: https:https://www.linkedin.com/in/jkroeger123/

Website: https://hivesight.so/

Follow Ben on Social:

LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/

Love this episode? Subscribe to the Next Gen Sales Leaders Podcast for expert insights on B2B sales, GTM strategy, and leadership. If you found value in today’s episode, please leave us a review.

Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-justin-kroeger