AE Prospecting: Yes or No?
Ever wondered why your outbound prospects ghost you faster than a bad Tinder date? You're not alone.
In this week's episode of B2B Outbound, hosts Chris and James sat down with Kevin Baumgart, founder of Set Sales and a sales veteran with over 20 years of experience. From selling copiers door-to-door in downtown Chicago to coaching high-growth tech companies, Kevin's seen it all.
Meet Kevin: The Sales Coaching Veteran
Kevin's journey started in the trenches – literally knocking on doors in Chicago with nothing but a briefcase full of business cards and a Rolodex for contact management. (Remember those?)
"I got kicked out of buildings and got locked in a stairwell on the 17th floor of an office building in downtown Chicago," Kevin recalls with a laugh. "Yeah, there's definitely some PTSD from that experience."
But that grind taught him everything. After cutting his teeth in door-to-door sales, Kevin transitioned into the startup world, helping early-stage software companies from pre-seed to series B scale their sales operations. Now, through Set Sales, he provides one-on-one coaching, fractional head of sales work, and custom training curriculum.
The #1 Challenge Every Sales Team Faces
When asked about the most recurring challenge he sees, Kevin doesn't hesitate:
"Opportunity creation. Lead generation. That new opportunity creation building that consistent pipeline."
It's not process optimization or closing techniques – it's getting quality opportunities in the door in the first place. As Kevin puts it, echoing wisdom from a VC board member: "Nothing happens until somebody sells something."
The Great AE Debate
This one's a hot topic. Should your star account executives be prospecting, or should they focus purely on closing?
Kevin's take is refreshingly practical: "Every org is different."
For early-stage companies with limited resources, AEs might need to wear multiple hats. But as organizations mature, Kevin advocates for specialization:
"If I have a really solid AE that is so good at running the sales process and getting deals over the finish line, I don't want them to do one prospecting call. I want them focused on that all day, every day."
The key? Clear role definition from day one. No surprises, no "I've paid my dues" attitudes.
Outbound vs. Inbound
Here's where things get interesting. Kevin breaks down the fundamental difference between converting inbound and outbound opportunities:
Inbound prospects know you. They reached out. They can usually articulate their need clearly.
Outbound prospects? Not so much. They haven't raised their hand, which means your sales process needs to be completely different.
The Discovery Deep Dive
For outbound opportunities, Kevin emphasizes going way deeper on discovery than you might with inbound leads:
"So many sales organizations do a really good job of uncovering needs and pain points, but they don't dial in impact behind that need and challenge."
It's not enough to know they have a problem. You need to understand:
- The impact on the business
- The impact on the team
- The impact on your champion personally
The Demo Disaster
Kevin has strong feelings about generic demos: "I see way too many demos that are, 'Hey, here's the functionality' and they go through all the pieces of functionality and every demo looks the same. It irks me."
Instead, your demo should be laser-focused on the specific pain points and impacts you uncovered in discovery.
The Tech Revolution: What's Working
The conversation naturally turned to the latest sales tech trends. Kevin's excited about tools like Gong, Clari, and conversation intelligence platforms:
"The days of not being able to analyze and review calls and look at data in the sales process and understand shortcomings and where funnel bleed is... sales leaders have such a different role today."
On AI voice agents? Kevin's cautiously optimistic but realistic about current limitations: "The quality is not there. There's a massive gray area from a legality perspective."
The Virtual Assistant Game Changer
One trend Kevin's particularly excited about? The rise of virtual assistants for sales teams:
"Instead of hiring a $70,000-$90,000 sales ops person, now they can hire 4, 5, 6, 7 virtual assistants."
He's seeing account executives with dedicated VAs helping with pipeline management, CRM updates, deal analysis, and proposal generation – support levels that were unthinkable just a few years ago.
Kevin's Golden Rules for Closing Outbound Deals
When pressed for his top advice for converting outbound opportunities, Kevin offered two game-changing insights:
1. Master Your Discovery Process
"If I had to give one piece of advice, it would be focus on discovery. Script it out, message it out, understand everything that you need to uncover prior to that discovery process."
Kevin emphasizes that when he does win-loss analysis, it almost always comes back to something that happened (or didn't happen) in the discovery stage.
2. Define Your Next Steps (Seriously)
"I find way too many salespeople end a call and there isn't defined next steps. Most importantly, time on the calendar with an invite sent with them accepting that invite."
Kevin believes getting ghosted isn't entirely the prospect's fault – it's often because we haven't done our job defining clear, valuable next steps.
The Process Evolution Challenge
In a world where tools, tactics, and technology change daily, how do you keep your sales process fresh without causing chaos?
Kevin advocates for treating your sales process as "a living, breathing document" but warns against constant changes:
"Yes, we should make improvements. But I think we got to be calculated and dialed in and communicate with the team... that doesn't mean we have to jump on every new tool right away."
His recommendation? Quarterly reviews of process and tooling, with clear communication to the team about any changes.
The Bottom Line
Outbound selling isn't broken – but it requires a fundamentally different approach than inbound. Success comes down to:
- Deeper discovery that uncovers not just pain, but impact
- Structured processes that guide prospects through each stage
- Clear next steps that keep momentum alive
- The right balance of human touch and technological efficiency
As Kevin puts it: "Use the insight you've gathered from discovery calls and refer back to it the whole way through the process."
Ready to Transform Your Outbound Game?
Kevin's insights are just the beginning. If you're struggling with outbound conversion rates, inconsistent pipeline, or want to build a sales process that actually works, this episode is essential listening.
Want to connect with Kevin? Find him at setsales.co or reach out at kevin@setsales.com for coaching and consulting that turns outbound challenges into closed deals.
Listen to the full episode to hear Kevin's complete framework for outbound success, plus war stories from the door-to-door days that'll make you appreciate your current sales challenges.


Ever wondered why your outbound prospects ghost you faster than a bad Tinder date? You're not alone.
In this week's episode of B2B Outbound, hosts Chris and James sat down with Kevin Baumgart, founder of Set Sales and a sales veteran with over 20 years of experience. From selling copiers door-to-door in downtown Chicago to coaching high-growth tech companies, Kevin's seen it all.
Meet Kevin: The Sales Coaching Veteran
Kevin's journey started in the trenches – literally knocking on doors in Chicago with nothing but a briefcase full of business cards and a Rolodex for contact management. (Remember those?)
"I got kicked out of buildings and got locked in a stairwell on the 17th floor of an office building in downtown Chicago," Kevin recalls with a laugh. "Yeah, there's definitely some PTSD from that experience."
But that grind taught him everything. After cutting his teeth in door-to-door sales, Kevin transitioned into the startup world, helping early-stage software companies from pre-seed to series B scale their sales operations. Now, through Set Sales, he provides one-on-one coaching, fractional head of sales work, and custom training curriculum.
The #1 Challenge Every Sales Team Faces
When asked about the most recurring challenge he sees, Kevin doesn't hesitate:
"Opportunity creation. Lead generation. That new opportunity creation building that consistent pipeline."
It's not process optimization or closing techniques – it's getting quality opportunities in the door in the first place. As Kevin puts it, echoing wisdom from a VC board member: "Nothing happens until somebody sells something."
The Great AE Debate
This one's a hot topic. Should your star account executives be prospecting, or should they focus purely on closing?
Kevin's take is refreshingly practical: "Every org is different."
For early-stage companies with limited resources, AEs might need to wear multiple hats. But as organizations mature, Kevin advocates for specialization:
"If I have a really solid AE that is so good at running the sales process and getting deals over the finish line, I don't want them to do one prospecting call. I want them focused on that all day, every day."
The key? Clear role definition from day one. No surprises, no "I've paid my dues" attitudes.
Outbound vs. Inbound
Here's where things get interesting. Kevin breaks down the fundamental difference between converting inbound and outbound opportunities:
Inbound prospects know you. They reached out. They can usually articulate their need clearly.
Outbound prospects? Not so much. They haven't raised their hand, which means your sales process needs to be completely different.
The Discovery Deep Dive
For outbound opportunities, Kevin emphasizes going way deeper on discovery than you might with inbound leads:
"So many sales organizations do a really good job of uncovering needs and pain points, but they don't dial in impact behind that need and challenge."
It's not enough to know they have a problem. You need to understand:
- The impact on the business
- The impact on the team
- The impact on your champion personally
The Demo Disaster
Kevin has strong feelings about generic demos: "I see way too many demos that are, 'Hey, here's the functionality' and they go through all the pieces of functionality and every demo looks the same. It irks me."
Instead, your demo should be laser-focused on the specific pain points and impacts you uncovered in discovery.
The Tech Revolution: What's Working
The conversation naturally turned to the latest sales tech trends. Kevin's excited about tools like Gong, Clari, and conversation intelligence platforms:
"The days of not being able to analyze and review calls and look at data in the sales process and understand shortcomings and where funnel bleed is... sales leaders have such a different role today."
On AI voice agents? Kevin's cautiously optimistic but realistic about current limitations: "The quality is not there. There's a massive gray area from a legality perspective."
The Virtual Assistant Game Changer
One trend Kevin's particularly excited about? The rise of virtual assistants for sales teams:
"Instead of hiring a $70,000-$90,000 sales ops person, now they can hire 4, 5, 6, 7 virtual assistants."
He's seeing account executives with dedicated VAs helping with pipeline management, CRM updates, deal analysis, and proposal generation – support levels that were unthinkable just a few years ago.
Kevin's Golden Rules for Closing Outbound Deals
When pressed for his top advice for converting outbound opportunities, Kevin offered two game-changing insights:
1. Master Your Discovery Process
"If I had to give one piece of advice, it would be focus on discovery. Script it out, message it out, understand everything that you need to uncover prior to that discovery process."
Kevin emphasizes that when he does win-loss analysis, it almost always comes back to something that happened (or didn't happen) in the discovery stage.
2. Define Your Next Steps (Seriously)
"I find way too many salespeople end a call and there isn't defined next steps. Most importantly, time on the calendar with an invite sent with them accepting that invite."
Kevin believes getting ghosted isn't entirely the prospect's fault – it's often because we haven't done our job defining clear, valuable next steps.
The Process Evolution Challenge
In a world where tools, tactics, and technology change daily, how do you keep your sales process fresh without causing chaos?
Kevin advocates for treating your sales process as "a living, breathing document" but warns against constant changes:
"Yes, we should make improvements. But I think we got to be calculated and dialed in and communicate with the team... that doesn't mean we have to jump on every new tool right away."
His recommendation? Quarterly reviews of process and tooling, with clear communication to the team about any changes.
The Bottom Line
Outbound selling isn't broken – but it requires a fundamentally different approach than inbound. Success comes down to:
- Deeper discovery that uncovers not just pain, but impact
- Structured processes that guide prospects through each stage
- Clear next steps that keep momentum alive
- The right balance of human touch and technological efficiency
As Kevin puts it: "Use the insight you've gathered from discovery calls and refer back to it the whole way through the process."
Ready to Transform Your Outbound Game?
Kevin's insights are just the beginning. If you're struggling with outbound conversion rates, inconsistent pipeline, or want to build a sales process that actually works, this episode is essential listening.
Want to connect with Kevin? Find him at setsales.co or reach out at kevin@setsales.com for coaching and consulting that turns outbound challenges into closed deals.
Listen to the full episode to hear Kevin's complete framework for outbound success, plus war stories from the door-to-door days that'll make you appreciate your current sales challenges.