[SaaS & Sales Series] The Skill–Will Blueprint for Modern Sales Organizations With Bart Fanelli

Bart Fanelli is the CEO and Co-founder of Skillibrium, an AI-driven revenue operating platform that aligns learning, execution, and coaching to help organizations scale high-performance revenue teams. With more than 25 years of revenue leadership experience, he has played key roles in scaling enterprise software companies, including Splunk, during a period of significant hypergrowth. He has worked with organizations from pre-IPO through post-IPO stages and is the co-author of The Success Cadence. Bart is recognized for building structured coaching frameworks that combine operational discipline with human-centered leadership.

Here’s a glimpse of what you’ll learn:

• [4:23] Bart Fanelli on unifying revenue teams with an AI-driven operating model
• [6:18] 8×8 case study and aligning revenue teams around value mapping
• [9:12] Bart’s strategy for beating the Forgetting Curve so training actually sticks
• [14:04] Why proactive outbound is essential to escape obscurity and fuel pipeline growth
• [22:05] How becoming coachable transformed Bart’s leadership and accelerated his career
• [29:14] Mastering sales discovery and the Magnificent Nine questioning method
• [33:12] Common sales discovery mistakes and the importance of pre-call research
• [37:13] Overcoming ADHD and dyslexia through self-learning and mentorship

In this episode…

Scaling high-performance revenue teams while keeping sales, customer success, and leadership aligned is challenging. Fragmented training, slow onboarding, and the Forgetting Curve weaken momentum. How can AI and structured coaching build a unified, continuously improving revenue engine?

Bart Fanelli, a revenue operations leader and enterprise sales strategist, faced these challenges while scaling high-growth technology companies. With more than two decades of field and leadership experience, he has built repeatable systems that align sales, customer success, and executives around a shared cadence. Bart champions role-based playbooks and daily reinforcement within real workflows. He focuses on aligning “skill and will.” He explains that consistent coaching rhythms and candid conversations drive accountability, adoption, and measurable growth.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Bart Fanelli, CEO and Co-founder at Skillibrium, to discuss scaling revenue teams through AI and operational discipline. Bart shares the Magnificent Nine discovery framework and practical ways to beat the forgetting curve. He also explains how to build a coaching culture that sustains long-term growth.

Resources mentioned in this episode:

• Bart Fanelli on LinkedIn
• Skillibrium
• Splunk
• OutSystems
• BMC Software
• Behavox
• 8×8
• Sandler Training
• Harvard Business Review
• Skill Will Framework
• Master Continuous Sales Discovery
• The Forgetting Curve
• The Success Cadence by David Mattson, Tom Schodorf, and Bart Fanelli
• Succeeding When You’re Supposed to Fail: The 6 Enduring Principles of High Achievement by Rom Brafman

Special mentions:

• Tom Schodorf on LinkedIn
• Steve Rowland on LinkedIn
• Dave Mattson on LinkedIn

Related episodes:

• “[AI Series] AI Tools That Transform Your Business With Nicole Donnelly” on Inspired Insider Podcast
• “[AI & Agency Series] AI-Powered Lead Generation and Automation for Agencies With Ken McLoud” on Inspired Insider Podcast
• “[SaaS & AI Series] Future-Proofing Your Marketing With Jason Patel” on Inspired Insider Podcast
• “EO Atlanta | You Can Have It All With Ethan King, Co-Founder of Zeus’ Closet” on Inspired Insider Podcast

Quotable moments:

• “Hard conversations are the best way to scale companies. As long as you do it with passion or with adult-like tone, it’s never an implication on the person.”
• “Your ability and your willingness to learn the skills are what matter most. And that’s why the framework is exceptional for scaling high-performance teams.”
• “AI is amazing, but you can’t use it as a shortcut.”
• “I’m a firm believer. Give, give, give. And it will come back full circle.”
• “If you’re learning in a classroom and then your learning doesn’t match what you then go do in a corporate environment the next week. Within six days, you lose 80% of what you taught.”

Action steps:

1. Master pre-call research before every interaction: Research prospects, their companies, and industry trends before conversations to build immediate trust and avoid missed opportunities.
2. Embrace continuous learning within your workflow: Integrate learning into daily and weekly activities to reinforce knowledge, prevent skill decay, and ensure practical application on the job.
3. Use a unified coaching framework such as “skill and will”: Apply a consistent coaching model to objectively address ability and motivation, align expectations, and drive accountable performance improvement.
4. Prioritize intentional, high-quality outreach over volume: Focus on structured, personalized outreach efforts to generate sustainable growth and reduce overreliance on inbound marketing.
5. Have courageous, constructive conversations early and often: Initiate honest, empathetic feedback discussions proactively to resolve issues early and strengthen team culture and performance.

Episode Transcript

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here, Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Bart Fanelli of Skillibrium, and Bart before I formally introduce you, I always like to point out other episodes of the podcast people should check out. Since this is if you go to their site, Skillibrium, you’ll see that Bart and his company have this AI revenue operating model. So we’re going to talk about that. So when I look at some of the past episodes, Bart, there’s AI series and there’s also SaaS series because you kind of blend the two.

Some of the AI discussions that were good people should check out Nicole Donnelly we geeked out on, I don’t even know, like 17 different AI tools, how she uses them. Ken McLoud, same thing. Jason Patel started Open Forge, which is an AI solution, software solution, and Ethan King also shared some of his tools. And he kind of speaks all over the world too, on AI.

So those are some good ones on the SaaS side. One of them Co-founders of Zapier, that was really interesting. One of them Co-founders of Pipedrive. I think at that point they were 10,000 customers now. I think there are over 100,000 customers at this point, and just so many more.

So check them out on InspiredInsider.com. This episode is brought to you by Rise25. At Rise 25, we help businesses connect to their dream relationships and partnerships. We do that in a few ways. One, we’re an easy button for a company to launch and run a podcast.

We do the strategy, accountability, and the full execution. Bart and I were talking before we hit record. I started this back when I was a Chiropractor, and people were coming to me asking me to help them because I was doing this while I was running my chiropractic business, and that turned into a separate business. And then the other one is an easy button for a company is gifting. So we make gifting staying top of mind for clients, partners, and prospects.

Easy, affordable, simple, and even from a culture perspective, some people just, you know, we send to their staff. So you just give us the addresses, we do everything else. So we kind of call ourselves the magic elves that run in the background to make it stress free, to help people build amazing relationships. And that’s the number one thing for me. I’m always looking at ways how I can give to my relationships, and I’ve found no better way over the past over 15 years to profile the people I admire on the podcast and send them sweet treats in the mail so you can go to Rise25.com or email [email protected]. I am super excited to introduce Bart Fanelli. I’ve been binging his content actually, and it’s super valuable. He’s a revenue executive with over 25 years experience. He’s a co-author of a best-selling book, The Success Cadence, which you can check out.

He’s also the CEO and Co-founder of Skillibrium, which I mentioned, which is an AI revenue operating model. It basically brings together legacy systems, workflows, information silos, and it reduces complexity and overhead when you’re trying to scale high-performance teams. And what I’ve read and listened to with Bart, he knows how to scale high-performance teams. You look at, he’s cut his teeth on OutsyStems, Splunk, BMC Software, one of the companies, went from 60 million while he was there to 1.5 billion. He’s been, I think, part of pre IPOs, post IPOs and much more. So Bart, thanks for joining me.

Bart Fanelli: 03:43

Oh I’m I’m I’m excited that I’m an inspiration of some sort. You did a fabulous job introducing yourself. Thank you so much for that.

Dr. Jeremy Weisz: 03:52

I want to start off and we’re going to dig into you have so much great experience and even looking at the site, which I’m going to pull up in a second. Through Skillibrium, you know, you have these really cool tools like which I share. I, you know, would think everyone should go on and get there’s one of them’s downloaded for free. You should probably be charging for it. It’s a scale.

You know, sales discovery best practices. There’s a scale sales discovery data sheet, which we’ll talk about, but talk about Skillibrium and what you do.

Bart Fanelli: 04:23

Yeah. So thank you for that. And you know, you mentioned something. We’ll do that. But let’s talk about your one of your points was you like to give and you know, so open leaving everything open, allowing customers to access content or even let’s say on LinkedIn, giving people access to our coaching frameworks, our four box, which is what we have the most experience in.

It’s called skill and will. Those are gifts. Take them, and then usually it comes back full circle. Someone’s found it valuable, and then we’re engaging on something more meaningful. So, gating is not something we do.

We give it away. So. So you described it as AI revenue operating model. So I’ll simplify it as best I can. In revenue organizations, there’s usually a pretty broad gap in how someone is trained compared to what they’re really supposed to be doing in their job day to day, and then how their leader coaches and develops them.

And we’ve unified an approach where learning, doing and improving is AI assisted. It is highly specific and prescriptive by customer, by user, by persona. And it works extremely well. And it’s intended not to replace a bunch of systems of record, but we augment those systems of record and become, let’s say, the UI of choice, where our customers they access very specific learning for their based on their revenue operating model, very specific playbooks, and then very specific coaching frameworks all out of one system. So that’s what we do.

Dr. Jeremy Weisz: 06:07

So maybe we’ll talk about an example so people can kind of digest it a little bit. Maybe talk about 8×8 and what you do there. So by eight do.

Bart Fanelli: 06:18

So 8×8 is in a very competitive space call center or customer service. And they do a variety of different things with many different products. So we help them normalize the way they’re selling teams communicate and collaborate, a concept called “Value Mapping” as an example where a selling team and their leadership and.

Dr. Jeremy Weisz: 06:41

Their them here.

Bart Fanelli: 06:42

Yeah, that’s them right there where they all collaborate in a common way so that there is no confusion on how the team is supposed to operate day in and day out from their contributor all the way up to their senior sales leadership. Everybody’s on the same page. So we do all their learning curriculums. We did all their playbooks, we do all their coaching frameworks, and all of that is aligned so that they can speak consistently internally and face customers on brand and on narrative.

Dr. Jeremy Weisz: 07:14

Talk about I’m sure they have a lot of different staff members. Who’s it for? Is it for all executive team? Is it for the sales team who’s using it?

Bart Fanelli: 07:25

Fantastic question. In their case, it is all of the revenue-generating functions. So anybody that’s in a revenue org, and that would be sales sales engineering customer success. They’re all customer-facing. And from let’s say day one onboarding through skills and development of the way they run their business, same system all unified in their language from their senior most sales executive to their contributors in all geos and in all segments.

Dr. Jeremy Weisz: 07:58

So what does onboarding look like? Are you having to meet with them frequently and building out these custom learnings, or how does it work?

Bart Fanelli: 08:08

One time. So we usually engage upfront, and we build in their voice and based on their model, their operating model. And then our engine, our AI-powered engine allows them to learn, do and improve in one place. So we may work with them up front before we roll it out and do custom content. Or they might. A customer could just use the platform as it is today.

It requires no integrations, it does have content within it, it has workflows within it, and it has coaching frameworks within it. They’re more custom because they did a broad rollout to their entire sales organization, and they are doing very well. So, they’ve actually had three great quarters in a row. And I would say that is a combined collaboration between them, their leadership skills, and some of the wonderful people on their team that are doing great work.

Dr. Jeremy Weisz: 09:05

I mean, you’ve worked with some pretty large teams. I’m wondering what’s worked for getting adoption of these things.

Bart Fanelli: 09:12

Are the so so this is where usually most companies fall down. If adoption or learning has to match what the flow of work looks like as an example, and then it should be reinforced through coaching. So as soon as there’s a disconnect and you probably know this study, the “Forgetting Curve”. The “Forgetting Curve” was a study. It’s been around for a long time. Harvard

Dr. Jeremy Weisz: 09:40

I think I forgot the forgetting curve. I don’t

Bart Fanelli: 09:46

You probably did. It tells you that if you’re learning in a classroom and then you’re learning doesn’t match what you then go do in a corporate environment the next week. Within six days you lose 80% of what you taught. So it’s pointless. So the the best case scenario is learn only first principles that are applied daily, weekly, monthly and quarterly in the line of work based on your role. And then your leadership should coach and develop you based on exactly that.

Otherwise, you’re floating around and you’re existing and you’re not being productive and you’re forgetting. So we normalize the Forgetting Curve”

Dr. Jeremy Weisz: 10:23

So how do you with the Skillibrium, how do you get the team and managers and everyone to continue to use it. And you know, I guess this for any SaaS company, right? I mean, you want someone just on there and using it or they’re not going to think it’s valuable even if it is super valuable.

Bart Fanelli: 10:41

So there’s this concept called “The Intersection of Value” or “The Intersection of Efficiency”. If we know we have what’s called a pillar system and our pillars are agnostic. So we build customer specific content around pillars that have to be present in order to be successful in doing a job or a sales role from, let’s say, a five step selling process as an example, or we’ll call that a playbook. Well, a pillar first pillar might be anchoring on value. And there, there that is very specific to the prospector customer that we’re serving.

And they have to do it in their language on brand. And then their sales teams have to translate that very effectively to customers and prospects and partners, and everyone should collaborate the same way. And if that design principle is met and then the playbook, how they do their job that that they work in shows up and is based on those same principles and those same pillars. We get organic adoption because they’re using the playbook day in and day out on a daily, weekly, monthly, quarterly basis. And the coaching framework then looks back at the playbook as a reinforcement for skill and willingness.

And we know in industry, in SaaS and in any tech, what you want is the most productivity you can possibly get per person. And that’s what helps companies run more efficiently. And they don’t waste money. Well, we went through this wonderful well, you know, it was a wonderful it was a learning experience that was terrible. When we went through Covid, everybody forgot how to go be in person.

You know, everything became digital. Well, now what we’re finding is, you know, with the advent of or the on ramp of all the AI tools and post Covid, human to human is is a prized skill and most people don’t have it. So what we do through coaching, through leader leadership curricula and skills curricula, playbooks and coaching is we ensure that everybody is following the prescribed steps that the company using Skillibrium wants them to follow to show up the right way in front of their prospects or customers. And and we measure to that. So that’s that.

What that does is it drives adoption by default. Seller and leader talk about those steps and those skills. They get rated. They get to take their curriculums again to be proficient or remediate those skills if they don’t have them the way they should. And then most importantly, I if we have someone on the team that isn’t willing to learn or is going through a hard time, it is that connective thread, the leader and the contributor being aligned in a system and operating the same way they get to navigate that together.

So. And rather than someone being put on the hot seat or put on a plan or something of the like, the leader’s usually in tune with what’s going on very quickly. So we get high level efficiency and we get a high level of productivity out of customers that use the platform.

Dr. Jeremy Weisz: 13:44

In, like when API goes in. Is there a certain recommended cadence that the manager is like, okay, we’re going to have because a lot of it too is accountability, right? Is there like, okay, we want you meeting with the different team members once a week to check in on what they what’s what’s that look like and what’s your recommendation for that.

Bart Fanelli: 14:04

Yeah, it’s different for every industry and every customer. So I’ll give you a general example of what the best practice is. So in an enterprise, you know, I’ll say that the biggest risk or flaw is that most companies die in obscurity. And the reason is they rely solely on their marketing engine to drive demand that comes to them. And that’s not really the best case scenario.

We want that to still happen, but the selling team has to have some proactive outbound based on a repeatable process that’s based on quality. So it’s never volume. It is always intentional, professional and prescribed. So as an example, if I’m in the enterprise and I’m in I work for a company, let’s say Behavox. It’s another one of our customers and I’m a seller then I should have to go and find unique personas to present the Behavox message to on a regular basis.

And I should measure that and we should train and provide the narrative so that everybody can be rehearsed and do that really well. And then Behavox can measure that to ensure productivity follows the behavior pattern. And that’s what they do and that’s how they use the platform.

So unique personas is something that sales teams at every level should be required to meet on a, on a weekly basis. And if they do, they won’t die in obscurity. So Behavox does they have a really cool offering in a a very important industry. You know, where where they’re transforming the way their customers in financial services maintain compliance and avoid risk.

And they serve those customers using a proprietary AI product that they’ve been building for years. And it works exceptionally well. It is a modern way to to for them to deliver value to their client base.

Dr. Jeremy Weisz: 16:08

So how else does he use this platform?

Bart Fanelli: 16:14

So they use two parts of it. So they have a learning curriculum that are defined for their industry by role as a baseline. So the sellers, the leaders, sales engineers, they have the same foundational baseline that they’re taught. And they are served through the platform’s learning curriculum that matches their coaching framework. Their coaching framework is “Skill Will”.

So their leaders and their team members talk about the skills on a quarterly basis, and they rate their capabilities on those skills objectively. And if they need remediation, they can go right back to the learning curricula and learn it. Or they can rehearse together as a leader and a contributor. So best case scenario, 100% adoption when they rolled out. Probably the suggestion was or feedback to us was this is the first platform or product we’ve rolled out where we had 100% adoption, and it’s because it is designed to complement them in the line of their work, rather than just be training as an example.

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