Why Traditional Sales Metrics Fail and How AI Can Help With Jack Siney, Co-founder of FrontRace

Jack Siney is Co-Founder and Chief Revenue Officer of FrontRace, an AI-powered decision intelligence company focused on uncovering the activities and behaviors that drive business performance. As a seven-time entrepreneur with five successful exits and 25 years in B2B SaaS and technology, Jack has led teams of more than 100 sales reps and closed more than $500 million in sales. His practical approach to AI is grounded in experience spanning US Navy contract negotiations and building companies such as Advanced Public Safety and GovSpend, which became a leading provider of government purchasing data before its acquisition.

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

• [2:02] How Jack Siney’s experience in government procurement shaped his approach to buyers and data
• [4:42] The entrepreneurial lessons Jack learned from seven companies and multiple exits
• [6:56] How strong teams and recurring patterns help businesses scale
• [8:35] Why decades of sales technology have failed to make forecasting significantly more reliable
• [10:49] The two sales problems that inspired the creation of FrontRace
• [17:08] How FrontRace connects and normalizes existing company data to uncover success patterns
• [19:37] Why business leaders should move slowly and deliberately when adopting AI
• [28:52] How resilience and persistence help entrepreneurs survive difficult periods and uncertainty

In this episode…

Sales organizations have invested heavily in technology, yet many still struggle to forecast accurately and understand why their best performers consistently outperform everyone else. The real drivers of success may be hidden in small behaviors, timing decisions, relationship-building habits, and process variations that traditional dashboards fail to capture. How can leaders use AI and their existing business data to uncover those invisible patterns and turn them into repeatable performance?

According to Jack Siney, AI thought leader and the Co-founder of FrontRace, companies should begin by understanding and organizing the data they already have rather than rushing to purchase another AI platform. FrontRace connects and normalizes data from tools such as CRMs, email, messaging, and video systems, normalizes that data, and analyzes the small activities associated with wins and losses. Jack argues that the differences between elite and average performers are often found not in headline metrics such as call volume but in dozens of subtle behaviors. By identifying those patterns, organizations can improve coaching, forecasting, and decision-making while applying AI to measurable business problems.

On this episode of the Top Business Leaders Show, Chad Franzen welcomes Jack Siney, Co-founder and Chief Revenue Officer of FrontRace, for a conversation about scaling businesses, uncovering the hidden drivers of sales success, and adopting AI strategically. Jack explains why traditional sales metrics fall short, how FrontRace analyzes high performers, why clean data matters, and how resilience and strong teams fuel entrepreneurial success.

Resources mentioned in this episode:

• Chad Franzen on LinkedIn
• Rise25
• Email the team at Rise25: support@rise25.com
• Jack Siney on LinkedIn
• FrontRace
• Gong
• ChatGPT
• Claude

Quotable Moments

• “There are a million great ideas in the world. The hardest part is whether you can operationally bring one to life.”
• “Can you get 100 customers? To me, that’s the magic benchmark; once you reach 100, you’re off and running.”
• “The difference between your best people and your average people isn’t the big things. It’s 20 little things.”
• “The magic is in the data you already have. If your data isn’t right, better AI won’t make the answer right.”
• “If you have the stick-to-itiveness to get through the difficult periods, things often work because most people eventually quit.”

Action Steps

1. Identify the small behaviors behind top performance: Study how your highest performers sequence tasks, communicate, follow up, and build relationships rather than focusing solely on traditional KPIs.
2. Act when problems become patterns: Treat a single issue as a possible anomaly, but when the same customer or operational challenge appears three times, develop a deliberate response.
3. Clean and connect your existing data before investing heavily in AI: Bring together information from your CRM, email, messaging, video, and other systems so AI models are working from reliable inputs.
4. Test AI against measurable business problems: Start small, establish what success looks like, and verify whether a solution produces meaningful ROI before expanding it across the organization.
5. Build around people you trust: Surround yourself with teammates who have complementary skills, challenge assumptions constructively, and can stay aligned through both successful and difficult periods.

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Episode Transcript

Intro: 00:04

Welcome to the Top Business Leaders Show. Powered by Rise25 Media, we feature top founders, executives, and business leaders from all over the world.

Chad Franzen: 00:20

Hi, Chad Franzen here, co-host of the Top Business Leaders Show, where we feature CEOs, entrepreneurs, and top leaders in the business world. This episode is brought to you by Rise25. We help B2B businesses reach their dream relationships and connect with more clients, referrals, and strategic partnerships, and get ROI through done-for-you podcasts. If you have a B2B business and want to build great relationships, there’s no better way to do it than to profile the people and companies you admire on your own podcast. To learn more, go to Rise25.com or email us at support@rise25.com.

My guest today is Jack Siney, a seven-time entrepreneur with several successful exits and a nationally recognized sales leader. He is the founder of FrontRace, a decision intelligence platform that helps companies identify and measure what drives success and turn it into real-time guidance for revenue teams. Jack works with organizations deploying AI across sales and operations, bringing a practical operator’s perspective on how to turn AI into measurable results. Jack, thanks so much for joining me today. How are you?

Jack Siney: 01:24

Thanks for being here. Has a long intro. Listen, I appreciate my last name. My whole life has been screwed up in so many different ways. So the first name, it was good.

So did I.

Chad Franzen: 01:33

I got Jack Siney, right?

Jack Siney: 01:36

Yeah. Siney great rhymes obviously rhymes with heiny. So my whole life there’s been a lot of permutations of my last name. And so first names normally folks get. So I appreciate the flip-flop for the good.

Chad Franzen: 01:49

Good. Well, it’s great to have you today, Jack.

Jack Siney: 01:52

Thanks for having me.

Chad Franzen: 01:52

Appreciate you started your career in government procurement with the US Navy. How did that experience kind of shape the way you think about buyers data and business problems?

Jack Siney: 02:02

Oh, sure. I think like most folks, I went to school on the Eastern shore of Maryland, a small school and, and, and when you grow up in the Mid-Atlantic, if you’ve never been in that area, a lot of stuff revolves around the government and how the government works, the federal government. And, and so one of the things they do is they reach out to some of the schools, and they have this program where they help you learn government procurement. And so I got into that program right out of when I graduated undergrad. And so it definitely throughout my career, I’ve been involved in the government process on either the government side or the vendor side almost my whole career.

So it certainly was not planned, but it’s played out that way. And I didn’t even plan to go work for the Navy. It was just an opportunity presented itself. And here we are.

Chad Franzen: 02:44

So, tell us a little bit more about your journey between, you know, that time and the founding FrontRace.

Jack Siney: 02:53

Sure, sure. So I started my career on that side and then went to I got my MBA and came back and I started working with PricewaterhouseCoopers, trying to work on some government projects. How do we be more efficient? A kind of a constant mantra with the government, and then ran into a gentleman who was working on some technology in the public safety space. And so kind of flipped to the other side of helping government agencies, public safety agencies operate more efficiently.

We put some technology in the laptops that are in the police vehicles here in the late 1990s, early 2000, pretty, pretty common now, but back then was very innovative. And so we helped them operate better in the vehicle, and did that for about ten years. And then working with those agencies and seeing all the different ways they bought and all the anomalies in that, it really led into our next venture, which was gov spend. We aggregated government purchase orders for government contractors to really research and figure out, hey, if I’m going to go sell to the city of Houston or the city of Saint Louis, who do they work with already, and what things do they buy and how much do they pay for them. And so that’s what the government spent.

We did that again for ten years and was fortunate enough to have that company acquired. And that led into what as you mentioned now FrontRace, which is the ability. Now, hey, now that I, I, I can operate and I’m in a certain function, how do I use everyone’s focus on how do I use AI to be more efficient on the operational side, which is an interesting challenge because for us, I’m sure we’ll dive in. The AI on the tech side is doing amazing things on the business side, just more challenging to really drive efficiencies. And so that’s what FrontRace helps companies do.

Chad Franzen: 04:31

Awesome. So you founded seven companies, exited five. What lessons from those experiences have directly influenced how you’re building FrontRace or have built it so far?

Jack Siney: 04:42

Gosh. Amen. You know, I think I’m a sports guy. And so for those who are in sports, that’s the things that don’t work. Stick with you way, way harder than the things that work well.

And so I’ve been, as you mentioned, I’ve been fortunate enough to have some decent success, but it’s certainly the things in the. I had a company during the.com era. That went south in my kind of side business world; I’ve had a couple of challenges. And so those lessons of how to get financing. When you close a business, why and what happens, stick with me much harder than the successes.

And so I think one of the biggest things in the entrepreneurial world is, kind of the stereotype you hear, which is finding good people to work with. And the rest of it will kind of figure itself out. And so I think sometimes when folks are starting a company, we get hung up on NDAs and keeping the idea proprietary and, and all these other nuances. But the reality is there’s a million great ideas in the world, a million, maybe billion ideas. And the hardest part is operationally, can you get it done?

Can you bring it to life? Can you at whatever your initial idea is, I promise you, the thing that hits the market, or certainly the thing that helps you scale in the market typically is much different, right? And so the ability to hire good people around you so that they can see that help you grow, do things efficiently because you can’t touch everything all the time. And so can you operationally deliver the idea that’s in your head. And so encourage folks to focus on that part of it much more than the I gotta, can I get the right funding or I gotta get an MBA, MBA?

Can I keep this idea secret for so long? You could share your ideas. You could put it on a podcast, you can put it on the internet, and then the challenges can you, can you operationally deliver it in a way where customers want to continue to purchase it? And the last thing I would just say, I always say to people, young entrepreneurs when I meet them is, can you get 100 customers? That’s the magic point in my mind.

Entrepreneurially what? Everyone has a plan. Like what? I have 10,000 customers, I’ll do advertising, we’ll sell subscriptions and we’ll have and you’re like 10,000 customers. I mean, yeah, that would make you one of the biggest companies.

It’s like, can you get 100? Can you get 100 people, 100 companies to pay you for what you’re doing. To me, that’s the magic benchmark. And once you get 100 customers, then you’re off and running.

Chad Franzen: 06:56

What have you learned about maybe the difference between building a business and building a business that can scale?

Jack Siney: 07:03

Oh yeah. No, not not to repeat what I said, but so much of it is the people part. It’s just having good people around you. And one little axiom, I think we, you know, we try to abide by when you’re and when you’re an entrepreneur, especially if you’re creating something new and you have to educate the market, there’s a lot of things going on. You know, we had this little accident where like, if something comes up once you kind of like that’s maybe an anomaly and whatever comes up twice, you kind of take a note of it and be like, oh, we’ve seen this.

Now when you see it a third time, it typically is a thing that you have to address, whether that’s from a customer standpoint with your internal operation, with your finances. And so I just when you see things a third, a third time, typically what you can have a bunch of anomalies, right? I wouldn’t, wouldn’t respond constantly to every little thing that happens. But if you’re trying to scale a business, once you’ve heard feedback from a customer for a third time, or once you’ve dealt with an internal operational challenge for the third time, those are normally the things you’re like, oh, we got to fix that, or we have to address it, or we have to have a good answer for it or what have you. And I think sometimes people run around all the time trying to solve every problem.

You can’t solve every problem. But if you hear it for the third, third, fourth time, it’s something you really should take note of. Find a fix for it, or find a way that you’re going to at least respond when people raise that item for your company.

Chad Franzen: 08:22

So you’ve been in B2B SaaS and technology for 25 years now.

Jack Siney: 08:27

Too long, too long, way too long.

Chad Franzen: 08:29

How has your definition of a high-performing sales organization changed?

Jack Siney: 08:35

Oh goodness gracious. You know, I’m not sure this is going to exactly address your question, but I, at my age, I’m 57 now. It’s just so interesting at this stage of my career to watch what happens on the sales side. You know, sales get a bad rap sometimes. And some of that’s true.

Some of it’s just a rumor. But what’s really interesting to me the talking points we always strategically talk about internally, which is we’ve been now on the tech side or on the business side, the sales side, we’ve been at this having a CRM and a tech stack for about 40 years now. So CRM showed up in the 80s. We are now 40-plus years into that. And what’s really shocking is we’re no better today, forecasting and telling the market or telling board what we’re going to do than we were 40 years ago.

So with all, if you think about it, with all this tech- you know, Salesforce and HubSpot and all the other Pipedrive and ways to manage your pipeline and Slack and messaging and all these sales rev ops tools- it’s hundreds of millions of dollars, trillions of dollars we spent over the last four decades. And the reality is if we just look at the bottom line results, we’re not much better, in fact. ChatGPT and Google say we’re worse than we are. We were years ago, which is really shocking if you think about all the time and money. So then you’re like, okay, almost everyone has a dashboard or some kind of set of metrics you’re looking at, and you’re like, what’s interesting about those?

They’re not directly correlated to us having success, like whatever they are, like calls or size your pipeline or outreach or prospecting or whatever you think of your company. There is some correlation, but it’s not a direct correlation. They’re merely flags. They’re merely data points to say, oh, are we on the right track? And so it’s so almost shocking that we’re at this point, we still don’t have a great correlation in the world of sales between, hey, we want to know what we want success to be and how do we create that.

There’s still a lot of unknowns in that world, which is unbelievable at this point in the process.

Chad Franzen: 10:43

Is that the problem then in sales management that has led you to help found FrontRace?

Jack Siney: 10:49

I appreciate that. Ten bucks I’ll say. So that is a little bit of an internal setup. So at our last company, we worked with companies that sold to the government. So we had the opportunity.

We saw every size company in every vertical, right? Big, small, every, every vertical cell of the government, one say one shape or form, one form or another. If you’re unaware, the government is the biggest customer in the world. But if you don’t sell to them, you should. They spend more money than any client you’re ever, ever going to go after.

So every vertical has companies trying to sell to the government, whatever their services are. And so seeing all that, we had the opportunity to see almost every company, regardless of how big they were and or how small they were, the same two issues all the time. And we had it internally, which is what I mentioned earlier. We have a pipeline and a forecast. We’re unable to deliver on that in a way that is reliable enough to make us feel secure in our job or make the board happy.

It’s everyone’s battle. Like, what are we going to do this quarter? Or what are we going to do this month? Right. And sometimes their law can be problematic.

But even if you miss high, especially if you’re in public, the street does not like that. Right? So it’s like every company is battling this. How do I forecast better and deliver more reliable results? And then the other dynamic, if you’re in the sales world, if you’ve been in the business world, you’ve experienced this.

If you have on average ten sales reps, so pro rata, whatever that is, you have 2 or 3 that are crushing it, 2 or 3 that are crushing it, and everyone else is kind of average or below average, right? And the 2 or 3 that are crushing it aren’t just 10% or 20% better. They’re like three x better or five x better, right? If the average is 100 K, they’re doing 500 K or four. You’re like what?

And so every CEO or every head of sales is trying to study these people. They shadow them. They have these people do training for the rest of the team. They’re trying to replicate what these people are doing. And most of the time it’s very unsuccessful.

So those two issues we’ve seen over and over and over again. And yes, to your point, the reason we created FrontRace was to try to help solve those two issues for companies. How do we forecast and deliver in a more reliable way? And how do we find out what our best people are doing and share that with the rest of the team so that everyone gets better and we’re better as a company? Those are 100% the two issues that we confront and, and help companies with.

Chad Franzen: 13:10

So I’ve seen that front raise talks about revealing the invisible drivers of success. What are those and why are they hard to identify ? Yeah.

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