Sales Leadership Lessons No One Talks About | Matt Nucifora (Dandy)

Carter (00:00.944)
Hey Matt, give the people a quick intro. Who are you? What do you do now?

Matt Nucifora (00:05.302)
Hey Carter, thanks for having me. I'm Matt Nucifora. I spent the last 11 years at HubSpot. I actually had my last day eight days ago. And last almost six years have been in sales leadership, really helping to scale HubSpot as an organization, obviously helping to grow people. Recently, I made the jump to lead enterprise sales at Dandy, where we're fully digitizing the dental industry. So definitely a little bit of a shift, but.

Super happy to be here and wrapping up my first week in office, which is pretty dope.

Carter (00:36.4)
Like you said, you were at HubSpot for 11 years and you got promoted nearly every year. What do you think drove that kind of consistent progression? Like why were you promoted as opposed to others? What separated you from the other people?

Matt Nucifora (00:50.552)
Yeah, I think, I think there's a couple of things, right? Like whenever you're looking to get promoted, you want to understand what mastery or at least like excellent performance looks like in that current role. And especially for inline promotions, one of the things I loved about how that was measured at HubSpot super objective, right? Like if you're doing 110 % of your target in a given period, typically 12 to 15 months, then boom.

Auto trigger for that next level, which is huge, right? I think the second piece there is for anything outside of an inline promo, right? So not just like AE two to AE three, but how do you go from AE to team lead to let's say small business manager, which is the move I made 2019 to 2020. It's starting to do that role that you want next. I think people talk about that a lot, but like table stakes is doing hundred, five hundred, 10 % enroll.

What are the things that you can do to show, like I'm coaching, I'm helping to develop my teammates. I'm starting to really work some of those muscle groups that would demonstrate what a great leader would look like. Same deal if you're looking, I don't know, like let's say from a commercial to a mid-market role. Well, being able to demonstrate how you run a more complex multi-threaded sales process, that really maps super well to that.

Carter (02:12.752)
You're coming into a new industry at Dandy. What is the first thing you do? And is there a big learning curve going to a new industry or do the skills transfer pretty well?

Matt Nucifora (02:24.472)
So I am fortunate at Dandy to be able to apply a lot of sales management and coaching and sort of business acumen that I've developed over the almost 14 years now I have in the professional world. But I would say like it's a system shock in a good way, right? It's very intense and the move from a persona selling to marketers and sellers, which is kind of very close to what

tech salespeople are already thinking about to selling to dental support organizations and dentists and the clinical side more generally. It's definitely been a feet to the fire, you know, trial by fire just in this first week. I would say in my first like 30, I can kind of talk through a 30, 60, 90, but in the first 30 days, the focus is just on listening, observing and not just shadowing calls, not just listening to

call recordings, we use a platform called attention. That's been great. But also like getting a sense of what good looks like from some of my reps and from some of the other people leaders and just really starting to understand the buyer persona. So if you're selling to let's say a 40 practice organization, the CEO or the business manager, COO, what have you is probably going to have some different ideal outcomes in mind in different pain points than the

you know, office manager at a individual practice, but sort of being able to understand like what those pain points are. That's, something I've been really attempting to understand deeply over this first week. The other piece that's been kind of cool, because this is, frankly, the first time I've made this leap, in a leadership role, I had worked at a few places prior to HubSpot, but as an IC. So, you know, like as a leader, the, really cool transferable thing is.

being able to listen for things like give to get and negotiation best practices and sort of like where to hold the value of the product and hold that line in the sand versus like where some sort of flexibility is possible. All of that is incredibly transferable and probably more than you'd even think. So I think like there's two pieces, right? The heavy lift is understanding the industry vernacular, which is a lot, right? I'm definitely hearing some terms that I've never heard before.

Carter (04:49.082)
Riot.

Matt Nucifora (04:49.89)
but then really being able to understand like how businesses would like to make more money and understanding some of the things that are preventing them from being as profitable as they'd like and ultimately how that might map to the dandy solution.

Carter (05:03.47)
Okay, yeah, that makes sense. To bring it back to HubSpot, when an AE would need help on a deal that's not moving forward, what's the most common thing they're getting wrong?

Matt Nucifora (05:15.894)
I like to think I kind of refer back to the Sandler selling rule. Like you didn't lose a deal when they tell you that's just when you found out. So whether it's a stuck deal, whether it's a completely closed lost or ghosted deal, I'm sure you've seen this Carter like there's something that happened one to maybe three calls prior in the process that led to that ghosted stuck. No pain, no time, no urgency.

issue that we find ourselves with. there's usually a discovery issue at hand. And I think that's a really big problem to put out into the ether. If we break that down into discovery, yes, you want to understand some of the basics like MedPic and Bant and all that kind of stuff. And those qualification gates are really important. But if we really focus on that need piece, there's a few different areas there.

that all drive urgency and importance, right? So like need is not just a checkbox, need is what are the goals that this business has? How do they plan to overcome them? What's their current state? What's their future state? And where's that gap to where they wanna be? So if you can kind of work backwards and identify like, hey, like, I don't know, we want to do an incremental $2 million in revenue this year.

And right now we've got a path if nothing changes to do about a million. And whether it's X solution or something else, like we know we need to make some sort of a change in order to hit that goal. And if not bad things happen, people get fired because we just missed our target by a million dollars against a $15 million revenue business, whatever. That's where the magic happens. But that's also where the stall deal happens.

Carter (07:02.8)
Yeah.

Matt Nucifora (07:10.155)
I think there's two kinds of scenarios in which that doesn't. I'm a big believer in accountability. So obviously, like if I'm coaching a rep, I want to uncover, hey, why weren't we able to uncover this kind of pain? Why weren't we able to unpack the driver and the urgency that actually makes this thing move and makes this business tick?

And you're going to deal with situations where there's a business who you just like weren't able to get to that aha moment. Maybe it's because it was the wrong kind of business. Maybe they truly don't have any pain. They're doing really well. They don't need to make a change. It's a tough sell. Maybe you were talking to the wrong person who doesn't understand what those executive priorities would be. So you got to get a little bit more multi-threaded. There's a bunch of different scenarios where that's going to be the case. But I think really what it all comes back to is like

Carter (07:42.044)
Mm.

Matt Nucifora (08:00.778)
If you're talking to the right kind of business and the right person and creating a really strong point of view that opens up the conversation doesn't just turn into a game of 20 questions. Like you're probably going to uncover business pain. That is the urgency driver, not discounting, not, like I could really use this deal this month. Yeah. A percentage of deals will close because of that. But usually the stuck deals, there was no compelling event that required a change. Path of least resistance is always doing nothing.

Carter (08:26.15)
Mm.

Matt Nucifora (08:29.271)
But if the pain is larger than whatever that sort of friction is to change, then you're probably going to be able to make something happen and probably be able to make something happen now. And you almost certainly won't get ghosted when those conditions are true.

Carter (08:42.328)
And you said a little bit about this, but how do you coach an AE on your team who's underperforming? Like, what does that look like? What does a coaching session look like when you're maybe doing a one-on-one with them or telling them what to do?

Matt Nucifora (08:55.713)
Yeah, mean, frankly, one of one of those very common areas, there's a bunch. But let's say I'm seeing a trend if I'm going through data and I've got a rep, it's called the Rep Bob. So Bob's got a pipeline of 10 deals and six of them have stalled out or ghosted.

we're going to use that as an initial hypothesis and drill into all of those six. Now, maybe I just take a listen at a five minute snippet, have the rep send me a few like, hey, send me a five minute snippet where you were talking through goals and like a reason why that next call even needed to happen, why you scheduled the next step. And then you start to uncover a few other layers, right? Like maybe it's, I didn't have a next step. Okay, cool. Like that could be an issue. Maybe it's, like, yeah, they want to grow. Want to grow what?

Do they want to go from 12 million to 12.01 million? Like you don't need to invest 10 grand on software to grow that tiny bit, right? So I think it's like really starting to understand the themes across all of those different conversations. The second layer is maybe it's not discovery at all. Maybe it is a rep who has a crazy good close rate, doesn't get ghosted and has skill that I would put like top 10 % of the org. They should be a P club rep. And the problem there often might be

a will on the front end, right? Like sometimes the best closers and sometimes the best sellers, right? The most talented are not necessarily the grittiest when it comes to creating their own pipeline. Or maybe like they're actually self-sourcing some pipeline, but they're kind of lone wolves and they don't collaborate with their BDR to generate more of that pipeline. That tells me maybe it's skill, maybe it's will, maybe they just like don't see enough value from the BDRs they've partnered with to help drive that pipeline and create the amount.

of top of funnel so that their high conversion rate can do the rest of the work to get them over quota. I think the rule most critically here is I need to use the data to understand the biggest opportunity, right? Like you cannot try to coach and develop a rep on four things at the same time. If you're trying to make a world class Michelin star dish,

Matt Nucifora (11:17.697)
You don't want have four pots going at the same time because it's really hard to create that top level performance on all four, right? You just want to focus on the one thing that's going to have the biggest impact. so like if you're using that data and if you realize, hey, like this person's crap at doing objection handling or maybe there's just like there's no agenda. So they lose control of the call. The only thing you're going to do, whether it's for a week, a month, a quarter is focus on that one thing.

until you see the skill starting to turn. Once it does, your work is probably good and you just want to continue to trust but verify. Once that good behavior is shown on five, six calls in a row and the rep starts to see the impact of like the why and how this is impacting those deals and helping their close rate, helping their quota attainment. Yeah, then it might be time to move on to the next one. But if that initial behavior starts to slip, you do want to go back to that as well.

Carter (12:12.792)
Okay, that makes sense. There's this I don't know if you've heard this, but there's like this old timey sales guy, Frank Becker, he was friends with Dale Carnegie. He wrote this famous, like popular sales book. And that was one of his big takeaways only focus on one like getting better at one thing at a time.

Matt Nucifora (12:30.408)
I am not familiar with Frank definitely have heard of Dale. I don't think anybody can be in modern sales not hearing of Dale or Zig Ziglar or those kinds of, kind of folks. But yeah, I think. I don't know. It's like if I'm sure you've heard of the term in baseball, like a five tool player. If you're really strong at everything except for base running, but like your batting average fall off a cliff last year, it's probably harder to move the needle on base running.

Carter (12:47.707)
Yeah.

Matt Nucifora (12:59.466)
You don't need to be a fantastic base runner or fast player at all to be a great baseball player. But if you're noticing slipping on like batting average and you're doing worse than you have in the past, that's probably all you're gonna focus on is just great contact. Same idea on sales, right? Like some of the best sellers have an area of weakness, but if there's certain metrics that start to slip, that's really where we wanna course correct and just focus on that one thing that isn't as good as it used to be.

Carter (13:28.012)
In your, I wanted to talk about stage two capital. Your work with stage two capital is really interesting. When you're helping founders with go to market, are there certain patterns you see come up a lot or is it a lot of different situations that everything's different?

Matt Nucifora (13:44.417)
I, I think it's an interesting problem because you have businesses that are just starting to reach product market fit, right? Like they're going zero to one. Oftentimes technical founders are going to, and this is really tricky. Like technical founders may be diff, maybe most troubled with hiring salespeople because technical founders may oftentimes sort of get like brushed back.

at the type of challenging sales personality that's going to succeed, right? The, the, let's say sales rep who is actually asking a question. Why does that matter? Tell me more about why that's important. That actually might not mesh with that technical founder personality at all. So oftentimes a technical founder could then be inclined to hire the, I don't know, like safer pick the person who's a little bit more of an order taker personality who isn't willing to challenge. And that almost almost always leads to poor outcomes.

So I consider like, especially working with seed startups and thinking through consulting. Yeah. Like that hiring piece is really big because the sales DNA that's going to succeed in a startup oftentimes will butt heads a little bit. And that's not a bad thing. I think friction can be really good, especially in a challenging startup environment. The second piece there is process, right? So when you think about these brilliant technical founders, or even let's say like you have an excellent

go-to-market leader who has been in the professional world for two or three years. They may have succeeded in this kind of ambiguous startup environment, but their ability to create a like science of scaling type of process just isn't there because they might be incredibly talented. How do you scale that? Right? You might not be able to find top 5 % sales DNA with the people that you're going to be hiring for your startup that has $500,000 in funding, but

Carter (15:15.866)
Mm.

Matt Nucifora (15:40.897)
There are certain traits, know, figure it out factor, commitment to win, accountability, resilience, all of these traits map really well to top sales talent. And then you have the different sales process items that I was laying out before, right? How are you creating great quality pipeline with the right people at the right accounts? How are you progressing those deals with urgency and real business pain, not just nice to haves? How are you closing on time with the right negotiation tactics that don't set the business

Carter (15:55.004)
Mm.

Matt Nucifora (16:10.518)
you years behind because you were giving up huge margins or you were doing really unscalable like deal desk tactics. All of those facets may not be familiar to that top seller. Right. And so I think like, but from a hiring and scaling piece, that's the most exciting part as someone who's been around, go to market at a bunch of like rocket ship companies. That's almost always.

Carter (16:32.677)
Yeah.

Matt Nucifora (16:35.69)
the thing they have to nail to go from seed to series A, ultimately to series D to IPO, whatever that might be. And it's really fun. You know, I think like, yes, there's an investment component in any sort of venture sort of situation, but I don't actually see it as something that's like necessarily a massive payday. I it as an opportunity to give back to the startup community and help some really talented people.

And if there's equity along the way as part of working more closely with that company, great. But it's not the primary reason I do it. I I like to help people to grow.

Carter (17:09.724)
And I know you got to hop off pretty soon, but I was curious, there things, because I know you said you're investing in these companies, are there things that you look for? We were like, oh, I'm going to invest in this one and I'm just not going to invest in this one or get any, or is it you work with them and then they give you equity because you're being very helpful.

Matt Nucifora (17:26.878)
Yeah, the model is more so and this is what I love about stage two. Like I don't have to make those bets. I'm not a VC. What would I at some point do some angel investing, you know, independently? Maybe I hope to have a future exit at Dandy and be in a cash position where like I can I can sprinkle some cash on angel investments. But I think like it's more so of the portfolio companies that stage two supports of which there are many. It's like being able to

Carter (17:43.94)
Yeah.

Matt Nucifora (17:56.522)
get involved with the companies that I think I can add the most value to, right? Like I think it's very easy. Let's say, think about like a massive, massive private company and open AI or a Databricks. Those companies would have IPO'd and already been public like years ago. If we were talking 2014, 15 companies take a little bit longer to go public. There's a lot of incredibly successful private companies, but taking that a step further, like

those companies because they're so mature, they don't have those same sharp edges. What value can I add in an organization like Databricks? Not much, right? But when I think about that seed company, let's call it, know, Acme.ai. Acme.ai, maybe they're pre revenue or maybe they're doing 150 grand and they've got 500,000 in funding. If even a little bit of consulting can help them go, not even from zero to one, but can help them

fill the funnel with five opportunities worth 300 grand each. And even just going from instead of one of those closing two of those close, right? That's a massive revenue uplift. It's like literally multiples of their current revenue and can also set them on the right course to make those future sales hires and to continue that sustainable process of creating, progressing closing and then renewing those customers. I think like bigger picture, the thing that motivates me across

all lines, whether it's HubSpot, Dandy, whether it's consulting with startups, it's how do we continue to capitalize on the things that are going really well, but then also like find that next lever, that next thing that's really gonna be able to help individuals and customers grow better.

Carter (19:37.168)
Okay, perfect. Well, I think this is pretty good. I will end it here.

Matt Nucifora (19:41.207)
Thanks, Carter.