S1E6:  How a Standup Comic Became HubSpot's Best Closer

[0:00:00]

In the nonprofit space, they move at generally a slower pace overall. And it's being attuned to that and being understanding of that. If you're thinking more about closing the deal or more about your quota than you are like what do they need and when do they need it by, that's how it's going to come off.

[0:00:18]

Welcome to the Domin8 Podcast. On this show, we talk with HubSpot sellers about their latest wins, pulling back the curtain to explore the challenges they ran into, the sales strategies they use to win the deal. I'm Stephen Saberin, Senior Partnership Manager for Aptitude 8, the world's top tactical HubSpot consulting firm.

Today on the Domin8 Podcast, I have a guest who's mastered two worlds most wouldn't try to mix. He's known as the funniest man in software, spent eight years on stage as a comedian, landing spots on Comedy Central and making the finals at the Boston Comedy Festival. But what really makes this individual stand out is what he's done offstage, especially in the world of software. He's one of the early hires at a little startup we all know as HubSpot, 16 years ago, when it was just an idea in a company that fit inside a single room. Over those 16 years, Dan's seen it grow into a global force and has had a front row seat for all of it. These days, Dan's still combining strategy, storytelling, and comedy while selling HubSpot.

Dan Sally, I'm super excited to have you here. I've got to start with the obvious. How does a standup comic end up helping build one of the biggest names in B2B SaaS?

[0:01:20]

Great question, and thank you for having me. So I started in sales and standup at the exact same time, and I will tell you both take tenacity and both take a very high tolerance for rejection. They worked really well together. And I will tell you there has never been any situation I've ever been in in a sales capacity that has been worse than my worst gig. None. Absolutely none. So from that perspective, I feel exceptionally safe where I am now, off the stage and selling.

[0:01:53]

In standup, you have seconds to read a room and adjust. Do you feel like that carried over to sales and made it feel easier?

[0:02:00]

Oh, big time. My dad was a trial attorney, so he had a lot of experience in high-pressure public speaking. The advice he gave me when I was doing standup was: they don't know what you're going to say. So the only person who knows if you messed up is you. The ability to adjust, the ability to know when things aren't going in the right direction and pivot and get people back on your side, those are all things I learned in standup and things I still apply today.

[0:02:35]

Comedy is essentially storytelling under pressure. How has that shaped the way you approach complex sales conversations?

[0:02:49]

One of the big things I learned with standup, and one of the things I apply in sales, is having an economy with my words. Thinking about what is the clearest, briefest way I can get a concept across. In standup, it's about keeping people engaged, getting to the laughs, keeping the pace moving. In sales, you're fighting against people's attention spans. And in the case of more complex sales, especially now that HubSpot is more of a platform sale, you're throwing a lot at people in usually an hour's time. The simpler you can make that, the better.

[0:03:23]

One thing I heard recently is to talk in sprints of no more than 10 to 15 seconds to make it a volley. That sounds like exactly what you're describing.

[0:03:35]

Yeah. I think sometimes what happens is we get so comfortable with what we're selling that you almost take it for granted that the person on the other end of the line knows everything you're talking about. The reality is they're all brand new to this. You really have to pace the conversation according to the audience you're speaking with. More savvy prospect, you're going to move a little quicker. But somebody who's brand new to whatever it is you're selling needs more time for education. You have to keep things briefer, more digestible, and check in to make sure they're following along.

The one thing that's tougher about sales than standup is that in standup, if the crowd isn't laughing, that's a problem you can see immediately. But on Zoom calls, everybody's just sitting there nodding their heads. If you're not checking in and getting a pulse for where they are, you might very well be losing them and not even know it.

[0:04:46]

How do you make that early checkup to test how much they understand, their background with CRM or HubSpot specifically?

[0:05:02]

A lot of times you can infer it. If this is a competitive sale and they have an incumbent provider, you generally know they're already familiar with the software itself. Industry can be a good indicator. There are some industries that are just more tech forward than others. And then of course there's the individual. Getting a feel for: have you bought software before? Is this your first time, second time, third time? And in some cases, you could be speaking with a group of people, in which case you really have to move according to the slowest quartile of the audience to make sure you're not missing them.

[0:05:40]

You've been at HubSpot for 16 years, it's changed a massive amount. How has that changed the evolution of how you're selling?

[0:05:58]

We were really a much simpler tool when I started. And I want to say this because we're recording: I found out about HubSpot on Craigslist. There was a job posting, I looked it up, and I instantly got the value. They moved pretty fast. When I started, we were more or less an SEO tool with a blog attached, a landing page creator, a little email, and some analytics. I had the fortune of being able to learn the platform as we grew, when we incorporated sales tools and CRM, I learned that. When we brought in Service Hub, I learned that. Piece by piece.

In terms of selling, it can make qualification a little more challenging because you're dealing with a really broad cross-section of needs. When you're speaking with multiple teams, you have to decide: am I going to try to do this in one marathon call or break it up into audience-specific calls? I'm a fan of the audience-specific calls because nobody has the attention span for a two-hour call — including me when I'm running the demo.

[0:07:53]

A lot of sellers don't have the advantage of growing up with the platform. What would your advice be to someone going from small biz to mid-market or mid-market to enterprise?

[0:08:12]

Don't try to learn the whole platform at once. Learn it piece by piece. A lot of times when we launch a new feature, the way I learn it is when I have a chance to sell it. I'll sit for an hour, play around with the tools, go into the knowledge base, and get myself familiar with that subsection before the demo.

The other thing I'd say, beyond the feature side, is really understanding how to deal with a larger team. A lot of times we're looking at the demo for a specific persona's problem. The concern of a marketing manager is going to be different from the concerns of a CMO, different from a sales rep, different from IT and InfoSec. You have to address all those different needs and personas to make sure it lands. And beyond the demo, getting used to checking in with each of those individual people throughout the sales process and making sure what you're saying is personalized to their role and what they're most concerned about.

IT doesn't really care if a tool is easy to use. They don't care if it unifies data. What they care about is: is this going to make more work for me? Is this secure? So in my communications with IT, I'm really focused on that. Whereas with a marketing manager, I'm focused more on ease of use and ease of reporting.

[0:10:50]

Nomenclature is the connector piece, right? It makes things real to the prospect.

[0:11:02]

Yeah. I spend a good two hours prepping my demo portals for a specific use case. I really like to make sure that this looks as close to what it's going to look like when the customer is actually using their own HubSpot portal as possible. Using the prospect's terminology and incorporating that directly into the portal. So there's no gray area. They don't have to use their imagination. They can just come right in and say, "Okay, this is what we look like using HubSpot."

[0:11:38]

That deal we won together, it was a nonprofit. In that world, they don't have contacts and deals. It tends to be members. It's a different set of nomenclature than a B2B or B2C company.

[0:11:56]

For sure. Definitely speak in their language, because it's definitely a different space. They have a different set of concerns, a different set of priorities. Things like ROI — they're important, but they're not as important in the nonprofit space. Every industry has to be approached a little differently. Buying cycle is one key difference. But give us some background on how they came in, the challenges, and how you ended up navigating that initial conversation with them.

[0:12:44]

For the sake of confidentiality, we'll allude to the company, but this was a major nonprofit. They had actually worked with us on a smaller scale before, so they were already familiar with us on the marketing side of things. We were included in a CRM evaluation, between us and Salesforce. I think we're still very much the upstart in the CRM space. Salesforce has an overwhelmingly large amount of market share. So it's just great — as somebody who worked here when we were in an incubator — to be brought to the table with Salesforce.

When we started the conversation, it was very clear this was more of an internal comms play than donor marketing or volunteer engagement, which is what we're often pulled into in the nonprofit space. Number two, there were lots of different constituencies. System admins, InfoSec folks, folks who were actually in charge of working with different partner organizations outside the nonprofit. It was a matter of telling a story that resonated with the core user but also addressed some of the bigger problems they were having on the system side and the data consistency side.

[0:14:00]

When you first got involved, what did you find was broken or missing? And what did they think they needed versus what they actually needed?

[0:14:13]

The issue was they had a bunch of different divisions involved in connecting with partner organizations, and each of these divisions had their own CRM or their own system, Airtable, spreadsheets, Monday.com. A couple were using Salesforce, one was using us. The issues they were running into were primarily around coordination. Two teams would be in touch with the same outside partner, communicating with that person unaware of the other person's communications. They were stepping on each other's toes, creating confusion, overcommunicating. It wasn't the best look. They really wanted to consolidate that under one platform.

[0:14:57]

One of the things I've noticed about the CRM space is that even today for a lot of larger organizations, it's still an IT-driven process. People are looking at it from an IT perspective: does this solve the problem of unifying data? How do we deal with security? How do we deal with user permissions? A lot of times what they miss in that process is: is this something the team is actually going to be able to use?

The good news is they were already aware that user adoption was going to be a big deal. That was really where we were able to come in and ultimately win, because from a pure nuts-and-bolts functional perspective, Salesforce or HubSpot could do the job. But Salesforce was going to require 10 more admins and 100 additional clicks to get the same thing done in HubSpot. We won because it was going to be way easier to administer, way easier to implement, and way easier for end users to adopt. We weren't talking about nontechnical folks, but we weren't talking about folks who necessarily wanted to live and breathe in a CRM either. They just wanted something easy that they could get their job done in.

[0:16:03]

Was the ease-of-use angle something they came in with, or something you directed them toward?

[0:16:10]

They came in with concerns more about adoption. And I think we were able to bridge that into ease of use. Everybody has a story about a platform or piece of software that they purchased and then nobody ever used it. It's like the proverbial piece of exercise equipment with your laundry hanging off it. Everybody always has an adoption problem or adoption story with some software. Sometimes people understand that means ease of use. Sometimes they don't. So a lot of times it's up to us to say, hey, the big issue you're going to have with adoption is making sure people understand how to use it.

They were a little friendlier to it because they already had teams in quote-unquote easy-to-use tools. Monday.com, Pipedrive — really easy to use. The problem with those tools is they just don't scale. One of the advantages we have is that we have that ease of use, but we also allow folks to scale.

[0:17:22]

Walk me through the stakeholder mix and who the final decision maker was.

[0:17:33]

I'm going to confess right off the bat, I have no idea who the final decision maker was. I really have zero idea. I tried to sus that out. I think it was a decision by committee, and that's something different about nonprofits. They tend to be more consensus-driven than B2B orgs or private companies, which will work by committee but ultimately typically have somebody who puts their stamp of approval on it. These folks were way more consensus-driven.

The mix was project managers, folks who were going to be in charge of getting people onboarded. Then IT and InfoSec folks, most concerned with integration, user permissioning, and data protection. And then we had what I'd call systems admins — the folks ultimately responsible for keeping the thing humming. What we did was break that up into separate calls. IT and InfoSec had their own call to answer all their questions. Oddly enough, we had more calls over their concerns than we did with the project managers. The CRM side was pretty easy. Then it turned into the wiring underneath — user permissions, integrations, stuff like that.

[0:18:47]

Any champions on the IT side?

[0:18:53]

They were all really great to work with. Very amendable. But they kept us at arm's length and were very clear this was a level playing field between vendors. I wouldn't say we had a champion or somebody really pushing for us. It was really up to us to prove the value.

One thing I'd say to anybody selling to a mix of IT folks and end users or project admins: you have to be good at selling to IT. And IT is familiar with a small subset of vendors. The easy button for IT is Salesforce or Dynamics — way easier for them to say yes to those two because they're familiar. Those two organizations do a lot of work marketing to that persona. With us, we really had to win them over, because that's one area where we're not as well known yet. Part of the reason is that the software is designed to make IT's job easier. Ideally, HubSpot doesn't have any involvement from IT or just minimal work. Whereas if they take on Salesforce or Dynamics, that's part of their job. They're married to that system forever.

[0:22:36]

How do you get ahead of the IT conversation early in the process so it doesn't catch you off guard later?

[0:22:41]

The first thing I typically do in discovery is get an understanding of what things look like from beginning to end. We like to work backwards. Okay, so your ideal implementation date is X — let's talk about how long it's going to take to get this set up. From there we determine when they need to start. Then we can work backwards and say, okay, what does the approval process look like? What does InfoSec look like? What does the procurement process look like? Legal? We cover all the bases so we can start to tee up what we're going to need to speak to and when.

In some cases, IT is along for the ride from the get-go. I actually prefer that to the other side, where they decide they want it and then bring in IT at the last minute. Speaking with empathy to the IT persona, they're dealing with people breaking stuff all the time, clicking on links they shouldn't have. That's their whole job. So a lot of times when they hear, hey, we want to go with this vendor and need to get started in two months, they're immediately pumping the brakes. All those questions and concerns pop up at once. The earlier you can get them into the process, the better.

[0:24:05]

I love working backwards from implementation. We map out the entire discovery — who needs to be involved, what calls need to happen, which departments need to be included. That gives everyone, including IT, the confidence that we've done this before and we're going to take everybody's needs into account.

[0:24:29]

And it makes everything easier on the back end too. If you have a date when they need to get started by, or you can anchor that to something critical to them, it's a whole lot easier to move the process along. If you understand all the different steps needed before you can get started, it's a lot easier to progress the deal.

One of the potholes I see a lot of folks get into — either new to sales or just starting with more complex sales — is they don't get that understanding. Instead they're moving with an assumed timeline of demo, security call, sale. That leads to a lot of friction, tone-deaf messaging, and things that make the sales experience unpleasant for the buyer. And especially in the nonprofit space, they move at a generally slower pace. If you're thinking more about closing the deal or more about your quota than you are about what they need and when they need it by, that's how it's going to come off.

[0:25:37]

Was there any point where you had to intentionally slow the discovery down to make sure it didn't break down further along?

[0:25:49]

No. They were ready to be really thorough and methodical. Just to offer a contrast — you do get some situations where folks want to jump right into the demo. I never want to appear like I don't want to show the software. But I also don't want to waste everybody's time. When people just want to get to the demo, it's really a matter of saying: hey, we can spend an hour, we can spend all day looking at all the features, but if I don't understand what matters to you, I could hit every feature you don't care about. Let's save time. Rather than doing three demos to get to the one you want, let's do one discovery call and then one demo that really nails the use case.

[0:26:29]

Would there be any scenario where you'd do two demos, a first to give them a taste and a second that's fully tailored?

[0:26:42]

Yeah, 100%. It's not standard sales best practice so I'm not going to advise everyone to do it, but you have to feel it out. There are some cases where folks want to see something before they pull in their entire team. If we have an opportunity where someone's interested but we need other stakeholders for approval, and we may not get those stakeholders without showing something first, then I'll show something. High-level discovery with the understanding we're going to do a deeper discovery call after. That generally works, and if it doesn't, it usually means it wasn't going anywhere anyway.

If I were advising anyone new to sales, I'd say don't do that. But after a while, you get a nose for when to go off script. Sixteen years, you start to learn a thing or two about a thing or two. I've earned it.

[0:27:44]

Most complex deals have a pivotal moment where things could go sideways. Was there a point in this deal with the most risk?

[0:27:58]

For us, there wasn't necessarily any area where things would go sideways with this specific deal because they were very forthcoming about their needs and their evaluation criteria. We knew what we were speaking to.

The risk for us was that they were definitely vendor neutral throughout the process, and I was cool with that. I respected the fact that they wanted to run a fair and level evaluation. The risk was getting into as involved a sales process as we did without a full understanding of where we stood against the competition. When it's just us versus an RFP or a list of requirements, we can say we meet all these requirements and the risk is mitigated. When there's a competitor in there, you're never quite sure where you are.

The one thing I've learned to do over time is really allocate my time to where I feel the greatest opportunity will be or where I'm going to get the greatest leverage. If I know we're maybe further behind, second or third choice, I know I'm not going to allocate the same amount of time I would if we were first choice. In this case, we were always competing for first place. There was never a clear sense of where we stood, and that's the risk you take, but with this one, it was worth it.

[0:29:32]

So it was just HubSpot and Salesforce? And then they had some incumbents like Airtable and Monday?

[0:29:38]

Yeah. I don't think they were ever seriously entertaining those. They knew they needed something with scale, and that was us and Salesforce. And they were using Monday as a CRM, which, you'd be shocked at some of the size of orgs I speak with who are using that sort of mishmash of different tools. In this particular org's case, it made sense because there was some autonomy across the different teams. But I've seen sales teams of a thousand people working off spreadsheets. So as long as people are doing that, I've got job security.

[0:30:26]

Nonprofits can be difficult to get a temperature check on. Was there any point where you felt the shift from being a strong contender to being the contender?

[0:30:45]

Yeah — like at the very end. I hope this comes off as an extreme compliment because they ran such a professional evaluation process. I don't think I knew until maybe two weeks before we got the official thumbs up that we were getting it. And that was after all the calls were done. Then they were like: hey, we don't want to say anything just yet, but we think you all are in a pretty strong position. I would ask them constantly. I'd say, listen, I wouldn't be doing my job if I didn't ask, how are we, where do we stand? They gave me the Heisman every single time until the last moment.

[0:31:21]

Looking back, is there anything you would have done differently?

[0:31:27]

I hate to say this because I know this is supposed to be a learning moment, but with this specific deal, I think we did everything we should have done and did it all in the right sequence.

Getting back to my roots in standup — nobody ever wants to hear about the show when you kill it. Everybody wants to hear about when you bomb the worst. When you see a comic bombing, just know that in the back of their mind, they're thinking about how they're going to tell all their standup friends about it afterwards. Those are the stories people want to hear. This particular case was one where we nailed it.

If I had to offer something more prescriptive for anyone listening, in a lot of cases we view our sales process almost as a set of requirements, almost like an RFP. If I get this, then I give that. So if I get all the stakeholders, then I give a demo. I need to know timeline, I need to know who signs. All of that is true and sound, and you should be getting all that information. But you also have to understand that all that information exists to make you feel better. It doesn't deliver any value to your prospect at all. Your prospect knows this. They don't need to have that information. You do.

What's really important to understand about any sales process, especially more complex ones, is you really have to view it as an exercise in risk management. What you're managing is your limited time. The risks are any vagueness in the process. Those checkboxes you're supposed to mark off before you proceed to the next step — they're all designed to keep you from spending too much time on folks who aren't qualified. In this specific instance, there was an acceptable level of vagueness we had to navigate, and that was the toughest part.

But as advice to anyone selling: think of those qualification questions, think of everything from timeline to compelling event, as little pieces of evidence as to how much time to invest. If you do that, you're going to gear your process much more toward the prospect. You're going to frame those questions in a way that matters to them rather than matters to you. And you're going to know exactly where you should be spending your time.

[0:33:58]

If someone is early in their HubSpot sales career, what's the biggest mistake they should avoid on deals like this?

[0:34:11]

The biggest mistakes are, number one, not having a clear understanding of the prospect's timeline and why that timeline is important. If you understand when and why, you understand most of what you need to know about whether that deal is going to close or not. If the when and why are compelling, you can backfill the rest. If you don't understand the when and why, you really run the risk of wasting your time. And with a complex deal, these are a lot of calls, a lot of prep time, long processes. You can burn up — and I've done it. I've burned up a lot of time with deals that weren't going anywhere. For every hour you're spending on a deal that isn't going anywhere, that's an hour you could spend prospecting for new deals or prepping for deals that have some legs.

Really gain an understanding of why the prospect is looking, why that's important, and when that problem needs to be solved by. You can backfill the rest from there.

[0:35:13]

Last question. What's something about you, personally or professionally, that most people either don't know or wouldn't expect?

[0:35:20]

I'm a big language geek. When I started at HubSpot, we only had the office in Cambridge and had a ton of leads coming in from overseas. They needed somebody willing to get up early in the morning and talk with folks in Europe. At the time I had a bunch of small kids and hadn't slept through the night since 2007 anyway. So I was like, fine, I'll do it. It worked really well with my schedule — I was working from 5 in the morning until about noon. Really child-friendly hours. And I really got used to it, really liked it.

Then I got to a point where I thought: if I'm going to stay in this role, I should know another language. I talked to our international recruiter and he said Brazilian Portuguese is in high demand. So I taught myself Brazilian Portuguese. Got competent enough to have a conversation — I can't sell HubSpot in Portuguese, but I can get around. I fell in love with learning languages.

Right now, my side project is building an app to learn Hungarian using a lot of different AI tools, a lot of vibe coding tools. I don't think we have time for me to explain why I want to learn Hungarian. But as you can imagine, not a lot of resources to learn Hungarian exist, so I just decided to build my own. It's also allowed me to get really familiar with the potential for AI to do custom coding and build apps. I've gotten to do some API work. My technical chops have gone up quite a bit. So now when my sales engineer and the IT person at one of my prospect companies starts talking about APIs, I don't have to put myself on mute and zone out. I actually know what they're talking about and can add some value there.

[0:36:58]

I love it. Dan, thanks for joining us. This was really fun. I really appreciate you breaking down how everything worked, why it worked, and selling in this complex environment with larger nonprofits.

[0:37:31]

Likewise. Thanks for having me.

[0:37:37]

Thanks for listening. You can find me, Stephen Saberin, on LinkedIn if you want to keep the conversation going. Check out aptitude8.com to learn how we're helping HubSpot sellers and solutions teams win more complex deals. Until next time — keep selling, keep learning, and keep dominating.