GTM Navigator: Nailing Your Discovery Calls

GTM Navigator is our ongoing series where we break down the essential components of nailing the right go-to-market strategy.

In this episode, Lauren Houpt, Associate at Fin Capital, chats with Jonathan Geller, Founder of Glider, a company that accelerates sales for B2B SaaS startups by driving faster deal cycles and building high-impact lead generation strategies.

Drawing on his background in sales strategy and product-led growth, Jonathan breaks down his playbook for running discovery calls that consistently convert.

Jonathan is a seasoned revenue leader who served as the founding sales hire at multiple venture-backed startups. Over the past decade, he’s helped scale three companies from $0 to $10M+ ARR, contributing to acquisitions by Vimeo and Ströer Media. The startups he’s helped build have collectively raised nearly $1B in capital. Now, Jonathan and his team serve as a bridge and specialize in helping Seed to Series A companies land enterprise clients, accelerate revenue, and build repeatable go-to-market engines.

Key Questions Discussed:

• What’s the best way to prepare ahead of a discovery call?
• How do you structure your discovery calls - from the opening to the close?
• How do you balance gathering information while building rapport?
• What techniques work well for uncovering pain points when prospects are hesitant to share
• How should you position yourself at the end of the call and set clear next steps?
• Any tips for effective note-taking during and after the conversation?

Transcription (edited for clarity):

Lauren Houpt (00:01): Welcome to Go-to-Market Navigator by Fin Capital. This is our ongoing series where we break down the essential components to nailing the right go-to-market strategy. My name is Lauren Houpt, and I am an Associate here at Fin Capital. Today we're joined by Jonathan Geller. He is the founder of Glider, and we're super excited to have a conversation about the best practices to nailing all your discovery calls. Thanks for joining us, looking forward to it.

Jonathan, welcome. Thank you so much for joining our go-to market navigator. We're really excited to talk about nailing your discovery calls today. Can you just start off with your background & your previous experience, so the audience knows where you're coming from?

Jonathan Geller (00:46): Thanks so much for having me, Lauren. To share a little bit about myself, I've been a founding sales hire three different times in my career. I’ve climbed the ladder from AE to sales leader. Two companies I've worked with were pretty much pre-revenue and went on to be acquired by big publicly traded technology companies. One of them was Vimeo. The company that they purchased was called Wibbitz. Another was Ströer Media, a German-based research company, which purchased Statista. So, I helped lead these companies in revenue. I scaled one from a team of six to 200. I joined the other, Stratista, as the fifth US hire. That company has a global team of 1,300 staff. So, sales is absolutely in my blood. My father spent 35 years selling wholesale paper goods door to door in Brooklyn, New York to restaurants. I did that as well.

Fast forward, I've closed 32 million bucks in revenue over the past decade for VC backed startups, including multimillion dollar deals with the likes of IBM. The reality is, I know what it takes to build traction in the early stage, and that's my edge based off of these real experiences. I love the process, and I’m always ready to roll up my sleeves and drive results for my clients. Honestly, I find that there's nothing better than closing deals and showing that there's life and blood in the early stage. My mission for my company and my team is to help jumpstart sales through B2B SaaS companies with a focus on pre-seed, seed, and series A with a focus on zero to 5 million in revenue.

Lauren Houpt (02:19): Awesome. Thank you. That's super helpful. I think it gives our viewers great context as well into this conversation. To really launch things off, I would love to hear your approach going into discovery calls. I think discovery calls can occasionally be intimidating, especially if you're a one-person sales team. What are your tips and tricks on how to prep in advance?

Jonathan Geller (02:41): I'd say first off, Lauren - the idea is to help them, to give first, and to build a relationship. Obviously, you have a product, software, goods or service to provide, but let's diagnose the situation, learn about them, and seek to understand before being understood. A lot of founders are incredibly proud. They have amazing software. They're able to raise meaningful money from a VC like you. So, they're really kind of chomping at the bit to share the latest and greatest and show off the goods of their product. 

Take a quick step back. Discovery is incredibly important. It's not a cute process to just build rapport. It's truly there to learn. So first off, as far as preparation, going into a discovery call, I'd say review their LinkedIn page. Of course, their tenure, their background, their scope. If it's a founder, pretty obvious.

If it's somebody else you kind of want to learn about their world, I'd say be prepared to take a ton of notes. I reminded myself for example, Lauren has 110 early-stage seed to series A companies. You have 10 series B, two pre-IPO companies. Which should make you think, “Wow. Jonathan actually listened to me the first conversation we had. Good for him. I can trust him. He listens to me at least a little bit. He's not like everybody else.”

So, a little further company, Crunchbase company site, of course, how large is their team? It kind of gives you some sense of how much money they're working with to some extent. What does the company do? What is their value proposition? You're speaking to somebody that lives and breathes this stuff, learn about that, right? Mutual connections, of course, all notes from previous conversations. If this is your second conversation, then prepare case studies as far as we have certain wins in FinTech, certain wins in construction, tech, whatever it may be.

Then again, just to rehash the mindset and the overarching goal, Lauren, is to seek to understand before being understood. When people feel heard, they're calmer. When you get them to stop thinking, “you're out to get them,” they're more inclined to trust, to tell you something you didn't know. And now you know something you didn't know, and at least you're putting yourself in the ring to extract more information from them. You're not really there to agree.You're there to understand their flow. So that's kind of going into a discovery call.

I will say, as a quick add-on, if it's a second conversation and how do you get into a second conversation, I really always like to start with information to level set. For example, even if I spoke to Lauren yesterday and I want to share information of what we know type of thing - if I can articulate my buyer's challenge, it's a good quote that I share all the time. “If you can articulate your buyer's challenge as well or better than they can, they'll automatically assume you have the right solution.” I believe it was Chris Arlo who said that,who's excellent. So yeah, worth noting.

Lauren Houpt (05:42): I totally agree on the trust part for sure. So glad you nailed that one in. That’s a great segue into another question; how do you structure your discovery calls specifically from open all the way to close?

Jonathan Geller (05:56): Great question. So, first and foremost, this sounds incredibly cheesy and my younger self thinks this is probably corny and not necessary, but setting an agenda is super important. In fact, Gong has a statistic that says calls with a clear agenda are 2.3x more likely to close than calls without an agenda. What do I mean by an agenda? For example, “Hey, Lauren, just to kind of level set, I always like to ask if it's okay to set an agenda” and then to basically get Lauren's blessings as far as what the agenda may be. “Here's what I have in mind. I have no idea if this is a fit, but this may be a perfect fit. We may be able to move mountains together. I may not be able to help at all, but we're here to learn. And the best way to accomplish that is to talk through your current sales process, your current gaps, kind of biggest challenges, some goals that you have for Q3, Q4.”

Then you're coming to the conversation, without them thinking “oh he's not out to get me”, but instead “he's respectful of my time. He asked me if I have the next 40 minutes, the next 20 minutes to speak.” And we're off to the races and I'm kind of an open book here. So,I'd say quick agenda, two minutes on that. Calls with a clear agenda are 2.3x more likely to close. Spend 10 plus minutes on a discovery conversation, which means, again, all things which we'll get into in the next question here, their situation, their pain, their impact of that pain, what's a critical event that we need to be mindful of, what's a decision criteria, so on and so forth.

Finally, I’d say be very aware, whoever you're speaking to is very proud and they could go off on a tangent, but you do want to leave the last five or ten minutes of this 30-minute conversation for the next steps. Typically, the discovery is about 30 minutes and to get into sell mode, it doesn't need to be more than five, ten minutes. You could save that for a call two, but that's really important here where if you kind of get caught up in a 30-minute discovery, that might be par for the course. 

For the larger 50K+ deals, you may want to spend that entire 25 minutes after the agenda going into the discovery, but you do want to show some form of value to get them hooked and to get them onto the next conversation. Quickly to recap, two to three minutes on the agenda, 10 to 15 minutes on discovery. If the deal size is less than 20K, I'd say to share the price, some semblance of the price would be one way to do that. And then next step is to kind of land another conversation later in the week or later or the next day.

Lauren Houpt (08:53): Awesome. Yeah, I will say as someone that talks to a lot of sales folks, I love when people enter the call and they say, “Hey, do you have this much time?” Sometimes there's a hard stop, sometimes people can go over. It makes a big difference when people join calls that way, I'm really glad you called that out. It goes back to that trust piece as well, which trust and respect go hand in hand for sure.

I know you alluded to this, but next question, which I think we'll really get into the meat here, but what are the most important questions you aim to get answered during a discovery call?

Jonathan Geller (09:38): Totally. Obviously different software is going to breed different types of questions, but I'd say I run the SPICED methodology. None of it is necessarily like rocket science, but you do want to make sure you extract this information from your prospect. First thing is the situation. Learn about their current world. How big is their team? What are they looking to solve? Some of their goals, who's involved their situation, simple enough, their world, try to extract that information from them. Then their pain, what are some of their challenges? Not only what are some of their challenges, but what are some of their challenges, that they’d regret not solving three months from now, six months from now? It puts a little bit of a timestamp on things.

Then you could peel back the onion a little bit. What's the financial impact of that pain? Well, what happens if we don't solve this pain in the next three months? How much time are you spending on this? How much time are you or your teammates spending on this? What's your take on what's causing these issues and why is it not clicking? That's really the need behind the need to some extent, which I think is really, really important because you're going to get some information, but it's really important. You begin to understand from the prospect's world what's going on in the business that's causing these issues. What's going on in the business that's driving this to be a priority now? Because if it's not a priority now, no worries.

For example, I might even ask, “Hey Lauren, where are these challenges on your priority scale?” and you may say, “you know what, Jonathan? They're a pain in my butt, but they're actually not that important.” So when I follow up two months from now, and Lauren's pretty slow to respond, surprise, surprise. She told me that these aren't really all that important and don't need to be fixed over the next three to six months.I need to listen to that and follow that as opposed to knocking on your door over and over again. Now, on flip side, this is where you really open up “what's going on in the business, Jonathan, that's driving me to prioritize this now? Well, my founder is upset about this and my VP's talking about that, and we have a goal to hit this revenue in the next six months. If I don't, then I'm going to look like an idiot in front of my team next time I present.” That's the need behind the need. And now I'm talking, I'm hearing from Lauren's own words share that these are the ramifications this challenge is having.

I think those are a couple of really important questions that get the need behind the need. Then you also want to share what's the impact if you don't hit these numbers. Also, again, the cost of inaction. So that would be the pain. Then it's the impact; what's the financial impact of that pain?

And then the last two, the C and the E of the SPICED criteria is the critical event. And then lastly is the decision criteria. So, I understand the financial impact of that pain, but when does this need to be solved for? What’s the critical event? When do these decisions typically take place? Example here is asking “Lauren, it seems as if you've probably done this a hundred times before. How does this typically work as far as who's involved and when?” Where you might say, “Oh, you know what, Jonathan, our fiscal year is kind of weird and it ends at the end of January as opposed to end of December.” These are the things that as a seller, especially as an enterprise seller, you really want to learn. Otherwise, you're kind of, like “Hey, Lauren, what's the latest? What's the latest?” As opposed to really understanding when these decisions are typically accounted for.

Taking this critical event for example, if I know Lauren makes these decisions and they need to fit this into the budget by December 31, I need to get an answer from Lauren by the end of October because she told me that legal takes six weeks or that we need to run through procurement for two weeks. So for us to have a decision by December 15th in order to get 50K out of you upfront, which is kind of traditional SaaS, which is what we're charging for, or which is what we're striving for here, then I want to know that plan and map that out with you together. Noting here that I’m not against you but can collaborate on that. These are the things that very, very important, which you can extract from conversation number one. Then lastly is the decision criteria. So, Lauren touches base with Jonathan and shares the scope of work with Jonathan, who's kind of a decision maker, for example, but then Jonathan needs to kind get the blessings from Lauren and learn how that navigation process looks like through thick and thin, and you want to again extract that information off the bat

Lauren Houpt (14:50): A thousand percent, and thanks for adding some additional flavor to that as well. I think that leads nicely into our next question. We've talked about how you gather information, what questions should you try to get answered during these discovery calls, but how do you balance getting information while also building rapport on the call? Curious your thoughts there, because a lot of EQ that goes into this too.

Jonathan Geller (15:16): Totally, a hundred percent. You're very, very rarely going to sell anything without the rapport being solid and the trust being strong. You don't need me to share that with you, but it comes from being a good listener and comes from paying close attention. It also comes from seeking to understand before being understood. It's always a balance. You're here to be a partner, but also show them that you're going to make them look like a star, make their world a little bit easier, make their team's world a little bit easier, and help them grow their business. They also need to like you. Sure, you also need to show value, show that you've done this a million times before, even in the early stage. It's only a couple of times before, right? Maybe you have a couple of pilots, maybe you have a couple of trials going, but you need to show that this is something that has worked before.

We have proud investors. I'm a proud founder, and people feel above all connected when they feel understood, not just chatted up. Going a little further, how else would I balance gathering information versus building rapport? I'd say those are a handful of different things that I would focus on. Obviously being an expert in your field, being an expert in your own business and your own product, but also in their world as well. It goes back to if you can articulate your buyer's challenges as well or better than they can, they'll automatically assume you have the right solution for them.

Lauren Houpt (16:43): Totally agree there. Awesome. Well, I know we also touched a little bit on how important it is to understand pain points and the challenges that your potential buyer is facing. And sometimes it can be a little cagey, it can be a little bit awkward. What are some techniques that you use or that you've seen work really well in uncovering those pain points when the prospect might be a little bit unwilling to uncover those?

Jonathan Geller (17:12): I'd say some quick techniques that I like to share is that it's okay to, on one hand be wrong, but I say that to say you're allowed to make some assumptions. For example, even if I'm incorrect, try and take a couple of stabs at what their problems and challenges may be in their world and let them correct you. You're not here to know their business better than them, but people feel empowered when they can actually correct people. So, if I share with Lauren, “Hey, it seems as if this may be a challenge, that's okay.” She may actually feel empowered by defying me. And then what you're doing is really giving her the opportunity to open up a little bit more about her world. Chris Voss, he's an amazing author. He has an awesome book that I love and recommend. He says, make assumptions and it'stotally okay. Get the other side to say no, right? Because if I can get Lauren to say no, she's more inclined to feel strong and empowered and actually share more insights with me. 

That's my job here, certainly in the discovery where if I could extract information from Lauren, I'm that much better off, so that when I do get to demo mode, I’m sharing a solution that fits the need for Lauren. That would be one tactic and a little bit of sales psychology that helps you extract more information, I'd say, as opposed to asking why questions. Well, why are you doing this, Lauren? I'm not going to get very far, because Lauren's going to share probably a one, two word answer of why she did that, and she's actually going to feel accused. Whereas if I share something a little bit more and I say, “Hey, Lauren, can you walk me through this?” or “Tell me more about that” - the what and how questions, you're that much more inclined to, again, share more of your world with me, all in the realm of me just trying to get a little bit more information from you. Where again, if I go to the why questions, you're going to be, “whoa, who is this person? I'm 10 minutes into the conversation. Why is he talking about why or why is he asking me why I did this or why I did that?”

For example, for myself, if I want to get a little bit more into the nitty gritty of how much a company has in runway, it's a little bit more sensitive. Maybe theydon't want to share that information with somebody inside an hour of conversation. But then the empathetic route is always a good one. “I'm not here to step on toes. I'm not here to do anything other than help your business”. With a frame of, “would it be a bad idea, Lauren, to share your runway with me?” you might say, “Well, no, Jonathan, it wouldn't, but I need you to sign an NDA.” Okay, that works. Or at least, “no, Jonathan, not at all. This is my runway”. Or another example would be, “Lauren, would you be opposed to sharing how much revenue you have thus far?” “Well, no, I wouldn't be opposed.”

See here, I'm giving you the freedom to say no to me, but I'm also sharing a little bit more. I'm also giving you the peace of mind that you are in control and that you could say no to me. And then when you say no, you feel pretty good about that stuff.

I find those to be pretty good tactics. I'd say a bit further as far as uncovering pain points, again, the need behind the need as well. This is kind of where those trusty questions really come in where, “what are the ramifications this challenge is having on the business? What's going on in the business that's driving this to be a priority? Now, what's your take on what's causing these issues? Why is it not clicking? You're going to hate me for asking this, but help me understand the ripple effects this has on the business. What if this stays stagnant type of a thing?” Again, also great stuff from Chris Orlob. I get a lot of good stuff from him.

Lauren Houpt (21:20): Great. I appreciate that. Totally agree on all of those different tactics, especially whenever the buyer feels like they're in control.I think you hit that spot on. Okay, so now we're getting to the end of the discovery call and you're getting ready for those next steps. How would you suggest positioning yourself at the end of these discovery calls? How do you take those next steps without sounding too pushy? Curious your thoughts there?

Jonathan Geller (21:53): Yeah, a tough one. I'd say first and foremost, you want to come across, you're not here to push for anything. You're here, frankly, as an authoritative voice to help their business grow and make them look like a superstar, right? I'd say post discovery, give them a quick recap. Here's what we know, here's what I learned. Sum up what they've shared with you. Sum up a little bit about as far the little semblance of what you gave them about your own product and service. And before you wrap up, kind of recap what you've heard, key challenges, key goals, that's going to make them look awesome, whether this is a potential fit. And then I'll say something like, given everything we've discussed, would it be a bad idea to set up a call next Thursday at 2:00 PM to go over X, Y, and Z? And I could take 15, 20 minutes to have my solutions engineer show off the product for you, period, shut my mouth, and then they're going to open up, share a little bit more. I'd say it's really important to land that conversation at the end of the call that's obvious but also share a couple of times. Whereas if you kind of leave it to chance and have them run to their calendar, they're going to be scrambling. And then time's going to be up, be pretty firm, offer two, three times and schedule the meeting actually on the end of the call.

Lauren Houpt (23:14): That sounds great. And then Jonathan, from your sales experience, what's your approach to note taking and capturing insights? I know some people don't like having the AI note takers in the room, others love it, some people do handwritten notes. What are the best tactics that you've seen work?

Jonathan Geller (23:36): I vehemently encourage note takers. I think you can extract incredible amounts of information super quickly automatically. Even as a follow-up, the information that you can extract from these note takers is incredible. You can super quickly share what we know, and I would strongly recommend still taking a ton of handwritten notes and compliment to that. We're on this conversation here. We have a note taker, but I still want to take down a ton of notes. Who's the champion? What's Lauren's situation? What's the risk of if we don't do anything, what's next steps look like? Did I bring up pricing? What packages is he or she most curious about? All these things I really want to jot down, and my note taker will still capture that and summarize that for me after, but I still want to jot down the main points.

So yeah, would highly recommend a note taker, taking a ton of notes right after the conversation. It might be a little tedious, but I definitely want to spend 15 to 30 minutes writing down my chicken scratch into my CRM and sharing all those important pieces of tidbits. That way, when I circle back with Lauren, I know she has an awesome dog, what the name is, she has a wedding in Montana. These are the little things that, make your prospect think “hey, this person didn't just look at me as somebody to sell to. It's rather he actually cares about me, pays attention to detail, cares about my world, and isn't just trying to make a buck.” Right after the call, spending 15-30 minutes or so, cleaning up my notes, logging the highlights, putting together a recap email. Lauren was kind enough to share 30 minutes of her time with me, I want to thank her for her time. Share a recap email of what we learned, putting together what we know. That way, when we speak again, hopefully within the next few days, that's pretty much outlined for me. Then share a rough scope of work. If I did get into the product at all, maybe it was an hour long conversation and I got into the product a little bit. And also, in agreement too. I don't know if that's too soon. You obviously want to be sensitive to that. But at the end of these conversations as well, in the interest of setting up another conversation, also share, “Hey Lauren, would it be a bad idea if I share an agreement over for your review, so you have the whole picture in front of you?”

Otherwise, surprise, surprise, the deal will never get closed if you never send out the agreement. Now, again, that's not rocket science as well, but you do want to help lend a helping hand to getting these deals pushed forward. If you never send an agreement or a scope of work, they have nothing to internalize, nothing to mull over and the deal won't ever get closed. Then it's a week after the fact, and then you're sending an agreement. Time is the killer of all deals, you want to get that out as fast as possible.

Lauren Houpt (26:33): Definitely. Awesome. Well, I know we'rekind of coming up on time here. Jonathan, really appreciate all your insights. If you want to quickly share how founders or other folks that are watching this could get in touch with you, maybe you could schedule some one-on-one time to dig into things further. If you have any closing remarks, feel free. But I really enjoyed the conversation today and thanks again for all the insights you shared.

Jonathan Geller(26:57): Yeah, thanks so much. I mean, I'd say above all, thankfully, mostly VC referred clients here become highly recommended by top VCs, including Insight Partners and Union Square Ventures and Fika Ventures. So, if you are thinking about hiring perhaps a full-time sales leader or a sales manager, or your first two or three AEs, or your first 1, 2, 3 BDRs, we serve as a bridge, right? Now would be a great time for us to work together where we could bring in product market fit and reinforce that product market fit, help you refine your ICP, bring in a million bucks top of funnel, help you close a couple hundred thousand in ARR to help you get to that X round with the likes of Lauren and her team at Fin. Or to help you get to your first million in ARR or help you get to your $2 million in ARR. That would be a great time for us to work together! You can find me at [email protected].

Lauren Houpt (27:57): Awesome. Really appreciate it.