Ep19: Beyond the Checklist: Earning the Right to Ask Questions in Sales Conversations with Nick Bontrager

Celeste Berke [00:00:00]:
Hello. It is Celeste here on The Sales Edge Podcast. I'm excited to talk with Nick Bonn. He's about to launch his own podcast. We met on LinkedIn. Thank you so much for being a guest today. Tell us a little bit about your current seat, and then we'll dive into this, sales podcast that you were launching.

Nick Bontrager [00:00:20]:
Thanks, Celeste. So pumped to be on. Thanks for having me on. Account executive at Drata. So we do security compliance for Startups and mid market large companies. So started my journey 5 years ago as an SDR in the multifactor authentication space and Worked my way up to AEs.

Celeste Berke [00:00:37]:
A lot of times when I'm talking to those who are in a sales leadership role, we forget that the majority of our team and, like, the meat of the people who are helping us get to where we need to be really start in this SDRAE space, and they're usually the ones who are not only customer facing, but they're hearing what's going on, like boots on the ground, What is changing, how the customer journey is changing, and how ticked off buyers are that most Sellers are coming from a product approach. You're in an interesting space in that multi Factor authentication ticks people off. Don't get me wrong. Salesforce, every time I log in, I gotta go to another, but it is there to help us. So I'm curious how because you're you're now about to advise some SDRs and also you've come from that seat. How do you move away from talking about products, especially for new sales reps within an org when it's like what we want to do because it's for SafeSpot and what we know.

Nick Bontrager [00:01:45]:
Great question. I don't know if I'm a glutton for punishment selling things that people just don't wanna talk about. Right? It's People ask, what do you do? I'm in sales. What do you sell? Multi factor authentication or security compliance. I'm a nerd like that, but There's a real need for it. SDRs do focus a lot on product. And I think, in a lot of situations, companies push product knowledge so much on their SDRs that that's what they focus on, and they're brand new in their selling careers. Right? So they don't know any better.

Nick Bontrager [00:02:13]:
They're going through a bunch of enablement videos. And don't get me wrong. You you should know your product. But start with the buyer and start with the pains that they have. And as an SDR, a really good way that I did that was talk to other account executives, not other SDRs that were going through the same types of training. Like, get Outside of that organization or find the SDRs that that are buyer centric and that that know those problems. That's definitely something I Think that a lot of SDRs that are getting promoted right now, they're focusing on the pains versus I can talk about this feature with you on this 32nd cold Yeah.

Celeste Berke [00:02:47]:
It's interesting because there's there's obviously a lot on LinkedIn right now in the SDR space. Companies who are hiring SDRs that seems to be the most open position within a company. It's really stemming from this place where economic times have changed. The big well has dried up. You can only be new and fancy for so long with people flocking to you about your product, and now you really have to build a case for change. And a lot of that is now coming down to SDRs going outbound. Not even SDRs, AEs as well, going outbound in this shift of 80, 90%. I talked to a company the other day.

Celeste Berke [00:03:27]:
A 100% inbound, and I'm, like, thinking to myself, your time is coming.

Nick Bontrager [00:03:31]:
Only a matter of time.

Celeste Berke [00:03:33]:
This focus on you call it pains. I like to call it problems. I have a big bruise on my shoulder right here. I don't want my husband coming up and poking that. I know I have a bruise. It's not life Threatening, so not gonna worry about it. How Like, the SDRs that you work with, how are you advising them when they do go down that technical path? How are you calling that out so that they can change that behavior and feel more comfortable talking about problems and more elevated business conversations when they're so new in their career.

Nick Bontrager [00:04:10]:
Yeah. I think that's a good question. And really, it in our industry, what we sell, just to I won't go too far into the weeds But basically, the main pain or problem that folks face is as they move up market, they start to have conversations with enterprise companies. And these enterprise companies are asking them, are you SOC 2 compliant? Are you ISO 27,001 compliant? What are you doing to keep my data secure? How do I trust you? That's the main thing. Right? He's building that trust. And we can talk about automation with Drata in all these different features. But at the end of the day, the SDRs that are really crushing it and doing well, they're the ones that actually understand that, okay. This is a revenue opportunity for our customers and also our buyers to unlock different markets, to move To larger deals because that's that's really the value of it.

Nick Bontrager [00:05:04]:
And I think our our enablement team's doing a pretty good job of pushing that Problem centric approach. And definitely seen a shift in the last couple of years have been inbound. It's been kind of the rosy Sunny days in SaaS, and now it's it's definitely harder. Money's dried up. Money's more expensive now with interest rates. And And, really, there's a a stronger shift towards outbound. So our team has started to lead with that problem messaging as opposed to the feature messaging, which is definitely The big thing on LinkedIn right now, or at least it was a couple weeks ago, was so out for 2024. Oh, so in for 2024.

Nick Bontrager [00:05:41]:
And so the The feature pushing is is so out.

Celeste Berke [00:05:46]:
So out. You're right. We're not that far into 2024. It's still still out, and I would assume with everything that's happening with email, it'll be even further out if you go that route. And it's interesting because you're in this space. So in gap selling, We when we do our training, we have a slide that's specific to what you all are facing, which is kind of just like risk analysis. So a lot of times in, like, cybersecurity, any type of compliant, you're not dealing with something that may have happened. A risk that it could happen.

Celeste Berke [00:06:18]:
Whereas a lot of other buyers are experiencing something in their current state. And it's similar to my dad's a physician. He has malpractice insurance. Well, what happens should you get hit with a malpractice claim. You have to play that out, and it's very rare that you would experience that. I think my dad 45 years in the business, maybe 1 malpractice his claim and his whole career with someone who that worked for him, but on his malpractice. But he buys that insurance because If you get hit with a claim and you do not have that insurance, like, the risk does not outweigh that reward or vice versa. The people that you're selling to probably don't even understand it.

Celeste Berke [00:06:57]:
Many of them know we have to do this, but we don't know why or, like, what it is. It's a different language. So really educating them on if this isn't happening now, This is what could happen. If it's happened, how many times does it happen, and then what are those impacts to the organization? I was on a call this morning, and this is where the team was missing. They could get the technical problems, which is where many sellers live. We all love our products. Business problems? Okay. Maybe turnover, churn, like, things that you can't fix like this.

Celeste Berke [00:07:35]:
The impacts is where they were having a really hard time with, and I would assume for some younger BDRs, maybe even some VP's of sales CROs. That's what we miss is what is the impact to the organization? That's where the motivation to buy or changes. It lives within those impacts. We can't clearly define those. Alright. So I went off on a tangent there. You, 5 years in now, Seen a lot of stuff. Mhmm.

Celeste Berke [00:08:01]:
Obviously, problems over product and features. You told me prior to this You were starting a podcast. Tell us about that. Where did this arise from? What is the concept?

Nick Bontrager [00:08:15]:
Yeah. So it arose out of a little bit of extra time on my hands during maternity leave. Good time. I'm back this week. But, essentially, I asked myself over paternity leave. Okay. What what am I building for for myself, for my wife, for my son that is outside of, you know, Strata in the career and, and all of that. And it really came down to, okay, I've been posting on LinkedIn for a while.

Nick Bontrager [00:08:40]:
I enjoy the interaction. Enjoy the community. What if I go all in on that? What if I start to build this brand? And then that brought me to the question, okay, what can I actually teach on? What can I teach people? And I have been in SDR. I was in SDR for 2 years and got promoted out of that role into an account executive selling role. And so that is what I wanna help folks with is the new sellers, the young sellers, both in their SDR roles and the new AEs. I wanna help them Take their next step, but specifically those SDRs who are looking to get promoted. And so here shortly, I'll be recording the 1st episode of the Promotable SDR podcast. So it'll only feature guests that have been promoted from an SDR role up and out within the last couple of years because I wanna keep it recent.

Celeste Berke [00:09:27]:
This is a great niche sadly for both you and myself because what is happening or what I'm seeing in conversations with individual contributors as well as sales leadership is we don't have any training within the company. Everybody's able to do their own thing, and what we find is that reps are either leaving, they get complacent, you start seeing quota slip, Maybe there's negative surveys around culture. Yep. There's a lot of chatter online or on he's like dark webby type of communities where people are fed up with the lack of, I can't show up and throw up at my job. Like, I need tools, resources, training in order to get me to where I want to go. And if it's not being offered here, I'm gonna look elsewhere. What would you say to companies that aren't offering Any type of training methodology plan. What is their risk? Tell us about their risk.

Nick Bontrager [00:10:36]:
Yeah. The risk. I think you hit the nail on the head, right, is the risk is attrition. People leaving, I know that I'm not happy if I'm not growing, And I have a clear line of sight of where I'm going personally, and I think it's a massive opportunity To attract talent with a road map. I'm a very road map oriented person. When I joined Duo Security back in the day, that was my 1st SDR role, There is a well defined culture of promotion internally to the selling role to the full AE role. So much so that there were really cool traditions back when we went to these crazy things called offices, that they would hang up a jersey Of the SDR who got promoted from an SDR to an AE role, it would have the the year that they were promoted in their last name. And so every SDR that came into that, you know, selling area for SDRs would see those jerseys.

Nick Bontrager [00:11:32]:
And it's like, that is the kind of culture that you wanna instill Because these are folks that if you're hiring the right people, they're uber motivated to make moves in the organization, To learn the product, to learn the pains, and honestly, can be some of your best sellers. So that's why I'm really excited about the podcast, because I'm gonna get to talk to those, Exactly. Those folks. And a lot of a lot of people have moved out of those roles and are doing amazing things.

Celeste Berke [00:11:58]:
And and they learn a lot. So let me ask you. Mhmm. In that company, your 1st company where there was a lot of internal promotion, celebration around that Mhmm. You know, emphasis sounds like on that training and development piece. Will or skill? A new SDR comes in. Which one is going to have them on that trajectory do you believe? That's, like, obviously, self diagnosing. I mean, we don't know.

Celeste Berke [00:12:29]:
But, like, will or skill?

Nick Bontrager [00:12:33]:
Yeah. I mean, It's gonna be Will that can turn into skill, I think, is really how that would roll. Sure you have some people that come in and are I'm not personally one of those, but, like, those that are coming in extroverted, they're super comfortable talking to strangers. I wasn't that way when I was in this role, in the SDR role to start. So for me, it was Will that turned into skill eventually over rep tons of repetition and training and Call shadowing and picking the brains of the top performers around me to get to the level of where I wanted to go. So definitely, I'll I'll answer the question kinda Not one or the other, but it's will that can be the skill.

Celeste Berke [00:13:13]:
I trained a lot of people in my life and usually could after a while, after I got into sales leadership and had some time under my belt, I would much rather take someone that had the will than the skill. I think it's easier to teach skill. It's much harder to teach will. So I'm there with you, but I I do believe we're at this place of companies that are seeing Some of these indicators, right, churn, low win rates, or decline, and are just pumping more into the top of the funnel versus peeling back the onion layers and saying, do we have a people problem? Do we have a process problem? Do we as you mentioned, do we have a culture problem? I saw someone post today on LinkedIn. She talks a lot about, like, content and brand building, and she was saying, like, bro, Nobody cares about all the internal stuff going on with their organization. Right? You use that for Slack channels. If you are an organization where The CEO put something out, and then everybody's regurgitating it. This isn't developing people.

Celeste Berke [00:14:14]:
They're it's not giving them a voice or a brand, and we're seeing that, and I'm assuming a direct correlation between lower employee satisfaction, probably higher turnover, and I do believe that comes, like you said, from that road map from day 1, working with individuals 1 on 1 on this is what the opportunity looks like, This is the development plan to get here. Like, let's help cocreate this. How do we get that? And what happens is That is a very 1 on 1 personalization based on their will and their skill versus what I've been hearing from larger corporations, from individual contributors. My manager doesn't have time. I never talk to them. We don't have a 1 on 1. There's no oversight. So I I do think that we're we're in for some rough waters here.

Celeste Berke [00:15:05]:
So that aside. Alright. So you went from s t r a e. Tell me what if you're talking to your former self and you're putting on my Superman costume, this is the cape I'm wearing. What is your sales edge? What makes you unique?

Nick Bontrager [00:15:26]:
Yeah. So that's in been in development for the last 5 years. And I think one of the main things there's there's 2 main things, And they kinda they play well together, which the first is to not be overly focused on process when you're coming into Talk with a buyer. So it's really good to have a background and a process, but you're talking to a person at the end of the day. It's a relationship. It's something where You are figuring out where they're at in their journey, and then you're joining alongside them. And then that second side is being extremely focused on being buyer centric. So an example of something that I just started doing is in my follow-up emails after demos, tying those follow ups Specifically to one of the criteria that they've mentioned on the call.

Nick Bontrager [00:16:15]:
And I call that out when I when I send the message. Like, look. All my follow ups Or most, at least, of my follow ups are going to tie directly back to one of your buying buying criteria so that this is actually a useful Piece for you to actually read. And so being buyer centric and then people over process, but still having a process, Would say I'd say those are my my 2 edges.

Celeste Berke [00:16:38]:
What I hear you saying is really listening to your buyer, listening for clues that, like, those bread crumbs, something that's It's important to them, something that may be going on in their environment that would change the direction of where you wanted to go, whether that's timing, something came up, something that they told you personally, and really making sure that they feel heard is what I hear, and I love that because when when we show up with our buyers and do not attach to the outcome, and and this took me, like, 30 years to learn, maybe more. I still do it sometimes. Like, we're salespeople. We're we're salespeople. Like, those whatever they are. I I almost called them memes, but they're not. They're a little I don't know. I'm older.

Celeste Berke [00:17:25]:
A video on the Instagram. A reel. A reel. That's what it's called. Mhmm.

Nick Bontrager [00:17:30]:
There you go. We got there.

Celeste Berke [00:17:33]:
We tend to want to attach ourselves to the outcome. And what does this commission mean? And what does this mean to my quota? And we Constantly have to bring ourselves back. The buyer doesn't care about any of that. Right? They care about themselves. So how do we become more empathetic to what they're going through in their current state? And listen without attaching to an outcome. So it sounds like you're showing up authentically listening, detaching from an outcome, but then really rooting them back into something that they said so they can help draw that same conclusion that you did that they maybe didn't put 2 and 2 together. That Clearly has been learned from time in the seat. It's not something that the BDR who started out, you would have known.

Celeste Berke [00:18:14]:
You probably would have fit to your product.

Nick Bontrager [00:18:16]:
Oh, no. Yeah.

Celeste Berke [00:18:18]:
Alright. So I'm I'm loving that, this buyer centricity. I we keep hearing this phrase coming out. I think Keenan, Who Wrote App Selling is working on a 2nd book eventually that really comes from the buyer's standpoint, so it'll be interesting when it comes out. They've done a huge survey. I would assume it will say people prefer a rep free environment. Nothing new that we've heard, but I'm interested to see what those statistics are as it relates to buyer centricity versus taking a seller's approach, which most of us still do from time to time. I've also heard of a couple organizations here recently that will flat out say that they use BANT as a qualification method, which Gets back to that, like, checklist.

Celeste Berke [00:19:01]:
Answer questions that are self serving to me so I can move you through my buying process. Also icky.

Nick Bontrager [00:19:09]:
Buyers are tired of that. Right? Nobody wants to be walked through a self centered checklist that is clearly, you know, just for my benefit as a seller to understand. A much better way to position that is towards wherever you wanna put it into the call. You can say things to set expectations appropriately on my side or just be completely upfront about, I just need to know this. This is this is a selfish question. You earn the right to ask those questions after you've walked through the journey, and you've attached yourself not to your own outcome, But to the buyer's outcome, and then your outcome follows that. If it doesn't, your outcome isn't gonna be that great.

Celeste Berke [00:19:48]:
A bell. I would be ringing it here, and that is tough to show up present and listen. And they're just also difficult if you're working in an environment where there is no methodology, You're given a checklist. Right? You don't have anybody to model that behavior after. Those companies are doing themselves a disservice because our buyers are screaming, We don't want this. Please stop. So over these past 5 years and your progression to now where you're going to be launching your own podcast, Tons of sales, let's say, advice being thrown at us. You are on LinkedIn quite often.

Celeste Berke [00:20:28]:
I am too. I definitely get LinkedIn fatigue. So much comes at you with, like, do this. Don't do that. Do this. Today, we're doing this. Now don't do this. Yep.

Celeste Berke [00:20:37]:
It's hard to know which way to navigate. What is some really poor advice you've been given over the years that you would like to say, Please stop, or we have to bust this myth. This isn't working.

Nick Bontrager [00:20:51]:
I wanna go to the filter thing real quick, which is, yes, LinkedIn fatigue is so real, and I've had to, like, filter through as, like, these are the people that I wanna listen to because I know I've applied what they've done and it's worked, or also I can tell, like, they've spent time in the actual roles. And that's very important to be very stringent about maintaining that LinkedIn diet

Celeste Berke [00:21:13]:
and what comes with the feed

Nick Bontrager [00:21:14]:
because otherwise

Celeste Berke [00:21:15]:
it's just I like that.

Nick Bontrager [00:21:16]:
Yeah. You gotta be careful with what you're putting in with the LinkedIn Diet. But to answer your question, so I think one of the things it's it's It's good advice, but it can be taken too far. Is the up up front contract that folks put down on calls. So it's good to have an upfront contract with with buyers when you're on a on a call with them just to let them know what's going on. But it's being delivered, and it must be This long, and it must be rigid. And I think a lot of times when folks rush through the I'm talking to a person and they just go for that contract that they engage the buyer in that track of, okay, sales call. Here we go.

Nick Bontrager [00:21:57]:
I'm going through this as opposed to the new way, which is Providing an agenda, but also saying, okay. This is what I assume you're coming to us because this is what buyers come to us all the time for. Injecting some of that experience with other clients into that agenda and tying it back to The actual buyer as opposed to walking them through your checklist of what you want to accomplish in the call. So it's good to have an upfront contract, but, again, People over process don't it's it's important how it's delivered.

Celeste Berke [00:22:29]:
For anybody listening who's, like, a VP of sales, CRO, sales leader, first time in tech, Like, would probably be like, what the heck did he just say? Upfront contract. And this is something that I've actually learned through my time. So I'm a certified gap selling training partner, which means I'm like a trainer by nature. I've been in sales marketing my whole life. Training and selling, gap selling at the same time are 2 different things or 2 different skill sets. So I'm right there with you in the CLC Making flubs, asking a self diagnosing question, taking it back. You know? Oh, I went down the rabbit hole. Ask too many probing questions because it's an ever evolving thing.

Celeste Berke [00:23:09]:
We're honing our sales skills. What if someone is like, I don't what do what do they mean upfront contract? My team doesn't see that. Give us an example of a poor upfront contract.

Nick Bontrager [00:23:21]:
Yeah. Thanks, Les, for joining the call today. Here's the agenda. You know, typically, we spend a couple minutes going through, You know, some questions that I have for you. I'll jump into the demo, give you an overview, and then we can establish next steps after that. It It it even how I said that. Right? I've said it before. Right? And it's something that reps get in a very monotone way of delivering, and it just becomes You're sitting in your seat in an airplane, and they're starting to give you the oxygen mask.

Nick Bontrager [00:23:47]:
It's like engage, sales call mode. Right? As opposed to Celeste, thanks for taking the call. Typically, folks join calls with me for x reason or y reason. I really wanna dig in because I think based on your company, it might be the why reasons. I have a hypothesis behind that I'd love to share with you. Adding that tweak to show, 1, you've done your research. You actually care about the buyer, and you're not just trying to, walk them through your steps. Because they have their own steps and

Celeste Berke [00:24:17]:
That subtle shift that you have of being seller cent completely seller centric to that subtle shift in buyer centricity. Yeah. Definitely. I mean, I think that analogy they used from the airplane mode is, like, spot on. How many times do we do that? We're like, I've heard this before. I'm checking out versus really including them in that conversation. I love how you said that hypothesis as well. We love to use hypothesis hypothesis.

Celeste Berke [00:24:45]:
We do that in a lot of

Nick Bontrager [00:24:45]:
my

Celeste Berke [00:24:46]:
notes

Nick Bontrager [00:24:46]:
I've nailed it.

Celeste Berke [00:24:47]:
Where after a call, And that's something else people people often are like, well, hurry up and get me to the demo or get me to the pricing. When When you haven't uncovered all the information, you don't even know you can help them. So, typically, for me, it's at least 2 discovery calls, sometimes 3, sometimes 4. But I'd love to put in my notes, like, what information did I not capture? What am I really curious about? What hypothesis Can I draw from the information they gave me? What could be going on within the organization? I wanna dive deeper into that. So I love how you frame that by hypothesis. Alright. So we're coming up on time. I like to keep these, like, snackable.

Celeste Berke [00:25:28]:
So what's what's next for you? This podcast, who would you love to have on? Listeners, tell us about that so we can get some listeners lined up for you or Some guests I have for you.

Nick Bontrager [00:25:45]:
So what's next? So I'm recording a couple of episodes. I wanna get 3 or 4 recorded before I actually Publish. It's out on Spotify and Apple Podcasts right now. It just has a trailer. But if you are interested, you can go follow the podcast when episodes drop and just notify get notified when they're available. I'm looking for SDRs, former SDRs who've been promoted Into AE roles, into account management roles. Maybe it was 3 or 4 years ago, and you have Hit the fast track, and you're in a VP role or some sort of sales leadership role. I wanna talk to those folks.

Nick Bontrager [00:26:21]:
So that's that's really who I wanna talk to. And, yeah, it should Be out here in mid to late February if I can, really line up those guests. I got the first 3 lined up, so really really pumped about it. But, yeah, Spotify, Apple Podcasts. If you're interested in being a guest, you can shoot me a

Celeste Berke [00:26:39]:
DM on LinkedIn. That's something that you're working on, like, passion project, really bridging the gap. No pun intended. People who are in SERC want to get promoted, maybe are lacking tools, resources, training, mentorship. I'm I'm gonna throw a zinger at you that I sound like like my dad talking. I'm gonna throw a zinger at you that I didn't prepare you for From a professional standpoint, aside from the podcast, what is something you're working on this year in your role.

Nick Bontrager [00:27:14]:
I'm working on a lot of things, but this is the 1st year that I'm actually gonna build out my own Sales process. So I've been using Notion for a lot of this organization of different things I'm doing on LinkedIn, podcast at Drata, and And I'm building out my own sales playbook. So coming from top reps at Drata, top reps that I've worked with in the past and putting this together and really Applying it to my role at Drata with the ultimate goal of getting to that president's club at the end of the year in January. That's something that I'm working on in my role. It's kind of a a bigger, less tactical thing, but it's gonna be Filled with, a bunch of tactical stuff. So maybe, eventually, we'll make that available in some format, but that's what I'm working on Right.

Celeste Berke [00:27:57]:
Lesson Westworld

Nick Bontrager [00:27:59]:
in the

Celeste Berke [00:27:59]:
field, best practices, working on Yep. Building out your own brand, what that looks like, how that applies to the sales role. So I love it.

Nick Bontrager [00:28:10]:
I've been promoted from SDR to AE and been a top performer as an AE, so I know that Early realm really well. But now it's just a matter of, okay, let's let's perfect the deal management. Let's perfect to getting into those larger deals and managing those cycles. And so, Yeah. Maybe a book. I'm I'm working on an SDR promotion frameworks ebook right now too. So that's also a evenings and weekends project. So there's all sorts of info on that on my LinkedIn page too Awesome.

Nick Bontrager [00:28:39]:
Profile.

Celeste Berke [00:28:40]:
Well, it's been a pleasure. I know as a as a new parent, Your 1st week back, I appreciate you sharing some insights on what it's like to switch from seller centricity to being buyer centric. Also, that there is hope for those outside of an organization that don't provide any training to have individuals such as yourself to look up to, to ask questions to, to follow along with, so we're excited for that launch. And thank you for spending your afternoon with us here. I will share all of the links to your Spotify. I'll grab that so listeners can find you and follow along in that journey as it's going to be, I'm sure, riveting, tales from the SDRC and how to get promoted. I'm sure you'll have some doozies in there as well, like, What to do and what not to do. So appreciate your insights.

Celeste Berke [00:29:28]:
Yeah. This is what happens when you're, like, a gen y, gen x. You're on the cusp, but we have no clue what the teens are talking about these days, but also still use some of your parents' language that most people don't know either, zinger being one of those words.

Nick Bontrager [00:29:44]:
I might I might add that to the, yeah, to the frameworks just like little callouts.

Celeste Berke [00:29:48]:
Zinger.

Nick Bontrager [00:29:49]:
Zinger callouts. If you see that, you you inspired it.

Celeste Berke [00:29:53]:
Cool. Thanks. I got a lot of other random useless knowledge throughout my years, but it's been such a pleasure. Thanks for staying with us here.