Mastering Complex and Long B2B Sales Cycles

[00:00:08] Aaron Janmohamed: This is another episode of the Revenue Mavericks podcast. Where we interview top leaders in revenue and RevOps and sales and what have you and find out what they're doing right so that other people can can copy it and take credit for it. So I'm joined today by somebody I've worked with in the past Daren Reschke. You mind giving us a quick blurb about yourself?

[00:00:31] Daren Reschke: Uh, yeah, sure darren reschke. I have worked with Aaron in the past. We're to work together at insidesales.com uh three years Somewhere around there and 

[00:00:43] Aaron Janmohamed: what a wild time. Yeah. 

[00:00:44] Daren Reschke: Yeah, I know. Uh, not a lot to talk about there. And then, uh, now today, uh, senior vice president of sales here at Entrata, and I've been here just over three years.

[00:00:56] Aaron Janmohamed: And I appreciate you, uh, you being willing to join the podcast. So let's get right into it. The thing I care most about is just finding out what people are doing that's driving success. Um, and, uh, and try to expose Maybe best practices, frameworks, systems, whatever it may be that other people can replicate.

And, uh, obviously given your background, you've had a lot of success. I thought this would be a great opportunity to find out what you're doing to crush it. So I know you can't go back throughout your entire career. I mean, I think we estimated it as likely 4 trillion that you've been directly responsible for.

But maybe while you've been in Trata, uh, give us some sense of scale. You know, the amount of business, the deal size, the people in your organizations, Okay. 

[00:01:42] Daren Reschke: Yeah. So, um, when, when I came here, the intent, uh, of hiring me at Entrata was to build out our inside sales team. We've been primarily an enterprise field sales focused organization.

And so when I got here, we had, uh, five sales reps. They're primarily inbound sales reps and we were doing about 4 million, uh, a year, three years later, we're up to 23 today and Uh, we're going to do about 25, 26 million this year. So over that time, you know, year to date, my org's done about 43 million dollars.

Uh, our average deal size, we're about 130, 000 is what our average deal size is today. When I started, we were in like the 60s. So we've more than doubled our average deal size. And primarily, you know, when you go from five to 23 sellers, we're not a big demand gen type company. Um, it's an ERP system that we sell for multifamily housing property managers.

And so because of that, it is a lot of outbound hunting. And so less on the inbound, more on the doing remote sales. Um, we still talk about, if we can do all of it digitally, we'll do that. 

[00:03:05] Aaron Janmohamed: So you've had, you've, you've been able to scale up pretty effectively. We saw you do the same thing at inside sales. So one of the bright spots of the company is kind of the turnaround on the sales team and, and, and finding ways to be successful.

The thing that I've, I've always noticed about you is you, you seem to have this very strict, uh, discipline as it relates to data and people management. And I wanted to know, um, I w I would like to get into that, but is that where you start? Like you step into a new role and the first thing you're looking at is what's happening with our reps.

What are the key metrics? What are the things to track and how well are we staffed right now for success? Like And then you take it from there. Can you give me a sense of the starting point so that we can orient ourselves a little bit? 

[00:03:49] Daren Reschke: Yeah, I would say for me, a point of view as a sales leader, the most important thing I can do is be consistent and predictable if I'm, if I'm wildly unpredictable and not consistent, my team doesn't know what to do and so, and that comes from years of experience of having leaders who were consistent versus leaders that weren't.

And so my anxiety as a rep, yeah. Would always flow based on what my sales leader did. And, you know, there's plenty of other reasons to be stressed out in sales. I don't need to cause more stress as a leader. So that's my first goal. And because of that, then I build out my framework to mirror that. So, um, coming to Entrata, for example, the first thing I want to do is just understand what was their process.

If they had one, um, some sales floors, if it's like a transactional big sales floor, you know, sit down, put in these inputs, you'll get these outputs. And you just want reps to go and knock them out small cells Cycle or small cell cycle small deal size that works great, you know new sellers You got to have a floor like that here, you know more complex cells for sure Um, and where you're selling pretty much everything that a business would need to operate, uh, it's easy to get distracted.

And so having one regimented sales process, uh, wasn't really going to work based on the maturity of the sellers that I was managing here. They weren't new, they were seasoned sellers, they'd been doing it a long time. So really wanted to say, okay, what, what could I focus on and make consistent? And a lot of that is just number one, figuring out what their process is like, what, what, what do they do every single day and what are their goals?

And can I hold one on ones and a consistent basis, talk about what their goals are, consistently talk about how they're achieving to those goals. And then just be more of their accountability partner based on what they want to do. And so first and foremost, that's the first thing I want to do is just make sure I understand what that is and then consistently follow up with them.

[00:05:56] Aaron Janmohamed: The other thing I've noticed about you is that the ability to spot people or at least coach people to the point where they're high performing. You had a lot of high performers on your team. You seem to have a knack for Spotting those characteristics that led to high performance. Do you mind going into some of that?

Like, what are you looking for in, in, in reps that are, that are the best performing or what have you noticed about the reps that are the best performing? 

[00:06:17] Daren Reschke: Yeah. Uh, I would say you've always got reps that you've, you've got a couple of different varieties. You have the ones that will be the doers. So, Hey, go do this.

They'll do it. They'll, they'll do a great job. They'll come back and, and, and report how they did. You got to have those guys, people who aren't doers, they're going to move through your org quick, get them out. The problem is, is that they're only going to do as much as you tell them to do. And especially when, as your org gets bigger, it's easy to get distracted.

And so you've got less oversight of what they do on a day to day basis. Uh, the reps I feel like are the highest performing reps are the ones that are more entrepreneur minded. Yeah. Coming to me with, Hey. You're asking me to do this. I actually want to try this and that, you know, two or three other things that they want to do.

And so what I've found is if I can give them a little more autonomy to go try things, I can put the reins on them a little bit so that they're not doing everything that get them outside of the guardrails. But I'm not having to whip them to get going like they're more proactive instead of reacting to what I'm telling him to do.

And so if I can find a couple of people that behave like that on my sales floor, then they do a lot of the work for me as a leader and reps are naturally attracted to that type of seller. And then they start to behave like that person. So you want to have some of those on the floor leaders that help.

Yeah. Mirror emulate what you're asking him to do and it helps to groups 

[00:07:51] Aaron Janmohamed: when you were talking about process. 1 of the things you said was, uh, you're you're looking at maybe 1 component is the cadence of of 1 on 1s and how you can work with each rep individually. Um, is, is, is that your, your deal review or is that a separate, a conversation, like, are these one of the same thing, like your weekly deal review call with each rep, you're going through deals, but also kind of their personal process and making sure that there's some level of adherence, there's some training going on, is that kind of all inclusive?

[00:08:20] Daren Reschke: Yeah, I think one of the things that if someone says what's your secret sauce, I don't know how secret it is other than I'm just maniacal at doing it every single time is training. Like, a lot of people feel like I over train. Um, but I always kind of look at sports, you know, if training wasn't important, why do you have practice?

Yeah, so sales in the same way. It's easy to get, get lazy and do it your own way and feel like you've got it figured out. Um, so what, what we like to do, uh, we train as a whole entire sales team. My whole org trains three days a week. So we train from 11 to 12 and it will rotate through topics. It will be, uh, one day we'll be, uh, product training.

So especially at Entrata, we can train on products. One every Monday through the year and not touch all of our products. There's a lot to train on. So we've got a lot that we can do there. Uh, then we'll train on salesmanship. So one of the days we'll focus on, you know, closing or discovery or. You know, overcoming objections and it will generally be led by, uh, members of, of my, my sales leadership group.

Um, and it could be, you know, we do deal reviews at that time, like call reviews. So we'll listen to a call. Mostly what I'm looking for is what does the customer say on the other side of the call and then how do we react to respond? And then we'll stop and let everyone give feedback. I think that's super effective.

Like, especially on a floor where everyone sits around each other. We hear one side of the meeting. We don't hear the customer side. Yeah. And so I really think that's a, that's an important one. And you know, it's working when. You start getting reps, sending you calls. Hey, can we use this call for Wednesday Wednesday's training?

And they're, they're serving those up instead of, you know, you'll always get the guys that you pull their calls up the first time and they all just buried their heads and don't listen to this embarrassing. Uh, it's meant to be embarrassing at first, but that's not the purpose. You don't want to shame them.

It's more, everyone's going to make the same mistakes. Let's do a group learning session. So we'll do that. And then the final training will be. Generally around industry related related stuff. So competition or what we're seeing in the market, people will talk about that. And that's my cadence. Like I do it every week.

That's another one where I try to not cancel that meeting. I've also had leaders that have canceled meetings and pretty soon you get in the habit of scheduling your meetings during that time, because you don't think that your leader is going to hold it. 

[00:10:53] Aaron Janmohamed: Yeah. 

[00:10:53] Daren Reschke: So consistency is super important. Um, in terms of one on ones.

Um, I, I also like to do a cadence of one-on-ones, you know, one, one week it will be maybe rep focused, like te Tell me about what you're interested in getting to know them a little bit more, what makes 'em tick. Um, talk about things that maybe they're concerned about. Uh, another one will be goals and initiatives focused.

So these were your goals. These were the goals we set for the quarter. How are you achieving to those? We pulled the numbers. Look at that. Are the numbers telling the story? Uh, another 1 might be, um, development. So, if they've got sales development that they want to do, they want to move into the leadership or maybe a different role.

Then we'll, we'll spend some time to do that. And, and, you know, if we're doing a full, uh, full breakdown of, of their numbers. That one on one might be an hour. Some of these other ones might be a half hour, but again, the key is just consistency, like if, if they know that you're going to be asking those questions every single week.

They're going to come prepared and it's a way to hold accountability. Inconsistency is a great way to lose accountability of your team. 

[00:12:05] Aaron Janmohamed: I love that principle. Um, we, uh, we're about to launch a survey and one of the questions we asked in the survey, actually, it was a five part question, uh, specific to deal review calls and what goes on in those calls and.

It was interesting to see people rank the effectiveness of deal review calls on a number of different criteria. You know, did they help move deals through the funnel? Did they help identify and practically respond to risk? Did they help enable reps more effectively in their sales skills gaps? Did they help, you know, it's just a number of things.

When people, um, were focused on the right things, there was a direct correlation to revenue impact. So this idea of consistency you're talking about fully makes sense. But then I also wanted to get into your, your practical process. When you are going over deals, what are the things you're looking at? Is it like, when's your last conversation with the executive?

Do you have a champion? Is it kind of the typical things or are there, there are any unusual signals that you, you typically look for as, as an indication of either health or risk in a deal? 

[00:13:03] Daren Reschke: Yeah, um, I would say the traditional like, hey, you're buying committee walk me through that. Who are you working with?

Who do you know? Who do you not know? Um, what are the challenges that they're telling you? 1 of the things that I think was a shock to me when I came to Entrada was how much pain this industry is willing to put up with. Like, I'm used to selling to pain where there's 1 inconvenience and that's it. We're changing our software.

This sucks. Cause cost of change was so small and you know, we'd forecast deals. This one's coming in. Like there's tons of pain here. Get up to the last minute. You know what? We're not going to change. We don't want to make so and so's life hard. They've worked for us for 30 years. We've been running a terrible for 30 years.

They'll be just fine for another 10 until they retire. It's like, Oh my gosh. Okay. So scrap pain. So pain is important, but really what I want to know is let's get below the pain. Like, what are the motivators for the business that is worth the change? Because. We're changing every piece of software they would ever use every process they're ever familiar with.

We had to get deeper so that we really helped them understand the impact of operating the way they were. 

[00:14:17] Aaron Janmohamed: Yeah. 

[00:14:17] Daren Reschke: And you know, I always want to ask when we're going through a deal review, I'm like, what's the number one. And what is the number one thing? If we didn't solve anything else, that one thing, if we did it, they would move software and work with us.

And if we don't have it, that's like the first bullet I put in the deal. 

[00:14:35] Aaron Janmohamed: Yeah, 

[00:14:35] Daren Reschke: because you know that there's a thousand reasons why they're just going to stick with what they've got like we used to Do nothing more than anything. We don't lose the characters as often It's we're just going to stick with what we got.

And so that that's a critical piece that we're really looking into um Number two. The other thing I want to look at is I really want to know um Are you bringing insight that they hadn't been considering? As they're going to do their evaluation Because a lot of times we'll get into these RFPs where we're just answering a bunch of survey questions and it's really easy to commoditize with your competition because we're all answering the same way.

And if you can step back and actually change the way they're thinking about an issue or you're teaching them something that maybe they hadn't considered. We have the advantage of dealing with deal cycles every single day. This company that we're selling to, this might be the only time they've looked at software in the last 10 years.

And so if we can teach and educate, I think that also helps us, um, you know, gain trust and have a better chance at closing the deals that we've got. And of course like when was the last time you talked to somebody like i'm always digging in We use groove here. So I'll dig in. I want to see what are the emails that that we've sent.

Are they getting responded to? I yeah meaningful So i'm always looking at that. I want to see like last activity dates um today we just did deal reviews for what's coming in in december and Highlight a bunch of deals that have cooled off and why are they still sitting in december? You You know, let's let's dig into those deals and see how we can get warm back back up.

So I wouldn't say there's anything magical there. Other than again, consistency. Yeah, it is about the activity. But what kinds of activities are are we getting the results and the results are always conversations or is it just. Going through the motions. 

[00:16:32] Aaron Janmohamed: Yeah, makes sense. Um, you had mentioned the accountability piece earlier and I want to go back to that.

So, um, I imagine metrics are a big part of the accountability. You got to hold people to specific numbers as a clear indication that they're operating within the boundaries of the game. What are most important metrics for you? 

[00:16:51] Daren Reschke: Uh, so top of funnel, obviously, if you don't have deals that you're talking to, you've got to have an amazing close rate to hit your number.

And so that creates all the cushion. It also helps the rep hold on to deals a little bit looser. So not treat everyone like, you know, live or die, it helps them to negotiate better. So I want to see, I want to see those funnel metrics, um, for us when I got here, if we had one X coverage, that was great. We were probably going to have a good chance of hitting our number, but we were also only.

Putting in pipe, the deals that were actually, you know, going to be 75 percent plus of closing. So we've tried to expand that more. So we knew how much is really out there. We're driving for the two to three X coverage right now. We're about two. Um, 

[00:17:42] Aaron Janmohamed: Oh, but you still have a pretty good close rate then at that level.

[00:17:44] Daren Reschke: We do like we're about 44 percent right now, which I think is fantastic for logo. Um, but I also want to see like, where, where are these deals coming from? Um, I want to see how many people they're actually having conversations with. We're like any sales team where they're great at drilling a ton of emails out there, being more of a email marketer than they are a seller.

And yeah, I want to, you got to build relationships in our market. Make sure people know who we are and we know who they are, um, because their, their timeframe to change is going to be so unknown, uh, make sure that they're going to call us. So I'm always interested in that. How many of the accounts that are signed to you?

Have you actually had a conversation with in the last 90 days? Um, then once we get into deal velocity. That's super important, like, the deals that are in your pipe. Right now we're about, uh, we're about four months. So about a four month sell cycle from start to finish. Once they start to engage with us, if we're outside of that, that's definitely, you know, red flags.

I want to know like what's going on outside of that. And it doesn't mean that that's the gospel. Like it's gotta be four months, but it at least gives us that range. I'm really keen on keeping the averages. Like those averages aren't again necessarily like the hard and fast metrics, but they at least give us something to compare against So I want to know by rep what's their close rate?

What's their their deal size? What's their sell cycle? Yeah, we'll back into figuring out how much work they have to do how many Um activities they've got to create so they have a chance of hitting their number at the end of the year And we just I 

[00:19:25] Aaron Janmohamed: would imagine when you're this dialed into the pipeline and um and this this efficient Um, when you're asked to submit your forecast for the quarter, you've got to be pretty accurate pretty early, aren't you?

I mean, what, what is there a standard like by week one, week four, week eight, what, where do you have to be generally, uh, to goal when it comes to your forecast accuracy? 

[00:19:46] Daren Reschke: Uh, you know, we're I would say we're getting better. We're not as tight as we've been or as I should say, we're not as tight as I've been at other companies being able to forecast early.

Um, and the challenges here is, you know, in our enterprise are. We'll have seven, eight figure deals out there that can really swing your forecast one way or the other. Um, for me, we've got more deals that, that add up to our number. It said those one bills that one big deal that will throw off your whole entire forecast.

But for us, you know, I want to be, you know, if, if we're going by the quarter, once we're into a month, two of the quarter. I want to have like a 90 accuracy to my forecast. 

[00:20:33] Aaron Janmohamed: Yeah. 

[00:20:34] Daren Reschke: Um, with us, we could have deals that we don't even know exist in the first month of the, of the quarter that will close by the end of the quarter.

So now that there's probably about 40 percent of my pipe that I don't know is out there in month one, my forecast will kind of move. But for the most part, if I just put in the math on what our average close rate is, uh, we, we hit pretty close. 

[00:21:01] Aaron Janmohamed: That's pretty good. So good, decent benchmark. Well, in our survey, we found that, uh, you know, the highest probability of hitting targets are with teams that have about an 82 percent accuracy by week, I think is week eight.

So by the end of the second month, which is kind of surprising, I thought it would be higher, like, 20% variability and with just one month ago seems like a little bit of, a little bit of a range, but that's, that's more of, of an average. It seems like best in class teams are able to get to that 90% range by the first part or second week of, of, of the second month of the quarter, which seems a little, little bit more in line.

[00:21:38] Daren Reschke: Yeah, I, I think. I think it also kind of depends on your market. Like if you're companies that buy software a lot, I think they usually have procurement teams that, you know, move at a certain cadence and it's a little bit easier to be predictable here. The challenges that we have is our customer base just doesn't evaluate software often.

Yeah. So much of us is teaching them how to evaluate first of all, but then second of all, keeping them on time. So they understand the impact of missing their dates. Uh, something as simple as a sewer backing up on a property will derail our whole entire, you know, million dollar deal. And sometimes you just can't account for that.

[00:22:20] Aaron Janmohamed: Well, um, I have one last question, um, which is, uh, uh, about leadership. Um, I've noticed that there seems to be a pretty good bet. If you've got a rep that's crushed it for a number of years, you can put them in a leadership position and, or her in a leadership position. It stands to reason that they would crush it as a leader.

It's not always the case. Why is that? Like, why do some people crush it as reps, but can't translate that at scale as a leader? 

[00:22:46] Daren Reschke: Yeah. Um, I've observed a couple of things. Number one, uh, it depends on what kind of sell you're asking to do. I've seen some sales orgs where your leader is just a glorified closer.

And so everyone on their team is BDRs and that's okay. Like, but you're also going to, they're going to be capped by how many deals that they can go and sell, but they're not going to grow closers. Um, so you have that side of it, uh, the other side to, um, to be a leader, you kind of have to sign up for, I don't know, like a lot of HR work that you're not considering you're managing people, which are wildly unpredictable.

Yeah. Dell's reps, especially you have a bunch of red type eight personalities. You've got to try to manage the egos. And you'll get a top performer who's a top performer because they care about themselves and hitting their number and we're coin operated as sales reps. And then you put them into a leadership role where they've got to win the hearts and minds of their team and they don't want to do it and they fell miserably.

You know, I can name people at every company. I've worked at that have failed that way and try to usher them back as quick as possible to where they're going to make the most money and love their job that there are others to where. It's interesting because we're, we're interviewing right now for a leadership role on one of my teams, and, uh, we're going through the process of entering, uh, interviewing our, our own sales reps.

And we've got top producers that are all interviewing. And it's interesting to see the mindset of each group. Like you'll get, you'll get the ones where you ask them like, uh, a company broad question and like, Hey, how, how do our, how do our orgs, uh, operate better? Like, what can we do? And some reps will take that from the long view and say, oh, here's how we all work together in harmony.

Others reps will say, well, if your company or your org would do this, this, and this better than the relationship would be better. And so it's more about them instead of about the other person instead of themselves. And it's a clear indication that you're going to be, you're going to be the one that's pointing the finger and you're going to be the sales department.

That's pointing the finger at marketing because they're not giving you good leads instead of, Hey, how can we partner together and be better? And I think that intrinsic perspective makes better leaders. Um, I would also say sometimes your best reps are also your, your most disorganized reps and disorganized sales leaders make for chaotic sales teams.

And, uh, so I don't know, those are some observations that I have. 

[00:25:38] Aaron Janmohamed: That's really helpful. Well, Darren, thanks so much for your time and your perspective. Always a pleasure.

[00:25:45] Daren Reschke: Yep. You bet.