Hot Takes

You’re Thinking about Sales Development Wrong with Ian Wroobel


Sales Development organizations are vital to the success of most sales functions, but it seems to be one of the hardest areas to get right. These organizations are the lifeblood of sales opportunities for your sales teams and often are the pipeline of talent that eventually move into full closing roles.

Despite the importance of this role, there are a million different opinions when it comes to structure, purpose, enablement, and metrics for these organizations. This lack of consistent vision for the sales development GTM is severely hindering the potential of this function for your organization.

During this 15-minute session, Ian Wroobel will outline how to create a GTM for sales development that prioritizes desired outcomes and ultimately drives more business for you.

[Transcript] You’re Thinking about Sales Development Wrong

Although transcriptions are generally very accurate, just a friendly reminder that they could sometimes be incomplete or contain errors due to unclear audio or transcription inaccuracies.

Gary Amaral

Product track here at Hot Takes Live 3. Thank you so much for sticking around, for taking in these sessions, and for all of your insightful questions. Please keep them coming. I’m happy to facilitate that for you.

After our quick lunch break, we are here with Ian Wroobel, soon-to-be sales director at a leader in data and AI. That’s a little bit of a tease that information will be coming out shortly, but Ian is here to tell us how we’re all thinking about sales development completely wrong. Is that right, Ian?

Ian Wroobel

Yeah, that’s definitely right. It’s something I’ve been passionate about for a while, so I’ve worked as a sales development rep. I’ve managed sales Development. I’ve worked with them as a sales director or Enterprise sales rep for the last four or five years, so something I’ve been pretty passionate about that I think there’s hopefully some takeaways from this that if you’re building one out or you’re working with one today you know that you can take away from.  

Gary Amaral

Awesome, Ian. I’m gonna throw up your deck right now feel free to jump right in; I’ll be back at the end to put you on a hot seat with some questions.

Ian Wroobel

Perfect, cool. So I’m going to talk today about why, essentially, you’re thinking about sales development wrong. There are multiple different ways to think about it, and there are multiple different avenues within sales development to think about, but I’m going to talk specifically about essentially the vision or what I think is required to make sales development successful from a vision standpoint today. 

As Gary mentioned, I’m a Sales Director, Enterprise account director, or whatever you want to call me. I’m actually in the process of leaving one company, and I’ll be joining a leader in data and AI. Then just a quick, interesting fact, I’m actually live from London right now, so moved from Los Angeles about two years ago. 

Kind of the origin for this, and if you’re kind of in the sales development world or you’ve spent quite a bit of time on LinkedIn, you’ll see there’s a lot of discourse right now around lead generation, cold calling pipeline growth. Really, That’s ultimately what’s dominating the conversation about how to drive sales development success. 

However, from my perspective, I think the real challenge of building and scaling sales development lies with the mission of the organization itself. Really it’s the focus upfront of how you’re actually building the organization, and I think the talk today, or my perspective today, obviously will be a bit different in the sense that I’ve never fully built sales development organizations, but I’m hoping to give a bit of a different perspective as someone that’s worked in them, managed them and ultimately worked from an inside and field perspective with sales development. 

So hopefully, it’s a bit of a different perspective, but what I’ve noticed from kind of my time in doing this is there’s a misalignment with business school. So lead gen. versus development is sometimes at odds. What that effectively means is a good example of this within a sales organization. I think there are essentially two primary functions. One is driving a new business, and one is developing your reps for the future.

You're Thinking About Sales Development Wrong With Ian Wroobel

You can do both at the same time, but inherently I think there are certain things that are at odds with each other. A good example–if I have a sales development rep create or set up a discovery call and I bring on an AE; Immediately, that AE is going to want to jump in and take over the conversation, and to their credit, they’re probably more knowledgeable to the product, the industry, the customer, but what that effectively does though is it leads to probably better quality of that call. 

Ultimately it’s probably going to go in a better direction having someone’s more experience take it, but at the same time, you’re then also having somebody that set up the call does not necessarily get the same value in terms of being able to basically learn from that situation. 

The second thing is, ultimately, I’ve seen quite a bit of blurred lines between quality and quantity. I think there’s a big need to treat sales development like you would a sales organization. 

Ultimately that’s how you’re going to get sales development reps really, I think, bought in and trained up in the way that you ultimately want.

You know, sometimes, again back to the first point, there’s some overlap in terms of lead gen versus development–as a development perspective, more ‘at bats’ is great, but from a lead gen perspective, you could be wasting a lot of time on poor quality leads or things that don’t turn into opportunities. 

Sales development seems to be one of those organizations where there are constantly changing priority structures and metrics, and I think that’s one of the biggest things that’s leading to an issue of quality and focus.

Then the biggest thing, or one of the biggest, is the lack of enablement and coaching. I think this is the organization where you need the most of this, not necessarily just giving them the opportunity to come in and just figure it out on their own. I think it’s one of the things just massively hurting businesses in terms of sales development.

As we kind of move forward. Effectively, a sales development organization could be one of your most valuable assets. It’s not just another problem to throw bodies at–I think that’s sometimes what I’ve seen–so having a vision for prioritizing the lead-generated AE progression is the foundation to build on. 

You're Thinking About Sales Development Wrong With Ian Wroobel

Ultimately it doesn’t matter what your ultimate goal is it could be something totally different from a sales development organization, but I think it’s key to have that goal in mind up front and build towards that vision or essentially work backward from that vision rather than saying, ‘Oh, I need to create more pipeline. Let’s hire some more SDRs and go at it right.’ Working backward and having that vision creates a lot of consistency throughout.

The second point being consistent enablement and coaching is key to facilitating quality over quantity and both lead gen and AE progression. So being able to train new reps coming in is absolutely paramount to being able to drive them towards whatever outcome you ultimately want within the organization, and I think there’s a lot of focus on, “Hey, just let them hit the phones, let’s reach out.” 

Ultimately SDRs or ADRs, whatever you just call them, are the first point of contact for your company into customers, and you want them to be trained up on the industry. You want them to be trained on not just your product but the broader ecosystem associated with it. 

Then ultimately–we’ll talk a little bit at the end–developing the right compensation strategy is massive, and I think anybody that doesn’t believe that compensation drives behavior is honestly fooling themselves. The compensation strategy is absolutely paramount to getting the outcome that you set in bullet one.

So I guess the question is why it matters. You know to some, this is common sense. Quality pipeline judges better conversion rates and more revenue. Ultimately I think there needs to be a thought process of sales development in the mission of the broader revenue organization of a company, it’s driving more quality revenue. 

You're Thinking About Sales Development Wrong With Ian Wroobel

Prioritizing rep progression facilitates a consistent pipeline of future sellers. I think one of the biggest things, and I’ve seen this working at a company like Oracle, which had a massive sales development organization, their goal with that organization was largely to be able to build that pipeline of sellers for the future. Teaching them the right things up front and enabling them correctly upfront:

  1. It leads to better retention rates. 
  2. It also leads to better performance of the reps that actually move into sales roles. 

Number three is that a strong sales development organization allows experienced AEs to focus on closing. I know that’s a bit of a hot take, and I’ve as an AE myself, or in my AE roles, I’ve always been a big believer of “I need to find the business myself,” but if I can get some stuff from marketing, sales development or other sources, that’s great.

I think the reality is that if you have AEs, that are so busy that they have inbound leads or leads from the SDR organization that are really truly quality, I don’t think that’s a bad thing you’re paying AEs a lot more money to be closing business.

I think a strong surveillance development organization really can have is hone in on actually closing and working on deals and opportunities. 

I think that the last thing is if you’ve ever worked in a sales development org, especially with younger folks coming out of college or university,  depending on where you are. Having the right vision leads to more motivated sales reps, and that was one of the biggest challenges I had was motivation in that job is tough.

It’s a really difficult job it requires a lot of day-to-day repetition, it requires getting told ‘no’ more than anybody else in any kind of organization, and I think finding ways to keep your sales reps motivated I think is paramount to your success. 

Then in practice right, and I want to be clear. The point of this “In Practice,” and again I’ve been transparent that I haven’t necessarily done all these things, but I think these are some of the things that I’ve seen that, hopefully, if you take away, hey, maybe there’s one thing I can implement right these are a couple of things that I’ve thought about.

You're Thinking About Sales Development Wrong With Ian Wroobel

If we start at the beginning right, determine your long-term goals of sales development and drive towards that consistently. So we’ve talked about that in the last couple of slides, but having that as your driving factor is massive. 

Number two is to hire first-line leadership that’s sold before or had a strong ability to be customer-facing. I think there’s a massive opportunity for your sales development team to learn from their immediate manager. I think having somebody that’s been in their shoes or sold at that product or the tech or the company, especially in a very tech-centric world it’s candidly difficult. 

There are a lot of challenges with the technology, there are challenges in terms of being able to understand why a customer would find any value in the technology. I think having that as a leadership principle in terms of hiring is massive to help drive towards ultimately the outcomes you want.

This is kind of an interesting one, but I believe in prioritizing sales development reps to follow the entire deal cycle and actually incentivize it as a metric, but this might be something that upfront you’re paying reps for that you might not see any inherent value. 

I think making sure that your reps are incentivized to stay with opportunities they find throughout, and they get to see experienced sales reps come in and close deals based off the work that they sourced. It’s a fantastic way that doesn’t really cost you anything. 

Still, it helps get reps way more up to speed because anytime you move from sales development to sales, there’s a massive learning curve in terms of being able to go from ‘Hey, I found an opportunity’ to ‘Hey, I closed an opportunity.’ Being able to see more and more of those ‘at-bats’ is extremely helpful. 

Going back to a bit on the enablement, it’s not just ‘Let me teach you my product, and you go sell.’ They need to understand, or you need to be able to communicate consistently the industry, the value that the product has to the customers, and essentially the foundations that you need. 

A good example of my time at Oracle; when we came in as sales development reps, we learned a lot of ‘what is this database technology,’ but 99% of the people had no idea what a server was, or computer was or what the basics of the industry were. Not having that foundation meant that you’re just regurgitating the same key points or whatnot, you’re not able to have real conversations, and you’re not able to understand. 

So I think prioritizing that is massive, making sure you have a clear path to promotion. Sales development reps want to move up; they want to move into new roles, making sure that they understand where they can go from there. 

Listening to your reps, I think sales development reps are great for understanding where the business is at and what kind of feedback they’re getting. You know, listen to understand their challenges. 

Then around compensation, just a couple of ideas I had, things that you want to prioritize, but things like meetings, progressed opportunities, and close deals. Give sales development reps a kicker or something in terms of closing a deal or a deal they find closes; that’s a massive incentive for them to find a real quality pipeline. Not just pipeline to hit numbers, number of meetings facilitated, or sat in on a sales cycle. 

Back to the point, number three or conversion rate of opportunities. I think, ultimately, the key here is prioritizing outcomes versus activity. Again the discord is a lot around activity, and I think it really needs to be more about outcomes. When I was a leader, I couldn’t care how you got 10 meetings a week, but if you got 10 quality meetings a week, that was fantastic. 

The last kind of key takeaway is that ‘investing in sales development with the same focus as direct sales organizations provides long-term dramatic and measurable value.’ and that’s it.

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Hot Takes Live


Catch the replay of Hot Takes Live, where 30 of the top SaaS leaders across Marketing, Sales, and RevOps revealed some of their most unpopular opinions about their niche.

These leaders shared what lessons they learned and how they disrupted their industry by going against the grain (and achieved better results in the process).

Gary Amaral

Awesome, Ian; thank you so much, bud. We got a few minutes here for Q&A. I got two questions to come to mind. One, you mentioned about like a path to promotion. I found historically that many people in that BDR/SDR role, they’re like super new most of the time, right? Like it’s a new-to-work type, and they have a very unrealistic time frame. Have you found that in the past, and how do you manage expectations around that?

Ian Wroobel

Yeah, I think they do, but I also think sometimes there’s no clear path to that next step. That’s given, and I think sometimes it’s the uncertainty of having that feeds to your point—some of the unrealistic expectations. If I don’t know how long it takes or what I need to do to get to the next level, there’s this on the back of that. There’s the mentality of ‘I want to get up as quickly as possible.’

And to be fair, I was that same way. And I think, in hindsight, the fact that I had to take extra steps or I had to spend a little bit longer in roles ultimately was to my benefit, and I think that’s a challenge you have to work, you know, with leadership to be able to coach to.

Because when you’re fresh out of college or university, it’s a lot of instant gratification, you want to get up and move as quickly as possible, but you know, having that clear path helps at least set the expectation.

Gary Amaral

Cool, and then the last minute or two here. 

I think you’re bang on in terms of people tend to gravitate towards building calm structures or management structures around activity, and really what we care about is managing the outcome, right? 

The tension comes from how much the rep, the BDR or SDR, or whatever they’re called, is in control of that ultimate outcome. You’re trying to find a house, a healthy balance between, ‘Hey, I know it takes effort, and I want to reward the effort. But ultimately, I care about the outcome, so here’s a taste.’  

So how do you find the right balance between those two things?

Ian Wroobel

Yeah, and I think there are metrics that we know lead to some of the outcomes that you want. Certain activity metrics potentially, meetings, metrics that we use, and pipeline opportunities. 

I think inherently, the problem is you can’t view sales development completely separate from sales and say, ‘Well, if they just hit all this activity metric, they’re going to be happy and motivated.’ From what I manage, the reps love to see deals close, and I think what you do is instead of saying that’s the only priority, you can’t just comp on closed deals. It’s not realistic or fair.

Giving that extra incentive or the above and beyond incentive for those kinds of deals, I think what you’ll notice is you’re still going to have the activity metrics, you’re still going to have people hitting the phones and potentially producing quantity over quality to a certain extent, but I think you’ll see that shift start to push into them doing their own qualification, them understanding what a real opportunity looks like, and a little bit more enthusiasm motivation seeing their hard work turn into something. So it’s I think it’s a gradual conversation. You can’t do one or the other entirely.

Gary Amaral

Awesome, Ian, thank you. We’re at time. Really appreciate you joining us; this topic was super interesting. For those listening who maybe want to reach out, or they maybe just want to keep an eye on you and see where you end up landing, what’s the best way to what’s the best way for them to do that?

Ian Wroobel

The best way is on LinkedIn; I definitely would love to connect with anybody. Happy to have conversations around this. I think it’s something I’ve seen and been very passionate about, so thank you for the time today, and looking forward to anybody who wants to reach out and connect.