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Sales Engagement Evolution with Wes Baker {Hey Salespeople Podcast}

Looking at the reply rates of a campaign is the gold standard for measuring email effectiveness. However, Wes Baker argues you should instead focus more on sentiment.

As the Senior Manager of Demand Generation at Jitterbit, Wes is responsible for streamlining inbound and outbound channels using their sales tech stack and shares his knowledge and experience on this episode of the Hey Salespeople podcast. 

Jeremey and Wes discuss where sales engagement is at today, tips for measuring effectiveness, and how he sees artificial intelligence (AI) and machine learning  (ML) changing the future of sales. 

wes baker podcast

Listen to this episode for answers to questions like: 

  • How should you approach mid-market accounts versus enterprise accounts? 
  • What are the holes in sales engagement platforms? 
  • Why is being an SDR one of the hardest roles in sales? 
  • What can AI and machine learning bring to sales engagement? 
  • What should a campaign’s ratio of positive to negative replies look like? (It’s not what you would think!)

Listen here, and keep reading for some of the highlights from this episode below.


Managing Sales Development Teams

Jeremey: When you moved into managing the sales development rep (SDR) team, what were some of the things that you view as keys to success and leading team to meet and exceed quota?

Wes: When I actually was put into this role, my VP of Sales told me, “Wes, you have three things to focus on: people, process, and technology. Exactly in that order.”

I absolutely loved that. I took it to heart.

The first thing I did was I made sure we had the right team. At that point in time, we didn’t… and I knew we didn’t. Some of the SDRs I was working alongside were just in it to hang out. They didn’t have that grind in them. They just weren’t happy there. So I said, “Okay, let’s have a discussion. Let’s talk about this. Is this the right thing for you?” It took me a while, but eventually, we did move those people along.

Then, we brought in the next first wave of individuals who I was able to interview. We worked with recruiters and different channels to find these individuals. We were trying to find people with the entrepreneurial spirit that want to make something out of themselves and are the go-getters. It’s hard to find talent, but that was was a big focus. Getting people that were hungry.

That was probably why [people, process, and technology] were in that order. Because that was the biggest reason for my success in the SDR management role. I hired really great SDRs and they’re actually all still at JitterBit today. Most of them are doing inside sales. I have one over in product marketing, one in product management, and a couple on the CSM team.

Hire good talent. People that are striving for that success goes a long way and they help you get to the next point.

Jeremey: We’ve done some data science where we looked at SDRs who are successful, and success is defined as moving from SDR to AE inside of their company. Whether you realize or not, your actual background is one of the green flags, if you will. Oftentimes people who were account executives, often in a smaller organization, who are looking for the opportunity to get into a better industry turn out to be great SDRs.

The Future of Sales Engagement

Jeremey: People understand sort of the current state of sales engagement. You’ve got phone, email, social, and potentially direct mail types of integrations. If you were to wave a magic wand, what are some of the changes that you would like to see this industry evolve toward?

Wes: The biggest problem right now that we’re all experiencing, especially as email marketers, is the amount of spam we all get. Reply rates are low. No one wants to answer emails. I can’t clear my inbox. I don’t think anybody can clear their inbox anymore. It’s absolutely terrible.

A big reason for that is because everybody is hyper-obsessed with reply rates. ‘How can I get this person to respond to me, I’m going to send them a random gift card, and hopefully, they’ll answer and go use the coffee card to talk to me.’ I’ve been sent a soccer ball recently. And I’m just like… I’m not interested. I don’t need a soccer ball.

We’re hyper-obsessed reply rates, which is good because that’s how the conversation starts. The problem is that we’re all so focused on these reply rates that we lose focus on the metric that really does matter – more positive replies. We need positive replies and people that want to speak with us. We need to make sure we’re targeting the right persona.

Tracking Sentiment

What I’m most excited about is for AI and machine learning to get to the point where they’re able to detect the sentiment of a reply. People are going to be making sure that they’re talking to the right persona; the one that actually wants to speak to them as well. It will tell marketers if they’re saying the right thing or not.

If I have an outbound cadence and it has a 20% reply rate, I think that’s good. Super high. I’m going to think “Wow, this is working!” The CMO or VP of Sales are going say, “keep using that cadence!”

Let’s flip it to see the sentiment. 2% of that is positive and 18% is negative. People are saying, “no, I don’t want to speak to you. No, I’m not interested. No, I’m not the right person for you.” Your perception of that cadence is completely changed, right? Now maybe you have a great content writer you can leverage to use the best email tactics to get them to respond. She’s doing the writing, and hitting them up five times a day.

Jeremey: I get most excited about that. Because I know with AI and machine learning, that’s the next thing that’s coming. I ask companies today, how do you track sentiment? A lot of people don’t actually do it. That seems pretty crazy.

Wes: The only way that I found to effectively do it today is how I do with our campaigns. We’re running a very large manufacturing campaign right now. I hired a summer intern and I literally have this intern go through the entire cadence and look up what every single reply was, and tag it.

What is positive? Did they book a meeting? Did they refer somebody? Did they want to engage with us? Was it a neutral ‘Not right now? Maybe later? No, thanks?’ Or was it negative ‘Take me off your list. I can’t believe you’re doing this. This is the worst practice ever.’ That’s been very effective for us because we can pivot our message and change our messaging.

Jeremey: If someone replies, it seems most likely that it’s a positive reply. I’m not going to waste my time on the recipient end to send a negative reply. Is that what your intern has found? Or are there actually are a lot of negative replies?

Wes: What I generally see is there are actually a lot of negatives. I actually call it neutral. Negative is if they unsubscribe. Unsubscribe is like “I never want to hear from you guys. Take me off.”

We put a lot of marketing effort into this; months and months of work. I’m seeing a 10% positive,  15% semi-positive. Those are pretty much referrals, and then 50% of that is neutral. People that are just saying they’re not interested. “No thanks, maybe later.”  25% is negative… I actually think that negative is still really high.

That’s the one I want to get down because I don’t want to piss people off. This campaign is a very very large campaign, so we’re getting thousands of replies for our team. If 25% of those are not happy with what our messaging is, that needs to set the indicator lights off. This is the metric marketing needs to get that number lower.

This being a manual process and having an intern, it’s great for the summer because we have all this data for the summer. However, this turns off when summer is over. Then we lose insight into how our campaigns are performing and whether we should be changing our messaging. 

THERE’S A LOT MORE AFTER THIS! Listen to the full podcast for more on sales engagement.


If you have a passion for the art and the science of sales, are looking to further your career, or just want to hear some great, practical tips, ‘Hey Salespeople’ is the podcast for you. Subscribe so you can follow along as Jeremey interviews the brightest minds in modern sales to bring you immediately actionable advice. Listen and subscribe here.

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