Jan 22, 2021

Read Time 6 min

How to upsell customers with confidence featuring Bryan Neale


You sign up for a Customer Success gig and now your boss wants you to upsell…and expand…and have all those price increase conversations?

“But I didn’t want a job in sales!” you internally curse.

In our webinar, “Selling for people who don’t love sales,” Bryan Neale, founder of Blind Zebra Consulting shares how selling and taking great care of your customers actually go hand in hand. Bryan explains how we think about selling is just as important as our tactics and execution.

The Q&A portion of the webinar covered topics including what to do when a customer ghosts you, how to handle conversations on price increases, and much more.

Upselling strategies for Customer Success managers with Bryan Neale

At the start of the webinar, we polled our audience to find out what their No.1 fear was when it came to selling. More than half (63%) said they feared coming across as too pushy – likely since we’ve all felt the annoyance and discomfort of dealing with an overly aggressive or eager salesperson. This was followed by 20% of respondents who cited a fear of failing or getting a “no” from a customer, and 17% who fear not having an answer to a question and appearing incompetent.

Q: How do you set a clear future meeting date when using chat or email as opposed to phone or in-person conversation?

A: Authenticity is a core feeling that we carry with us. So, we speak from an authentic place. If we’re in Slack or a chat, or something like that, we just say what the truth is. So, if you’re trying to set a clear future date, I would say to them in the chat “Hey, can we hop on a Zoom call or the phone for 30 seconds to look at our calendars and get something booked? Or we can do it in chat, either way.”

I would just ask them to hop out of that. If you can do it in the chat, do it in the chat. There’s no [rule that] you have to use the phone or anything like that. The main thing is just getting it.

You can type what we just talked about too. You can say, “Hey, I’m trying to be super efficient here. I don’t want to be chasing you around. If it’s OK, could we look at a date to reconnect? We need 15 minutes. Let me know, and I’ll send some dates over in the chat.” They say, “Sure. Sounds good.” Then you immediately send dates over and they say, “Tuesday at 4 p.m. looks good.” You say, “Great, I’m sending you an invite now. Let me know when you get it.”

Q: How do you set a future meeting date if your customer is ghosting you?

A: When you’re getting ghosted multiple times, here’s the generic coaching: you either have to change the message, change the channel, or change both.

Change the message means if you’ve been doing the “Hey it’s me, just checking in” that goes silent real quick. So, your message has to change.

Channel has to do with the modality. Have you been [using] email, email, email, email? Then you need to break that pattern; you need to text them and see what happens. Call them. Leave a voicemail. All with good intention; we’re not being pushy. We’re trying to serve them. We can’t serve them if they don’t talk to us.

We are huge fans of using video to do this. There are lots of software packages. Covideo is based here in Indy. BombBomb is one of them. Vidyard, that’s another. [Those] are kind of the three big ones that we know about. Use video to do that. They’ve got a great way; you hold up a little sign that says, “Hi Brian.” You write that on the sign. You do your video, and it emails it to them. We found huge success in getting responses when you’ve been ghosted multiple with video. If you ever want to talk about that, you can either email me or my wife Stephanie. We can give you a sample.

Q: What’s the furthest out you’d schedule a clear future date for a meeting?

A: Usually, it’s closer to the meeting. We’re running a process. We’re rolling through it. It’s usually within weeks, maybe a month and a half or so, but usually within weeks.

I would be comfortable, if someone is in the mix, to set a clear future date for anytime going forward. There’s no harm in that to me. Then I apply common sense. I [was asked] this question yesterday. Their customer asked to talk in November 2021. [That’s] 10 months from now. And they asked me the same question. Should I set a clear feature date? I see no harm in it.

But if I had to bet, I would put low odds that that meeting happens the way it’s supposed to happen. But I could be wrong.

Usually that 30 to 45 days is what this would be for. [QBRs] are typically scheduled. We like to have those scheduled on the calendar for the year as opposed to chasing them around a week before: “Hey, it’s time for your QBR. Let’s look at the time.” I’m not a fan of that. I like to have them set for the year.

Q: Should you always keep sales calls separate from routine customer calls, such as business reviews?

A: Context setting is what you do here. I am a fan of these being separate. I’m not a huge fan of the sales being blended in with normal CS conversation. I think that’s hard for you, and I think that’s hard for your customer. There needs to be a line. To context set, you might say, “Hey, I want to have a conversation with you next week. I want to talk about a couple other divisions of yours that we’re not working with. I’ve got a couple ideas I want to run by and get your take on.”

So, that’s the subject. That’s not existing; that’s new. I love those to be separate, and I contextualize them like that.

Even if I’m in a normal conversation about CS stuff – I’m talking about usage problems or onboarding – I say, “Hey, can I switch gears on you for a second?” Everyone’s going to go “Sure.” Then I say, “Not today, but at some point here in the next week – maybe we can look at calendars after this – I’ve got a couple of ideas for the other division ABC over here. I wanted to run them by you and get your take on some advice on that. Can we even look at calendars now? Or I’ll send you some dates to talk about that.” They’re very separate. Use language to shift gears. I don’t like blended. That’s my strong opinion.

Q: Should Customer Success Managers be comped like sales reps?

A: Comp is such a funny thing. First of all, I’m a big fan of non-monetary compensation. A lot of us are these days, where it’s about culture and purpose and things like that. That’s way more important sometimes than cash. I like to think about what I’m compensating for and what kind of culture I want to create. Because the comp plan will create the culture in some way, shape, or form.

If I want a bunch of CS people doing a bunch of sales, then I might comp them on behavior. If I say that if they have an upsell conversation, they get a bonus or something like that, I’m going to get what I comp for. The big mistake there – and this is if there are any VPs, managers, Chief Customer Officers – you have to know if your team is motivated by money, and I’m telling you most people are not.

We actually do an assessment that measures this and less than 50% of people have money as a high driver. Do not assume that everybody wants to make more money. [Managers] do that “Hey, here’s a bonus. Here’s a spiff for you. You do this, you get a thousand bucks.” Then the managers get upset: “Why didn’t the CS team do this? They could have made a thousand bucks.” It’s because they’re not motivated by money; it’s not their deal. They might be motivated by days off. Or, let them go adopt a pet or something like that, something purposeful. Comp the team to the culture.

Q: How should you approach a conversation about price increases?

A: I hate these myself. These are uncomfortable conversations for most of us, mostly because in America – from the time we’re born, we can talk and walk and everything else – when it comes to money, we are programmed to not talk about it.

You don’t ask people how much they make; it’s rude. You don’t ask people how much their house cost; it’s rude. You do not talk about money. Oh, you’re in business? You have to talk about money the whole time. It’s totally countered to how we’re raised.

Authenticity comes out. I acknowledge verbally, in my context statement, that these are uncomfortable situations for me (if they are). For me, they are. I say, “Hey, I want to have a pricing conversation with you. Fair warning, it’s a little uncomfortable, but I want to walk you through what it is, get your reactions, and see where we land. Here’s what’s going on.” Then, I just explain what’s going on.

Real strong advice here: do not defend a price increase. You do not have to defend a price increase. Most CS people think they have to say, “Prices are going up 14%, but here’s why.” Don’t do that; just let it be. Let the customer react to it. You’ve got abundance and attachment. Just be with it; good intention. They’re going to land where they’re going to land. You just have a good, open, and neutral conversation.

Increase your upsell potential by getting the timing right

Pinpointing the most ideal time to present your customer with an expansion opportunity can’t be left to intuition. It must be a well-orchestrated act.

Discover how ChurnZero customer, SalesIntel, grew its net retention by 133% by using customer buying signals and usage data to perfectly time its expansion outreach in our blog, “Is it magic, or ChurnZero? SalesIntel reveals the secrets of its expansion success.” You’ll learn how you can apply the same strategies to your own expansion pathways.


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