Sam has worked for some of the most notable names in the Bay Area, including ON24 and LinkedIn, and spent years as an individual contributor in net new Enterprise sales before moving to scaling teams and revenue in executive leadership. She is the creator of #samsales, which has a significant following on LinkedIn for her tangible sales tips and actionable advice for sales executives and teams.
Sam has been named a Top 50 Woman in Revenue, consistently ranks as the most read author for countless publications, is proud to be one of the faces of LinkedIn Sales Navigator’s marketing campaigns, and was named a Top Ten LinkedIn Sales Star 2020.
In her interview she shares her best tips and tricks for having meaningful sales conversations along the whole buying process.
Don't want to read? Watch the interview on YouTube!
Hi Sam, great to have you here today. I'm looking forward to talking to you about having meaningful sales conversations across the whole sales cycle. So, having great prospecting, outreach, having good demo calls, discovery calls, and really connecting with your prospect and customer along the way. Before we get started, maybe you can quickly share who you are and how you've ended up in sales and why you love sales.
Oh my gosh, how much time do you have? Well, first, thanks for having me so lovely to speak with you and on my favorite topics, no less. But my background I've been in enterprise new business sales for about 15 years almost now, which makes me feel so old at this point, but I think like many of you I fell into sales, and it wasn't a career I dreamed about, you know. I wasn't a six-year-old thinking, "I'm going to be a salesman," probably more along the ballerina track, which never worked out... But I fell into sales, and I think what I really love about the idea of selling is that we are solving a challenge for people. So this isn't about me selling a product like skincare or something where I'm hopeful that you'll buy it so that I can make ends meet. This is about looking for an opportunity to solve a true challenge that our buyers have. So, whether it's a technology, a revenue gap, or efficiencies, we have such an opportunity to help our clients to look for what keeps them up at night or what their biggest issues are and then to plug that gap together. I also think that many people love sales just like I do because your effort right in sales really pays off in terms of your financial reward. I was actually just speaking to somebody today who is formerly a teacher, an award-winning teacher, and her pay is identical to somebody else who is a teacher that might just kind of phone it in every day. Whereas sales, the more exceptional you are, the better you do.
That's completely true. I totally understand that. I've learned that your favorite acronym is s-m-y-m-k. Like, show me you know me.
Yeah, s-m-y-k-m. I think you know this really bleeds into every part of sales. Show me you know me. And I think what's interesting about this is that so many people just don't do their research in advance of meeting someone. I speak to sales reps all the time who don't think that they need to do any research before discovery calls. They think they can just show up and wing it because they're super senior, and they know what they're doing. But kind of the show stopper here is, if you show up to a call with a brand new client, a prospective client, and you say, "Hey, you know I'd love to hear about your challenges," and if they say, "Great, but tell me what you know about me first," and then you're like oh my god crickets. Because you didn't do your research in advance. So I think "show me you know me" can bleed from starting up the discovery, not only the discovery call, but also the outbound emails. So, what are we writing in our outbound emails? How are we showing them we've done our homework on them? How do we show them that we've done our research before a discovery call, and then how do we continue to show that we know them throughout the entire sales process? This really bleeds into every fiber and every step.
I guess we all have busy schedules, right? You have a busy schedule, I have a busy schedule, and I guess all the salespeople out there have. And "show me you know me" sounds like a lot of work, like doing a lot of research. How is that possible? How can I do that at scale if I have a full schedule?
Well, so that's a great question. Here's what I'll say: If we show up to that discovery call, the thing that we work the hardest to get, and we show up, and we've done no homework on that person, we're going to exponentially increase the odds of us not furthering that meeting because the person's going to be turned off. So I think this is one of the most critical elements. Whether we have time for it or not, or think we have time for it or not, it's a critical element to see the success. It's as if a rep said, "Well, I'm really busy, and I don't have time to do proposals, but I still want to close a deal." But you have to do a proposal. It's a standard part of the sales process. Think about it in your own perspective: If I had shown up to this call and I didn't know anything about your background, perhaps I didn't know your location, or perhaps I said, "Where are you located?" Your first instinct might be to think, "Well did you look at my Linkedin? Can't you see any of my background? You should have done your homework." Right? Same thing for our prospects. The times that people get on the phone and they're like, "Oh, where'd you go to school?" and I'm like, "It's right there on my profile." So I think 10 to 15 minutes of research in advance before you send out your outbound campaign or before you get on a discovery call, will make all the difference. Don't forget to research not only the company that you're speaking with, but also the person. We want to know that person. Where they came from, who they know, where they went to school? All that jazz.
Exactly. So I think it's pretty common at the moment to say it's not about selling something, it's about building relationships. Now I saw you say your superpower is connecting with people, which I guess is super handy, especially in sales because your job is to connect with people all day. But as someone who's not naturally extroverted and is in sales, how do you get this connection quickly and easily to build a relationship?
So I think there is so much to unpack there as well. A couple of things I would say. One, the connection piece, and building that rapport, I think it's an art. Two, I think it's something that a lot of people undervalue or don't think is a necessary part of the sales cycle.What I'll tell you is one of the most common things I teach: It's the idea of being better at sales is not just working harder, but it's really about being different. So what are the small things that we can do to be different? Like doing our research, being a connector, informing rapport - that's what makes us better and different at our jobs and helps us stand out. On the connector piece: I talked to my fiance about this a lot. He's more on the balance of extrovert and introvert, but one thing he absolutely hates to do is network. And he's like, "What do I do when I show up to network?" "How do I connect to people?" "I just hate it, it makes me very uncomfortable." And the tip that I give him and that I would give all of you guys is just asking questions. It doesn't have to be about you, it doesn't have to be about you sharing or telling a million things about your own private life or your own professional life, but simply show up with some meaningful questions. Tell me a little bit about your perspective, so being a natural introvert, where is the hurdle there for you?
I think it really depends. Especially in today's world where we have so many different channels: you have email, you have Linkedin, you have networking events... I think it's easy to connect online. It's different being at an event where you have to go to them and address them proactively. So I think those are two completely different worlds. And to get out of this basic small talk like, "Oh, the weather today is great." I think the challenge is to really dig deeper.
I think the weather component that you touch on is an interesting thing. We talk a lot about building executive presence on calls. Executive presence really is making those connections. Not talking about the weather, unless of course there's like some monumental weather thing happening like a blizzard or a hurricane and then it's newsworthy. But one of the things that I would do to connect with people, especially before you meet them, is to look at what you can find out about them online. I look at Linkedin if there's nothing there, I'll see if they have Twitter, if then there's nothing there, then I'll just google their name... And I'll just see: Have they written articles? Have they spoken at conferences? Have they contributed a quote to something? Like is there anything I can find that would help, and then I use that when I jump on the call and just say, "Hey, I saw you know this," or, "I noticed this." Just as a way to say, I've done my homework. I've shown them that I know them and just to build that connective thread. And I think it's as complicated as it has to be.
What was the best outreach cold outreach you've ever received? Do you remember it?
Great question. There was a gentleman, who still hasn't gotten a meeting with me, but it's because there's just no product fit, but he literally followed my advice. He put a few things that he knew about me in the subject line to capture my attention right. The subject line is the most important part of our email. If we don't nail that, forget it. And then, throughout the email, he weaved in things that he'd read about me or direct quotes from things I'd said. And I'll tell you that is no small effort. And he really tried to do his homework, he really tried to connect with me and just say, "I've done my work, can you help me." Now while I haven't taken a meeting with him, I did reward the effort by connecting him to three different individuals that I thought could use this product. So we think that's another thing to think about. We're so busy, we have so much on our schedules, how do we have time to scale this and do show me you know me? The right executives who appreciate the difference and the effort you made will try to connect you with somebody who could help you even if they have no need for your product. So think that effort will pay off at least one way or another and at least with a handful of executives, if not all of them.
That's good advice not only for the people reaching out but also for them receiving outreach.
Right yeah? What about you? What's something really good that you've seen from an outreach perspective?
A lot of people still send presents like some funny socks or cookies or whatever with a funny quote on it - That's something that I remember because it really sticks out compared to all those emails and Linkedin requests. So I'm a big fan of those. Of course, it's harder with everyone in home office but still, I think it's a great idea.
Well and I think I'll give a shout-out to a gentleman named Derek. So Derek leads a sales development team at a company called Lessonly in the states, and Derek got my home address. He just asked for my mailing address, not in a weird way of like "Where do you live" but, "What's your mailing address?" And he had temporary tattoos made that said, "Show me you know me," "The urgent bird gets the worm," and one with a pineapple. So he took all three of my background images and just made me something to say thanks for putting content out on LinkedIn all the time. I mean, that will stay in my mind forever.
That's great. I never got anything that good.
One day, so that's the goal.
But you're not only a pro in things like outreach and prospecting. I know you recently launched a master class about discovery calls. So what I noticed in discovery calls, there are two types of people, two kinds of calls. There are those that talk a lot themselves and the prospect is like, "Okay, is he actually interested in my challenges and goals?" And on the other hand, there are people that have their checklist and ask one question after the other: Budget, decision-maker.... and not really having a real conversation. How do I find the balance?
Yeah, so I think a few things about discovery. Just like you said, we're asking a firing range of questions; we're going through our list of what we have. I think about a discovery call like a first date. You know, I think everything in sales can go back to dating. To your first example, if you show up and you talk about yourself the whole time, just think would you do that on a first date? And if the answer is yes, we should have a separate conversation - to help you with your dating life because that's never going to work. But the second thing is if you come to your first date with a firing range of questions: Do you want to get married? Do you want to have children? What's your financial credit score? Like all of these things, you're not going to help somebody. The idea is for us to get to know each other. And especially on the discovery call, as a salesperson, it's our job to lead the call and to understand the challenge of the other person. I think if we reset the idea of the discovery call, it's not about uncovering BANT, it's not about covering what the exact next steps are, and who the decision-maker is - It's really about uncovering the challenge. Our one job on a discovery call, especially the first one, is to solve that challenge of the buyer either by something that we do or by referring them to somebody who can help them do whatever they're looking to do. And I want you to think about that: If we show up to the call and we just ask these questions, it's selfish. Instead, if you and I were on a discovery call together and I said, "I could tell you a million things about #samsales, but I would love to hear about you first. Can you tell me a little bit about your challenges, the landscape over there, your team... I'd love to start with that first if that's okay." What I'm doing with that is I'm saying three things: One, I'm going to tell you about me, but you go first. Then I'm giving you some footholds to think about, like your team, your challenges, the landscape, etc. I'm kind of filling that awkward silence while you think. And then the final thing is just saying if that's okay. Because there could be a chance you come on the call and say, "I actually have a bunch of questions for you. I already know I want to buy you. I just need to make sure you answer these questions." But nine times out of ten you're going to get someone who's going to say, "Sure, let me tell you about our side." And that's when the magic happens. Because they're telling us everything that we need to know to sell to them. And the one more important thing that I'll tell you there is: don't interrupt that stream of consciousness. Most reps hear the first thing that we can solve, and they're like, "Oh, let me talk about that." Be quiet. Let that go, and then, as soon as they're done talking, we go back, and we filter our way through all the things they mention.
How important do you think honesty is in this process? If I have a qualification call and I notice maybe it's not the perfect fit... what would you say? Would you be honest to the prospect, or would you try to push your product to them anyway because you need to hit your numbers?
Sales, and especially this kind of sales, is a long game. So I think what's important is that we always have our foot on the gas for prospecting. So we have tons of opportunities. So even if this isn't a fit, that's okay. Like book yourself a hundred first dates for that month. That way, you don't have to focus on the first day to try and get to the end game. But the other thing to think about is that honesty is incredibly important. If they're talking to me at #samsales and they're saying, "You know we really need a consultant to help with sales operations and revenue operations." Could I figure that out? Maybe. Is it my strong suit, what I love? No. But would I want to bring that revenue anyway? Sure. However, what I'm going to do is be honest with them and say, "That's not really my forte, here is my forte. When you need help with this, come talk to me. But, I have an excellent consultant that I can refer you to. If you already took time to speak to me and you trust me enough to give me your time, maybe you'll trust my recommendation, and I can help you do something." I will tell you that honesty will pay off. Because you get to help somebody else hopefully that you know they can help them. And, you're honest with the person when they would probably expect you not to be because you want to make a sale. And when they're ready to buy your services or know somebody who will need your services, they'll refer you in a second just because you were honest. And full selfishly in the end, even if we try to push that deal forward, they're probably going to figure out that we're not the right person for them, and we'll have wasted hours upon hours, making proposals and having calls for something that wasn't going to happen in the end anyway. Think about a mechanic. If they are like, "We could fix this for you, but it's unnecessary." You're like, "I will come to you for the rest of my life. I love you."
There are situations where I notice we're not the right fit, but, of course, there are situations where I think it's a perfect fit, but the prospect says it's not the right fit because of the wrong timing or maybe lack of budget. So, I need to nurture this lead. We at Ciara had a lot of discussions about that topic in the past weeks. I reached out to a couple of people in my network and asked them how they do it in their companies to compare best practices. And what I noticed: no one was really sure if they were doing it the right way. How would you set up a nurturing process for sales?
Great question. One of the things that you said before perked my ears up. The idea of "We don't have the budget for this." So I think one thing to think about is that depending on the size of the company that you're going after - like if you're pitching #samsales and we say we don't have the budget for a hundred thousand dollar solution, we probably don't have the budget as much as we wanted - but if you sell to commercial-grade companies and you hear "we don't have the budget," I want you to think about two things: One, it may be that they don't have a budget outlined for this exact thing, but it doesn't mean that they don't have money. And if they don't have the budget or if they don't have as much budget, we also haven't proven value. It is almost never about the budget. It's about proving value, really solving a challenge. And then helping your buyers figure out how to find money from different teams, from different initiatives, cross-functional partners... there's so much work we can do there. So when you hear "We don't have the budget," be like: There's budget, I know there is.
On the nurture side, here's one of the very easy game-changers to think about: Let's say they're saying, "The timing isn't right but perhaps in 90 days could you reach back out to us?" One thing I hear people say is that their polite pushback is, "What will be different in 90 days?" I personally hate that question because it feels very conceited. It feels very judgmental. Here's the thing: If you did proper discovery and you really understood what's going on with the client, you know why they need to wait 90 days. Or you can kindly say like, "Tell me a little bit about the initiatives you have over the course of this quarter that make 90 days more feasible?" Because then you'll get some information possibly that you didn't get. But let's say regardless we know we have to reach out in 90 days. So we have from zero, which is today, to 90 to nurture them. What I find most individuals do is they say, "You got it. I'll reach out in 90 days," and they set a reminder in Salesforce for day 89, and then on day 89, they follow up, and they're like, "Veronika is now the right time to chat?" and you're like I just want to jump off a ledge. So here's what I would say: think about how to nurture that prospect in a smart sequential way. I say with 90 days, every two and a half to three weeks, I like to send a piece of evergreen content or something smart that I already have teed up. When sending that content, think about a few things: One, it does not need to be all work-related. This should not be anything that's pushing them back to #samsales. The mechanism and idea of nurture is to give something of value and to remind them that I exist as a human and that hopefully, they want to buy from me. So this can also be Harvard Business Review articles, things from Forbes, from the Wall Street Journal, the New York Times, whatever you want. Every two and a half weeks, send something along. And the components of this email are very simple, "Hi Veronika, I saw this piece in the Harvard Business Review it made me think of you because..." And then I'm tying it to something you and I have talked about. Then I'm giving you my opinion on it, not a novel, just one or two sentences like, "I read through this here's what I loved about the article..." And the closing is the most important part. There is no ask whatsoever; it's just a closing: "Hope you find this helpful," "Hope you're having a great week," "Happy weekend." Because if you instead close it with, "By the way, do you have an extra 15 minutes to chat?" people are going to see right through you, they're going to be turned off, and it's going to be a wasted effort. So just use that as a lever to nurture, drive value, and remind the person that you exist.
One other thing: Don't forget the power of Linkedin. That's an extra lever. I have a top 50 prospect list. Every Monday morning, I'll go to 10 people on my list, and then the next 10 next week, and the next 10 next week... I'll go to their LinkedIn and see if they've posted anything recently or commented on somebody's post recently, and I'll add my thought leadership. Not something like, "Cool post, Veronika," but I'll actually give something that's in my brain because then I'm allowing myself to have my subject matter expertise shown and to stay top of mind with my prospects.
So you've got a lot of leverage that you can pull there in the 90 days.
You said two important things now: First of all, you said nurturing is not really about promoting the product and scheduling the next meeting but about showing you're human and you want that they buy from you as a human. And second, you said you shouldn't forget LinkedIn in all this process. So combining those two things, how important in your eyes is personal branding on Linkedin?
I think I couldn't speak more highly of it. And what I will say is you a couple of things you've got to think about: It takes time. It really takes time to develop that brand. There are so many people who say, "Well, if I post something today on LinkedIn am I going to get business out of it?" No. If you go to the gym today to work out, you're not going to lose weight and build 60 pounds of muscle. Like it takes time. But when you get there, it pays off in spades. So, what I would tell you is to keep in mind that building a personal brand is who you are consistently for better or for worse.
If you want to start building a personal brand on Linkedin, if you want to start sharing content, you want to start your own hashtag like #samsales, just do it. Don't make an announcement because this is where I see people fail. They're like, "Every Monday, I'll be posting this," and then three weeks go by, they get very excited about posting for three weeks, and then they fall off the bandwagon. And that brands you as somebody who cannot follow through. We will sometimes miss posting on Linkedin, we'll miss building that branding effort sometimes in one week or maybe in a few days, and that's okay. As long as you haven't committed to doing something like that, nobody's going to be looking out for that and looking for basically you not following through on the commitment. The thing that I would say is if you start to post content on LinkedIn and build a personal brand, you want to think about it in a couple of different ways. About 70 of your content on LinkedIn should be your own thought leadership. Something that you are giving away as valuable content, as teaching someone something, as a perspective. And in that 70 percent, you should also be engaging with others. Go to people's posts - my posts, other thought leaders posts, your clients' posts, your prospective clients' posts... - and comment and add thought leadership. Just the power of that is huge in terms of personal branding. And I'll tell you as a quick hack: If you want to speed up the process of your name being exposed out there, go and look for people like myself, who have an inordinate amount of followers on LinkedIn, and comment on our content. When you do that, you get access to four different audiences: myself, anybody who commented, my network, and your network. With one post - it's huge. Spend 10 to 15 minutes a day doing that, and you'll be in great shape.
Now the flip side, where's the other 30 percent. The 30 piece comes in when you are doing anything that's self-promotional. So an award you won, a product release, a case study of your client, or you're speaking at a conference, an article you wrote, all that stuff. Keep the bulk of it as thought leadership and engagement with others, selflessly, and then work in the little promotional parts here and there in the other 30 percent.
That's really good advice. I need to start working on my own LinkedIn brand. But I'm one of those people that always forget to post and stuff, so...
Well and I'll tell you, so here's my 30 percent, here's my shameless plug: If you go to our website samsealsconsulting.com, there's a section under our solutions called "Shorts," and it's an annual subscription, very inexpensive, and you get access to all of our video content on there for anything that you want to know about. How to get around budget, how to build a great profile, how to use LinkedIn to search for a job... there's so much there and tons of content to be added.
I bet it helps. I already watched a couple of videos and went through a couple of posts, and I really can recommend it to everyone watching.
Thanks, thank you.
I guess we have a lot of really good advice for frontline sellers already, so maybe one more sales leadership-related question. As a sales leader or sales enablement manager, how can I enable my reps to have more meaningful conversations? Especially in a remote setup where I not necessarily can jump into every call and guide them? How can I support them?
So I would say two things: On the meaningful conversations, think back to what we talked about the discovery calls. Just teach them how to open that conversation up. To me, again, the goal of that discovery call is solving the challenge, not working through our own questions. And if we start a discovery call with, "Tell me more about this," we will have a much more meaningful conversation. The other thing is active listening. Forrester research did a case study and looked to see the number one thing the B2B buyers want from their sellers. And it's active listeners. So active listening is the act of asking a question, getting the answer, and then using the information from the answer to ask the next question. Again, if we join a call and we're working through our firing range of questions, we're not actively listening, and our buyers see that. So I would say listen to recordings, even try to have a conversation with them, and see if they're active listeners. And if they're not, make that one of the sweet spots that you work on.
The next thing I would say to look out for meaningful conversations is the question behind the question. My first job out of high school was as a lifeguard at Walt Disney World in Orlando, Florida. One of the things that we were taught on basically day one is that Disney's most popular question is "What time is the three o'clock parade?" Well, it's at three o'clock. So here's the thing: If you are most reps, you're going to say, "It's at three o'clock. Does that answer your question?" And the buyer is going to say, "It does, thanks." And then they're going to move on. If you are looking for the question behind the question, it's to say, "The parade's at three o'clock, and I have a few things to tell you about that, but first, tell me a little bit about why you're asking."
We're trying to look at the situation in front of us when somebody asks that: is this a family, do they have children, is somebody in a wheelchair, are they short, are they tall, are they trying to get out of the park, do they want to get to a ride...? What are they really asking? Because it's not what time the three o'clock parade is. It's just their crutch for asking that, for what they really want to ask. So think about that. If your prospective client says, "Do you have an app?" "Do you integrate with this?" Anytime they ask a question, think to yourself, why are they asking? Even if it's obvious, ask anyway because you get tons of information out of that, and again, it's leading to better conversations.
It seems like Disney is a good sales school.
Oh my gosh, they're the best. I advocate everybody to go and work for them and learn about customer service because holy moly.
Okay, perfect, Sam. I think that's it for today. I think that's a wrap. Thank you, it was really great; there were so many valuable insights.
Thank you, thank you so much for having me. Very truly feel free to connect on LinkedIn. If I can ever be of help or if you ever have questions, feel free to hit me up there; I'm pretty responsive. But there are so many resources on our website too. Totally free and all sorts of stuff. And Veronika, thank you so much for having me.
Thank you, Sam.