EPISODE 407: Sendoso Gets $100M Funding; CRO Sam East Explains How it Impacts Sales Efforts

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[EDITOR’S NOTE: This is a replay of the Sales Game Changers LIVE Webinar sponsored by the Institute for Excellence in Sales on September 15, 2021. It featured Sendoso CRO Sam East.]

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SAM’S TIP FOR EMERGING SALES LEADERS: “Be conscious of the things that you cannot affect within your sales process. As you’re in a sales process, if you’re hitting a brick wall, you’re in a challenging situation, make sure that you’re very aware of, “What can I do to change this and what are the resources that I can leverage around me to help move forward? What are the things that frankly, are completely out of my control?” If you waste one second worrying about those, it’s one second that could have been spent on things that actually are within your sphere of influence. I think that’s increasingly important for how we sell today, because there is a lot more that’s out of our control. Not everything is down to you, so that’s something that I’m preaching a lot to my sales teams, my sales leaders. Just focus on the things that you can really impact, don’t sweat everything else.”


Fred Diamond: We’ve got Sam East today, he’s the Chief Revenue Officer from Sendoso. Sam, it’s great to see you, thank you so much for being here. Interestingly, Alice Heiman, who’s one of our frequent guests on the Sales Game Changers podcast brought up your company’s name back when she was on the show in November of last year. We talked a lot over the years about some strategies for making virtual go much more successfully by personalized interactions with customers, which we’re going to talk to. But we have to talk about what happened to your company yesterday. Congratulations for Sendoso, good to see you. Why don’t you tell us the news? Tell us a little bit about Sendoso and then we’ll get right into the interview.

Sam East: Fred, firstly, thank you so much for having me. I really appreciate it. As you say, I work as Chief Revenue Officer at Sendoso and our big news was that yesterday we announced that we have raised a hundred million dollars Series C, it was led by SoftBank. Really exciting day for everyone in the company and also our customers and prospects, because obviously, a lot of that money gets reinvested in the product, in the support that we give our customers. Exciting news for everyone.

Fred Diamond: We’ll talk about that. Of course, it was private news until yesterday, but now it’s been public so we’ll ask some questions about what that means from a sales leadership perspective. Let’s get right to it. First, tell us a little bit more about Sendoso. What do you guys do? Then you had this big shift, but tell us about how things are going in your sales organization and what some of the big priorities are.

Sam East: Sendoso is obviously a venture-backed company based out of San Francisco. We also have offices in Scottsdale, Arizona, in Lahore, Pakistan, we just opened a new office in Dublin, Ireland as well. We’ll continue to expand into Europe and other markets in the coming quarters and years. Essentially, Sendoso is a platform with which sales professionals and marketers can send pretty much anything, at any time, to anyone as part of their sales activity or marketing activity. We plug into existing technologies that sales professionals and marketers might be using, such as Salesforce or ADM-type platforms. We allow our customers to send gifts or direct mail or really anything that is highly personalized, but at scale.

To your question around how we’ve been doing, obviously, the Series C is a combination of an absolutely fantastic few years of growth for us. We were only founded five years ago, I’ve been with the company for a couple of years. In that time, revenue, we had more than double last year, another double this year, the size of the team has grown from about 150 folks when I started to about 450 today. There are similar levels of growth within the sales organization. It’s been a really fun rocket ship ride over the past couple of years and this funding, if anything, just puts more fuel into that rocket ship. It means that we should be accelerating even faster.

Fred Diamond: Tell us the value of what you do. We do webinars every single day – which we convert, of course, to Sales Game Changers podcasts – and gratitude comes up a lot. Gift-giving comes up a lot, finding new ways to touch people. That’s always one of the big challenges, how do you get through all the clutter? We talk a lot about phone calls and prospecting and it’s very difficult to get to the C-suite. We talk about combinations of marketing, emails and social selling, etc., but your technology, your technique is something different. Tell us briefly, what is the real value? So that our listeners understand.

Sam East: Gifting or – and I struggle with this word all the time – reciprocity, this is not a new sales technique. What we’re trying to do is really bring that into the 21st century. If I think about my first sales job out of school, it was pretty much the least sexy sales gig you could ever possibly have. I was selling cleaning and catering disposables to universities, schools and big institutions.

Essentially, what that meant was I was selling pallets of bleach and toilet rolls. As I used to go on my appointments, whenever anyone would place an order, I would always bring a big box of donuts in for everyone at the office of that customer. They knew after a bit, when we place an order with Sam East, we’re going to get some donuts. Just in an increasingly competitive world where you’re trying to get differentiation between you and everyone else, those little things, those little ways of creating authentic relationships with customers or prospects goes a long way.

If we bring that forward to where we are today, when all of us are living in this world with way too much digital communication, inboxes absolutely full of emails – which has happened even more, since a lot of us now are working from home or in some sort of hybrid situation – it’s really difficult to get your message across to either prospects or customers and stand out. That’s what Sendoso is for, it’s to allow our customers to stand out, cut through that digital noise, and if you’re a sales professional, make an authentic connection with a prospect or customer. Send them something that means something to them with a handwritten note at a touch of a button.

Fred Diamond: At the top of the podcast and webcast we announced that you all just got a hundred-million-dollar investment, congratulations. Let’s change some of the tenor of the questions as the guy who leads sales there now. How does that shift what your sales approach has been? We typically ask, what are your top priorities right now? Has the investment changed your priorities as a sales leader? What are your priorities right now and how has this big news shifted your thinking over the last 24 hours?

Sam East: Certainly, when you get these big rounds of investment, expectations are only going to go up. That’s for sure. But at the same time, having gone through many of these rounds as a growth state sales leader in my career, I think it’s really important firstly to recognize what got you there in the first place and recognize the people that contributed to the company’s growth and success that led to that round of funding. I think that was the first thing that I and the rest of the exec team at Sendoso really wanted to focus on.

Sure, we’ll get to the future, that’s an exciting place for us to go. But firstly, let’s recognize what got us there and let’s make sure that we use that DNA, that culture, and bring it forward into the way that we’re going to grow and develop in the future. Don’t forget what got you there in the first place.

The second thing is we were growing anyway, but this level of investment means that in terms of people, we are going to have to grow exponentially over the last couple of years. I’ve always thought that the very best sales leaders, their #1 priority should be hiring great people. If anything, that just became my #1, #2 and #3. Having seen companies that sometimes struggle with these big rounds of funding, often that’s because they bring down the bar in terms of who they’re bringing into their sales organizations through a need to scale really quickly.

Frankly, those are all of my priorities right now. It’s making sure that we’re hiring the right people, that we’re supporting those folks as they come into the organization, we’re hiring the right leaders and that we have the right onboarding training and playbooks to ensure that as we scale, we’ll continue to hit the levels of production that we need across the sales department.

Fred Diamond: We have our first question here which comes in from Christine, and I believe Christine is in the Washington DC area. “Sam, congratulations on the investment. What are the top sales professionals doing right now?” Sam, a word that we use a lot is elite, elite sales professionals, and it’s gotten harder to be a successful sales professional over the last 18 months. It’s crazy that we’re doing today’s show in September of 2021 and the pandemic has been raging for 18 months, it really is insane.

We’ve noticed over time that you have to have gotten better to stay in sales. I’m going to shift the question a little bit, what are the elite performers doing right now and also, what are the elite leaders doing? You mentioned a few minutes ago that you were also looking to bring on different levels of leadership, per se. Elite, what does it mean to you and what are the elite sales professionals doing right now?

Sam East: Firstly, thank you for the question, Christine. Let’s talk about elite sales professionals firstly. I don’t think that what makes great sales professionals has changed fantastically over the past 10, 20, 30 years. That said, I think that the very best sales professionals are just able to emphasize areas that are more important to customers and prospects today than they were 5 or 10 years ago. The two words that immediately come to mind are curiosity and creativity.

Ultimately, we all know that our buyers are making 40%, 50% of the buying decision before they get to talk to you. If you go in without the level of curiosity required and you go into those conversations essentially with your own preconceived ideas of your value proposition and how it pertains to that customer, then you may as well be an automated message. You’re not adding anything to the sales process.

The real elite sales professionals, at least in my team, are unbelievably curious and are able to really engage with prospects and understand what’s important to them as opposed to what’s important to us. I think the second thing is creativity and we just talked a little bit about Sendoso and how that can help your creativity. I have so many stories and examples of how our customers and also our AEs here at Sendoso have leveraged our technology to engage with, to reengage with prospects, to broaden the number of people that you’re talking with at a particular company. Looking at new and creative ways to engage outside of just picking up the phone or sending emails, I think that’s absolutely key for elite salespeople.

In terms of elite sales leaders, I think more than anything right now, it’s about building authentic relationships with your teams. Gone are the days when you can manage AEs thinking of them as walking quotas who are only motivated by paying the mortgage. Even more in these challenging times when we don’t get to spend so much time face to face, building truly authentic trust-based relationships with your AEs and having them know that you’re going to go out to bat with them is absolutely key because it’s difficult. It’s difficult to be a salesperson sitting in the same office day after day, and if you don’t feel like you have a leader that really has your back and is investing in you, then it can be even more challenging.

Fred Diamond: To flip it a little bit, what is your advice to your sales leaders on how to coach junior sales professionals? It’s been really interesting. Imagine if you started your sales career 18 months ago and typically, you would go to an office and you’d have 10, 15 other junior sales professionals starting the same time. You go through your onboarding, you get your territory, you get trained, you figure it out. Everybody’s been doing this from home if they’ve started their career in the last 18 months, it’s been hard. You haven’t had that comradery. What’s some of your advice for leading junior sales professionals right now?

By the way, I love the idea about creativity and curiosity. We’re actually going to be doing a show in the December timeframe specifically on curiosity for sales professionals. And of course, every Friday we call our show Creativity in Sales specifically because that’s what you need to do. So, people leading junior people. What is some of the advice to make them more successful?

Sam East: It’s a great question. I think that’s something that all sales leaders are finding challenging right now. One of the things that we’ve done really well at Sendoso is to work to create that office environment, and an environment of learning – not just from your manager but from your peers and the people around you. “Great call”, “I love the way that you said that” or, “What would you do if you faced this objection?” Create that environment in a virtual space. We’ve leveraged a lot of technologies to make sure that our folks were able to listen to each other’s calls, share success, and just build that team environment even though we were all feeling a little bit isolated right now. I think that’s the first thing.

The second thing, and this is something I know that you’re very focused on as well, is to really spend time coaching and working with AEs on the mental side of the game. That’s always been important, but I think in these particular times, making sure people feel engaged, supported, and that they understand that there will always be things outside of their control that if they spend a lot of time focusing on, ultimately, will take them in the wrong direction. I think probably those are the two things that are most important. Creating that virtual environment and secondly, really putting the time in to coach new, less experienced AEs on the mental side of what is required to be an elite performer.

Fred Diamond: Let’s talk about the conversations. A lot of the coaching that we have with our sales organization is how to talk to your customer, how to ask the right questions, how to understand the value you could provide. Preparation’s a big word that comes up a lot. Talk a little bit about what are some of the conversations like that your sales organization is having with their customers, and what are customers thinking these days?

Again, we’ve been doing a webinar every single day since the pandemic kicked in. We’ve been smack in the middle of lockdown, we’ve been smack in the middle of vaccination, reopening, etc. Give us a little bit of sense right now of what your conversations with customers are looking like right now.

Sam East: We’re in a fantastic position at Sendoso in that we sell to revenue and marketing leaders, we sell to people like me. Also, we are helping our customers with a wide variety of different use cases up and down the sales and marketing funnel. Whether that’s plugging into someone’s ADM campaign or helping an SDR team drive more meetings or helping salespeople engage or reengage with prospects, or field marketing, or account management customer success. Lots of different use cases.

I think that the main thing we’re seeing from our prospects is that more and more, prospects are looking for one technology or one solution to help them with multiple different use cases. That puts a lot of emphasis on my sales team and our sales org to go hunting for trains, to go and find those use cases and really build far more broad value propositions for our customers, not just a point solution that’s helping someone with one piece of the puzzle.

I think the second thing we’re hearing a lot is customers, as you just described it, Fred, are struggling with this changing environment. Six months ago, I think we were all feeling like, “Great, let’s talk about post-COVID. What’s that going to look like?” Now we’re talking about, “Hang on a second, where are we?” So, making sure that we as a company and we as a sales team are able to ask the right questions, to understand where our prospects are along that journey with what’s going on with COVID and everything else, and make sure that we can make our value and our product really fit where they are right now. I think that’s key, because everyone’s feeling a bit different about the situation right now. Some people are feeling extremely encouraged and positive, and I definitely fall into that camp, but I know there are a lot of other folks that aren’t feeling so great about the moment. You need to make sure that you understand where they’re at and where their organizations are at, and that you can match your proposition to exactly how they’re feeling at that place.

Fred Diamond: Sam, you mentioned in the beginning that Sendoso was a VC-based company, a funded company. You mentioned curiosity and creativity, talk a little bit about why somebody would succeed in sales at a company like yours, as compared to another company like an Oracle or a company that’s been established, more enterprise-based. What are some of the characteristics of somebody who would come to a company like yours and succeed?

Sam East: That is a great question. I’m sure books have been written about that one. Firstly, I would say that many of the skills that allow sales professionals to be successful at big, established enterprise companies are the same. It doesn’t matter what you’re selling, and I’m yet to meet a lazy successful salesperson or I’m yet to find elite salespeople that don’t have confidence or curiosity. There are certain things you need across the board.

I think working in a VC-backed startup environment, there are two or three things that are absolutely key. Number one is you need to be extremely okay with change, with selling through ambiguity. If you need to know exactly how everything is going to go and if you need to be reassured that that process is always going to be the same, then startup probably isn’t for you.

But if you are intellectually curious, if you’re excited about change and about how that’s going to change your sales process and what you do on a day-to-day basis, then startup is for you. Because the only consistent in startup world is change. Second thing is you need to be excited about making a more significant impact and being a bigger part of the puzzle than maybe you would be if you’re working at a more established company.

For example, when I have a board meeting, we’re talking about individual deals and individual sales professionals. Therefore, you need to want that exposure and you need to embrace the ability to make an even more significant impact than if you’re in a team of a thousand, two thousand, ten thousand sales professionals.

The final thing is being in a startup really puts a lot of emphasis on your ability to marshal your internal resources. Again, not every part of the playbook has been built, not every path is clear for you to see. If you’re unable to leverage whether it be marketing product, customer success, all the other folks that you’re working with to ensure that your prospects and customers get what they need, then you’re going to really struggle. That’s a big part of what it takes to be successful at a startup.

Fred Diamond: Sam, what are reps doing wrong? Again, you’ve worked with a lot of reps over the years. You’ve managed them, you’ve seen some great ideas about what they should be doing to do right. What are they doing wrong? What do they continue to do wrong?

Sam East: That’s a great question. I don’t want to give you the boring answer which is just the inverse of what I said that they should do. There are certain things I see again and again. Fortunately, most of these things can be corrected if you’re self-aware and you’re willing to make change to the way that you’re working. The #1 thing, and I hinted at this a little bit earlier, is to believe that a sales process is all about you. It’s all about the things that you’re going to tell your prospect, it’s all about some piece of marketing blurb that you read about your product, a feature or its benefits. It isn’t about you. The best sales professionals understand that it is about their customer, it’s about their prospect.

I was actually on an interview with a potentially new rep the other day and we were talking about, he’s sales methodology and also how he viewed himself as a salesperson. I think I asked him a question about, what would your sales epitaph be? What would people say about you as a sales professional? He said, “I make it all about the customer.”

That’s an easy thing to say. I said, “What does that mean? Tell me more about that.” He said, “Well, I listen back to the recorded phone calls of pretty much every new engagement I had with a prospect, and I’m really proud of the fact that when I aggregate all of those calls, I’m talking somewhere around 30% of the time.” That level of self-awareness from a relatively junior sales professional to understand how important that was, I just thought that was fantastic. The inverse of that is salespeople that get on calls, show up and throw up. That is more and more not what prospects are needing right now.

Fred Diamond: That’s a great point. We actually like to say that if the customer does 90% of the talking on a sales call, then it’s a great sales call. Of course, if it’s a demo, it should be a little bit different. Good for that young man for having that self-awareness. As a follow up, what do you think customers are expecting from you? For the people that are listening today, again, we have sales leaders all over the globe, talk about from the customer side. Your business is high-touch. You’re literally sending things that should make a customer feel good, you’re sending them some kind of personalized gift or something like that. What do you think customers expect from sales professionals right now?

Sam East: I’ll go back to The Challenger Sale here which is not a methodology, but a mindset that I have a lot of time for. Which said that in tougher times, and I think this is a touch time for many of us as sales professionals, customers are looking for experts in the field, they’re looking for people that are adding a level of intelligence and insight on top of what your product or service does. That they’re able to really engage with you and learn something. It’s not just about a sales process, it’s about learning about the space you’re in, learning about the prospects and challenges your prospects face, engaging with them on those and hopefully, adding some level of insights. That’s what prospects are really looking for right now, insights.

Fred Diamond: It’s been a challenging time for everybody for a whole bunch of reasons which we’re all familiar with. Give us a positive, give us something specific. Of course, the company got a hundred million dollars yesterday, that’s very positive. But seriously, as a sales leader, give me one really positive thing that has come out of the last 18 months for you.

Sam East: I think there have been many positive things. I think that the best type of exercise is the most impactful type of exercise. I think that tough times, if anything, strengthen those muscles that should be strengthened. Having sold through 2008, having sold through the bubble bursting in 2001, I know that sales professionals who are able to sell through tough times come out at the other side leaner, meaner and stronger. They just have a far more comprehensive and far more market-ready set of skills that allow them to really appreciate and make the most of a good time.

I think the other thing, and this is something I’ve seen at Sendoso. This sounds like a bit of a paradox, but I think that this time that has pulled us all apart and put us into our offices and our bedrooms on calls like this, it’s actually forced us to work hard to be closer together and be intentional. “I’m going to spend time talking to Joe, I’m going to spend time talking to Cindy, Sammy and Sally.” You really have to be intentional about reaching out to peoples spending time and building relationships with them within your own teams and within your own companies. I think that can only be a positive thing.

Fred Diamond: Sam, thank you so much, you’ve given us so many great ideas. Not sure if you know this, but I mentioned this in the beginning. Sendoso has come up a number of times on the Sales Game Changers live, we’re at over 400 episodes right now. Gratitude is something that we’ve talked a lot about, especially in 2020 and the ability to say thank you to a customer with something interesting and personalized is something that’s of value. Something that’s not just personalized but means something to the customer, showing that you know something. We always talk about not something that’s branded with your company, but something that would be specifically applicable to them.

We actually used your technology, we have an award event every spring, typically. We used Sendoso to send personalized gifts to our sponsors and the people who helped us and it got a tremendous response. Congratulations for the great work your company is doing to help sales professionals be successful. As we like to do at every Sales Game Changers webcast and podcast, we’re looking for an action step. You’ve given us 15, 20, 30 great ideas on how sales professionals and leaders can take their career to the next level. Give us one specific action step for reps to take today to ensure their continued success.

Sam East: I’ve been thinking about this question a lot and it’s such a great question. I could probably talk about this for the whole of the podcast episode. I’m going to break it down to something I think is really simple and really easy, and something I hinted at a little bit earlier. Be conscious of the things that you cannot affect within your sales process. Be conscious of what they are. As you’re in a sales process, if you’re hitting a brick wall, you’re in a challenging situation, make sure that you’re very aware of, “What can I do to change this and what are the resources that I can leverage around me to help move forward? What are the things that frankly, are completely out of my control?”

If you waste one second worrying about those, it’s one second that could have been spent on things that actually are within your sphere of influence. I think that’s increasingly important for how we sell today, because there is a lot more that’s out of our control. Not everything is down to you, so that’s something that I’m preaching a lot to my sales teams, my sales leaders. Just focus on the things that you can really impact, don’t sweat everything else.

Fred Diamond: That’s not just a great lesson for sales, that’s really a great lesson for life. I talk to a lot of sales professionals and they ask me, because at the Institute for Excellence in Sales we help sales leaders acquire, retain, motivate and elevate top-tier talent so I talk to sales professionals and leaders every single day. Sometimes I hear, “What’s your biggest challenge, what’s your biggest complaint?” I’ll say, “You’re never going to solve that one, it’s too bad.” That’s great advice. Sam, thank you so much for your time and for your insights.

Transcribed by Mariana Badillo

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