Episode 121 : The Art of Creativity and Empathy While Leveraging Technology

Kris Rudeegraap is the co-founder and CEO of Sendoso, the leading Sending Platform. Kris has more than a decade of sales experience and has spent time at Talkdesk, Yapstone, and Piqora. During that time, he discovered that creating meaningful engagement through direct mail and gifting was an effective way to drive demand and increase sales – which helped inspire the idea for Sendoso. Kris is a California native and CSU-Chico alum currently residing in the Bay Area.

Questions

  • Could you share with us a little bit about your journey, a little bit about who you are, tell us what a leading Sending Platform is? What’s that all about? And just how you got to where you are today?
  • Could you share with us just based on your experience, and also your business as an entrepreneur and a leader, what are maybe one, two or three things that you think salespeople need to do to retain their customers?
  • What are maybe one or two things you think that somebody could do to enhance or build on that skill? How can you build on being more empathetic as a human?
  • Could you give us maybe some recommendations as how companies can leverage more collaboration software and use it to their advantage? And how can employees be open to adapt to this and be able to succeed, especially with something that they are not very comfortable with?
  • How as a leader in all of these that’s happening, can you ensure that your team is thinking creatively? They’re thinking outside of the box? How do you get to inspire them, especially when you’re not in the same physical space with them? How can you really get them motivated and pumped up that they are excited to come up with new ideas and innovative solutions to make the business move forward?
  • Could you share with us maybe what’s the one online resource, tool, website or app that you absolutely can’t live without in your business?
  • Can you share with us maybe one or two books that have had the biggest impact on you? It could be a book that you read recently, or maybe something you read a very long time ago, but it still has an impact on you today?
  • Can you share with us maybe what’s the one thing that’s going on in your life right now – either something you’re working on to develop yourself or your people?
  • Could you tell our listeners where they can find you online?
  • Do you have a quote or saying that during times of adversity or challenge, you’ll tend to revert to this quote, it kind of helps to keep you focused, or kind of gets you back on track. If you get derailed at any point in time. Do you have one of those?

Highlights

Kris’ Journey

Kris shared that before starting Sendoso, he spent about 10 years in software sales in San Francisco. And so, he was really trying to break into new accounts, send emails to prospects, and really saw that there was a lot of digital noise and email was a hard channel to be super personalized.

And so, that’s really where he decided to start sending out handwritten notes and he’d send little gifts, he’d send little packages with like company swag and all that stuff was really great, it was just super hard to do and very manual and very time consuming.

And so, he dreamed up this idea of a sending platform where you can click and send a button inside of tools like Salesforce or HubSpot or other tools. And then behind the scenes, it would do all the fulfillment and all the hard work for him.

And so that was the original idea and that’s what inspired him to start Sendoso about 5 years ago, and really a sending platform is a couple components. One is it allows you to send out really anything and everything, corporate gifts, their direct mail, their company swag, there could be flowers, cookies, ice cream, gift cards, digital experiences, you name it, they can send it. There’s also team management and budgets, there’s integrations, there’s fulfillment all under one platform.

Me: Sounds good. So a big part of what Sendoso does are, what you do is sales? 

Kris shared that sales, that’s how he got started and a lot of their customers are using them for sales. But they also have a good amount of companies using them for post sales. So customer service, customer success, marketing, and even HR too.

Tips on How Salespeople Can Retain Their Customers

Me: So what I like to find out from you is could you share with us just based on your experience, and also your business as an entrepreneur and a leader. What are maybe one, two or three things that you think salespeople need to do to retain their customers? So I know sales is about getting new customers, but how do you ensure that you retain your existing customers? How do you have that relationship, the customer relationship management component? Maybe what are two or three things that you think is critical based on your experience?

Kris shared that he’d say one is really being human and building rapport and think about it as not a business to business, but a business to a human and how do you build that relationship.

Two is really just getting creative with how you engage folks. So not just using email, but using other means to build that relationship.

And he thinks the third is really leading with empathy and putting yourself in your buyer’s shoes, and really encouraging authenticity and really understanding what the buyer really needs.

How to Build on Being More Empathetic as a Human

Me: Okay, so those are three really good points. Now, let’s say for example, you’re dealing with sales reps that don’t know how to exercise empathy. So as a Customer Service Trainer, I have found based on research and experience that empathy is not one of those skills that you learn when you’re growing up, it’s really a skill that you develop as you get older, as you get to understand yourself, as you get to understand emotions in other people. But some people just still are not able to exercise empathy to its fullest extent. What are maybe one or two things you think that somebody could do to enhance or build on that skill? How can you build on being more empathetic as a human?

Kris shared that he would say one is finding training and learning courses, so going out of your way to find ways that you can really learn about how to be more empathetic and kind of study and learn and kind of take what you’ve learned and start practicing that. He’d say that’s the first thing is really going out of your way to learn more.

And then he thinks the second is, people might not be as empathetic in business, he thinks a lot of people are naturally maybe empathetic in their home life and maybe understanding what are those key things you’re doing in kind of your home, non-work life that could be empathetic, and how could you translate that into more business like environments.

Me: That’s a good one. Because it’s the same skill, same behaviour, you’re exercising in a personal environment so you need to just transfer that into a professional environment so that you can really understand where the other person is coming from.

How Companies Can Leverage and Adapt Collaboration Software And Use it to Their Advantage

Me: So a big part of customer experience also is understanding that we’re in this space now where we have to be pivoting, I think that was a big word for 2020 and it’s definitely come over into 2021. And just being able to be flexible using the different technologies that exist out there to serve our customers.

Agility is also something that a lot of organizations are looking to do with their teams. So could you give us maybe some recommendations as how companies can leverage more collaboration software and use it to their advantage?

And how can employees be open to adapt to this and be able to succeed, especially with something that they are not very comfortable with?

Kris stated that he thinks that to Yanique’s point, one is taking the time to really time block on your calendar to learn more.

We live in a world where people work, and maybe don’t do enough in terms of like education or re-education, so he’d say purposefully putting time on your calendar for learning and development is key.

And being cognizant of that, say, “Hey, next week, I’m going to block two hours, and I’m going to learn this or I’m going to practice using this software,” which might sound like how do you have enough time to do that, but he thinks it’s taking that time, it’s almost like taking a step sideways to take 10 steps forward, versus kind of always being in an environment where you feel behind. So, he would say that is one scenario.

He’d say two is just maybe, depending on your level of leadership, really just the culture of the company, or the executives can be really driving this agility and so, he thinks it starts at the top. And really, if you can demonstrate agility at the top and really make that a key part of your company culture, it can really benefit everybody.

How To Inspire Your Team to Think Creatively

Me: Leadership is very important, I’m glad you touched on that just now in terms of getting people to really step up to the plate. So you have these teams and even though they’re working from home, I’ve heard so many complaints where people complain that they’re just exhausted, they’re burnt out, literally, just between family, depending on what age the kids are, and then just keeping the home in order, and then being on all of these Zooms and Microsoft Team meetings constantly at your computer.

But then outside of those meetings, you have the actual work to get done and it’s just a lot.

  • How as a leader in all of these that’s happening, can you ensure that your team is thinking creatively?
  • They’re thinking outside of the box?
  • How do you get to inspire them, especially when you’re not in the same physical space with them?
  • How can you really get them motivated and pumped up that they are excited to come up with new ideas and innovative solutions to make the business move forward?

Kris shared that one thing that comes to mind is making sure that you are upfront about a flexible work life balance and right now it’s harder than ever to be flexible, because you kind of live and work in the same room, so to speak.

And so, he thinks it’s purposefully making sure people are stepping away, even if it’s just a staycation and you’re staying home, you just put your laptop away.

So, they really try to inspire that, they even have a twice a year employee bonus that if you take a vacation or a staycation, they’ll give a $500 bonus each time to spend on that and so they’re kind of paying their employees to take breaks and keep that flexible work life balance.

And so, he thinks that’s one area, making sure you keep your work life balance strong so that it really keeps your mental state in a really good place.

Two, he’d say is like, how do you get creative or have more fun with some of your Zoom meetings and so, they’ve incorporate things like Zoom wine tasting events, or they’ve done like dinner making class over zoom and so they bring in special guests to some of these Zooms, and maybe change it up a little bit so it feels a little bit more unique, and adds a little bit of flair. So he thinks that’s an interesting way.

And then there’s other ways as it relates to just helping getting people out of their comfort zone, and maybe connecting people with other teams. So they’ve tried to institute more of like cross team collaboration or getting people involved in kind of mini, what they call tiger teams, or project teams, they kind of are taken away from maybe their normal day to day and exposed to new parts of the business where maybe they can bring their new level of creativity.

Me: That’s really amazing. So I like the idea of dinner, what was the suggestion, you bring in a special guest and that person would prepare dinner and everybody kind of follows along?

Kris confirmed and stated that they’ve done like a special checked guest that comes in. They did one where was like a cheese making class, there’s a wine tasting event where you could wine taste virtually. So it makes some of these Zoom meetings just a bit more exciting.

Me: So do you do that in the middle of the day? Or is that an additional Zoom meeting that is tacked on to the end of their day?

Kris stated that it could be both, he thinks for the wine tasting one, they typically would want that to be more like a 3:00 pm or 4:00 pm or 5:00 pm.

And so, it’s typically still during business hours, but it just says, “Hey, have some fun with this and kind of meet more of your team and have a have some fun.”

But some other ones could happen during the day too as well. And it’s more of a way to kind of think creatively versus just be in the same exact kind of Zoom fatigue.

Me: Yeah, I agreed. That’s really cool, very creative, very innovative, and it does stimulate a different parts of the brain, which will definitely help them to not feel like they’re doing the same thing over and over and it gets mundane. And just as you said don’t feel motivated.

App, Website or Tool that Kris Absolutely Can’t Live Without in His Business

When asked about an online resource that he can’t live without in his business, Kris shared that from a collaboration perspective, Slack, it just like keeps them all collaborating, that is probably the one they couldn’t live without.

One that he really loves is an app called Feedly, and it basically brings together hundreds of different blogs into one app that he enjoys reading.

And it’s a great way for him to stay creative and really be immersed in a lot of different contexts of ideas. And he typically wakes up and do some reading in that app and then he’ll typically go to bed and do some reading in it. And it just gives him new perspectives across a myriad of different topics.

Books That Have Had the Greatest Impact on Kris

Kris shared that he’s a huge podcast listener and actually give him the biggest inspiration and impact. And so, he’s all in on podcasts and a couple podcasts that he’s just obsessed with.

So he’d probably say he listens to podcasts, maybe daily, he would read books maybe a few times a year, so he’s much more engaged with podcasts and a couple that he loves, one’s called Dare to Lead with Brene¢ Brown and another is called Acquired, another is called Follow Your Different and then a classic, another one, How I Built This.

Me: Oh, nice. May I ask what kind of topics they discuss predominantly on those podcasts? Are they more like self development podcasts? Or are they business podcasts?

Kris stated that he would say a bit of both, part of them are business related, but also, they also include talking to founders at times too, which gives you kind of personal inspiration as well. So he thinks it’s part personal inspiration, part business, and then part just kind of interesting topics.

What Kris is Really Excited About Now!

Kris shared that one thing that he’s doing that is, now that they have close to 400 employees now. One of the things he’s doing is just random meetings with employees, and he created this new Slack channel called Ask Kris Anything and then he meets with 3 to 5 random employees each week.

And so, that’s something that he’s doing just so that he can really understand how they’re scaling the business and learn from everybody. And so, that’s been something that he has been doing recently that he’s really excited to continue.

Where Can We Find Kris Online

LinkedIn – Kris Rudeegraap

Website – www.sendoso.com

Email – kris@sendoso.com

Quote or Saying that During Times of Adversity Kris Uses

When asked about a quote or saying that helps him get back track, Kris shared that he would say that the one that comes to mind that he remember the end that he thinks about often is,

Entrepreneurs spend a few years of their life like most people won’t, so they can spend the rest of their life like most people can’t.”

“Unknown”

And so, he thinks it kind of hints on that like there’s tough times for an entrepreneur, but if you make it, your life will be changed forever.

And so, that’s one of his favourite quotes. The other one he thinks is a popular quote by Wayne Gretzky is, 

“You miss every shot you don’t take.”

Wayne Gretzky

And he lives by that too, you got to take risks, you got to challenge yourself, you got to do stuff and get out there. And so, that’s also an inspiring quote for him too.

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