[00:00:00] Rosalyn Santa Elena: Welcome to the Revene Engine podcast. I'm your host, Rosalyn Santa Elena. And I am thrilled to bring you the most inspirational stories from revenue, generators, innovators, and disruptors revenue leaders in sales, in marketing. And of course in operations. Together, we will unpack everything that optimizes and powers the Revene Engine. Are you ready? Let's get to it.

Many times companies are started when a founder is faced with a problem that they're trying to solve, or there is some kind of aha moment that is pivotal in the journey. But other times founders like Ted Blosser, the CEO and co-founder of WorkRamp are intentional in determining the right company with the right fit and the right vision.

In this episode of the Revene Engine podcast, Ted shares his story of how he built his company with an overall vision, but also with a strategy and a plan for execution, which he shares in a baseball analogy with innings. Ted also shares so many great learnings and actionable insights around building an amazing company, helping your team and your customers.

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So please take a listen and learn from this authentic inspirational leader and all around. Nice guy. So super, super excited to be here today with Ted Blosser, the co-founder and CEO of WorkRamp for anyone who's not familiar with WorkRamp work gram is the all-in-one learning management system that allows you to build content.

And deploy training to your internal teams, your customers, and your partners, all on one platform. So welcome Ted. And thank you so much for joining me. I'm super excited to share your story and also learn from you

[00:03:02] Ted Blosser: Excited to be here Rosalyn. Hopefully you don't hear. I just had a new baby, so. That's a crying baby in the background, in this recording.

[00:03:09] Rosalyn Santa Elena: No problem at all. I have two dogs and one dog always makes an appearance on the podcast. So no problem at all. And congratulations on the new baby. Super exciting.

[00:03:19] Ted Blosser: Thanks, it is our third. So, so not our first time. So we're getting through it.

[00:03:24] Rosalyn Santa Elena: That's awesome. Well, and yeah, I have a stories to tell you on that one. I have three as well. So of course mine are older, but definitely we'll have to share some more stories there too. So let's start by talking a little bit about your journey before WorkRamp. All right. Can you share a little bit more about your backstory? You know, I know you were an account executive, you were a product manager, you've done different things.

So if you can share a little bit about that, that'd be great.

Yeah,

[00:03:47] Ted Blosser: for sure. So I personally have a pretty eclectic background. Coming out of college, I actually studied electrical engineering and then randomly got into sales. After cynical, after I graduated Santa Clara university. So I did sales at Cisco great training ground.

This was back in the day when big tech companies were sending you to go get trained for about a year in some remote site, in the comeback into the field. So that was really. And then from Cisco actually went and did failed startups. That was my first startup expense. And then when I came out of that, I said, Hey, I need to go learn how to really do this whole startup thing.

Cause I wanted to do another company which ended up becoming work cramp. And because of that, I knew I had to build a broad skill set. So the first thing I did was, was get it back into sales, but more on the SAS side. So I'd never done SAS sales. And then afterwards, I actually went into product management because I knew I had to learn how to build products nights and weekends.

I was coding. Sites just for fun. Cause I want to learn development and I had a technical background from school. And so I felt like, Hey, I had all this experience leading up to starting a company like WorkRamp. And so that was the background. That was a nice journey which took, took, let's see how many years it took about about almost nine, 10 years to, to really get the eclectic experience I taught.

Before starting WorkRamp itself. And it's definitely give me some a leg up while, while founding a WorkRamp.

[00:05:10] Rosalyn Santa Elena: That's awesome. That's awesome. So oftentimes, you know, companies get started, you know, when a founder is faced with a problem that they're trying to solve, or maybe there's some kind of aha moment, right. Or some event that happens. Was this the case with the WorkRamp and kind of what led you to starting the company?

[00:05:27] Ted Blosser: You know, I, sometimes I wish that was the case. It wasn't like I ha I grew up with, with parents that were professors and I love the education category or, or experienced something really visceral in my, in my childhood.

But it wasn't like that. It was actually more when I w when I failed at my first startup and said, Hey, I want to go. Learn how to do this and go start another startup. So when I was at box, that was where I was learning kind of the SAS market. I said, Hey, if I want to start a company again, I have two criteria.

And for me, the first criteria, which is actually probably the most important parts of. What's to build an awesome company. And so it was really about bringing people on board, building the culture building just a really great organization where people would, I would call it quote, unquote, skipping to work every day.

So that's kind of my number one criteria. And then the second criteria was really looking for a gigantic. That we felt was underserved, had bad players in, it was in the SAS space. Cause we knew SAS really well that we can actually add a differentiated experience with it. So we were actually on the hunt for market like that.

And when we stumbled upon the learning market, Because we looked at a lot of markets. We said, Hey, this is the market. This, this market almost has an infinite total addressable market. The players in here are really bad and really stodgy and every company needs it and we can, we can offer a big impact.

So we kind of married those things, those two things together. We found our domain name online in 2015, and then. Went off and started working. So that was kind of the origin story of, Hey, it wasn't really an aha moment. It was really, Hey, what was that criteria? We satisfy that criteria and that's where a WorkRamp was born out of.

[00:07:09] Rosalyn Santa Elena: I love that. It's a very, actually very thoughtful and very diligent kind of calculated way of creating, creating a company. So now, like almost, I guess it's been about six years, right? So six years later, how has your vision, I guess, for the company evolved and. What does that look like? Has it changed?

[00:07:27] Ted Blosser: Yeah, that's a, that's a great question. I would say. Yeah. This is funny. I, we are six years old, but I like to say we're about three years old. Cause it took us a while to get to that kind of infamous product market fit. So it took us a while to get to product market fit and but the whole time it was funny.

We did a. We did a kickoff the other other month. And I actually found a picture that had all these stickies up above my desk, not a picture from 2015. And the vision was essentially the same empower every employee to reach their full potential through learning, I think is a slightly different variation of that over the years.

But the vision was always the same. Now the journey to get there has kind of has shifted and moved. And so, and what we really realized we had product market fit, and this is the buy-side gifted startup founders is that you might have a grand vision, but you need to have a strategy. And then you need to have execution on how to get there site essentially.

Hey, how do you start small, even though you have a great vision and then grow to that larger vision. So for us, the way that played out was, Hey, we always had this big vision, but we need to start small. So we actually started onboarding and we actually started and go to market team. Once we got a good enough brand recognition, good enough traction that we expanded to support teams.

Then we expand it to HR and L and D teams. And then two years ago, we expanded all the way out to customer education and partner education. And so we always knew that our long-term vision was the same we own power all professionals to reach their full potential, but the steps to get there. Was essentially a journey and we still have a I call it word any three of basically nine right now, where I'm very specific with that, with the team that, Hey, we're still in early innings here.

There's still a lot of things we need to do to achieve our long-term vision.

[00:09:18] Rosalyn Santa Elena: So as part of that story you were sharing that quote right around WorkRamp empowers every professional to reach their full potential through learning. And I think continuous learning. Yeah. Right is incredibly important, right? To us as you know, personally, as well as professionally, but especially in building teams, right.

Teams that are going to be successful today and can scale for tomorrow. So when we talk about revenue, teachers is kind of where you focused initially early on in the journey around, especially on sales, right? Enablement is just like a key strategic differentiator, right? In your organization's ability to accelerate revenue.

So what have you seen, I guess, in the market in terms of trends. Around sort of this enablement of go to market. And have you seen it evolve and kind of, where do you see it going?

[00:10:01] Ted Blosser: Yeah, that's a, that's a great question. I would say, I'll take, I'll take one step back, actually, and talk about it at the organizational level.

And I'll kind of feed it back into kind of enablement teams. I think there's, there's three big trends we see with all companies and this is kind of across the whole org and it actually feeds really well into enablement orgs. And so there's really three things. One is. Every company we see is going through massive digital transformation.

And so there's real transformation really means everything in their business is getting upended right now. It's it's how do you serve customers is getting offended, how you communicate internally is getting offended. How you recruit talents, getting up in. Your business processes, even the paper that used to flow an office is getting offended.

And so that's a big thing happening in all. Companies need to figure out how to do that. The second big thing is remote centric work. And so it doesn't mean every company has to go remote first world, but it really means, Hey, are you ready to have remote workers in your staff and in your operations? So COVID brought that on.

As we know. But, Hey, how do we continue pushing remote centric? Whether that is a full-time remote for everybody, or, Hey, you just have some offices that are remote. Everyone needs to figure that out. And then lastly, the, this is the probably biggest trend of the three is the war for talent. And so we know over the next decade that having the best people on board, the best sales reps, the best sales managers.

Every company that what you're really competing for over is not really money anymore because it's money is actually easy to come by or funding, but it's really around how do you get enough people in the door to help further the mission and the vision? So those are kind of the big three macro trends and the common theme across all three of those.

One of the highest leverage activities you can do as Andy Grove said always the paranoid survive. That for a manager, the highest leverage activity you can do is really training and so, and enabling. And when you think about those three trends, And enabling your people is probably the biggest thing you can do for all three of those trends.

For digital transformation, you have all these new processes, you've got to get people like, for example, if you will, on new Salesforce process for digital transformation, you better make sure your people know how to do it, or else it doesn't matter. The war for talent. You have to make sure that Hey, people are progressing in their careers.

And they're getting trained to go from SDR to BDR, to AE E right. And then that remote centric work, you can't tap someone on the shoulder and be like, Hey, how do I enter in this steel correctly? Or, Hey, I got this competitor in this deal. What do I do? And that's all about training as well. And so that's the big trend we're seeing is that when I talk to other CEOs is, Hey, a lot of this is, Hey, I need to get the right people in the door.

I need to get them trained up. I need to get them enabled. And so that's what, that's the big trend. I kind of answered your question in a roundabout way, but that's the. That we're seeing overall.

[00:13:00] Rosalyn Santa Elena: Yeah. Yeah. And that war for talent really resonates with me right now, as we're trying to, as I'm trying to build out a team. Right. And then getting those folks that you have already in your current team enabled and sort of, you know, scaled right. Upscale them basically, and get them to where they want to go. So yeah, I.

[00:13:21] Ted Blosser: Talking to this leader the other days, like Ted money, is it money in a fig? Is what he said. He's like the biggest problem is really not, not having head count open or not the pay it's about, Hey, how can you attract the right people right now?

It's super hard. Whereas a year ago is all about some of the tactical things. Now it's just, I just need to get someone in the door. That's the right fit for them.

[00:13:43] Rosalyn Santa Elena: Yeah, yeah, 100%. So, so this may kind of feed into this a little bit, but what are some of the biggest mistakes that you're seeing revenue teams making in sort of their approach to enablement and to training and some of the things that you talked about.

[00:13:59] Ted Blosser: It's kind of funny, I'm learning a lot. So we hired an Stephanie , she's actually a former customer of ours and now she's amazing. She's teaching me, she's taught me so much about enablement. Cause she's seen it so many times and I would say there's two, two big mistakes and she's even educating me on these mistakes because we could easily step into them.

One mistake, which is actually, so actually on two ends of the spectrum that we see. So one is you either don't give enablement enough power. And I don't know if you've seen this where you kind of stick it or tuck it under product market. It's more of an afterthought. You hire it probably once you have 50 sales reps, it's like, oh yeah, we probably need someone to help with onboarding and, and you can easily see, Hey, where are they placed in the organization?

How much power they have? How senior of a role are you hiring? I'll see a lot of org. So you say, Hey, we need enablement and they just go hire a really junior person, maybe switching from the BDR regs it's enablement because they want to. And so that's kind of one end of the spectrum. I actually see that mistake a lot and actually see the other end of the spectrum.

Which is not so much where it's like ham hiring and giving them too much power enablement, but it's more, I'm hiring an enabled. Maybe it's a right level person, like a director to start, but they have unrealistic expectations and they give them too much. So they basically say, Hey, I went through everything in the kitchen sink in this enablement role because I have nowhere else to place it.

And so they might give internal events to enablement. They might say, Hey, I have a competition problem. Go solve that. Or they might say, Hey, I have this more of a rev ops problem. Go solve that. And just literally everything they'll even PMM type of activities, they'll toss their way. And so one thing Stephanie has taught me is like, Hey, every quarter a director of enablement can maybe handle one, two big initiatives every quarter.

Right? And so it's important to make sure that you prioritize their time and that you don't give them too much stuff that's outside of their scope. So those are the two classic mistakes that. Which is too junior and you just don't have the right person in place or, or you're not investing in it enough, or you get at the right person place and you just overwhelm them.

And they're like, I can't be successful with all this stuff. So those are probably the two biggest mistakes I see with customers. And you kind of want, I think the perfect blend. And I think Stephanie is doing this here at WorkRamp is you have the right person who's elevated. She reports directly to essentially our VP of revenue.

Rocky pat, and she's very good at saying, Hey, I'm going to take off these to take down these two big priorities. I have a few other tasks cooking, but here are the two big things I'm doing.

[00:16:43] Rosalyn Santa Elena: That's awesome. That's really great advice and definitely very useful for sure. So let's talk a little bit more you know, I think a lot of enablement offerings, you know, they focus on just sales, right?

And as we talked about your platform really focuses on all calls. Learning internally and externally. Right. So can you share a little bit more, you talked about the innings and kind of the, the longer roadmap of where you need to go, but maybe share a little bit more about your vision there. You know, how has that kind of product differentiation really helped WorkRamp be successful right around accelerating revenue growth and obviously expanding within your customer base?

[00:17:17] Ted Blosser: Sure, for sure. You know, that's a really interesting, we had this fork in the road a couple of years ago and. And we looked at the learning corporate learning space, which is gigantic, as I mentioned before. And we, we basically said, Hey, this, this fork in the road, you're either going to go heavy into sales LMS, and kind of build a niche solution for sales and go to.

Or what you do is you consolidate all the learning happening across an organization. It's still very strong in sales, but you bring together other departments in an org to have a more cohesive story. As you can guess, we chose the latter route and we call this the learning center of excellence. And we have this nice chart.

We show to clients, both, both prospects and clients that. That shows, Hey, you have all these different learning pockets in the org. You have learning on the go-to market team. You have learning with your customers and partners. You have learning in your HR team, right? And everyone is speaking a different language, different subject matter experts, contents getting out of date or not being used properly.

And what the learning center of excellence does, is it consolidates, your learning content, your learning philosophy, and most importantly, importantly, you're learning culture. Within an organization. So that's why we call it the learning center of excellence. So we push our customers to say, Hey, everyone does have a different learning needs.

The way HR wants to do learning, which is very, self-served very focused on retention versus how sales does it, which is, Hey, I need to go sell my product more efficiently. They have different needs. We want to have a product that serves both needs, but has a fundamental. Underlying layer that actually allows those teams to collaborate with each other.

And that spans all the way out to your customers, right? That same content you're training your technical SES on your technical customers probably want that same content too. And so that's a big trend. That we're seeing on the market. So it's essentially a fondant Lang that you're saying you hear a lot about that on bundling and bundling.

We think we're moving into a bundling phase and we want to be at the forefront of the bundling of learning. And we're calling that the learning center of excellence and it has a huge impact because go to market could then. Even more resources at, at play, if it's part of the broader kind of learning center of excellence within a company.

[00:19:37] Rosalyn Santa Elena: Got it. Got it. Yep. So you touch a little bit about kind of what customers are looking for. So I want to talk a little bit more about customers, right? As we were talking about probably a little bit before we started recording, but you know, buyers were looking to consolidate, we're expecting a lot more companies don't want a vendor.

They want, they need. Right. Someone who's going to really help them be successful. And I know WorkRamp was the recipient of a number of T2 awards, both in HR software and in sales software. And I love G2 because it is from the customer's perspective, right? These are actually users who submit these reviews.

So I think that those awards are always very meaningful, right? When you hear directly having so many innovative brands as customers, right? You've got box, you've got outreach and read it and lattice and all these other customers that are, you know, leveraging. Solution and partnering with you, you know, what is your philosophy, right.

Really around driving customer success, driving that value. And how has that contributed to revenue acceleration?

[00:20:35] Ted Blosser: Yeah, that's a, that's a great question. And one of our four key values and we truly live and breathe it as is customer focus. And a lot of companies say that, but not everyone kind of walks away.

I've been at companies that say that, and it's like, you have a customer issue. You kind of sweep it under the rug a little bit, but for us, we truly believe it. I would say there's a few things that contribute to. At least our customer success. So far one is we, we try to meet and talk with as many customers as we can to really drive our roadmap.

And so it's actually the, the counter-argument to the famous kind of Steve jobs, quote of like, Hey, if I just listened to my customers, I would have a faster horse. I would have build a faster horse, but we actually kind of live and breathe that where, Hey, we listened to our customers at times. Okay.

Personally, I, I, I adhere to the philosophies of like a Jason Lumpkin and a mark Benioff that constantly talk about, Hey executives, especially in this virtual work world, get in front of as many customers as you can hear about their pain points. I would say, when I look at my schedule in the day, I get a ton of energy.

When I see that customer call on my schedule, and I know I have to prep for it by come out of that with so much more energy and so many, so many ideas. So that's probably probably the first thing. Get in front of as many customers as you can. And that's not just the executive team, but that's all the way on down.

Don't just send that email. Don't just send that slack message on our VIP channel, but it's Hey, get in front of your customers and really engage with them. Probably another, another big thing is I'll call it structural programs. Customer successful. So I assume I used to back in the day, think that our CS team, as an example, could just do it all.

I would hire superwoman or Superman or super person CS CSMs, and say, Hey, do implementations, do the technical calls, do the renewals, do the QVR is you're great. Right. And what I realized is that's actually a disservice to clients. And what we realize is that if you can specialize and do parts of the customer life cycle, while the customers will greatly benefit from that, a great examples.

When we split up our CSM team into essentially the implementations team instructional design team and what we call client outcomes, team focus on the outcomes that customers want to track. When we saw that split, we saw a dramatic increase. In our gross retention rates and our net retention rates or our upsells as well, our customer happiness and sees that scores.

So there's a lot of structural things that help and those get complimented with things like, especially in your world dashboarding metrics, insights into how those customers are doing and how each team is doing. So, for example, we track down to the day how long it takes for our average implementation.

And then probably one last big thing on customer success. I like to bring up is, and this was actually a, I picked up the idea from David sacks, the head of craft ventures. He wrote this really cool blog post. This was about 18 months ago. About what he calls the cadence and the cadence revolves. It's basically how to operate a SAS startup.

And it revolves around what we call the lightning strike. So the lightning strike is like your apple key. For your company and also for your customers. And what's really cool about this is his, his theory, David Sachs. His theory was that, Hey, if you innovate every quarter and at minimum, have a touch point with your customers every quarter around your product, around your customer success, they're going to be extremely well taken care of, and that will compound.

And so what we've done as a company, we've done this now. Six quarters. For six quarters is every quarter, literally on the.in the middle of the quarter, we will have what we call a a lightning strike the button. And this is where we invite all of our customers to this. We have a nice live stream and we show them, Hey, what's our vision of the world.

We've been listening to you. Here's the product we built and let's build even better relationships moving forward. And we've got a grave reviews from that. So hopefully those are, those are three three ideas for the audience that. That really say, Hey, how do you actually push the needle on customer success?

For us talking customers the kind of specialization as well, and then things like the lightning strike have really helped. That's awesome.

[00:24:55] Rosalyn Santa Elena: Thank you for sharing that. I think that's super helpful. I think that's definitely going to give some ideas to folks who are listening, who maybe didn't think about, you know, things that they've probably or may have thought about, but never really implemented and didn't really understand the value.

So that's super helpful. Thank you. You know, as. The Revene Engine, the podcast, right? I'm always hoping that others will learn right. How to accelerate revenue growth and power, that Revene Engine. So a lot of the tips that you've given around customer success around enablement, all of these around even how to build a business, right?

All of those things are super valuable. So thank you for sharing that. You know, as a CEO and founder, you know, is there anything that you wish maybe you knew earlier? I mean, you talked about kind of the failed first failed startup, and I think you took those learnings in already, but is there anything that you might, you know, you wish you knew earlier, or maybe you might do differently, you know, if you could do it all over again?

[00:25:47] Ted Blosser: Yeah. I would say. If I can do it all over again, you almost can't avoid this. I talk about the have you, have you heard of the kind of startup trough of disillusionment? Have you seen that chart or it's like a startup starts and it drops off. This is something that Paul Graham kind of pioneered where it's like, Hey, you start a startup.

It's super exciting. And you get that tech crunch article for your first fund. And just drop off a cliff, that's called the trough of disillusionment, and then you kind of crawl your way back in, into an actual company. And so those, that definitely happened to us. That was about two to three years in the early days of WorkRamp.

And I think one of the things that we did wrong was prematurely thinking. We have product market fit and prematurely scaling. And so one of the things I always tell founders is like, Hey, you listen to all this cool startup podcasts. You're going to go through Y Combinator. Like we did. And you just think you're onto something you got to get on other podcasts, you got to get loud on LinkedIn and you got to hire people, spend that money and you need to take an honest, look at yourself and say, Hey, is what I'm building the correct thing.

And if, if not, how do you pivot to the correct thing? Or how do you keep experimenting to get there? And I've seen founders who kind of go index to too much of one direction or the other one that can't stick with an idea. Jumping around every, every week you talked to them and then some that are just too stubborn about their original idea.

You need to find a fine balance. And so if I, if I had to do it again, was, would be, and there's, there was some hires we made that we made and I almost feel bad for this. Because we just weren't ready as a company. I almost did them at the service for hiring them, but by wish looking back on it, that is very true to ourself on product market fit.

And when we were ready to scale and when you do feel it, you will feel there's a night and day difference of Hey, pushing a product on the market and for it getting pulled. And so we're definitely when we in 2018 is when we really started to get polled. And that was the one thing I could tell my younger self is.

Don't prematurely scale. Don't hire people. Don't spend money until you figure out, Hey, what do customers really want? What is their demand for? And then once you get there, then you could scale what a shade that three years, and a lot of gray hair in my head here. If I, if I had taken that advice.

[00:28:09] Rosalyn Santa Elena: I love that. I love that. That's really good advice. So thank you so much for joining me, Ted. But as we wrap up before I let you go, I was asking all of the guests two things. One is what is that one thing about Ted that others would be surprised to learn? And two, what is the one thing that you want everyone to know about you?

And what I've found is that sometimes it's the same thing. When I talk about. But so, so what is, you know, something that others might be surprised to learn about you and the other is what is it something that you really want people to know about you and take away?

[00:28:43] Ted Blosser: Yeah. So one, one surprising thing about me.

I'll, I'll talk about both, maybe in a professional context. You'll probably find some non-professional stuff like my, my my sports and hobbies that you could take out, but professionally. One, one kind of thing. That's really interesting. I love building things. A lot of people don't know, but I coded up the first version of WorkRamp and I always tell my wife, even, even during our honeymoon, one of my favorite things to do is code.

And so if I could retire at a beach one day, when I'm in my sixties, I'd be coding. And so it's kind of comes back to my passion where, where I love building products. I love getting into the weeds. And even, even now, today, I'll, I'll even ask the engineer who just built a feature. Hey, what'd you use as a library?

Or why did you build it? Build it that way. And so that's probably one of my favorite things to do is build things. And now, now we get to do it at scale with customers. To your second point is probably different. I think, I think the one thing that. I love people to know about me is really, I love leading.

I think there's a lot of people who kind of stumble into the CEO position or might reluctantly take it. But I, I generally love weeding and it's really from, from when I started my professional career, I was always reading leadership books. I was always listening to CEOs as reading.

CEO's we're positioning things and there's just some ultimate satisfaction. And for me, it's not about the power or the responsibility around, I even talk about it in my title, chief enablement officer, it's really around enabling people to be their best and watching them thrive. We had this employee the other day who slacked me was like, Hey Ted, he's a sales rep.

He's like Ted, because of this great year I had, you've been able to. Help pay for this new home I just bought and he was able to go buy this new home. It just so rewarding getting that slack message from. And so that's, that's the rewarding part of, of the job. And that's something I love doing is just the leadership portion of it.

I'm not perfect at it. I'm always trying to learn. I learned from mentors, but but it's one big part of that. The, the role that I really love today.

[00:30:46] Rosalyn Santa Elena: Oh, I love that. I love that so much. Thank you for sharing that. So thank you so much for joining me, Ted, as always, it's a pleasure to connect with you and speak to you.

And I just felt like I I'm super, super appreciative of just all of the. Learnings. I think there's lots of good tips here and lots of good advice and I'm super excited to see what's next forWorkRamp.

[00:31:06] Ted Blosser: Awesome, thanks for having me Rosalyn.

[00:31:08] Rosalyn Santa Elena: Thank you.