By Matt Heinz, President of Heinz Marketing

Yet another great episode of Sales Pipeline Radio in the books.

Weekly, we cover a wide range of topics, with a focus on sales development and inside sales priorities heading into and throughout the year. We’ll publish similar highlights here for upcoming episodes.  You can listen to full recordings of past shows at and subscribe on iTunes.

This week, Manny Medina, CEO at Outreach SaaS joins us to discuss:  Can You Trust Your Sales Team with Technology?  Outreach Thinks So

He’s the CEO and founder of Outreach, a fantastic sales enablement and sales engagement and acceleration platform.

We have a great discussion… at one point I tell Manny, “You’re opening up the kimono a little bit, things that not everyone thinks about or has to experience but I appreciate you sharing…”

You’ll love Manny’s answer to this question: “What should companies be looking for? What should sales leaders be looking for in platforms to ensure they’re getting results and ensure that it’s additive to their productivity versus negative?”

You’ll also hear what he thinks is one of the most common mistakes he sees sales operations teams make.

And, listen to the end to hear some great examples about a couple of their core values:  Grit and Diversity.

More about our guest:

Manny co-founded Outreach in 2014 and now serves as CEO. Prior to Outreach, Manny was employee number three on Amazon’s AWS team, and led the Microsoft mobile division from launch to $50M in annual revenue. He holds an MBA from Harvard and a Masters in Computer Science from the University of Pennsylvania. Manny is a model of vulnerable and transparent leadership to his employees, from his heartfelt weekly email to his employees, to the traditional Friday get-together where the whole company shares their highs and lows of the week. He is a proponent of saving the planet by consuming less and purchasing second-hand whenever possible (he might be the only CEO to take the stage at industry events in shirts purchased from Goodwill). Manny grew up in Ecuador and now lives with his wife and three children in Seattle.

Paul:  Welcome everybody. It’s time again for another episode of Sales Pipeline, the only show that’ll let you grab your board and surf along as we take a look at the latest and greatest ideas and insights and rumors with our host Matt Heinz, who’s coming to us from Washington, D.C. today.

Matt:  How you doing, Paul?

Paul:  I’m doing … you know, maybe I shouldn’t bring this up but I have to as a journalist. You were a journalism major. I’m a journalist here at OC Talk Radio. I have to have you address the rumor that you’re in Washington to secretly meet with the president to become his new economic advisor.

Matt:  Well I was going to ask you because you mentioned rumors that you were going to share. Apparently that’s the rumor. No, that’s not why I’m here but thanks for asking. I am coming to you live from the business center of the Hilton Garden Inn here just actually a couple blocks from the White House.

Paul:  There you go.

Matt:  Was in town for an event with Marketo that we just wrapped up earlier today and heading back home a little bit later tonight back to the beautiful Pacific Northwest, but not before we get another episode over Sales Pipeline Radio in the books. So thanks everyone very much for joining us today. We are here live every Thursday at 11:30 Pacific, 2:30 Eastern. The 2:30 Eastern a little more relevant to me today. If you’re joining us live, thank you so much. We got an amazing live audience that we actually do have Paul, every week. They listen to us live. It’s amazing.

Paul:  I know. They want to know answers, so they tune in to hear about the latest.

Matt:  Because they’re looking for rumors. We’re going to have answers today for sure. For those of you that are joining us from the podcast, thank you for subscribing. You can get us at the Google Play and the iTunes Store, and every episode of Sales Pipeline Radio, past, present, and future is available at Every week we are featuring some of the best and brightest minds in B2B sales and marketing and today is no different. I’m really, really excited to finally get on the show Manny Medina. He is the founder and CEO of and we’re going to be talking about sales and technology and moving from big companies to startups and a lot of great stuff. So Manny, thank you so much for joining us today.

Manny:  Thank you. Thank you. We’ll be happy to have you back here in the Pacific Northwest. It’s 40 degrees and raining as it should be in March.

Matt:  Oh my gosh. From what I understand, once I get back starting I think Friday night into the weekend we’re supposed to have mid 60s weather and March in our house is garden infrastructure month. This is the time when we’re starting to build stuff out. I got spring training on the radio. It’s a good time to start to get outside a little bit more. But want to talk a little more about what you guys are doing. Manny is running a company called Outreach. They are one of the fastest growing companies in sales technology. Manny, maybe start, just give people who aren’t familiar with Outreach, tell them what Outreach is and what problems you guys solve for sales professionals.

Manny:  Absolutely. So Outreach is a sales engagement platform, and what that means is that your reps needs to perform activities every day that includes reaching out to prospects, following up, booking appointments and moving them through the pipeline. What Outreach does is it gives you an actual set of action tools that your reps connect to really quickly. So imagine a rep that needs to make a few phone calls and then follow up with an email and then follow up with another phone call. Outreach puts a lot of that automation in place so that the rep doesn’t have to follow up on his own. He is actually very diligent in actually executing this follow up and getting through his pipeline and booking those meetings. So Outreach gets you about 30% meetings lift for any sales or organizations that uses Outreach.

Matt:  And just full disclosure, we are fans of Outreach. We’ve got clients in Outreach. We actually use Outreach now ourselves internally and I can tell you just firsthand even though we have a very small install of Outreach given our size of our company have been very happy with just the efficiency it’s been able to generate for us. I’m curious, when you graduated from business school you spent 10 years working at a combination of Amazon and Microsoft and this is what you chose to do after that. So eventually I want to talk a little bit about what it takes to move from Microsoft and those types of environment, but why this? What drove you to this problem to solve with a startup as your first foray out of sort of enterprise technology?

Manny:  We had a previous startup that was in the recruiting space and when that got a little bit of funding and we were moving slowly into the right and up in terms of revenue generation, but it wasn’t fast enough. We were running out of cash. So there came a point in our lives that happened sometime in the third quarter of 2014 where we were staring at our bank account and we only had about two months of cash left. So at that point we had a choice to make. Either we go all out and figure out a way to get money back into the bank or we prepare to shutdown. So we decided to go build a tool that would allow us to sell our way out of this problem.

Now the four co-founders of Outreach are all engineers and designers, so we decided that we’re going to go and use our engineering and design jobs to generate more meetings because you know that that’s a precursor for sales. If we could generate more meetings, we felt pretty sure that we can dig our way out of the problem and get cash again. So we built a tool that essentially did two things. One of them was it created a quick personality spatial window so that we can send a lot of emails out that had a one-liner opener and that alone would counter act the whole email with a personalized email. Imagine that with two windows, one of which has you compose for you to write something up and the other one that has every single optic of that individual live, like a LinkedIn address, a Facebook, a Google+ account, whatever you needed to sort of find some relevancy in that line that you’re about to write and write it quickly so that we can crank out through personalized emails quickly.

The second piece that Outreach did originally or that we did originally before we founded Outreach was that then that email would get followed up meaning we will look into the mailbox, look for a reply and if there’s been a reply it will follow up. So we used that to generate meetings and we had a small team of about two sales people. And that’s who allow us to book about 10 meetings per rep per day. So very quickly we went from floundering to being swimming in meetings.

Now the problem was that if we were getting into those meetings and we were selling recruiting services and we were offering sort of a very high response rate that we had for candidates and using that candidate pipeline to sell to companies, people were not interested in our candidate pipeline. They were interested in this tool that got us into that meeting and the tool that we’re getting to generate it. So that’s sort of the a-ha moment after 10 of those or 15 of those we realized that the market was not really buying our recruiting product but they really wanted to buy the pipeline generation product. So we pivoted the company and we launched Outreach for sale and the rest is history.

Matt:  That is such a good story. We’re talking to Manny Medina. He’s the CEO and founder of Outreach, a fantastic sales enablement and sales engagement and acceleration platform. And I have to ask, in hindsight, I mean obviously good move in making the pivot to a business that clearly is the right place at the right time. It’s succeeding and growing. I think you know the origins of Slack which many of us use for internal operations has a very similar origin story. It was a design firm that was doing design work and created a tool to communicate with each other internally and realized their clients had a need for it. So in hindsight great pivot. How difficult was it to recognize the need for the pivot in that moment? I don’t want you to give away things that you may not want to make public, I’m just curious discussions internally was it a difficult decision? Was it a scary decision at the time to go from what you knew that you were selling to something that was really very completely different?

Manny:  Oh it was an incredibly difficult decision. When we realized that we were generating a lot of meetings, I was getting this feedback but cash is not showing up in the bank and my co-founders and starting to sort of freak out.

Matt:  Yeah.

Manny:  And there was this one call I remember taking from talking to a customer. I spoke to a customer, went back to my car, I was in San Francisco and my co-founder is saying how great this went and how this is turning into a business and they were like, “Yeah, about that, we are inventorying everything and we’re going to have to put it on eBay.” And that was sort of the crucial moment where I had to put on my pitch hat again and pitch my own team about this viability of this new idea. That was one of the hardest things I had to do in my life because I have to convince them that even though we didn’t have any cash and even though we have to put a ton of effort into turning this into a forward-facing product because the previous product was not customer facing yet. So that the biggest asset that we really had was a group of four very talented individuals with a great idea in an enormous market, and that is a dream come true for any investor. We just needed to go and execute.

Matt:  Yeah.

Manny:  That was sort of the genesis of the turnaround, but it was hard for a little bit because then I had to go and actually get some money from investors again and telling them like, “Remember that thing that we were doing before? Forget about that. We’re doing this other thing.” And it took a little bit for us to get going, but it was incredibly hard.

Matt:  Yeah. First of all, thank you for sharing that story. You’re opening up the kimono a little bit, things that not everyone thinks about or has to experience but I appreciate you sharing that. For those of you listening that haven’t read the book The Hard Thing About Hard Things by Ben Horowitz, he shares a lot of stories similar to that where sometimes in hindsight you’re like, “Wow, that business did really well and look at all these great successes and great choices,” but some of those decisions are in the moment not exactly easy and the reality of your ambitions versus the cash in the bank that can allow you do some of those things. That’s one of many hard things about hard things.

Talk a little bit about, and extension of that, going from a big environment like a Microsoft. You were there for 10 years running a bunch of different organizations. What was it like transitioning from a company that’s big, that’s known and with resources to really starting over and starting from scratch in a startup. Was that a challenging transition and I guess also what are some of the keys you recommend for other people that may be thinking about making that transition to be successful as well?

Manny:  That’s a great question, Matt. I think the biggest transition pain that I had going from Microsoft to my own company was the fact that at any company of any size that has been around for a while, you have a brand name, even if your brand name is not big. Microsoft’s brand name was one of the top five brands in the world. So there was no meeting that people wouldn’t take with me. I was selling Windows 12 to carriers and anybody … I would email anybody or call anybody, they would take my meeting. That was not the case at Outreach. And actually, that’s one of the reasons that we invented Outreach because we had to follow up. You have to find a way to get through the door. You have to try many different people and avenues within the accounts to actually get a crack … open the door a crack so that you can get in. That was the hardest thing. That was a lot of humble pie that I had to eat there.

The second piece was that when you are at a big company that is doing relatively well, you are insulated from the vagaries of the market and the vagaries of failure. And failure that can kill you. Microsoft can buy a company worth $200 million, burn it to the ground and move right on. We don’t have that kind of luxury. We have to be right a lot more than we have to be wrong, and when you come out of Microsoft, you come out thinking … or out of Amazon or any big company, you come out thinking that you are never wrong because you see success around you the entire time. When you go into startups, failure becomes a daily thing and you have to get used to it instead of learning how to fail fast, how to fail smart, how to learn from the failure and get back up again, use the failure to your advantage, that was the biggest learning and biggest positioning point of me coming out of Microsoft into our own environment.

Matt:  Yeah. That makes a lot of sense. Someone told me once that they spent a lot of time at Microsoft and went into a startup and they said that one of the biggest differences in when you’re in a big company, you can spend more time focused internally and you’ve got enough gravity and momentum in the business sometimes that works out. When you’re at a small company, when you’re starting from scratch you have to focus externally and your decisions all carry more weight. I think that knowing that and making that transition can be a challenge for some folks.

Well hey, we’re going to have to take a quick break here, pay some bills. We’ll be back with more with Manny Medina. He’s the CEO and founder of Outreach. We’re going to be talking a little more about sales technology and understanding when it helps, when it hurts. Talk about growing a business rapidly with integrity and keeping your values intact and much more. Thanks for listening, we’ll be right back on Sales Pipeline Radio.


Matt:  Inside the beltway, the belly of the beast, it is a nice day here but freezing as I look out the window and see everyone walking by with their stocking cap. It may be spring training. It may be warmer weather somewhere, but definitely not here not yet. Thank you very much everyone for joining us. Coming back to Sales Pipeline Radio. We have some great guests coming up over the next couple weeks. Next week we will have Jonah-kai Hancock. He is the vice president of marketing at Tune, great little start up in Seattle. We’re going to be talking about marketing technology and a little bit of account-based marketing. They’re one of the most aggressive adopters of sales and marketing technology that we know and they’ve got a pretty interesting framework for how they not only how they evaluate technology but also ensure its success inside organizations. So excited to have Jonah-kai.

And then the following week we have Alli McKee. She is the founder and CEO of a company called Stick. She is integrally involved in their sales process. She is also an improv specialist. She’s taking classes and doing a lot of improv work, so we’ll be talking about the intersection of improv, startup sales, and the role of improv skills in the sales process as well, so much more coming up in the next couple weeks the Sales Pipeline Radio.

More today with Manny Medina. He’s the CEO of Outreach, and full disclosure we are an Outreach user. We are a happy Outreach user. It’s amazing how quickly once we got it on board and got it integrated, it’s amazing how quickly it just became part of our process and part of the way we’re sort of helping get more engagement from prospects and as well as from customers. It’s been fantastic. I think a lot of people, Manny, look at technology and they see the opportunity with a lot of these tools but I’ve also seen people that have increasingly indicated a little bit of a backlash on technology wondering if some of it can be counterproductive, if there’s some technology that people adopt that actually because of what it takes to use that technology is counterproductive to their results. What should companies be looking for? What should sales leaders be looking for in platforms to ensure they’re getting results and ensure that it’s additive to their productivity versus negative?

Manny:  That’s a great question. My advice to sales leaders out there is that they should have a process in place. They should have a playbook that has some degree of options and understanding throughout the organization before they start getting heavy on technology. We see technology go sideways when they bring us in or they bring whatever vendor in and without knowing what they want to accomplish with it. What is it they’re looking to lift? What is it they’re looking to stop doing? What is it they’re looking to optimize? And in the concept of what is framework. Pick your framework. So for instance, we recently did some training with command of the messaging from Force Management, and now that gave us a framework for us to start deploying our assets all the way from product into our product marketing team, into our enablement team, into our sales team and et cetera, and that at least puts a little bit of our rail into how we operate.

The same thing should be done with any organization, be that challenger or be that some private coaching. Whatever you need to sort of create the persona that you’re going after, how they like to be communicated, what experiments you’re going to run and how are you going to sort of get to that customer needs to be in place before you bring in a technology partner. The technology is just going to put a rocket booster to your current profits. It’s not going to make the profits. It’s not going to teach them anything. What it’s going to do is it’s going to make them faster and better at what they are already doing. And that’s sort of the main thing.

The second thing is that whatever tool you buy, whatever sort of platform you decide to adopt, make sure that it has some component, some learning component meaning that it presents a way for you and your management team to learn from the actions that your team is taking. Meaning is the tool is helping you do X, Y, or Z better, phone calls better, emails better or office management better or document management or closing pipeline, whatever it is, make sure that you can measure different planes within that framework so that you are constantly improving and make sure that you spend time understanding what it is you’re doing and why is it you’re doing it.

One of the most common mistakes that I see sales operations teams do or sales teams do is that they come in with a very heavy belief, kind of like a doctrinal order or religious belief about a particular thing that they have to do because the customers like to be communicated and it’s not until you test it against something else that you don’t learn. So the most important thing is that your team is always learning, it’s always testing, it’s always finding out what way your persona likes to be sold and adopting that and moving right on. Hopefully that answered the question.

Matt:  No, I love that. That’s a great answer and a great framework and we will certainly continue to share this up on as well as a great way to think about technology usage and really evaluating those tools and how they can be successful for you moving forward. Got just a few more minutes here with Manny Medina, the CEO of Outreach and definitely encourage you to check out Some great resources up there. They’ve got a fantastic blog and a lot of other resources, and if you go there right now you are very likely to see a video and a promotion for Unleash.

Last year kind of out of the blue, Manny, I mean you guys created one of the most buzzed about sales conferences of the year. I was not able to make it last year, but I have yet to talk to someone that wasn’t just blown away by the quality of the conference and it’s coming up again in May. I think it’s May 6th through 9th, 2018 down in San Diego. Talk a little bit about what people can expect from the conference this year and who are the roles, who are the people that should be checking this out and getting registered?

Manny:  That’s another great question. So let me tell you a little bit about the story of Unleash. So Unleash was a response to a need to have a sales conference where a sales professional can come and be inspired and be energized and learn something and take that home. We didn’t see in the market, other than the big sort of affairs with booths and vendors, we didn’t see in the market something that fulfilled that need and we decided to go ahead and fill it. As you know, this company has a few important elements from the Tony Robbins organization that help us sort of hone in on what is our persona going to be in a conference. What is it we want to deliver? How do we want to make people feel?

So this year, the theme is going to be peak excellence, and that is how do you show up every day at peak excellence at your job and how do you perform as a rep. Your job is hard. You get told no many times. Your commit number may not be the number that you’re coming through with. How do you get back on your feet and sort of get back into that peak excellence mindset? And peak excellence covers many things. It’s your tooling, your attitude, your mindset, your preparation, your training, all that comes together in one conference and that’s what we’re going to be talking about.

And the easiest way is just to go to Unleash at and register for the event. It’s going to be mind blowing. As you know, we have signed up the Navy SEALS to come in to training every morning and we have signed on Jocko Willink, the author of Extreme Ownership, to come and give us a talk and this is mixed in with a new Outreach releases, which is Outreach Amplify, our new machine learning platform, and a number of other things that it’s just going to be bigger, badder ass than last year.

Matt:  I love it. Yeah. I’m definitely looking forward to being there with you guys this year and it sounds like you guys have a lot of exciting stuff coming up. So definitely check out or just go to the home page and you can find more information and register there. You talking about sort of peak mindset, I know this is something that bleeds over into your organization as well. You guys have grown very quickly, taken advantage of the market opportunity but I know that with that bracketed growth it’s been important for you to grow with integrity and to grow with values and maintaining a good culture. Talk a little bit about what it takes to build and maintain an ideal culture in the midst of aggressive growth. That isn’t always an easy thing.

Manny:  No, absolutely. Actually, that is the first thing that breaks with rapid growth if you don’t mind it. A couple of things that I think we did right is that we gathered our early team back when we were about 50 people and we gathered as many people as we could into our room and we decided to sort of list what are the core values of this company. What are we going to stand for? Who are we going to be? And you would think that’s something that comes from the founders, but it didn’t come from the founders. It came from everybody. The funny thing is that it was a quick exercise. It took about two hours to come up with five core values, the initial five core values that we came up with. And after that, what happened is that those core values need to be discussed, need to be tested, need to be challenged. And that needs to be a point of conversation at all times. So every time that we get into an all hands, there’s always a question around the core values. I initiate a conversation across the company on what does that mean.

So for instance, one of our core values is grit. Like grit sounds great and it sounds like something you would do when you’re passionate about your goal and you go after it on a regular basis with a lot of energy and enthusiasm. But grit can also break things and also drive the wrong behavior. So for instance, many times our support team or customer success team will do something that is on the platform but it’s not quite right but it solves the customer’s problem by gritting it out. Instead of sort of taking that well the problem was stated and bringing it back to our process and we can actually go ahead and solve it, grit can also sort of cut the other way. By recognizing when a cultural or when a core point of view sort of cuts both ways is when that point becomes real. You know what I mean? When it stops being dogmatic and something that the CEO says all the time so that you can feel good about yourself, but when you actually go and do it.

So for instance, another core value for us is diversity. But we don’t just talk about it. We go and measure it. You know what I mean? And then we talk about the company as like how many diverse candidates are we bringing into the pipeline and are we feeling good about that pipeline? How many percentage do we have on C, how many of our candidates are doing well? How many of our candidates are in management? So having women and people of color and making sure those people are being successful, are being recruited and they are being placed, that’s how you actually live the core value of diversity. So that’s sort of the bottom line, is that for you to really live the core value you have to test it. You have to put it in front. You have to discuss it. You have to sometimes even disagree with it and measure it most importantly.

Matt:  I love it. I love it. Well we’ve covered a lot of ground here today. We’re going to have to wrap up today’s episode of Sales Pipeline Radio. I want to than our guest Manny Medina. He’s the CEO of Outreach. Learn more about him, the company, the conference, Unleash at We will have a recording of this episode on demand at in the next couple days if you want to listen to this again. Appreciate the candor and the openness for a lot of diverse set of topics today. So thanks again to Manny. We will see you all here next week again live, 11:30 Pacific, 2:30 Eastern with Jonahkai Hancock. We talk about marketing technology and a framework for evaluating the success of technology in your stack moving forward. For today, for my great producer Paul, this is Matt Heinz. Thanks so much for joining us. Sales Pipeline Radio.