Hey there! Welcome to the Marketer Of The Month blog!

We recently interviewed Manny Medina for our monthly podcast – ‘Marketer of the Month’! We had some amazing insightful conversations with Manny and here’s what we discussed about-

1. Consolidating sales tools: Simplifying tasks for sales reps

2. Efficiency enhancement: Aligning workflows for optimal client interactions

3. Leadership synthesis: Medina’s blend of Amazon and Microsoft strategies

4. Pioneering sales execution platforms: Outreach’s AI-powered edge

5. Customer-driven innovation: Refining AI for enhanced sales performance

6. Value-oriented innovations: Boosting sales efficiency with tangible solutions

About our host:

Dr. Saksham Sharda is the Chief Information Officer at Outgrow.co. He specializes in data collection, analysis, filtering, and transfer by means of widgets and applets. Interactive, cultural, and trending widgets designed by him have been featured on TrendHunter, Alibaba, ProductHunt, New York Marketing Association, FactoryBerlin, Digimarcon Silicon Valley, and at The European Affiliate Summit.

About our guest:

Serving as Outreach’s CEO since 2014, Manny Medina co-founded the company and played pivotal roles at Amazon’s AWS and Microsoft’s mobile division, contributing significantly to revenue growth. With an MBA from Harvard and a Masters in Computer Science from the University of Pennsylvania, his leadership style is defined by transparency and innovation.

EPISODE 154: Workflow Wizardry: Outreach’s CEO Manny Medina on Aligning AI Ambitions with Sales Success

The Intro!

Saksham Sharda: Hi, everyone. Welcome to another episode of Outgrow’s Marketer of the Month. I’m your host, Dr. Saksham Sharda, and I’m the creative director at Outgrow. co. And for this month we are going to interview Manny Medina, who is the CEO of Outreach.

Manny Medina: Great to be here. Thank you.

Don’t have time to read? No problem, just watch the Podcast!

Or you can just listen to it on Spotify!

The Rapid Fire Round!

Saksham Sharda: So let’s start with the rapid-fire round. The first question is, at what age do you want to retire?

Manny Medina: I don’t have a retirement age.

Saksham Sharda: How long does it take you to get ready in the mornings?

Manny Medina: Oh, I jump out of bed and I’m ready.

Saksham Sharda: Most embarrassing moment of your life?

Manny Medina: I woke up.

Saksham Sharda: Favorite color?

Manny Medina: Blue.

Saksham Sharda: What time of day are you most inspired?

Manny Medina: Between 5:00 AM and 7:00 AM.

Saksham Sharda: How many hours of sleep can you survive on?

Manny Medina: Six.

Saksham Sharda:  Fill in the blank. An upcoming technology trend is _____.

Manny Medina: Is a tech fad.

Saksham Sharda:  The city in which the best kiss of your life happened?

Manny Medina: Quito, Ecuador.

Saksham Sharda:  Pick one- Mark Zuckerberg or Elon Musk.

Manny Medina: Elon.

Saksham Sharda: The biggest mistake of your career.

Manny Medina: That’s starting our reach earlier.

Saksham Sharda: How do you relax?

Manny Medina: I meditate.

Saksham Sharda:  How many cups of coffee do you drink per day?

Manny Medina: A lot. I love coffee.

Saksham Sharda: A habit of yours that you hate?

Manny Medina: Sometimes I bite my nails.

Saksham Sharda: The most valuable skill you’ve learned in life.

Manny Medina: Listen.

Saksham Sharda: Your favorite Netflix show.

Manny Medina: The Wire.

Saksham Sharda: Early riser or Night Owl?

Manny Medina: Early riser.

Saksham Sharda: One-word description of your leadership style.

Manny Medina: Do not show, not tell.

Saksham Sharda: Top priority In your daily schedule.

Manny Medina: Talk to customers.

Saksham Sharda: Ideal vacation spot.

Manny Medina: Any beach in Italy.

Saksham Sharda: Key factor for maintaining a work-life balance.

Manny Medina: What is work-life balance?

Saksham Sharda: Memorable career milestone.

Manny Medina: When we pass a hundred million.

Saksham Sharda: The last song you’ve been listening to

Manny Medina: Anything by Jay-Z. I forget which one

Saksham Sharda:  The last movie that you saw that had an impression on you.

Manny Medina: I don’t remember watching a movie, but I watch a lot of Star Wars at home, so maybe one of the stars. Like a Socha or Mandalorian. I re-Watch Mandalorian.

The Big Questions!

Saksham Sharda: Alright, well that’s the end of the rapid-fire round. All right. The rest of the questions you can answer now with as much ease and time as you like. Okay. The first one is, what strategic initiatives or advancements is outreach focusing on to meet the evolving needs of its users? And how do you envision shaping the future of sales technology?

Manny Medina: Yeah, so in sales technology, the main challenge right now is that after CRM there has been a blow-up of applications. So now you need 10 applications to do two jobs, and all that needs to be consolidated into a single platform. So one of the initiatives for us is to bring as much capability into a single pane of glass to make sure that the rep doesn’t have to go from the app to their jobs.

Saksham Sharda: So in terms of user experience, how’s outreach enhancing its platform to accommodate the growing complexity of sales processes and the increasing demands for personalized efficient interactions with potential clients?

Manny Medina: It’s that we need to understand what it is the rep wants to do and wants to accomplish, and then put that into a workflow that uses both software and AI to get that done as fast as we can. At the end of the day, the job of a sales professional is to spend time with customers and to either, you know, drive a customer activity or drive a customer outcome or go get more customers. So if you’re not doing those two things, then you’re not, you know, you’re not using your time. Right. So that’s what we’re focusing on is how we get, you know, sales reps and managers to spend more time in front of customers and win-win more often.

Saksham Sharda: So you have an extensive background from leading Microsoft to Windows phone business development teams to engineering Amazon’s compensation system. How have these diverse experiences shaped your approach to the role of CEO at Outreach?

Manny Medina: I took ideas and leadership styles from each of those companies. So you know, I beg to borrow things from both Jeff and Andy at Amazon. And, you know, from their leadership styles, I borrow a few things that I use myself. And then when I was at Microsoft, you know, I learned a lot about, you know, having patience and playing the long, long game. In both companies, they did the same thing. Because at Amazon AWS took, you know, 15 years to turn, you know, to turn into anything. At Amazon, they are relentless in the pursuit of the cloud. So I think in both places, I learned, you know, how to establish a vision and get people behind it and sort of execute on it with, you know, with patients.

Saksham Sharda: So given this, well some differences between the corporate cultures of Microsoft and Amazon, how have you integrated the best aspects of both into your leadership approach at Outreach?

Manny Medina: I mean, you, you take what works for us. So at Amazon, it was this belief that you were the smallest large company out there. So you always acted like a startup with a lot of urgency, with a lot of you know, with frugality and with a lot of thought in how you make decisions and use data. And, Microsoft, it was about how you build a big business on the back of big partners, big customers, and how you land them. How do you align your roadmap, towards their vision so that you can create an ecosystem of large customers that propel you forward? You know, Microsoft was a more sales-driven company than Amazon was a tech-driven company, and I think the mix of both is what makes us at Outreach, you know, really great.

Saksham Sharda: Outreach is described as a platform that helps revenue organizations create and close more pipelines. How have you strategically positioned the company in the competitive landscape of sales execution platforms?

Manny Medina: So, first of all by being the first one to be an execution platform, we were the first company to bring all the assets together into a single execution, experience. And then it’s by making sure that each of those experiences has imbued, you know, any type of AI, whether it’s generative or not, to make sure that that part of the execution gets on faster and influences the other part of the execution. So in sales, how you build a pipeline determines how you’re gonna close it, and how you’re gonna close it also influences the kind of pipeline you need to build. So you have this virtual cycle that you have to be that you have to be feeding at all times. For us, it was about building it and then iterating on it faster with more intelligence than anyone else in the market. And that’s how we win.

Saksham Sharda: So in what ways do you leverage all this data and customer feedback to continually refine and improve the strategic direction of Outreach?

Manny Medina: We do something called action outcome comparison, which is, a term that we coin that if we look at a sales action and we look at the outcome or lack of outcome, then those two create a pairing that feeds, a language model or a machine learning model. And then out of that feedback loop is how we iterate and we create things like detecting sentiment, trying to figure out whether a call went well or not trying to figure out whether a deal’s moving forward or not, trying to use that prediction and forecast. So the ability for us to capture all those pairings and then feed that into the difference is what’s, you know, been driving the platform forward and ahead of the competition.

Saksham Sharda: Can you highlight any memorable achievements or milestones during your tenure as CEO of outreach that have significantly impacted the company’s growth and success?

Manny Medina: I think it was when we ship we had, a product capability that is a knowledge AI assistant that is an imagine an AI assistant top of your meetings and takes notes real-time and real-time answers questions. That was a marvel of both engineering and customer insight and customer obsession because up to that point, the majority of applications that did anything around the call were transcription tools and then did an analysis on the transcript as opposed to being on the call itself and in the call. You know, and we have to solve this fundamental problem, which is when somebody asks you a question, it takes, you know, about six microseconds to get to your brain and then another couple of microseconds for you to answer. So we needed to understand and pop a card in less than six microseconds for it to be useful. And for us to develop that technology was, you know, almost like landing somebody on Mars. It was incredible.

Saksham Sharda: And is there a situation where customer feedback directly influenced a pivotal decision within Outreach?

Manny Medina: Oh, all the time. We are constantly talking to customers obsessed with them.

Saksham Sharda: Any memorable instances here?

Manny Medina: Yeah, it was when we figured out that.

Manny Medina: What, you know, after talking to many account executives, we found out that the best account executive sells a vision of the future and then brings it back to today in the form of a plan. Capturing that plan in the form of both an account plan and a deal plan was the way that they were managing it. Usually, they were managing different things in notebooks and spreadsheets and slacks and Google Sheets. So when we came up with that insight and we sort of started wrapping around a lot of what we do around that insight, then we’re able to make, you know, all account executives successful. So there is, you know, a lot of customer feedback that didn’t come to us directly and say, go build X, but they say, look, my success, you know, users do a lot of plans, and then they execute on that plan. If you had a planning tool within Outreach, it would’ve helped me, you know, it will help make every account executive, you know, behave like the best ones.

Saksham Sharda: So considering this dynamic nature of the sales technology industry, how do you prioritize innovation in particular?

Manny Medina: You know, innovation needs to come in at the rating, which is absorbed. So it is, you can’t just innovate for innovation’s sake and throw, you know, stuff out there and see if it works. You need to make sure that our customers are getting value from it, unlike any other application we sell to, to revenue organizations and the revenue organizations need to see the value and something very tangible in the form of ROI or production or time saved. So for us, the innovation has to hit the mark in terms of like, is it delivering something very tangible otherwise it doesn’t get done.

Saksham Sharda: And how do you encourage experimentation and risk-taking within the company, if at all?

Manny Medina: It’s by, you know, everything begins from the point of view of the customer. So we have a, you know, everything has a hypothesis as to how we’re gonna inflect, you know, our customer’s efficiency or the productivity or time savings, etc. And then after that, we go and look into the future of technology and see what technology is cutting edge that could help us sort of like inflect on behalf of a customer. When you are operating at the edge of capabilities of technology, you’re gonna bring in some things that are not gonna work. So, you know, we have tried, you know, machine learning stuff that didn’t work or that didn’t, you know, deliver on the, on the promise. And, that is part of the job, right? Like, as an innovative company, you have to try, like, if you’re not failing, you’re not innovating on behalf of the customer. So failure is baked in a requirement for us to grow.

Saksham Sharda: Are there any memorable failures that you can think of?

Manny Medina: Yeah. So the first model for emails for detecting sentiment was a catastrophic failure because it kind of didn’t quite work well. And so we tried to solve it by creating a user experience where we say, Hey, we think this email has, is an objection, or is an intro, or some other sentiment for the email. And then when a model was wrong, we asked the user to correct it. Guess what? Users don’t want to correct anything. So if the model was wrong, the user just stopped looking at it and just moved on. So like, the idea of having a human in the loop for training the AI model is just stupid. But, you know, back then we thought it was brilliant and turned out to be dumb. So here we are.

Saksham Sharda: So delving into sales execution, could you elaborate on why organizations find it crucial and how Outreach contributes to their success in this aspect?

Manny Medina: Yeah, because sales are not unlike other things. Sales are not about a bunch of charts and accumulating data and giving you insight on the data and like talking about, you know, more knowledge of sales, sales is inflicted or is changed at the point of the rep in front of a customer or at the point of a manager in front of a rep. So execution is about that. It’s about the fact that it’s not storing data the way a system or record would. It’s about taking that data in whatever else you have and then taking an action and then having that action move something forward. At the end of the day, the reward for sales is revenue close to one. And if you’re not getting more revenue close to one and then you’re, we’re not making progress. So unlike, you know, other applications that help you be more productive or, you know, share more information, the goal of a revenue-facing application is that it delivers more revenue, otherwise, we’re not doing our job.

Saksham Sharda: So given the current buzz around AI, how does Outreach distinguish itself in the landscape?

Manny Medina: We’ve focused on what our customers need. So we don’t, we’re not gonna go build AI and then go make some big splash about it. Just for the sake of the AI, we’re gonna be building things that help our customers, you know, do more with less. So for instance, when we build our ability to summarize meetings, then we increase the amount of, the, increase the amount of time, a rep or a sales rep would have because the managers didn’t have to ask how the meeting went. They can just inquire within outreach, how did that meeting go? Outreach will give a summary with the bullet points and then answer any additional questions such as what features came up, what was the pain and what was the price conversation like. So the ability to give the rep and the manager more time is how we measure success and how we measure success of both software and how we measure success of AI. So when we come up with something new, we talk about it in the form of not the technology that is behind it, but we talk about the firm in the form of the benefit that it brought to the organization. So, you know, when we go from, you know, meeting summaries to deal summaries to the way to inquire, deal to the way in, acquire a family of deals, then you measure your success and how much time you’re relieving this rep and the manager for having to meet, talk about things because all that is available in the application. So it’s all about the value that you deliver to the customer.

Saksham Sharda: Right. So as we approach 2024, could you share one insightful prediction you have for the industry and how Outreach is poised to navigate or capitalize on this anticipated development?

Manny Medina: Well, it’s going to be about, you know, AI is gonna become useful for, for and it’s gonna make a real difference for, for both sales and, and their managers and the organizations. But the economy’s still gonna be tough. So, you know, we’re gonna have to get back to, you know, good old ways of landing customers and, and delivering value and obsessing over them because I don’t think that we’re gonna be in a recovery mode for another, you know, a few quarters.

Saksham Sharda: Alright, so the last question for you is of a personal kind. What would you be doing in your life, if not this?

Manny Medina: I would probably be a professor somewhere, I think.

Let’s Conclude!

Saksham Sharda: Thanks, everyone for joining us for this month’s episode of Outgrow’s Marketer of the Month. That was Manny Medina, who is the CEO of Outreach.

Manny Medina: Pleasure. Thanks for having me.

Saksham Sharda: Check out the website for more details and we’ll see you once again next month with another marketer of the month.