Sales Pipeline Radio, Episode 345: Q & A with Manny Medina



Learn about the importance of adaptability, prioritization, and leveraging AI to enhance productivity and stay competitive in the evolving business landscape.

By Matt Heinz, President of Heinz Marketing

If you’re not already subscribed to Sales Pipeline Radio or listening live Thursdays at 11:30 am PT on LinkedIn (also on demand) you can find the transcription and recording here on the blog every Monday morning.  The show is less than 30 minutes, fast-paced and full of actionable advice, best practices and more for B2B sales and marketing professionals.

We cover a wide range of topics, with a focus on sales development and inside sales priorities. You can subscribe right at Sales Pipeline Radio and/or listen to full recordings of past shows everywhere you listen to podcasts! Spotify,  iTunesBlubrry, Google Play, iHeartRADIO, Stitcher and now on Amazon music.  You can even ask Siri, Alexa and Google or search on Audible!

This week’s show is entitled, Why AI Will Redefine the Workplace, for the Better“.  My guest is Manny Medina, CEO at Outreach.

Tune in to learn how to:

  • Embrace Change and Prioritize for Success: In 2023, adaptability and disciplined focus are key to thriving. Prioritize wisely, as the era of overinvestment and growth at all costs has evolved.
  • Shift Focus from Tasks to Jobs: Disassociate tasks from sales jobs. AI can handle routine tasks, freeing salespeople to focus on building relationships, solving problems, and creating value.
  • Boost Productivity with AI: Sales leaders must harness AI to increase team productivity. Minimize the “swivel chair tax” and invest in meaningful customer interactions to stay ahead of the competition.

Watch the LinkedIn and YouTube video, listen in below and/or read the transcript below.


All right. Welcome everyone to another episode of Sales Pipeline Radio. I’m your host, Matt Heinz. Excited to have you here for our first episode of September. I dunno where the year’s gone. Manny, my daughter, my oldest child just started high school. I need time to slow down for a variety of reasons, but happy to be here on another Thursday. It’s for those of you who are joining us on Sales Platform Radio live from LinkedIn or YouTube. Super excited to have you here in the middle of your workday and workweek. If you want to join the show, you can do so live. Make a comment if you can have a question, a comment, a rebuttal. It’s a little bit of a family show, so keep it safe and the sane. But we can make you part of the show. We can ask your question live, give you a shout out here on the show. So if you want to participate, please do. If you’re watching and listening on demand, thank you so much for downloading and subscribing every episode of Sales Pipeline Radio all the way back, all 345 plus now, all available on demand at This is a real treat. Very excited to have with us today, the founder and CEO of Outreach, Manny Medina. Manny, how you doing?


I’m excellent, man. Happy to be here.


We were just joking before we got started here that as we record this in early September of 2023, I was talking to another CEO that you and I know, and he asked me how it’s going. I’m like, not my favorite year of all the years, and I think a lot of people can resonate with that. But you made a good point about sharpening the steel right now and knowing that you get through this, they’re going to be better, but knowing where to focus on things right now and I’d love to have you share some of that.


Yeah, I think that this is a year in which we come from a world in which we will do everything. We’ll do one of each. We will take on as many projects as we could, and our portfolio was very large and very broad with the hope that many of those things will pay out, and now we’re forced to prioritize. If you don’t have one or two things that you’re working on and you’re putting all your resources behind, you’ll be doing it wrong. The appetite for overinvestment, the appetite for waste, the appetite for growth at all costs has gone out the window. So now you have to be very ambitious of making sure that every dollar lasts and that the probability of things paying out is higher than average. So I like the discipline, I like the thought that this is a world in which you have to make your investments turn into cash in a very short period of time. And constraints actually free you to be more creative. The creativity and the constraints is far more exciting than the time in which you don’t know what to do with the cash. You did everything. So it’s not sour grape argument, just to be clear. It is more of a, this is a different world, but a world that rewards those who are ready for it.


I really appreciate what you just said. I think a friend of mine who I worked with at a number of startups who’s actually running enterprise sales at Smartsheet now, when we worked together, he had a saying at the top of his whiteboard that said, startups typically don’t starve. They drown. Right? They take on too many things. You try to do too many things. And a big part of strategy is choosing. And before we get into that, I want to talk about sales platforms and AI and the things we tend to talk about, but I love this topic. I think if you are prioritizing, if you are choosing the things to prioritize, by definition, you are leaving things on the table and someone else in your company in your world cares about those things, you’re no longer prioritizing and they will remind you of that, right? And that is an anxiety spiral that helps no one. As an entrepreneur, as a leader, I’ve just been so impressed at how you’ve built culture and driven the team and the growth at Outreach. How do you encourage your team to not only prioritize, but accept sometimes the ramifications of the things that you’re not doing?


Yeah, it is a really good question because there’s no silver bullet for it. And the whole disagreeing commit only works so many times the disagreeing commit is you have a cookie jar and you only have so many cookies in the cookie jar. When you can have somebody disagreeing commit before they’re like, alright, you’re just telling me what to do without selling me. And I think that one of the things that we did really well by having four co-founders as supposed to use one is that I couldn’t get my co-founders to do anything because see, I am the CEO because the CEO was the only job not taken, when we started the company, everybody else would pick a lane and the CEO was a lane that wasn’t picked. So the job for me to get anything going was to have to sell the idea.

So we got very used to selling to each other. So we couldn’t just say, we’re going to go do X, we’re going to have to, for me to convince my co-founders to do X or Y, I have to go sell them to the X and the Y, and I have to bring in evidence and I have to deal with the counter arguments and we have to spend time in this rock tumbling. And the tumbling and the friction of the ideas made the rock shinier over time. So we got really used to selling arguments as opposed to making arguments, selling ideas and selling propositions as opposed to forcing a proposition through.

In this time in which you have to leave things on the table, it’s actually better than that. You have to leave things on the table that other people are very attached to it and that your competitors are going to pick up and run with it. So not only are you going to get the noise internally from saying, Hey, I want to do that, it’s on the table, but your competitor is going to run and go with it. And then whoever had the idea, it was attached to the idea on the table’s going to say, look at the competitor is running with it. See, I told you,

And I mean, you have to be okay with that. You have to be, yes, it is on the table. Yeah, I know you like it. Yeah, I know somebody else wrong with it. Our bet is still this one, and the reason it’s still good is because of X, Y, and Z. And it’s okay to resell the idea. It’s kind of like rekindling the love with your partner. You have to do every once in a while, otherwise it goes stale. So it’s okay to resell the idea, but we have to be aligned. The one thing that is not a sacrificable thing is alignment. You have to be aligned. You can’t be doing this one thing in somebody else doing another. That is the case of that. That is how you die quickly.


That’s so good. If you haven’t read, and I want to move on to some of these other topics we wanted cover, but I can’t remember the exact title of it, but there’s an article, go Google like Legos on the table. Basically this concept of as you grow your business, there’s a million things you can focus on, prioritize what you want, leave the rest of the Legos on the table. Someone else may pick them up and decide that’s a priority. And those things, if you prioritize well as a team, as an individual, can move your business forward. But I love the concept of just focus, be willing to sort of say, there’s only so many times you can disagree and commit and shout out to Jill Richards who’s said here in the comments that saying no more than yes. That’s what focus is. Finding the things, saying no more often, saying yes to a small number of things, moving it forward.

Think a little bit to one of our other topics today is this whole idea of AI in the workplace, and I know I want to talk about what that implies around having a platform mentality in your sales tech stack as well. I feel like we’re in this moment where everywhere you turn, you read about the emergence of AI and the importance of AI and the future of ai. Yet at the same time, I find so many people that just want to have their head in the sand that are like, I don’t know what this is. I’m going to ignore it. I’m going to pretend it’s not going to happen. We’re very early days on this, but that juxtaposition is really interesting to me. Now that said, AI has been in a lot of tools we’ve had well before chatGPT. I know that ai, this is not a sales pitch, but I’m a happy Outreach customer. I know, and I’m thankful that there’s AI in the platform that I use and our team uses for sales engagement. But if you’re a sales and marketing leader watching, listening to this right now, how should you be thinking about AI in the workplace and why does that matter?


The first in instantiation of AI is to do a survey of your tools of whatever you’re using and figuring out where is AI helping, who is actually embracing and how is it showing up in the form of taking a task away or replacing a workflow with something else that was not done before? So for instance, in the course of Outreach, if you look at a task of building sequences, so our first instantiation of AI is of course the degenerative offering of writing the emails for you. That’s par for the course right now. But as you can see the progression of AI, you will see that Outreach will write your own sequences, so you don’t have to worry about that. It will automatically generate your AB testing. In the case of Kaya, it will generate your cards. And one of the things that we’re about to release is scoring.

So there is a scoring of the calls, but the scoring of the calls only happens post facto by a manager, and it has to be manual when reality doesn’t need to be. You already know what a great call looks like. So why don’t we create an AI scoring mechanism that actually helps to rep a score better during the call so she doesn’t have to score after the call and how a call went. It can actually improve as the call is going through and improve the score of the conversation based on the outcomes that you expect in the conversation. So the first thing you do is make sure that every one of your providers or your vendors, your partners are embracing AI themselves in a way that is more meaningful than the obvious. That’s number one. And that they’re doing a responsibly, right? They’re not exposing your data.

They’re not just connecting to ChatGPT and throwing your data out there because that becomes part of the public domain, et cetera. So make sure that that is happening. So that’s go do now. The second aspect of it is, look, the beautiful part of the AI and the scary part of the AI is it can be whatever you want it to be. And that creates a lot of either for those who are early adopters and innovators leaning forward and being like, alright, what can I make it be? And for those who are a little bit more on the pragmatic side, they’re like, show me first before I jump in too early. And when we go talk to our own customer base, it’s a little bit divided, some people will be like, yeah, give me all, give me now, give me fast, give me flying cars.

And some others are saying, no, no, no, no, no. I heard that AI hallucinates, AI makes it up. AI does these other things and I don’t want to be part of that equation. So what we all need to do as an industry is continue to sell the vision of whatever that vision is or as the vision is. There is no world in which there’s a general AI assistant for reps and managers. Right now the way it shows up is in the task, right? You’re going to do a call, you’re going to do a deal inspection, you’re going to do a forecast, and AI is assisting all those things. But panacea or the world that we imagine is one in which you wake up and your AI tells you, Matt, today you got two deals to close. You got three deals that got pushed out and the customer went cold.

So you need to reengage that conversation. You’re short on pipeline for next quarter and you have a QBR at the end of the week that you need to prepare for. Would you like to book your calendar full of those activities and organize your day accordingly so that your day is the most productive? And then once you go into each of those tasks, there’s yet another AI who’s guiding you through be optimized around creating a deck or running a meeting or running your call or getting prepared for your QBR. So that you see that there is a nesting of AI, one that is generalized for your day or the context of what you’re trying to do. And that is very task specific and things are going into that direction and it’s very encouraging. So we all need to A). move in that direction, and B). ask our vendors to start moving in that direction too so we can get the most productivity out of the applications that we buy.


So one of the number of ways I’ve tried to get people more comfortable and more out of the fear cycle of AI is to talk about like, Hey, listen, let’s assume for a moment you’re not going to lose your job. Let’s assume for a moment you’re going to be able to still pay your mortgage. You’re going to have something to do. We separate this idea of tasks and jobs. The job of marketing in 1960 is a little different than what it was 40 years later versus where it is now. The tasks are different. The job, the outcome is still the same. So if you think about a task, a job, and then the body of work to get there, if you are in sales, your job is not to write emails. Your job is not to follow a sequence. Your job is not to shoehorn your way into someone’s calendar. The job in the body of work is to build a relationship, create a win-win scenario here. So talk a little bit about the context of AI and also, I mean this kind of speaks to the importance of sort having a consistent approach to all those different tasks and jobs to do the body of work well.


Begins, I think I stole this from somebody else, it is mindset, tool, skillset. So it always begin with a mindset, and this is the problem, is that if you associate your worth, your self-worth with the tasks that you do, then you’re in trouble. So if you are a great email writer, if you are a great follow-upper you know what I mean? If you are a great preparer for meetings, those things are going to go away. It’s like I love washing dishes, but I’m not better than the dishwasher. I’m actually more wasteful. You see what I mean? I find washing dishes as a zen moment, but the machine is way better than me and more efficient, and that’s all sorts of things. So we need to disassociate ourselves from the tasks that we do and associate ourselves with the goals that we’re trying to achieve as a whole.

So as a sales rep, your goal is to solve a problem, identify the problem, solve the problem in a way that is win-win, build that relationship so you can get permission to solve the next problem. You see what I mean? And there is no AI that will ever replace that because there is so much that is very human to human communication that is sort of like fifth sense level stuff that we can’t code that won’t be replaced. So get good at doing that. So fix your mindset into an expansive way of seeing opportunities as opposed to seeing threats. When you buy a car, if you buy a Subaru, all of a sudden you start seeing Subarus everywhere. So if you fix your mind and saying, look, AI is a threat, you’re going to see threat everywhere and you’re going to see nothing but threats.

But if you fix it in your mind and saying, look, AI is an opportunity, then you start seeing opportunities everywhere. So you need to start fixing your mind. It’s like, what can you do for me and how can I identify more opportunities? Then the second thing is that you’re fix it in your process. Have to make it part of your process so you can feel good about doing it. So it becomes chopped wood carry water kind of stuff as opposed to being all, what is it going to do for me? Is it hallucinate? Is it going to do something weird? And the third part is it needs to be part of if you’re a manager or you’re part of an organization, it needs to be part of the organizational culture in that it’s okay for you to disrupt your job to find a better way to do it. That needs to be culturally acceptable that I’m going to break this process to come up with a better process because a better process gets into the outcome faster. So I’m going to stop there and see,


No, it’s really good. We’re talking today on Sales Pipeline Radio with Manny Medina, he’s the founder and CEO of Outreach. And I find it interesting that some of the same people that worry that the BDR function is going away because of AI are also the same ones who complain that their sales team doesn’t spend enough time actively selling that they spend all their time doing administrative tasks and writing new emails, and you got 14 different tabs open with 14 different tools to do 14 different parts of the process. And so it just seems to me like if we want the artists, the craftsmen, that our salespeople to do what they do best, if we want more active selling time, if we want the humanity and sales to be the majority of what they do, there’s a lean in moment there for AI, but also a lean in around really improving the process and not having 14 tabs open anymore.


Absolutely. And I think somebody at Verizon called this the swivel chair tax. There’s a real tax of going from an application to the user experience is different. You’re trying to remember where things we’re at. And the real impetus for all of us leaders is to figure out how to minimize the swivel chair tax and take tasks away from our reps so that they can focus on solving somebody else’s problem. See, the beautiful thing about sales is that your job is to get into somebody else’s mind and see the words and not being spoken. And to read between the lines is to get yourself into this hyper empathetic point of view where you are really understanding from your customer point of view what the problems are so you can actually craft a solution.

And the more time you have to do that, the better off you’re going to be. So I just don’t see a world in which we continue to do this nonsense of 20 point solutions to the five jobs because that is just not where the world is going. You see what I mean? So the outcome that we’re seeing is an AI that works on the back of a single platform where you can do your prospecting job, your deal qualifying job, your forecasting job, you run your meetings, you build your account plans, meet your action plans, and the AI just learns from all that and sort of continues to get better in helping you at your whole job, not just each of the tasks.


Yeah, I had literally earlier today, I had with a CMO who was just really struggling with getting their BDR function to work and be successful. And over the course of the call, I realized a couple things. First of all, they were focused on BDR as the function. I said, that’s not the strategy. That is a tactic. That is a channel that is a component of what is a bigger strategy, which in their case is like an outbound motion for target accounts. And I said if you’re setting it up to automate it and just do it automatically, you’re going to send a bunch of crap spam to a bunch of people that is not going to land well, as opposed to saying, what is our strategy for engaging in building value with this audience? We leverage machines and robots and tools and data to tell us who to call next.

I mean, no matter how complicated this all gets account-based motions, whatever. Every sales rep I know just has the same questions. Who do I call next and what should I talk with them about? Right? And the last thing you want to do is go spend, I remember back in the day spending 45 minutes doing research to leave a 30 second voicemail. That doesn’t sound very efficient. And yet people still do that. So I think about the machines, I think about the tools, I think about the data that can shorten that time that tell me not only help me make a better call and better conversation, but to fast track that information to me for me to go have more time in front of my customers as opposed to more time in front of my CRM and that swivel chair mentality,


Right? No, what’s really interesting, I hear this a lot, right? Is the BDR job going to go away? Is the SER job going to go away? New technologies do this, display some things and there’s more. The old technology ends up finding new uses. So for instance, we still see SDRs being productive when you’re trying to crack into new markets when nobody knows you, where a person to person conversation about what the hell is that you do and how I can help me in the general sense of my organization is valuable. So having a conversation at that level is super helpful in new customers. Or I also see SDRs and BDRs being helpful in expansion place. So there is a place in which you deploy it, but the general statements of like, oh, it’s working or it’s not working, lacks the context. What industry are you in? Is it oversaturated? Are you already a winner and everybody knows you? So the SDR incremental code is not going to help. So this general statements are just madening because this is the problem of social media that the pithy arguments wins the day and it lacks the consistency and the nuances that we as organizational leaders need to actually make a decision.


The last question I have for you is, and we’re September, right? And people are already starting to think about next year, which is smart, I think tend to think of Q4. If you’re a calendar fiscal year, Q four is quarter zero is the time. You should sort of get your mind right, as we talked about earlier, strategize and put some of those things in place. What are some productive things and practical things that sales leaders should be thinking about in prioritizing for their teams using technology and AI into 2024?


If you are not actively thinking about making your reps more productive and minimizing that swivel chair tax your competitor is. We are in a world right now that because everyone is to some degree frozen, you have to overinvest in that customer relationship. The winner in this kind of environment is status quo. So you have to figure out what is your key, your approach into that customer conversation that will unseat on status quo and get the conversation open, not even for your product, but just the conversation going. That could be an overinvestment in SEs, that could be more overlay reps. It could be a number of things. But for you to be able to make that investment, you have to get efficiency out of somewhere else. You won’t be able to just add headcount and call it good. You have to get your reps from being out on 50 to 60% participation to like 70, 80, 90% participation. And if you’re not planning for it, somebody else will. So you have to get your mind right, and you have to lean in and to make productivity gains so that you can invest in your sales cycle in a way that makes sense.


Well, when you say competitors, I think about that two ways. I think one, your direct competitors trying to sell to the same customers are adopting this technology, making it easier for your prospects to buy, creating a better experience with their sales team than your sales team, your other competitors, the other startup down the street that wants to hire salespeople, right? Right. And so dude, that 45 minutes just to leave a voicemail. That hurts, right? Because you’ve been there. If you’ve been seller, you’ve been there. If you’re doing your homework and doing it right, if some other company can offer you an opportunity to provide the right tool set to be just as successful or successful to do more of the job that you love, that’s going to be a competitive differentiator in the hiring market, let alone your competitive market in your go-to-market strategy.


Of course. And if you don’t have high performing reps, it’s just as bad as not having technology. This is not a static game. The game doesn’t end with technology or go to market. You have to have it all play nicely in sync.


Manny, I know how busy you are. I really appreciate you taking the time today to do this. Everyone, check out They’ve got a conference coming up here in Seattle. I’m super excited to get out for that one and just check out their content as well. Super good stuff, Manny. Thanks so much.


Thank you. And come to Unleash. See you all later.


All right, we’ll see you at Unleash. Thank you everyone for joining us today. We’ll see you next week on another episode of Sales Pipeline Radio. Take care.


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