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Why AI Will Redefine the Workplace, for the Better · Sales Pipeline Radio

• 0:01
  All right. Welcome everyone to another episode of Sales Pipeline Radio.
• 0:05
  I'm your host, Matt Heinz.
• 0:06
  Excited to have you here for our first episode of September.
• 0:10
  I dunno where the year's gone. Manny, my daughter,
• 0:13
  my oldest child just started high school.
• 0:15
  I need time to slow down for a variety of reasons,
• 0:18
  but happy to be here on another Thursday.
• 0:21
  It's for those of you who are joining us on Sales Platform Radio live from
• 0:24
  LinkedIn or YouTube.
• 0:25
  Super excited to have you here in the middle of your workday and workweek.
• 0:28
  If you want to join the show, you can do so live.
• 0:30
  Make a comment if you can have a question, a comment, a rebuttal.
• 0:34
  It's a little bit of a family show, so keep it safe and the sane.
• 0:37
  But we can make you part of the show. We can ask your question live,
• 0:40
  give you a shout out here on the show. So if you want to participate, please do.
• 0:44
  If you're watching and listening on demand,
• 0:45
  thank you so much for downloading and subscribing every episode of Sales
• 0:49
  Pipeline Radio all the way back, all 345 plus now,
• 0:52
  all available on demand at www.salespipelineradio.com. This is a real treat.
• 0:57
  Very excited to have with us today, the founder and CEO of Outreach,
• 1:02
  Manny Medina. Manny, how you doing?
• 1:04
  I'm excellent, man. Happy to be here.
• 1:07
  We were just joking before we got started here that as we record this in early
• 1:11
  September of 2023,
• 1:14
  I was talking to another CEO that you and I know,
• 1:17
  and he asked me how it's going. I'm like, not my favorite year of all the years,
• 1:21
  and I think a lot of people can resonate with that.
• 1:24
  But you made a good point about sharpening the steel right now and knowing
• 1:29
  that you get through this, they're going to be better,
• 1:31
  but knowing where to focus on things right now and I'd love to have you share
• 1:34
  some of that.
• 1:34
  Yeah,
• 1:35
  I think that this is a year in which we come from a world in which
• 1:40
  we will do everything. We'll do one of each.
• 1:42
  We will take on as many projects as we could,
• 1:45
  and our portfolio was very large and very broad with the hope that many of those
• 1:49
  things will pay out, and now we're forced to prioritize.
• 1:53
  If you don't have one or two things that you're working on and you're putting
• 1:55
  all your resources behind, you'll be doing it wrong.
• 2:00
  The appetite for overinvestment, the appetite for waste, the appetite
• 2:07
  for growth at all costs has gone out the window.
• 2:09
  So now you have to be very ambitious of making sure that every dollar lasts and
• 2:13
  that the probability of things paying out is higher than average.
• 2:17
  So I like the discipline,
• 2:20
  I like the thought that this is a world in which you
• 2:24
  have to make your investments turn into cash in a very short period of time.
• 2:30
  And constraints actually free you to be more creative.
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  The creativity and the constraints is far more exciting than
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  the time in which you don't know what to do with the cash. You did everything.
• 2:46
  So it's not sour grape argument, just to be clear.
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  It is more of a, this is a different world,
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  but a world that rewards those who are ready for it.
• 2:56
  I really appreciate what you just said.
• 2:58
  I think a friend of mine who I worked with at a number of startups who's
• 3:01
  actually running enterprise sales at Smartsheet now, when we worked together,
• 3:05
  he had a saying at the top of his whiteboard that said,
• 3:07
  startups typically don't starve. They drown. Right?
• 3:09
  They take on too many things. You try to do too many things.
• 3:12
  And a big part of strategy is choosing. And before we get into that,
• 3:17
  I want to talk about sales platforms and AI and the things we tend to talk
• 3:20
  about, but I love this topic. I think if you are prioritizing,
• 3:24
  if you are choosing the things to prioritize, by definition,
• 3:27
  you are leaving things on the table and someone else in your company in your
• 3:31
  world cares about those things,
• 3:32
  you're no longer prioritizing and they will remind you of that, right?
• 3:35
  And that is an anxiety spiral that helps no one.
• 3:40
  As an entrepreneur, as a leader,
• 3:42
  I've just been so impressed at how you've built culture and driven the team and
• 3:45
  the growth at Outreach. How do you encourage your team to not only prioritize,
• 3:51
  but accept sometimes the ramifications of the things that you're not doing?
• 3:57
  Yeah,
• 4:00
  it is a really good question because there's no silver bullet for it.
• 4:03
  And the whole disagreeing commit only works so many times the
• 4:08
  disagreeing commit is you have a cookie jar and you only have so many cookies in
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  the cookie jar.
• 4:13
  When you can have somebody disagreeing commit before they're like, alright,
• 4:15
  you're just telling me what to do without selling me.
• 4:18
  And I think that one of the things that we did really well by having four
• 4:23
  co-founders as supposed to use one is that I couldn't get my co-founders to do
• 4:27
  anything because see, I am the CEO because the CEO was the only job not taken,
• 4:31
  when we started the company,
• 4:32
  everybody else would pick a lane and the CEO was a lane that wasn't picked. So
• 4:38
  the job for me to get anything going was to have to sell the
• 4:43
  idea. So we got very used to selling to each other. So we couldn't just say,
• 4:47
  we're going to go do X, we're going to have to,
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  for me to convince my co-founders to do X or Y,
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  I have to go sell them to the X and the Y,
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  and I have to bring in evidence and I have to deal with the counter arguments
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  and we have to spend time in this rock tumbling.
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  And the tumbling and the friction of the ideas made the
• 5:07
  rock shinier over time.
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  So we got really used to selling arguments as opposed to making arguments,
• 5:13
  selling ideas and selling propositions as opposed to forcing a proposition
• 5:17
  through.
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  In this time in which you have to leave things on the table,
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  it's actually better than that.
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  You have to leave things on the table that other people are very attached to it
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  and that your competitors are going to pick up and run with it.
• 5:32
  So not only are you going to get the noise internally from saying, Hey,
• 5:34
  I want to do that, it's on the table,
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  but your competitor is going to run and go with it.
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  And then whoever had the idea,
• 5:40
  it was attached to the idea on the table's going to say,
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  look at the competitor is running with it. See, I told you, And I mean,
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  you have to be okay with that. You have to be, yes, it is on the table. Yeah,
• 5:49
  I know you like it. Yeah, I know somebody else wrong with it.
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  Our bet is still this one, and the reason it's still good is because of X, Y,
• 5:55
  and Z. And it's okay to resell the idea.
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  It's kind of like rekindling the love with your partner.
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  You have to do every once in a while, otherwise it goes stale.
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  So it's okay to resell the idea, but we have to be aligned. The one thing
• 6:08
  that is not a sacrificable thing is alignment. You have to be aligned.
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  You can't be doing this one thing in somebody else doing another.
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  That is the case of that. That is how you die quickly.
• 6:17
  That's so good. If you haven't read,
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  and I want to move on to some of these other topics we wanted cover,
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  but I can't remember the exact title of it, but there's an article,
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  go Google like Legos on the table.
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  Basically this concept of as you grow your business,
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  there's a million things you can focus on, prioritize what you want,
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  leave the rest of the Legos on the table.
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  Someone else may pick them up and decide that's a priority. And those things,
• 6:39
  if you prioritize well as a team, as an individual,
• 6:42
  can move your business forward. But I love the concept of just focus,
• 6:45
  be willing to sort of say,
• 6:47
  there's only so many times you can disagree and commit and shout out to Jill
• 6:50
  Richards who's said here in the comments that saying no more than yes.
• 6:55
  That's what focus is. Finding the things, saying no more often,
• 6:59
  saying yes to a small number of things,
• 7:01
  moving it forward. Think a little bit to one of our other topics today is this
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  whole idea of AI in the workplace,
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  and I know I want to talk about what that implies around having a platform
• 7:11
  mentality in your sales tech stack as well.
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  I feel like we're in this moment where everywhere you turn,
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  you read about the emergence of AI and the importance of AI and the future of
• 7:22
  ai. Yet at the same time,
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  I find so many people that just want to have their head in the sand that are
• 7:26
  like, I don't know what this is. I'm going to ignore it.
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  I'm going to pretend it's not going to happen. We're very early days on this,
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  but that juxtaposition is really interesting to me. Now that said,
• 7:36
  AI has been in a lot of tools we've had well before chatGPT.
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  I know that ai, this is not a sales pitch, but I'm a happy Outreach customer.
• 7:44
  I know,
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  and I'm thankful that there's AI in the platform that I use and our team uses
• 7:48
  for sales engagement. But if you're a sales and marketing leader watching,
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  listening to this right now,
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  how should you be thinking about AI in the workplace and why does that matter?
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  The first in instantiation of AI is to
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  do a survey of your tools of whatever you're using and figuring out
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  where is AI helping,
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  who is actually embracing and how is it showing up in the form of taking a task
• 8:17
  away or replacing a workflow with something else that was not done before?
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  So for instance, in the course of Outreach,
• 8:24
  if you look at a task of building sequences,
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  so our first instantiation of AI is of course the degenerative offering of
• 8:31
  writing the emails for you. That's par for the course right now.
• 8:36
  But as you can see the progression of AI,
• 8:38
  you will see that Outreach will write your own sequences,
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  so you don't have to worry about that.
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  It will automatically generate your AB testing. In the case of Kaya,
• 8:45
  it will generate your cards.
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  And one of the things that we're about to release is scoring. So there is a
• 8:51
  scoring of the calls,
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  but the scoring of the calls only happens post facto by a manager,
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  and it has to be manual when reality doesn't need to be.
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  You already know what a great call looks like.
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  So why don't we create an AI scoring mechanism that actually helps to rep a
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  score better during the call so she doesn't have to score after the call and
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  how a call went.
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  It can actually improve as the call is going through and improve the score of
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  the conversation based on the outcomes that you expect in the conversation.
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  So the first thing you do is make sure that every one of your providers or your
• 9:22
  vendors,
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  your partners are embracing AI themselves in a way that is more meaningful than
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  the obvious. That's number one. And that they're doing a responsibly, right?
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  They're not exposing your data. They're not just connecting to ChatGPT and
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  throwing your data out there because that becomes part of the public domain,
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  et cetera. So make sure that that is happening.
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  So that's go do now. The second aspect of it is, look,
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  the beautiful part of the AI and the scary part of the AI is it can be whatever
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  you want it to be.
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  And that creates a lot of either for those who are early adopters and innovators
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  leaning forward and being like, alright, what can I make it be?
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  And for those who are a little bit more on the pragmatic side, they're like,
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  show me first before I jump in too early.
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  And when we go talk to our own customer base, it's a little bit divided,
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  some people will be like, yeah, give me all, give me now, give me fast,
• 10:12
  give me flying cars. And some others are saying, no, no, no, no, no.
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  I heard that AI hallucinates, AI makes it up.
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  AI does these other things and I don't want to be part of that equation.
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  So what we all need to do as an industry
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  is continue to sell the vision of whatever that vision is or as the vision is.
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  There is no world in which there's a general AI assistant for reps and managers.
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  Right now the way it shows up is in the task, right? You're going to do a call,
• 10:42
  you're going to do a deal inspection, you're going to do a forecast,
• 10:44
  and AI is assisting all those things.
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  But panacea or the world that we imagine is one in which you wake up and your AI
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  tells you, Matt, today you got two deals to close.
• 10:55
  You got three deals that got pushed out and the customer went cold. So you need
• 10:59
  to reengage that conversation.
• 11:00
  You're short on pipeline for next quarter and you have a QBR at the end of the
• 11:04
  week that you need to prepare for.
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  Would you like to book your calendar full of those activities and organize
• 11:10
  your day accordingly so that your day is the most productive?
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  And then once you go into each of those tasks,
• 11:15
  there's yet another AI who's guiding you through be optimized around creating a
• 11:19
  deck or running a meeting or running your call or getting prepared for your QBR.
• 11:25
  So that you see that there is a nesting of AI,
• 11:27
  one that is generalized for your day or the context of what you're trying to do.
• 11:31
  And that is very task specific and things are going into that direction and it's
• 11:35
  very encouraging. So we all need to A). move in that direction, and B).
• 11:38
  ask our vendors to start moving in that direction too so we can get the most
• 11:41
  productivity out of the applications that we buy.
• 11:44
  So one of the number of ways I've tried to get people more comfortable and more
• 11:49
  out of the fear cycle of AI is to talk about like, Hey, listen,
• 11:52
  let's assume for a moment you're not going to lose your job.
• 11:54
  Let's assume for a moment you're going to be able to still pay your mortgage.
• 11:56
  You're going to have something to do. We separate this idea of tasks and jobs.
• 12:01
  The job of marketing in 1960 is a little different than what it was 40 years
• 12:05
  later versus where it is now. The tasks are different. The job,
• 12:09
  the outcome is still the same. So if you think about a task, a job,
• 12:12
  and then the body of work to get there, if you are in sales,
• 12:15
  your job is not to write emails. Your job is not to follow a sequence.
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  Your job is not to shoehorn your way into someone's calendar.
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  The job in the body of work is to build a relationship,
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  create a win-win scenario here.
• 12:28
  So talk a little bit about the context of AI and also,
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  I mean this kind of speaks to the importance of sort having a consistent
• 12:33
  approach to all those different tasks and jobs to do the body of work well.
• 12:39
  Begins, I think I stole this from somebody else, it is mindset, tool, skillset.
• 12:44
  So it always begin with a mindset, and this is the problem,
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  is that if you associate your worth,
• 12:50
  your self-worth with the tasks that you do,
• 12:55
  then you're in trouble.
• 12:58
  So if you are a great email writer,
• 13:01
  if you are a great follow-upper you know what I mean?
• 13:03
  If you are a great preparer for meetings, those things are going to go away.
• 13:07
  It's like I love washing dishes, but I'm not better than the dishwasher.
• 13:11
  I'm actually more wasteful. You see what I mean?
• 13:14
  I find washing dishes as a zen moment,
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  but the machine is way better than me and more efficient,
• 13:19
  and that's all sorts of things.
• 13:21
  So we need to disassociate ourselves from the tasks that we
• 13:25
  do and associate ourselves with the goals that we're trying to achieve as a
• 13:29
  whole. So as a sales rep, your goal is to solve a problem,
• 13:33
  identify the problem, solve the problem in a way that is win-win,
• 13:37
  build that relationship so you can get permission to solve the next problem.
• 13:41
  You see what I mean?
• 13:41
  And there is no AI that will ever replace that because there is so much that is
• 13:45
  very human to human communication that is sort of like fifth sense
• 13:50
  level stuff that we can't code that won't be replaced.
• 13:53
  So get good at doing that.
• 13:56
  So fix your mindset into an expansive way of
• 14:01
  seeing opportunities as opposed to seeing threats.
• 14:06
  When you buy a car, if you buy a Subaru,
• 14:07
  all of a sudden you start seeing Subarus everywhere.
• 14:09
  So if you fix your mind and saying, look, AI is a threat,
• 14:12
  you're going to see threat everywhere and you're going to see nothing but
• 14:14
  threats. But if you fix it in your mind and saying, look, AI is an opportunity,
• 14:17
  then you start seeing opportunities everywhere.
• 14:19
  So you need to start fixing your mind. It's like,
• 14:20
  what can you do for me and how can I identify more opportunities?
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  Then the second thing is that you're fix it in your process.
• 14:27
  Have to make it part of your process so you can feel good about doing it.
• 14:29
  So it becomes chopped wood carry water kind of stuff as opposed to being all,
• 14:34
  what is it going to do for me? Is it hallucinate?
• 14:36
  Is it going to do something weird?
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  And the third part is it needs to be part of if you're a manager or you're part
• 14:42
  of an organization,
• 14:44
  it needs to be part of the organizational culture in that it's okay for you to
• 14:50
  disrupt your job to find a better way to do it.
• 14:53
  That needs to be culturally acceptable that I'm going to break this process to
• 14:57
  come up with a better process because a better process gets into the outcome
• 14:59
  faster. So I'm going to stop there and see.
• 15:01
  No, it's really good.
• 15:02
  We're talking today on Sales Pipeline Radio with Manny Medina,
• 15:04
  he's the founder and CEO of Outreach.
• 15:07
  And I find it interesting that some of the same people that worry that the BDR
• 15:11
  function is going away because of AI are also the same ones who complain that
• 15:16
  their sales team doesn't spend enough time actively selling that they spend all
• 15:19
  their time doing administrative tasks and writing new emails,
• 15:23
  and you got 14 different tabs open with 14 different tools to do 14 different
• 15:26
  parts of the process.
• 15:28
  And so it just seems to me like if we want the artists, the craftsmen,
• 15:33
  that our salespeople to do what they do best,
• 15:35
  if we want more active selling time,
• 15:37
  if we want the humanity and sales to be the majority of what they do,
• 15:42
  there's a lean in moment there for AI,
• 15:44
  but also a lean in around really improving the process and not having 14
• 15:49
  tabs open anymore.
• 15:50
  Absolutely. And I think somebody at Verizon called this the swivel chair tax.
• 15:55
  There's a real tax of going from an application to the user experience is
• 16:00
  different. You're trying to remember where things we're at.
• 16:03
  And the real impetus for all of us leaders
• 16:08
  is to figure out how to minimize the swivel chair tax and take tasks away from
• 16:12
  our reps so that they can focus on solving somebody else's problem. See,
• 16:16
  the beautiful thing about sales is that your job is to get into somebody else's
• 16:20
  mind and see the words and not being spoken.
• 16:23
  And to read between the lines is to get yourself into this
• 16:27
  hyper empathetic point of view where you are really understanding from your
• 16:30
  customer point of view what the problems are so you can actually craft a
• 16:32
  solution. And the more time you have to do that,
• 16:37
  the better off you're going to be.
• 16:38
  So I just don't see a world in which we continue to do this nonsense of 20 point
• 16:43
  solutions to the five jobs because that is just not where the world is going.
• 16:48
  You see what I mean?
• 16:49
  So the outcome that we're seeing is an AI that works on the back of a single
• 16:54
  platform where you can do your prospecting job,
• 16:58
  your deal qualifying job, your forecasting job, you run your meetings,
• 17:01
  you build your account plans, meet your action plans,
• 17:03
  and the AI just learns from all that and sort of continues to get better in
• 17:06
  helping you at your whole job, not just each of the tasks.
• 17:10
  Yeah, I had literally earlier today,
• 17:12
  I had with a CMO who was just really struggling with getting their BDR
• 17:17
  function to work and be successful. And over the course of the call,
• 17:20
  I realized a couple things. First of all,
• 17:21
  they were focused on BDR as the function. I said, that's not the strategy.
• 17:25
  That is a tactic.
• 17:26
  That is a channel that is a component of what is a bigger strategy,
• 17:29
  which in their case is like an outbound motion for target accounts.
• 17:33
  And I said if you're setting it up to automate it and just
• 17:37
  do it automatically,
• 17:39
  you're going to send a bunch of crap spam to a bunch of people that is not going
• 17:42
  to land well, as opposed to saying,
• 17:45
  what is our strategy for engaging in building value with this audience?
• 17:49
  We leverage machines and robots and tools and data to tell us who to call next.
• 17:54
  I mean, no matter how complicated this all gets account-based motions, whatever.
• 17:58
  Every sales rep I know just has the same questions.
• 18:01
  Who do I call next and what should I talk with them about? Right?
• 18:05
  And the last thing you want to do is go spend,
• 18:07
  I remember back in the day spending 45 minutes doing research to leave a
• 18:12
  30 second voicemail. That doesn't sound very efficient.
• 18:15
  And yet people still do that. So I think about the machines,
• 18:17
  I think about the tools,
• 18:18
  I think about the data that can shorten that time that tell me not only help me
• 18:22
  make a better call and better conversation,
• 18:24
  but to fast track that information to me for me to go have more time in front of
• 18:28
  my customers as opposed to more time in front of my CRM and that swivel chair
• 18:32
  mentality.
• 18:32
  Right? No, what's really interesting, I hear this a lot, right?
• 18:35
  Is the BDR job going to go away? Is the SER job going to go away?
• 18:39
  New
• 18:43
  technologies do this, display some things and there's more.
• 18:46
  The old technology ends up finding new uses. So for instance,
• 18:50
  we still see SDRs being productive when you're trying to crack into new markets
• 18:54
  when nobody knows you, where a person to person conversation about
• 18:59
  what the hell is that you do and how I can help me in the general sense of my
• 19:02
  organization is valuable.
• 19:04
  So having a conversation at that level is super helpful
• 19:09
  in new customers. Or
• 19:13
  I also see SDRs and BDRs being helpful in expansion place.
• 19:17
  So there is a place in which you deploy it, but the general statements of like,
• 19:21
  oh, it's working or it's not working, lacks the context.
• 19:24
  What industry are you in? Is it oversaturated?
• 19:27
  Are you already a winner and everybody knows you?
• 19:29
  So the SDR incremental code is not going to help. So
• 19:33
  this general statements are just madening because this is the problem of social
• 19:37
  media that the pithy arguments wins the day and it lacks the consistency and
• 19:43
  the nuances that we as organizational leaders need to actually make a decision.
• 19:50
  The last question I have for you is, and we're September, right?
• 19:53
  And people are already starting to think about next year, which is smart,
• 19:56
  I think tend to think of Q4. If you're a calendar fiscal year,
• 19:58
  Q four is quarter zero is the time. You should sort of get your mind right,
• 20:02
  as we talked about earlier, strategize and put some of those things in place.
• 20:07
  What are some productive things and practical things that sales leaders should
• 20:10
  be thinking about in prioritizing for their teams using technology and AI into
• 20:15
  2024?
• 20:21
  If you are not actively thinking about making your reps more productive and
• 20:26
  minimizing that swivel chair tax your competitor is.
• 20:30
  We are in a world right now that because everyone is
• 20:35
  to some degree frozen, you have to overinvest in that customer relationship.
• 20:40
  The
• 20:45
  winner in this kind of environment is status quo.
• 20:48
  So you have to figure out what is your key,
• 20:51
  your approach into that customer conversation that will unseat on status quo and
• 20:56
  get the conversation open, not even for your product,
• 20:58
  but just the conversation going. That could be an overinvestment in SEs,
• 21:05
  that could be more overlay reps. It could be a number of things.
• 21:10
  But for you to be able to make that investment,
• 21:12
  you have to get efficiency out of somewhere else.
• 21:14
  You won't be able to just add headcount and call it good.
• 21:17
  You have to get your reps from being out on 50 to 60% participation to like 70,
• 21:21
  80, 90% participation. And if you're not planning for it, somebody else will.
• 21:26
  So you have to get your mind right,
• 21:29
  and you have to lean in and to make productivity gains so that you can invest in
• 21:33
  your sales cycle in a way that makes sense.
• 21:35
  Well, when you say competitors, I think about that two ways. I think one,
• 21:39
  your direct competitors trying to sell to the same customers are adopting this
• 21:42
  technology, making it easier for your prospects to buy,
• 21:46
  creating a better experience with their sales team than your sales team,
• 21:49
  your other competitors,
• 21:50
  the other startup down the street that wants to hire salespeople, right? Right.
• 21:53
  And so dude, that 45 minutes just to leave a voicemail. That hurts, right?
• 21:58
  Because you've been there. If you've been seller, you've been there.
• 22:01
  If you're doing your homework and doing it right,
• 22:03
  if some other company can offer you an opportunity to provide the right tool set
• 22:07
  to be just as successful or successful to do more of the job that you love,
• 22:11
  that's going to be a competitive differentiator in the hiring market,
• 22:14
  let alone your competitive market in your go-to-market strategy.
• 22:17
  Of course. And if you don't have high performing reps,
• 22:20
  it's just as bad as not having technology.
• 22:25
  This is not a static game. The game doesn't end with technology or go to market.
• 22:29
  You have to have it all play nicely in sync.
• 22:32
  Manny, I know how busy you are.
• 22:33
  I really appreciate you taking the time today to do this. Everyone,
• 22:36
  check out Outreach.io.
• 22:39
  They've got a conference coming up here in
• 22:41
  Seattle.
• 22:42
  I'm super excited to get out for that one and just check out their content as
• 22:45
  well. Super good stuff, Manny. Thanks so much.
• 22:47
  Thank you. And come to Unleash. See you all later.
• 22:49
  All right, we'll see you at Unleash. Thank you everyone for joining us today.
• 22:52
  We'll see you next week on another episode of Sales Pipeline Radio. Take care.