By Jonathan Costet

Zero to Won: Personal Branding in Sales with Jake Dunlap (Skaled)

Zero to Won: Personal Branding in Sales with Jake Dunlap (Skaled) In this episode, we chat sales culture and personal branding with Jake Dunlap (Founder and CEO of Skaled). Jake is a sales leader...

Zero to Won: Personal Branding in Sales with Jake Dunlap (Skaled)

In this episode, we chat sales culture and personal branding with Jake Dunlap (Founder and CEO of Skaled). Jake is a sales leader with over 15 years experience both as a VP of Sales and working in sales consultancy. In the show, Jake shares what it takes to build a winning culture today, why building a brand has become table stakes for sales leaders, his process for growing his personal brand, and sales tips that you absolutely shouldn't follow.


  • Culture happens on purpose: 00:55 - 03:55
  • People are always watching: 03:55 - 05:00
  • Don't hire for potential: 05:00 - 07:30
  • Having professional development conversations with your team: 07:30 - 11:00
  • Don't be a hero manager: 11:00 - 12:15
  • Personal branding has become table stakes: 12:15 - 16:00
  • Jake's process for growing his brand: 16:00 - 20:40
  • Keep a script: 20:40 - 24:34

3 key takeaways

#1 Onboarding matters

Companies spend too little time onboarding employees and don't put enough work in certain areas that should be prominent in a successful onboarding. For sales people, this translates into a thorough training on the product and the pitch, and too little talk about how to behave towards customers or other people on the team. While some blame millenials for high turnover in sales roles, Jake points the finger at organizations that still underestimate the importance of setting up employees for success in their roles.

#2 Progressing, on their own terms

It's not about your definition of progression. It's not one size fits all. As a manager, it's up to you to work with each individual on their own career path. Everybody needs to have a plan, and they need to know what that next step looks like in clear, actionable items on what it's going to take to get to that next step. To follow up on that, Jake recommends making time outside of pipeline and forecast reviews for professional development conversations and running them on a set cadence based on the tenure of the person or their career stage.

#3 Building your personal brand

As an influencer himself, Jake shares a few tips for sales leaders looking to start building their personal brand on social. First off, you're going to have to do it to attract top talent, to land your next opportunity, and to grow. Second, social doesn't necessarily mean video: text-only posts also work if you're not comfortable with video. Third, don't overthink it. You have conversations about your industry and insights into where it is heading every single day. And that is a gold mine of potential content opportunities.

Full transcript of our chat with Jake Dunlap:

In a nutshell, you and your team at Skaled help businesses operationalize their sales and marketing organization.  I was wondering, what are some of the attributes that you see today in booming sales cultures?

Jake Dunlap:

I think culture happens on purpose, and I think a lot of leaders, at times, take for granted that you are also lucky to have employees the same way that you feel like they're lucky to have a job.  I think, sometimes, in sales culture, it can be very, feeling like, "Well, we're paying at the top of the market, and people are making money."  And just understand that people aren't motivated just by money.  I would say that top sales cultures I see are where most of the staff is motivated by more than just money and really is focused on finding different ways to engage different folks.  That, to me, is probably the number one, where people feel safe, they feel cared for, and that they're motivated to help a company achieve a greater good versus just doing it for the money.

As a sales leader, what does it take to set up that culture to have that mindset really be at the forefront of your team's day to day?

Jake Dunlap:

I've been a VP of Sales many times over, too, so I can tell you both from my own experience and from working with hundreds of companies that we have, to me, I think it starts with onboarding.  Meaning, I think companies right now, it is pathetic how much time they spend in onboarding.  And onboarding is all about products stuff as opposed to, "Look, this is who we are.  This is how we behave.  This is how we act."  And I've even been guilty of this myself.  I know that I've messed up a time or two.  From my side, I think it starts with how you set the tone.

And, then, it's how you act and behave when you are in the business.  Are you only talking to people about their forecast?  Are you like, "Revenue, where's this deal at?"  Or are your sales leaders actually working with people to help them build skills?  And if you're not doing the latter more than you're doing the former, then it's really tough to have what I would think of as an all-time sales culture.  That's my two cents on it, that you have to have this kind of balancing act between caring about the numbers but also having a culture where people know that they're first and they feel safe.

And that's why I think churn right now is at an all time high in sales roles.  People are like, "Well, it's Millennials."  Like, "No, Dude.  It's not.  It's that onboarding is at an all-time low, and our trust in our people is also at an all-time low.  And that's why churn is high."  In organizations where I haven't done a great job of that, even at Skaled there's been times and periods where I haven't done a great job, I trace it back to that.  I'm like, "Man, I did not provide a very great experience for these people or a consistent experience."

Any kind of tips for sales leaders who are coming across these kinds of issues and seeing a lot of their top performers leave?

Jake Dunlap:

I think you just have to reevaluate the tone that you're setting as the leader.  People are always watching.  Always.  And, so, if you appear too hands off and removed from the business, they watch that.  If, instead, you're like the buddy leader and they think they can slack or get away with things, then they watch that.  And, so, I think you just have to be very, very mindful that you are setting the tone for the organization. This is not a democracy. This is a well, well, well informed leadership role that you are ultimately responsible for.  There's no passing the buck.

So, for me, I think that's really the big thing, just really taking that ultimate ownership.  I think, what is it?  Jocko Willink calls it "extreme ownership."  But that, to me, would be what I would think about.

Some people have also said in terms of thinking about culture and how it materializes in an organization is that what it really comes down to is two things - who you hire and who you promote.  When it comes to bringing in people through the door and into your team, what are some things that you need to look at in order to have the right people to make it work?

Jake Dunlap:

I'll speak from very first-hand experience.  I would say, where we missed that is, we hire for too much potential.  And I think that that sounds kind of counterintuitive, meaning, when you're at a growth stage like we are, we almost, we did 200% growth year over year.  Last year, we'll probably do 25%.  50% this year.  You need people who have been there and done it, and I think a lot of times you kind of hot air based on price, you know, what you think, saving $10,000 here, $20,000 there.  You hire for potential.  At times, you don't have time for it.  You got to be very smart about where you are in your evolution as an organization and then be very smart about the profiles that you hire for.  I think that's important.  And that changes over time.  And I think that's an important thing, too, that changes over time.  So, you have to be willing to evolve and know how your role and the role profile evolves, too.  I think that's critical.

So, what are some of the things that you look at?  Like track records, what companies they've been through, how long their tenure was?

Jake Dunlap: Yeah.  And here's what I would say.  I don't think, and again I'll just say this because I think I've been equally as guilty of it.  I don't think we spend enough time really being smart about the role profile.  Even like the job description of like, "What is this role actually need to do?  What are the things that we actually expect from this person versus some type of cookie cutter thing that's like not specific to our organization at this point in time and where we're at for the next 18, 24, months?" 

I think we under-invest right now and actually being very thoughtful about who's the right person for us right now as opposed to like a cookie cutter version.  Candidly, if you just spend more time there, you're going to most likely let more of the right people in the door.

And when it comes to taking those people that are in the team and keeping them engaged on the day to day, what does that come down to?  Is it like a lot of coaching, I imagine, a lot of opportunities for progressions, a huge deal where your business is at and whether they're seeing progression in terms of both the company and their role?

Jake Dunlap:

Yeah, and it's not about your definition of progression and what you want.  It's about their definition of progression.  And I think that is a big mistake, too.  It's not one size fits all.  Not everyone wants to be a sales leader.  Not everyone wants to be an enterprise sales rep.  Not everyone wants to be in customer success or account management.  Whatever it is, right?  So, it's really, "Do you understand what they want?  Do you understand what they need and what their next step is?  Are you working with each individual in your organization on their own path to get from point A to point B.  That, to me, is what you have to do.  You do need a consistent training program and a uplevelling program for every organization.  I'm a firm believer in that.  But more importantly, everybody needs to have a plan, and they need to know what that next step looks like in clear, actionable items on what it's going to take to get to that next step.

If I were to give a takeaway right now for our listeners, would something like, just mentally run through 5 or 10 people on your team and think about whether or not you can state what their idea of progression is.  And if you're not able to do that, you probably need to get back in there on those one-on-one's and make sure you're keeping track of this.

Jake Dunlap:

Yeah.  And I'm going to give you two caveats for that, too, that I think are actually really critical.  The first is, in your mind, when you're doing that exercise, you go, "Yeah, I know what John…"  You don't know what John cares about.  If you find yourself going, "Ehh, yeah…." like that, to me, it's an ultimate indicator you're probably directionally right, but you don't really know if… That's step one.

Step two is, "Always separate performance and forecast conversations from professional development conversations."  If I'm here to talk about your development, we're only talking about that.  We're going to spend time and we're going to go deep.  I'm not mixing in performance conversations.  I'm not mixing in your forecast.  So, I think you have to be very purposeful in the time that you spend with people.  Very purposeful about carving out that time as sacred time where that person feels like, "Man, we're really working on me.  It's not this hodge podge of stuff."  So, those are my two caveats to that.

And on that second one - professional development conversations - how often would you recommend doing those check-ins with the team?

Jake Dunlap:

Depending on the tenure of the person, monthly or quarterly.  People earlier in their career, you don't have that kind of clear career path or even personal...  For me, I like to focus on the personal goals.  I've got an employee here, a teammate here, and she's trying to get certified in a few languages and do other things.  And, so, we've got some of these multiple tracks.  And, so, I feel like it's really understanding for each person.  For her, monthly is a good cadence.  For another employee, 60 days might be the right cadence.  For another employee, 90 days might be.  But definitely not any longer than 90 days where we're having those conversations about growth.

We spoke a lot on the culture aspect, but when it comes to winning, I feel like that's kind of foundational, and one of the things that you say about how to manage a team is to have that winning mindset.  How is that something that you encourage on a day to day?

Jake Dunlap:

I think a lot of this stuff is easier said than done.  For me, for what you just mentioned here, I think you have to trust that you hire the right people and trust them to do the job but without being apathetic and kind of like not giving any feedback.  I think that's really the balancing act that most leaders get wrong is, they're either too up in people's sh*t or they're not, or they're, "I'm not a micromanager," and so, they're like overly hands off.  I think it's really trusting that you hired the right people to do the job, you hired them, trust them, to go out and do it and execute.  And, then, make sure that you're very clear on your expectations upfront.  And I think that this is where people get it twisted is that sometimes they think they're clear but they're not.  They're actually vague.  I know that I've been guilty of that.

So, I think that, to me, is the big…  If you give clear expectations, you hire people that you trust, then you have to trust them to get the job done.  And I think that's where a lot of sales leaders can't help themselves, but the hero managers can jump in and save deals where that's not how you're going to build people, is by saving them on every deal.

So, obviously, a lot of people know you through LinkedIn.  I think it's safe to say that anyone who keeps up with seven sales a day has at least come across a few of your videos.

Jake Dunlap:

I hope so, or they've unfollowed me at this point.  One of the two.

At is that at this present moment in time, it feels like everyone is kind of becoming an influencer, and that is increasingly blending in with their professional brand.  As a sales leader, do you encourage this in your team?  Because a lot of times, you get concerns like, "Well, what if this person leaves?  What does it mean to have these people communicating on their own terms on behalf of the company, each with their distinct voice?  How do we maintain a consistent voice?"  What's your take on that?

Jake Dunlap: 

Yeah, a hundred percent.  I am super encouraging and non-censoring of my team.  I encourage them to go out.  They'll ask me sometimes, "Jake, I'm thinking about this," and I'll give them my two cents on it.  But we have no filtering process on purpose.  Because what the future is, in 2020, 2021, is going to be about the personal brand in professional settings.  This is going to happen.  We're already seeing leading indicators.  And the other piece is how you engage.  Most salespeople, the only way they know to engage is to sell sh*t.  They only know how to "share my whitepaper," but the real trick is, how do you actually just share what you know, talk about an industry, talk about what's happening in the space, and then from there, how do you better engage with people? How do you actually build an engagement? 

You think about, all LinkedIn is is the 2019, 2020, version of your local Chamber of Commerce Rolodex.  And when you have that mindset going into it, my job is to build relationships.  But now, because it's LinkedIn, I can build relationships like this, huge, and that's the mindset that most people are missing.  They, instead, are looking at every little person as a prospect, whereas, I'm trying to build my own little local community or my own community around me, as opposed to the Chamber of Commerce.

There's a lot of stuff to unpack here, and I think that one of the first things was how to step out of that salesmanship and actually make it about something more valuable to your audience, as you said, speaking about trends in your industry versus a new whitepaper that your team may have published.  What are some other tips that you may have for sales leaders who are looking to get started in this and start building their brand?

Jake Dunlap:

One, you're going to have to do it.  If you are a sales leader today, you are going to have to do this for recruitment to make sure you attract top talent.  And you're going to need to do this to get jobs and to grow yourself as a professional.  It's just table stakes at this point.  I think I'm just going to put that on record.  The second thing I'll put on record, don't think that social media is video.  There are sales leaders that I know, there's two in particular, these guys are getting thousands of engagements on posts.  It's taken them nine months to a year to get there.  They have posted one or no videos.  So, I think, you don't have to focus on videos. You don't have to focus on videos.  So, don't worry about it.

And all of you sales leaders, let me tell you my process.  And that's what I tell everybody.  My process is very simple.  I wake up.  Maybe I had an epiphany from the night before or some sh*t.  That's not usually it.  I'm like, "Hey, what's a random conversation I had yesterday?"  Uh, that, I'm going to post that.  Like, I just talked about it.  Like, cool.  I had a difficult conversation with somebody.  I had a tough client conversation.  I interacted with aVP. of Sales, interacted with a sales….  You have these conversations all day long, and it's really just about sharing your insights around those and knowing that those insights are super valuable to people that aren't you.

You might think it's table stakes or stupid or simple, but there are so many people that have no freaking clue about half the stuff you're talking about.  That would be it.  The main reason people  don't post is fear.  They fear their boys will laugh at them, and they will.  Your friends are going to give you sh*t.  I promise you.  It will happen.  But forget them.  Don't worry about what they're going to think about you because you're trying to do your own thing.  You're trying to build your own career.  I don't have time to think about what Johnny Smith in New York thinks about me or Suzie Smith in San Francisco.  I don't care what those people think about me.  I'm focused on building a company, building my own business for the long term.  And that's really what LinkedIn offers right now. 

The second thing that you were touching on was, LinkedIn is your new Rolodex.  What's the mindset there, and how is that different from treating it as just another social media platform?

Jake Dunlap: 

That's an awesome question.  Let me give you a caveat.  If your buyers aren't on LinkedIn, or you like to sell medical devices or something, LinkedIn is less important to you.  But worry about Twitter or be the trade show guy.  There's other things.  But if your buyers are on LinkedIn, and I would challenge you, if you're in the B2B space, and that's really all I know.  If you're B2C, I don't really know a lot.  But if you're in the B2B space, this is really, really critical. 

For me, what I mean is that people are visiting LinkedIn every day.  I think it's like 40% of people on LinkedIn are like a manager level or above.  You have people interacting every day.  You have an opportunity to…  If you can get those people to follow you and you share one piece of content every day, you're constantly staying in front of those people.  You don't need to remember to email them, etc.  I cannot tell you, on a monthly basis, how many DMs I get, we get, of, "Hey, Jake, I saw your content from blah, blah, blah.  We need help with XYZ."  And it's not a push.  It's not like I'm pushing.  It's that now they're pulling me into the business.  So, that's the opportunity here.

Right.  It's a long game.  So, you need to be willing to put in that work, day in and day out, doing those first small steps and then kind of using that as a foundation and building from there.  When you think about what it means in a couple years' time to be doing this and to have these personal/professional brands completely merged into one, how do sales leaders prepare for those challenges, and how do they get ahead?

Jake Dunlap:

You alluded to this earlier, and I don't think I answered it, but recruiters have been living this world for forever.  Meaning, like, you know what would happen is, you would hire… Let's say, if you're in recruitment.  You'd hire a recruiter.  That recruiter would build up a network of salespeople or whatever things, and then they'd leave.  That was the status quo.  And you don't want them to leave.  And they leave in a Rolodex.  That's just what's going to happen here.  And you've got to be okay with that.  I'm okay.  If I have people on my team that become massive, huge, and they leave, that's on me.  That's on me for not providing the opportunities for them or seeing ahead or for whatever reason. 

So, I feel like, invest in the team, invest in the team, don't worry that a few people might leave and, "Oh, my god, they left with all our blah, blah, blah."  Like, "That's okay, because, guess what, I've got 50 other people that are crushing it the same way, and I'm not going to spend my time worrying about the two people that left."  And that's just life.  Guess what?  Those two people that left, they already had a Rolodex either way.  It's just visible now on LinkedIn.  So, that's it.  Don't worry about that.  Just invest in the people and helping them.

And just a final closing thought.  There's a huge amount of resources out there for salespeople who are looking to improve their performance, better their careers.  What's one piece of advice that gets handed out that really gets under your skin?

Jake Dunlap:

This one's ultra-annoying to me.  Sales, the discovery process, it's a conversation.  And, like, "No, it's got to be conversational."  I'm like, "No, it's a structured conversation."  The piece of advice that I think is very, very bad, it's very bad advice, is that if people are telling you it should be free flowing and you shouldn't have your questions written out in advance.  And this saving different things that come out of their mouth, not to jump from one thing to the next but to parking lot that, and then come back to it when it's appropriate.

If I'm in a conversation with somebody in the town acquisition space, for example, and I'm talking about your business objectives, and you mention, "Yeah, you know, look…."  And let's say I'm competing against Indeed or something, and you say, "Yeah, I work with LinkedIn and Indeed, da, da, da, da, da, but our goal is this and this," and then you go, "Oh, okay, so what are doing with Indeed?"  It's like, then you get sidetracked and you make the conversation tactical.  Say, "Look.,.."  I give this analogy all the time.  Like, Anthony Hopkins reads a script 100 times before he does a movie.  And you think you're so fancy that you don't have to read a script, that you don't have to, that you don't need a script, though.  You're Johnny Badass salesperson.  Having a structured conversation, as opposed to like, I get that little nugget and I say, "Okay, goals.  Let's stay on the goals.  Why is that a top priority?" And then when I want to talk about tools, then I reference it. 

So, if anyone is telling you to make it a conversation that you shouldn't have your questions written out, they're giving you horrific advice.  So, that is my number one thing that gets under my skin for sure.  There are other things, too, but…

And that's the takeaway right there " Spontaneity is good in the call, BUT..."

Jake Dunlap:

Totally.  Totally, spontaneity is good, and rewrite the questions in your own language.  But every time you jump around, you're going to forget to ask key questions.  And thousands and thousands of salespeople….

And then that just has an impact all along the funnel...

Jake Dunlap:

Yes.  I am probably…  I don't know how to approximate this.  I've tried a few times.  I would guess I've ran at least 5,000 sales meetings.  If I do not have messaging in front of me, still, still, and I consider myself an elite salesperson and sales leader, I will miss questions.  You have to have it.

Check out the full video on Youtube. For more Zero to Won, visit

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