PODCAST 58: Evolution of Scaling a Business and Shaping the Future of Modern Organization w/ Jake Dunlap

This week on the Sales Hacker podcast, we speak with Jake Dunlap, Founder and CEO of Skaled. Skaled is a modern sales-consulting firm that helps companies implement best in class sales and marketing processes and technology. Today on the podcast, he discusses how to scale a company while shaping your next startup in a modern organization.

In case you missed PODCAST 57: Career Progression as a Concentric Circle to Become Top Manager w/Ashley Grech

What You’ll Learn

  • The evolution of scaling a company
  • Shaping the future of a modern organization
  • How to better optimize your go to market
  • Why we need sales development

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Timestamps and Agenda

  1. Show Introduction [00:03]
  2. About Jake Dunlap: An Introduction [02:14]
  3. The Future of Sales [11:19]
  4. Cutting Through the Noise [16:45]
  5. Know (and Love) Your Sales Tech [21:56]
  6. Intent Data Is Your Friend [28:25]
  7. Know Where Your Audience Lives [30:42]
  8. A Man with a Plan [38:40]
  9. Influences [42:18]
  10. Sam’s Corner [44:59]

Show Introduction

Sam Jacobs: Hey everybody, welcome to the Sales Hacker Podcast. It is your host, Sam Jacobs. This week we’ve got a very special show. Jake Dunlap is the founder and owner of Skaled, which is one of the leading sales technology consulting companies in North America. He’s also an active presence on LinkedIn teaching how to use social media to enhance your brand and assist in the buyer’s journey.

Before we dive into that, we want to thank our sponsors. This week we’ve got a new sponsor called Conga. Conga is the leading end-to-end digital document transformation suite. With Conga, you can simplify documents, automate contracts, and execute esignatures so you can focus on accelerating sales cycles and closing business faster.

Our second sponsor is that unicorn that we all know and love, Outreach. Outreach is the leading sales engagement platform. It supports sales reps by enabling them to humanize communications at scale. From automating the soul-sucking manual work that eats up selling time, to providing action-oriented tips on what communications are working best, Outreach has your back.

About Jake Dunlap: An Introduction

Sam Jacobs: Today I’m delighted to have, perhaps the world’s biggest LinkedIn celebrity, Jake Dunlap. He’s the founder and CEO of Skaled, one of the fastest growing sales technology consulting and sales strategy consulting firms in North America. Jake, welcome to the show.

Jake Dunlap: I appreciate you having me.

Sam Jacobs: Tell us about Skaled.

Jake Dunlap: We are a consulting and strategy company to better optimize the go to market, sales process, account growth process, and look for outside help and support on how to do that. A lot of the work that we do is with executive leadership down to the front line teams. We focus on engagements, measurable impact, results, and making sure that we’re driving business outcomes, not analysis and assessment.

Sam Jacobs: Give us the highlights of your career.

Jake Dunlap: I went to college at Missouri State University. I worked at CareerBuilder where I got put through formal leadership development that I think a lot of startup leaders never get. I realize now how fortunate I was.

I saw an opportunity to do the work that I love, which is building teams, scaling teams from demand generation through customer success. But instead of doing it for one company, doing it for a lot of companies. I made a conscious decision that I did not want to build a lifestyle business, I wanted to build a company.

Early on, I realized the problems I wanted to solve, but I don’t think I had a clear vision for what it would be like. The first couple of years we meandered through. I learned to have a clear vision of where we wanted to go, who we wanted to be as a company. Whether you’re a CEO or a sales leader, having a vision for where you want to be helps get everyone aligned.

We wanted to become a consultant company. My journey over the last six plus years has been continuing to focus the business. We’re still expanding our product set, doing creative services. Continuing to focus the vision of shaping the future of the modern sales org, that’s the true north.

The Future of Sales

Sam Jacobs: What is the future of sales development?

Jake Dunlap: Everyone wants to generate more leads. Most sales organizations build their sales development playbook based off of predictable revenue, which is a process that ended in 2006. So the plays were: call, call, call, email, email, email.

Now that we’re doing account-based marketing and influence, the KPIs we measure success by have changed dramatically. AI is going to take out some of the basic email interactions.

For sales development people to be successful, they’re going to need a better understanding of how to go a little deeper in the funnel because a drift bot can take care of the basic qualification.

Sam Jacobs: Do you still think you need AE?

Jake Dunlap: Sales is gonna get involved further down the funnel. Conversational or some type of AI can take it to qualify at 10 or 20%, but it’s gonna have to be done in a different way. We keep going back to better qualification. Focusing on the need is what’s important, but these SDRs don’t know how to have a conversation about it.

Understanding and really addressing a need: is there a need, do I understand this business enough to know if this is a real need, etc? Sales is continuing to get squeezed, and is just gonna need to get involved later.

AI is getting good at basic conversations. You’re already talking to machines just as much as people and you don’t even know it. Where we can differentiate is in the quality, the nuance of the conversation.

RELATED: How To Build (And Scale) A Successful Sales Development Team

Cutting through the Noise

Sam Jacobs: What advice do you give on the communication channels and engagement touchpoints companies use to get to the conversation?

Jake Dunlap: Calls and emails are still fine. The problem is these channels are becoming saturated. Robocalls in particular are the biggest threat. In 2017, there were 30 billion robo calls, last year there were 50 billion. Unless we do something sweeping from a legislation standpoint, it’s going to be worse this year. On the email side, we’re sending almost 260 billion emails a day. Busy people are getting hundreds and hundreds of emails, and that’s something that we have to factor in.

We’re used to using calls and emails as primary levers. Now you have to think about how to integrate direct mail with that. How do you integrate potential advertising with their outreach? It used to be, go out and make it happen, figure it out. But as the noise ratio grows on these channels, your voice shrinks. Things like direct mail, video, other different ways cut through the noise.

Right now marketing is focused on putting together a blog post a week, and people’s attention spans are shorter and shorter. Your blog post dies in two days. There are 2.1 million blog posts produced every single day.

Know (and Love) Your Sales Tech

Sam Jacobs: You just talked about a complicated sequence of touchpoints. When I hear that, I hear complex and expensive. Is your answer, tough shit?

Jake Dunlap: Marketing looks at technology as a strategic investment that’s an absolute must. The problem is we’ve got to start looking at sales technology investments to make the team more effective first, and efficient second. Understanding these other components and how to integrate them into cadences is a must.

A lot of sales leaders right now are outsourcing their knowledge of what’s possible in sales tech to their operations team and that’s a mistake. There are over a thousand sales technologies. As a sales leader, you don’t need to know all of them, but you do need to know the ones that are moving the needle for other people.

Sam Jacobs: What categories of sales enabled technology or sales technology are you most excited about?

Jake Dunlap: If you are not using one of the major players in a sales engagement space, you are at a massive disadvantage. The real practical applications are actually in the sales process: how you nurture decision makers or influencers in the process, creating an IT stream or an operations team.

Every account management team should be using one of these tools. You have a client, they renew in twelve months, you want to touch them a certain number of times throughout that process. That is a great opportunity to put in place a sequence or cadence of activities.

We’re not getting enough out of these tools and using more automations. When I talk to clients, none of them understand the power of automation rules and how you can either put people into a more active sequence of activities or put them into a nurturing campaign. Don’t get me wrong, grit and all that stuff is important, but we gotta be smart. We can do a better job of letting the machines help us.

Intent Data Is Your Friend

Sam Jacobs: What is intent data?

Jake Dunlap: Intent data basically uses less obvious things [when considering] why somebody might have a higher likelihood of wanting to engage with you. Bombora has their scripts running on tens of thousands of sites and they know the IP addresses of different companies, where they’re coming from, and the types of articles they’re reading. Who is searching for this topic, who in these departments might have some level of interest in what you’re doing or might be a good person to reach out to.

We lock in on an industry, size, but also all these other little factors like how fast they’re growing based on certain data. Maybe the VP of Sales just left, or there’s different data that exists that companies aren’t using right now to better target who their ideal customer is. The machines are going to be better at finding those 72 variables for your company that are the right indicators.

As sales leaders, the problem is we tend to take a lot of our biases from job to job and implement the same pieces. I think machines can help us to eliminate some of those and keep the core that matters.

RELATED: How to Leverage Buyer Intent Data in your Current Sales and Marketing Processes

Know Where Your Audience Lives

Sam Jacobs: What’s your biggest piece of advice to a sales professional?

Jake Dunlap: Know where your buyers live and know how to communicate on those platforms. Whether that’s email, phone, LinkedIn, Instagram, trade shows.

Understanding what they want to do and where they want to communicate is critical.

If I were a salesperson right now, I would pick an industry and stay with it. We’re going back to the old school Rolodex days. LinkedIn is a global, everyday networking event. If you go to a networking event and build an audience in your specialty, you’re gonna be able to use that forever. Machines will never be able to replace that I have a direct line to Sam Jacobs and he trusts me or my content. You need to build that connected group of proprietary people, whether it’s on LinkedIn or other platforms.

A Man with a Plan

Sam Jacobs: How do you handle the ups and downs of building your own company and putting yourself out there?

Jake Dunlap: For me, it’s all about the plan and executing the plan. Having a forecast and being able to manage the business to the forecast sounds so basic. Looking at all the different parts of the business and thinking about different products and business units differently and coming up with a realistic forecast helps me to sleep at night.

The other thing is having the vision and belief. There are certain things where I know I’m 100% right. I’m super passionate about what I’m doing. I love sales. I think that’s a big part of it. If you don’t love it, you’re never gonna be great at it.


Sam Jacobs: We want to hear about the people who have inspired you, the books you’re reading.

Jake Dunlap: I just read Phil Knight’s memoir, Shoe Dog. As an entrepreneur, it was amazing. He talks about his journey, hustling to start Nike. If you’re gonna start your own company, it’s not all glitz and glamor.

I listen to Gary Vaynerchuk. Gary has a very positive, consistent message. If you want to understand where marketing and consumers are headed, listening to Gary’s podcast is critical.

There are a lot of people on LinkedIn who are doing interesting things. Just start absorbing it.

Sam’s Corner

Sam Jacobs: Hey everybody, it’s Sam Jacobs. This is Sam’s Corner. You can feel Jake’s passion and enthusiasm for the art and science of sales come through in our conversation.

What We Learned

  • The evolution of scaling a company
  • Shaping the future of a modern organization
  • How to better optimize your go to market
  • Why we need sales development

Don’t miss episode 59.

Thank you so much for listening. If you want to reach out to me, you can. I’m on LinkedIn as you know. If you’re interested in participating in the Revenue Collective, we’re looking for VP level or above folks at high growth companies in sales, marketing, customer success, or operations who are revenue operators. Email me or contact me on LinkedIn to learn more. Otherwise, thanks for listening.

Before we go, thanks again to our sponsors. Our new sponsor this week is Conga, the leading N2N digital document transformation suite. And of course thanks to Outreach, the leading sales engagement platform. I will talk to you next time.

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