Working Without Pants - Creative Entrepreneurship

Dan Englander is the founder of, and the author of Mastering Account Management and The B2B Sales Blueprint.

Dan is an expert on growing sales, and specifically, getting the most value out of existing clients, which is often ignored in sales.

We dive into his experiences in ramping up sales at one of the first video explainer companies and winning massive Fortune 500 accounts (like Verizon, Showtime, Bank of America, Venmo), before he started his own consultancy.

Highlights of this episode:

[1:44] In the blistering New York summer, Dan wears shorts to work from home, and will often stroll over to a coffee shop- it gets him in a different mindset and is helpful for separating tasks.

[2:20] Before he was the braggadocious founder of, Dan knew nothing about sales. As the first employee of Idea Rocket, he learned sales and made it work.

[3:50] His initial sales process was not cutting it.

[4:20] Things started to turn around. PPC and PR was effective, but winning the show opening for the Showtime Series Weeds help establish them as an authority.

[4:50] Fortune 500 companies find vendors the same way startups do. They won those initial big accounts by becoming a safe bet.

[5:45] The initial big wins gave them validation, and created a snowball effect.

[5:55] The main challenge for their first big sales was convincing them that something so unorthodox (at the time) as investing five figures in cartoon was a safe investment.

[8:15] As the market grew, the game changed from “buy a car not a horse” to “buy a Mercedes not a Honda.”

[8:55] Eventually, they got to a point (which most agencies get to) where the struggle was qualifying and prioritizing.

[9:35] How Dan goes about qualifying and prioritizing for better clients.

[11:18] Dan’s got different arrows in the quiver, that is 2 or 3 different sales processes for the different levels of clients.

[13:10] Establish immediate value by giving prospects a taste of what it’s like to worth with you.

[13:40] The biggest stopping point for many creative agencies is prep work. In order to overcome this, they would offer scripts to their videos, to get in the door and prepare the client.

[15:55] Account management is basically a role that combines client services and sales.

[17:04] Selling to existing customers should be easier than selling to new people, but its potential goes untapped, because most go about it the wrong, awkward way.

[18:25] Start with a partnership mindset. Don’t just randomly hit them up for new business. Build the next steps into your initial process. Be relevant. Find ways to help.

[20:00] Jake has found that quarterly reviews are a great way to reconnect and gauge the impact your work has had.

[20:55] Don’t send donuts.

[21:15] Partnerships are a long game- there’s more ways to pull value from an account than just selling the same product again.

[22:25] Dan discusses his approach to getting referrals from clients.

[24:10] What to look for in hiring a salesperson / account manager: if they could write well, they’re halfway there.

[25:34] Asking the right questions is the most important part of sales. Subject matter expertise is overrated.

[26:44] Aaron Ross stands out as useful to any company trying to implement a sales process.

[27:23] Neil Rackham was ahead of his time.

[28:55] While many young entrepreneurs want a step-by-step guide to succeeding, it’s more about the mindsets that enable success.

[29:35] Dan’s first book is the Chicken Soup for the Soul of account management. Check out the link below for a free copy.

[30:42] By the hard questions early on, you will save time and find more opportunities.


Resources from this episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

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Direct download: WWP_-_Dan_Englander.mp3
Category:general -- posted at: 10:19am EDT