From Zero to $20M ARR with Dailius Wilson

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Could you imagine being raised in an environment where it is all about sales? Dailius Wilson’s dad was a VP for Hewlett Packard, so DW grew up listening to his sales calls in the car every day. Even though his dad advised him against getting into sales, being raised in that way helped DW develop the drive and enthusiasm he needed to become the sales expert he is today. 

DW is a 4 times VP of Sales. He helps companies grow from zero to $20,000,000 in ARR. He is currently the VP of Growth at GetAccept. He is also a writer for HubSpot and is involved with many different groups and communities. He is joining us today to share his ninja skills and take a deep dive into what he has learned from the many adventures he has had in his life. 

Sales is a meritocracy. So you will be promoted quickly and earn well if you can deliver.

No matter what stage he has been through in his leadership journey, DW has always loved calling his customers on the phone and talking to them. He still does it today.

Regardless of if you are a VP of Product, Finance, or Sales, doing a little bit of selling is a great ethos for success.

DW feels that sales, marketing, and growth are all connected because if marketing works the first time, it will result in a sale. 

A captivating effective ad that ultimately converts is effectively a digital direct sale from the first marketing effort.

Although sales are vital, you can use every other skill you have in different areas to gain respect from others and show them that you are a well-rounded professional.

DW’s top 3 ninja skills are:

  1. Automating human processes. Think about how you can replace the steps in your day-to-day workflow with technical thinking and machines. That will help you work 10-20 times faster.
  2. Mastering content and copy. There is a difference between writing marketing copy and sales copy. You can add a lot of value by doing those effectively and in different ways. (Like doing a podcast.) As a salesperson, you will gain credibility if you write something authentic every month and share that content with the people to whom you are trying to sell.
  3. Continually improving and developing himself. It is vital to invest in self-improvement. You stand to gain a lot if you spend about 8% of your annual earnings on up-skilling yourself.

To automate your sales process if you are a founder or sales leader, use third-party proof points. You can watch a leading SaaS video or listen to a good podcast. Get inside your own business before making any decisions. 

If you are a founder, sales leader, or salesperson, think about exactly what gets done between 9 am and 5 pm. You might see people making calls without doing any research or making any introductory efforts, or following up in any way. Reps need to follow up on all meetings. 

As a leader, you need to partner with all the individual contributors, as well as the leadership in the business, to smooth all the processes out and ensure that as many processes as possible can be automated. Think about automating to the point at which you can personalize. It is possible to automate and personalize things simultaneously.

It is a good idea to automate your prospecting, if possible. 

If you are a leader in a business with around $1,000,000 in revenue, you should already have a strategy that works for product-market fit or a customer or industry that you are already selling to successfully. Use that as a blueprint. Then, think about 3-5 pain points that occur within that market, and direct your marketing, messaging, and sales points around those pain points. Talk to individuals about the problems they are experiencing. That will make your approach more organic and palatable.

95% of people can be up-skilled quickly and effectively when it comes to their writing abilities. Sales writing follows a predictable formula, so it helps to incorporate a structure in your writing. As you become more comfortable over time, you can start to deviate from the structure.

Scott Barker, a good sales leader, landed himself in a good position by focusing on telling the right sales stories and finding the right salespeople. 

The best thing for a leader to see is their people becoming better than them. That will lead to mutual respect.

Try to double your net worth or your knowledge every 12 months, even during difficult times. It helps to diversify your strategy and have multiple income streams.

Ask people you respect who influenced them. 

DW enjoys listening to Lewis Howes’s podcasts and The Masterclass.

DW’s number 1 tip for growing from zero to $20,000,000:

Take the pressure off sales and put it into closing. If more than 50% of your leads are coming from outbound, you will find it hard to grow. Learn to live by the 80/20 rule of bringing in 80% of your leads from inbound, and 20% of your big deals from outbound. If you live by that rule, you are sure to scale.

The steps you need to follow for growing from zero to $20,000,000 are:

  1. Build a category that you can own and dominate for what you do. If you create a new trend, your name will be the first to appear on Google.
  2. Invest in zero-cost growth strategies as much as possible, as early as possible.
  3. Find a way to keep people infused into your business, even if it means giving away part of your company. That will create brand loyalty in your employees and incentivize them to stay.

Links and resources:

Find Dailius Wilson on LinkedIn

Books mentioned:

The Hero’s Journey by Joseph Campbell

The Hero’s 2 Journeys by Michael Hauge and Christopher Vogler

To Sell is Human by Daniel H. Pink

Harry Potter by J. K. Rowling

Lewis Howes Podcasts

The Masterclass