Get offshore leverage

It’s a conundrum.  You have a laundry list of tasks and projects that you want to tackle, and you have finite financial resources.  You can’t do it all.

Do you hire someone to tackle everything, or get 10x better at one thing?

Here is what we’ll cover this week:

  1. Pros & Cons of hiring a “jack of all trades” or “specialists”.
  2. Launching offshore talent to save your AR collections.
  3. Day 1 of your company – build a Dataroom checklist.

Pros & Cons of hiring a “jack of all trades” or “specialists”

I’ve been in this situation many times on both our marketing and product/engineering teams.  I have basically 2.5 roles worth of work that needs tackling, but I have the money for 1 person.  I know in my heart of hearts that I will be diluting somewhere:

  • I can’t afford the best-of-the-best
  • There are no superhumans/hero’s that will save my department

Something has to give.

In my experience, here are the Pros vs. Cons in making objective decisions around this hiring conundrum.  I’ve chosen from both categories in the past, depending on the situation.  There isn’t always a right answer – just looking at the situation objectively.

 “Jack of all trades” someone that can get a department or project/initiative off the ground.  Great for 0 to 1.  I’ve used this to start a marketing department, or a CX department when we launch a new company or product.

Pros – get stuff done.  Tackle 75% of all the tasks you need in a department.  You just bought yourself a ton of time back.

Cons – generally speaking, nothing will be great.  It will be V1 of everything.  All you did is go 0 to 1, but you didn’t break the atmosphere and reach the moon.

“specialists” – someone that can take over a program/initiative to accelerate past anything you have today.  I see our customers dig into specialist roles once they have the basics in place.

Pros – go an inch wide and 5 miles deep on an element of your business.  Want your social media presence to 10x, hiring a content marketing specialist.  Need to boost your paid media campaigns, get a specialist for that role.  We’ve seen customers that hire for specific platforms like Shopify and YouTube.

Cons – You are now spending $1,000 – $3,000 a month to get 1 very specific element of your business improved.  Nothing else.  Choose wisely on how you can turn your investment into 10x – 100x.

Again, there is no right answer.  Just situational.

We have customers today hiring EAs and BDR’s offshore (I would consider “Jack of All Trades”) and customers hiring Senior Paid Media Strategists for YouTube (“Specialists”).

Launching offshore talent to save your AR collections

In 2023, I’m hearing from founders who serve the enterprise / mid-market, AR collections are starting to turn into a silent killer for the business.  I got trapped in this cycle 5 years ago, and it almost killed my 1st company Sales for Life.

At the height of my financial meltdown, I needed cash badly.  My customers scaled from a $50M – $100M company, to most of our customers were +$1BN enterprise organizations.  I thought it was normal to win a $100,000 deal and collect my money in 60-90 days.  I would watch our finance team struggle with vendor set-up, PO # collection, manage the Ariba or Spyglass vendor portals, and get our money months later.  I thought a DSO (Days Sales Outstanding) of +60 days was normal.

I told a new mentor in 2018 that taught me about the magic of DSO < 30 days.  Think about this scenario.

Day 1 you invoice the customer.

Day 29 they pay you in full.

Day 30 you pay your employees / operational expenses to service that customer.

You are no longer negative cash flowing to “service” (finance) your customers’ work.

That’s what was happening to me.  I would lose 2-3 months of expenses to service 1 month of work.

Win 20, 50, and 100 customers, and the only way to scale this financing operation is to:

  • Raise Equity Capital
  • Raise Debt Capital.

There is an alternative.

Offshore talent to help with AR collections.  Think of this as the final step in pre-sales / beginning of post-sales.  


My companies, and some of our customers, have or are about to hire offshore talent to manage the AR collections process:

  • Vendor set-up and confirmation
  • PO number chasing
  • Executing a 3-5 step email sequence to gain confirmation of processing, funds transfer dates, and remittance confirmation.

Would you spend $500/month to pull $100,000’s per month forward for your business?

I think so!

Day 1 of your company – build a Dataroom checklist

Years into my 1st company Sales for Life, we got approached by a few buyers.  Their team made a few initial verbal offers and sent us a Due Diligence checklist.  This list felt like I would take 100 years to fulfill, but we had 30-60 days to make this happen.  CRAP!  I don’t have anyone internally that could put all this together without me basically quitting my job to wrangle 5 years of documents together.

When we launched Pipeline Signals and Get Levrg, I knew I never wanted to be in that situation again.  I would take a few hours a quarter to organize your dataroom which would save me months of agony in the future.

This is a perfect project for your personal EA.  Your EA already has access to confidential information and you can assume has the discretion to manage this project.

When a future buyer comes knocking next time, you’ll be ready!

Don’t Forget – Download a Standard Operating Procedures template here.