Here is a thought exercise I like to run when I am prepping for key personnel decisions in any new startup. It is done on a whiteboard and helps open up the conversation between the founding team around whether to hire, contract or use software for key jobs/tasks.

The purpose is to show there are options and to get everyone’s prejudices out of the way before everyone goes and places ads for positions.

If run correctly, the team should all be on the same page with how they plan to fill the skills gaps and accomplish their goals as they grow.

Step 1 – List out the tasks and positions you believe you will need over the coming months by type;

Step 2 – Do a solid analysis of the options available to accomplish the tasks you’re trying to solve for using the keyword for the task plus “Outsourced…”, “Contract…”, “Software For…”

Step 3 – Create your whiteboard with the known options:

Step 4 – Go through each task with your team and create an open dialogue.

A forward with some personal opinions before we dive in: 

  1. Founders, especially early on, should take the vast majority of the customer support and sales tasks. This is not only a necessity in most cases but a best practice because that’s where they’ll find out what they need to change to reach product-marketing fit.
  2. Development resources should be focused exclusively on the product in the early days – getting it ready and improving the experience. Not on things like coding up landing pages for marketing campaigns.
  3. Regarding software and the stack, tech and product changes happen so rapidly these days so it’s crucial not to sign long software commitments with software that may be necessary for the future state of the company that day, but if you take another year to get to that future state, you will be stuck on a system you cannot use another 12 months. So it’s best to go with agile lightweight tools that can work together given your needs right now.
  4. Finally, although we as founders like to think we know the needs of our users/prospects better than anyone, we’re often wrong. The best founders out there base every decision of data and leverage the experience of advisors and specialists as often as possible so they NEVER have to use the words “well I think ____ so we should do ____.”

Applications / SaaS you can use in place of some human bandwidth:

  • for web scrapers.
  • for landing pages.
  • for white label API integrations.
  • for API connection and data workflows.
  • for one-way single app connections.
  • for data cleansing for Salesforce only.
  • for financial modeling for startups.
  • for powering chat.
  • for creating presentations.
  • for sales training and data.
  • for managing social post syndication.

Fine print about the chart:

  • Some of these tasks staying with the founding team depend if your founding team is either technical or sales-oriented.
  • The light grey are tasks I suggest stay with the founders in the early stages because they need to learn about their customers and know their systems better than anyone.
  • PPC management can be either a very good contractor or agencies. I prefer agencies because you often have to change to get the benefits of new/better and it’s difficult to part ways with an individual.
  • “Managed Web Chat” sits under hire and software columns because there are two options – bot/software (, or human-powered software (like and the answer depends on who you have on your team.