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Why Startup CEOs Still Have to Make Sales Calls

by Howard Tullman


It’s not your strength, or maybe not even what you enjoy doing. But being there to close the deal isn’t something you can simply hand off to the sales team.

At what point can a CEO turn sales over to professional salespeople?  Before that can happen, the company has to achieve two foundational milestones:

  • You need to know exactly what you’re selling—by doing it over and over again (and not as a one-off).
  • You need to know for certain that others can sell it consistently.

That only comes with the maturity of your product/service.  Until it reaches that point, stay in the field and keep selling.  Your product is still being developed on the fly and continually redesigned/reconfigured to better suit the real requirements and demands of customers.  The fact is, ultimately only you can make the critical design and development decisions and you’ll do a much better job of that if you are hearing it directly from the end users and not from a bunch of whiny salespeople.

I’m seeing more and more startup CEOs who discover way too soon that they don’t like the wear and tear, the travel, and the rejection that are all crucial parts of selling a new product or service.  So they retreat, thinking they can run their businesses while they’re sitting on their butts behind a desk back in the office. That’s not how this game works; that behavior is a formula for failure. You may not be an extrovert.  You may not even know the technology that underlies your business as well as half the other people in the company.  You are, however, the boss and today that fact alone means a lot, at least to the people who make the final purchasing decisions.

Remember—buyers are typically older than you, they grew up in strictly hierarchical systems where titles count, and they need to be made to feel important and respected if they’re gonna sign off on your deal. No offense to any of the members of your team, but customers don’t want to deal with the monkey—they need to see the organ grinder. That’s you. And they want you for all the obvious reasons:

  • People don’t really care how much you know until they know how much you care. Show up. It’s important.
  • Startup staffs are notoriously scattered and hurried—lacking focus and attention to detail. Customers want to know that you personally are connected, paying attention and directly engaged with their business, their concerns, and their problems.
  • Clients want to hear it from the horse’s mouth. Not second hand. They want commitments and assurances from you. Everybody knows that the sales guys will say anything and promise them the world.  They need assurance that you will stand behind your product or service and make good on your promises. The buck always stops with you.

Product Maturity

Once your product/service reaches those critical milestones, it’s time to kick yourself upstairs and focus on other things. I encourage CEOs who find they spend too much effort selling to optimize their time.  I suggest that they find competent sales managers and others who can tee up just the right meetings for them—not opening meetings which are a dime a dozen, but closing meetings where the deals get done.

Finding sales meat-eaters to fill managerial roles isn’t easy; they are the hardest hires for any startup, but it’s absolutely critical to have them onboard if you’re going to build a viable business.

When your startup is hiring talent, you need to avoid certain categories of salespeople. For example, stay away from what I call empire builders.  There’s a whole generation or two of sales management types whose experience comes only from large organizations.  I have found fairly consistently that they are the wrongest guys possible for a startup because they grew up in a system where they measured their value and their success by the sheer number of people they managed rather than the results that those folks delivered. Nothing kills a young business faster than bloat and bureaucracy and having too many sales people sitting on their hands and not selling is the worst kind of poison. So be careful what you wish for and who you hire for this critical job.

There’s no more challenging job than being the CEO. You are responsible for the health of each part of the organization and the trajectory of the entire venture.  Stay in the sales loop until your product/service matures.  Then focus on closing deals.  Customers need you to be there—to say what you’ll do, and do what you say.


 Howard Tullman is the CEO of Chicago-based 1871, where 500 digital startups are building their businesses every day. He is also the general managing partner of G2T3V and Chicago High Tech Investors, both early-stage venture funds; a member of Mayor Rahm Emanuel’s ChicagoNEXT Innovation Council and Governor Bruce Rauner’s Innovate Illinois Advisory Council. He is an adviser to many technology businesses and an adjunct professor at the Kellogg Graduate School of Management.


This article is an excerpt of one that appeared recently in Inc.

Image Credits – Getty Images, MS Office, Howard Tullman

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