Founders, Don’t Hand Off Sales.


Founders, Don’t Hand Off Sales.

At least not too soon. No matter how badly you want to.

I am asked the following approximately 2-3 times per month. It’s a common question from founder-owners of all sorts of companies. And it comes when they’re just starting, maybe finding product-market fit, growing, or really wanting to ramp up.

“Hey, I need a good salesperson. Do you know anyone?”

I shake my head and remind myself to charge them before I answer. Because they never want to hear what I have to say.

Don’t hire a salesperson.

Not when you’re just starting.

Not when you’re trying to find product-market fit.

Not when you’re determining where to allocate a precious 50 or 100 thousand dollars per year.

Not when it’s too painful for you to sell.

And they say, “Well, you’ve given me something to think about.”

They hire someone, and struggle, and burn cash, and then realize they just lost 12-18 months.


Salespeople are great.

They have a tough gig, and people in non-selling roles either highly prize these people, or despise them.

Some people realize, “Hey, those people getting their heads kicked in on the front lines are pretty valuable.”

Others just see (or used to see) the client lunches, the expensive conferences, and how much money they make.

They have a hard job. And good ones are worth their weight in gold. And that’s not a bad way to compensate them for the value they bring to the table.

But they aren’t all the same. Hiring someone to sell for you is not like hiring a bookkeeper or accountant, where there are clearly defined skills and agreed-upon standards of success.

(credit for that image to AboveTheCanopy)


This doesn’t mean you shouldn’t hire a seller at some point.

This doesn’t mean you won’t ever have a real need for one.

But for almost everyone reading this asking, “Is it time?” the answer is likely, “Not now.”


Because there’s nothing more important than selling.

Than finding customers.

Than understanding them deeply.

(Some will debate that raising money is more important, but if you have a real business that creates cash and customers, raising money is likely a one or two time event, not a full-time, forever job.)


The worst thing you can do is listen to your friend in your accelerator/incubator/forum/roundtable group talk about their great salesperson who saved them from extinction.

There’s a great story about PeopleAdmin in Austin, Texas. In the early days, no one could sell their product. They were burning cash and weren’t sure how long they could hold on. They had one guy, who became their head of sales, and then went on to become the CEO of AcademicWorks, who believed he could sell it. He did. And they built and eventually sold a great company.

Turns out that selling that sort of product to the sort of customer he did was his superpower.

You. Won’t. Find. That. Guy.

That is the outlier. The odds are stacked against you. You didn’t buy Bitcoin when it was $10. The odds you get in on the next btc at $1 are really low. It’s ok.

Find a workable path, instead.


For years, I’ve worked with founders and owners in business services.

All forms of finance. Marketing. Software development. SaaS. Fractional CFOs. Staffing and talent management. You name it.

Everyone wants a rockstar seller. (However, not everyone wants to compensate these people appropriately, though that’s a different issue.)

But some people realize, “Hey, I started this thing. My everything is on the line. I need to figure this out. I can’t afford to offload sales. It’s critical I can make this thing run.”

And they figure it out.

Even when they suck at selling.

Guess why?

No one can sell like an owner or a founder. No one else has the conviction, or the willingness to make it happen. No one else will do what it takes to keep the business going.

Prospects sit across from an owner or founder, and they see something in their eyes that says, “This will work.” It’s belief.

They hear it in their voice. They know, “Well, the buck stops with her, so let’s give it a go.”


Did you see Netflix’s Rise of Empires: Ottoman?

It illustrates a point about founders and hired guns, though we caution you against extrapolating too much from made-for-tv docudramas.

Here’s the deal: Mehmed II wants to take Constantinople. And he’s decided to do it.


Emperor Constantine (not the founder, but named for him) is worried about Mehmed’s 80,000 man army standing outside his walls. He’s got maybe 7,000 dudes to fight him off with.


But he can’t just give over a city after it’s stood for 1100 years. So he hires Giustiniani (we’ll call him “G” for short), a mercenary with a professional army. He’s defended something like 47 walled cities from sieges and gone 47-0. He’s a stud. Think Floyd Mayweather. If the money’s right, he’ll show up and win especially a defensive fight. He doesn’t need to knock anyone out, just wins.

(What a comparison.)

G is promised a nice island for his services.


Mehmed wants the city. Fights for it for over 2 months. Deals with near-mutinies, various factions in his camp, the slaughter of his army, and discouragement. But he’s not going to lose.

G does a great job fighting a defensive battle.

Constantine keeps asking him what he needs to win, and keeps giving it to him.

But spoiler alert: in the last battle, guess who leaves when injured? (And there’s no judgement, just an illustration.) Yep. G. Flees.

(He dies in a few days, but that’s beside the point.)

Guess who dies defending his city, with his people?

Yep. The namesake.

And Mehmed, who outsourced nothing (really) but forced ahead in the key success factor of his effort (leading the military in a conquest), got his city and renamed it Istanbul.


Enough plugging Netflix. I don’t even own shares. The point should be made.

So much is made of the magical skills of salespeople. Some (maybe 5-10%) actually have those skills. Most don’t.

But let’s look at stages in a firm’s growth where one is tempted to hand off sales.

  • Product-market fit. Don’t do it. No one can listen like a founder. No one hears a change in tone or notes the difference in inflection from a potential buyer like a founder. A founder digs to understand what’s really going on in a prospect’s mind and world and can conceptualize how a pivot in the positioning or structure of their offering will create a customer or group of customers, they can satisfy. A seller almost never will. They’ll come back to the office with a list of 14 feature requirements without an understanding of why those are needed, and what problem we’re really trying to solve. This is a job for a Mehmed, not a G.
  • Just starting out with something to sell and an understanding of product-market fit. You have payroll, right? Even if it’s just you living on savings. Or you have investors. And you have a reputation with employees, said investors, and lenders. Do you think a hired gun is going to care as much about getting it done as you do? They can walk away and get a job elsewhere, even if you have promised them the holy grail of equity. You, as a founder, are tied to that ship, baby. If it goes down, you go with it. A seller can walk. Who is really more motivated to get something done? Mehmed would get this done. G may say, “I need more money.”
  • But I am not good at this. I know, I know. It’s uncomfortable. But remember this: you had the guts to start or buy this business. That’s worth more than you realize. And getting your hands around selling and slaying THAT dragon – it’s just a logical extension of you being an entrepreneur. So suck it up, take some at bats, get better, and move forward. You’ll get good. You don’t have a choice. See the point above. Someone you hire can leave, maybe because you want them in the office and that’s too demanding or something. You? You’re married to this thing. Mehmed would find a way like he did when he carried boats overland to circumvent a blockade. G would get out on the last ship leaving a falling city.
  • We have some money and I’d like to invest in growth. Great! Invest in your ops. Or in great lead gen. Maybe in content marketing. Maybe in a phenomenal integrator. But trust me, if you haven’t nailed the sales thing, you’re not ready to hand it off. You don’t like that? Well, consider the following. Do you have a staged sales process that is more sophisticated than, “Create Lead; Discovery Meeting; Demo or Presentation; Negotiation; Close”? If not, you aren’t ready. If you don’t have a sense of your metrics, you’re not ready. If you can’t teach someone else a compelling and unique message that causes prospects to say, “Tell me more,” you’re not ready. You’ll burn cash. And frankly, if you aren’t ready to hire 2 reps, you’re not ready to hire one. Because at least one is going to flame out for reasons outside your control. Build defenses, raise an army, and avoid needing a hired gun.

Who else will care like you?

Listen to prospects and customers like you?

Dig into what was said like you?

Be hungry for finding the next killer product or service a customer may need like you?

Seek out the truth behind a customer request like you?

Press into each objection to uncover the truth like you?

No one.

There’s a time to hire a seller.

It’s when….

You’ve got steady business. It’s profitable. You can afford time to invest in this person. Probably 10 hours per week. You can close business all day, so if this person gets hit by an Uber, you’re ok. You’re ready to learn how to manage salespeople, with all that entails (motivation, coaching, accountability, and more).

And when you hire that person, it may not be a full-cycle seller. It may be someone who simply takes a portion of your sales funnel and can run it. Because it’s a system you’ve built.


If you hate what I’ve said, do this instead.

Find a co-founder who is as passionate and as invested as you are. And who loves to sell and do discovery. Give up whatever you need to so they have skin in the game and serious upside. That’s your alternative.







Want to talk more? Email me at

Adam Boyd