Don't pursue that good idea

It's tempting but it's probably also a distraction

When deciding what to do, asking "Is valuable for the company?" is the wrong question. Even "Is this a good idea?" is the wrong question.

There are no shortage of good ideas or things that would be beneficial for the business. I have a list of 100+ things that would obviously make sense for Pilot to do—but we aren't currently working on any of them.

What should you be asking instead?

The right question to ask is: "Do we absolutely need to do thing XYZ to hit our goals this {year, quarter, month}."

If the answer is no, you should probably put more firepower behind your must-win bets, rather than letting your team get distracted by these other good but not essential ideas.

(That's the most frustrating part of all of this: these other ideas are good, and you actually will build them at some point—just not now!)

When should you cross-sell?

Probably later than you think

I get it, the cross-sell is tempting. You’ve already done the work to acquire the customer, you have a great sense of what they need—why shouldn’t they buy it from you?

Here’s why you should probably wait:

1. It's not going to move the revenue needle for you much in the early days—your total customer count is small, and only a fraction of your customers will buy your new cross-sell.
   
   As an example, when I last looked, only 60% of our bookkeeping customers buy tax from us. Which is actually a pretty wild stat—they are essentially legally required to buy it, and almost half of them don't buy it from us, even though we're already doing their bookkeeping.
   

2. It's a distraction. Unless you're Parker Conrad, you probably should keep the main thing the main thing.
   

3. It'll always be higher-ROI to do later. See #1: the cross-sell's total value to you is basically customer count * attach rate * ARPU, and presumably if you just wait, this number will go up—because customer count is going up.

Basically, your time is probably better spent focused on growth or retention, rather than on maximizing revenue per user.

When is this not true? When should you pursue the cross-sell?

The biggest case that makes this not true is when the cross-sell helps sell the main product. We only started selling tax because we found that some percentage of people would not buy bookkeeping from us if we didn't do tax—they'd just go somewhere else that did. (If the cross-sell helps retention, the same argument applies.)

Be the sales rep you wish to see in the world

What profile should I hire for my first sales rep? Scrappy up-and comer or seasoned VP? Answer: Neither.

Q: What profile should I hire for my first sales rep? Scrappy up-and comer or seasoned VP?
A: Neither.

You are the first sales rep.

One of your only jobs as founder is finding product-market fit. Your company is a submarine and customer conversations are your periscope.

They're the only way you actually see what's going around you: what customers like and respond to about your pitch, what they think of your pricing, who else they're considering, what else they think is important, etc.

If you let someone else peer through that periscope and describe the world to you, you're going to get a filtered version of reality.

And if it ends up not working (or, more likely, when it ends up not working), you're not going to know why. Is it because the product isn't right and needs to change, or because the person you hired isn't the right fit for the role?

I sold the first 100+ accounts at Pilot myself.

Until you've come up with a repeatable sales process that actually works, you're not ready to hire the sales rep. You are the sales rep.

Responsiveness is key

When customers have questions—or worse, when customers have complaints—you get huge bonus points for quickly responding

Most people do not promptly respond to customer requests or questions. (Or worse: complaints.)

They’re coming from a good place on this. They think "I need to fully research the issue and then come back with a complete, well-formed response, 48 hours later."

The problem is: that's a really awful customer experience. Your customer has no idea if you’re working on it or just ignoring their email. (And if the request is urgent, imagine how stressful that feels.)

So what should you do instead?

Fire back a quick note: “I’m looking into it.” Or even better, “I’m looking into it and I’ll be back in touch with an update by xxxxxx.”

Lean into being small

You're a startup, and that's a good thing—use that to your advantage

You're a tiny startup and the prospect is also evaluating the giant brand-name company. How can you possibly win this deal?

By leaning into the fact that you're a small company.

“Yes, you'd be our largest account, which is why we're so eager to work with you all.”

As a customer, would you rather be the most important account for Small Company X, where you can literally email the CEO when something goes wrong, and where you can shape the roadmap to make sure your specific needs are well-addressed?

Or would you rather be customer 29341 at BigCo where it’ll be impossible to ever talk to a human or get the solution customized to meet your actual needs?

The folks who are actually going to be good initial customers for you will see the value in what you’re offering—and the folks that don’t probably would not have been good initial customers anyway.