Bryan from Entrepid here. We disagree with the advice of hiring a head of sales as your first sales hire. You are better off finding a someone with 3-6 years of experience to be the first hire as an IC. This hire (and maybe a few others) will help you grow the company to a point where you can attract a badass VP of sales / head of sales

This all depends on the capabilities of the current exec team. Generally my experience has been:

Exec team with mature sales presence/leadership = hire less experienced (3-6 years).

Exec team with immature sales presence/leadership = hire more experienced (6-10 years with opp to become a VP of Sales).

Good guide - thanks for putting together.

In our experience, the founder should close the first 3-10 enterprise deals on their own. When you chose to outsource, you may close some deals, but you lose out on the early customer product feedback.

The relationships with your early customers are key. You need to make your early customers your biggest fans to show how your product changed their business through references and/or mini-case studies.

Oh, I am definitely in on all calls at this point. And thanks for the rest of the advice, I am trying to follow it already.

Bryan from Entrepid Partners here... we find that highly targetted, outbound cold emails are actually the best place to start prospecting.

In our experience, if you do the extra work to personalize the email and focus in on why your product/service is relevant to the buyer's pain points, we've seen response rates as high as 30% with the majority of those replies turning into an intro call with the buyer.

Hi Bryan :)

>highly targeted, outbound cold emails...

...are neither scalable nor calls, in my mind. Here's my opinions:

1) I am currently manually building my own unsolicited email list for the purpose of marketing my b2b service. I have good, quality data sources with no bounce rates and right personas, but it is neither cheap nor simple to enter this data manually

2) even if I send these people highly targeted and well-crafted emails that are friendly and insightful and pithy, it is a slow process with diminishing returns...

3)... because most people add me to their spam filter these days. It is trivial to do so.

I would infinitely prefer to invest my time in creating excellent, viral content and offering users a free entry level service with few restrictions.

I would then spend all my time obsessively devoting myself to those users who have a big budget and greatly desire to receive communication from me.

Lastly, I dare say that someone who responds to a cold email will probably just end up kicking tires.

Tire kicking is automated away with my free demo.

Certainly more than one way to do this, but I agree with Bryan.

Highly targeted email lists are scaleable enough and there is plenty of tech to make them more personal than ever. I disagree a great deal with the idea that cold respondents "end up kicking tires." 100% of my marketing is cold email. 100% of the marketing I do for clients is cold email. I'm happy with my ROI and so are they.

Refuse to read Forbes due to their aggressive stance against AdBlockers

I'm not sure they have a problem with that... They save the page serving cost and they weren't going to get revenue for it anyways.

Do users have to verify using Plaid for every transaction if there are recurring payments? Those seem the riskiest if someone has insufficient funds on a tokenized bank account

No. Plaid tokens live for an extended period of time and can be used for multiple balance verifications.

Why use Square (not a traditional payments API company) and not Stripe, Braintree, or WePay?

This is a huge need as well

Taking a fee should not have any effect. Stripe (like other providers on Payment Facilitator / Payment Service Provider models) protect you from this risk / compliance

How much of this decision was based upon regulatory / payments compliance pressure?