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Tips for Founders Sales: Lessons from Starting Two B2B Startups (philstrazzulla.com)
153 points by pstrazzulla on April 6, 2020 | hide | past | favorite | 31 comments



"Working out of one of their offices side by side is a great way to hear how they talk, what they care about, etc."

I've heard this suggested occasionally, how does this ask usually work? Besides the fact that our clients aren't near where we're based, it feels socially strange asking to impose on someone's office for a day - I must be missing something.


Companies who are potential early customers are also usually growth stage startups themselves (100-500 people) and want to help out other entrepreneurs. Email the founders to tell them what you're up to, and tell them you won't be a drag on productivity. A company like this almost certainly also has extra office space as they rent for growth.


Honestly I felt the same way, but the trick is to pick a start up where you know how and are able to do this. Or find a partner who can. The most likely way to do this is to go to conferences, happy hours, and introductions from friends.

If you are writing software for accountants and don't know how to spend time with accountants you're screwed, if you are writing software for in house counsel at utility companies and you don't know how to hang out with them you're screwed, and this goes for pretty much any B2B startup.


I did this with our early customer by offering to help in a few different ways. Especially if they are geographically a bit more distanced then you can tell them you would be happy to be there for 1 or 2 days to do multiple things, like run a few workshops, have a coffee with their manager and meet with IT (all three just examples). It isn't a very strange question to ask to use a spare desk in between those things.


the obvious way is to adjust the product to their needs. like if you were consulting. so you go there, watch the user use your product, write code. rinse, repeat. of course you can do that only for the first ten customers


I just launched a bootstrapped B2B product today (also in the recruiting space). I've never sold a thing in my life before, but have suddenly been trying to learn how to be as effective at sales as possible.

Today I got some significant interest from a couple of fortune 500 companies and got some serious imposter syndrome. Any advice for dealing with imposter syndrome as a defacto sales leader with zero sales experience?


Imposter syndrome or just not sure where to go? If it's the latter, there's a structure to enterprise deals that you can usually follow.

1st uncover the buyer journey with some form of this question: "Just so I can help plan accordingly, let's imagine your company decides to move forward, what does the purchase process at your company look like?" Try to unearth all the steps they need to go through (is it out of their personal budget, department budget, VPs budget? Are there other groups we'll need approval from and what does their process look like? (IT, Legal, etc). How long does it usually take to close a purchase and get a vendor paid in your firm?

The goal is to uncover the end to end process that results in $$s early so you can plan accordingly. If the process takes 18months and requires deep IT and Legal approval - make sure you're priced high enough to absorb the pre-sales time & labor.

And when pricing comes up - if you have a well established market, then price within the norms (your champion isn't using their own money, they're using the company's - they just need to justify the cost). If the product is a new category, price the product to organizational value. If your product reduces the number of sourcing staff or multiplies their effectiveness - a typical strategy is to show the business impact. Perhaps Salary of HR hires saved + number of good hires * impact factor on business (whatever works best to show $$s of impact to the business). Then charge a fraction of that value yearly.

There are a bunch of great books on enterprise sales, but 99% of it after showing value is uncovering the purchase plan and helping nurture your champion (and possibly others) to accomplish the sale to their internal stakeholders for you.

And as a previous commenter said before - don't worry about pricing it perfectly. Fit the budget they have today and readjust next budget cycle or during next year's renewals.

Best of luck!


Yes, as a founder keep to the mindset that you don't have to really do sales. You can do a much more powerful thing: Do business by talking about the business with them.

Especially in the early days it's not super key to extract 100% of the potential budget from a client. It's much more useful to get to 80% of their budget and have a very strong relationship for feedback and to get referrals for new customers. You do that by doing business with them as a founder instead of applying hardnose sales tactics.


Just continuously think about 1) how much value you product brings and why this is good for them 2) most sales reps are pretty mediocre at best 3) many other founders have gone through this before.


No quick tips, but can highly recommend the book The Charisma Myth by Olivia Fox Cabane. It has some great exercises that help you build habits to overcome many things, including imposter syndrome.


A lot of these types of posts about B2B assume you are selling a product >$1k... there are lots of B2B that are for less than that and so you can't really apply most of these approaches.


If you're selling a B2B product for <$1K, you'll probably need the customer to come to you instead of you reaching out to them. This could be through strong marketing and branding.

I only have experience with >$1K B2B which implied outbound sales (company contacts potential customers).


These advices are good, though the same can be seen in other articles pulling recommendations together.

What would be good to see, are the conclusions and takeaways after applying these. What works for real, what was the combination which lead to the first sale, what is needed for repeatable sales.


These tips are OK, but they miss, in my view, two essential components. My background is ten years as CTO and sales lead from founding to cashing out at a B2B software startup.

The two key points:

1) Know your product. Know it inside out, what it can do, what it will do, what it can’t and won’t do, and why those things are the case. You should be able to answer any question, and you should know the metrics you’ll inevitably be asked about like your mother’s phone number. If you’re a founder doing sales, this is doubly important, as it not only answers the question, but shows that you are deeply involved in the business/product, which brings me to

2) Passion. If you’re passionate and excited about your product, even the most stone-faced pessimist will be wanting to sign a contract by the end of the pitch. Enthusiasm is contagious. Have your story and why you set out to provide this solution ready to go, and tell it. Narrative tells people why you’re passionate, and allows them to share that narrative, that passion.

I converted almost every pitch I made, to the tune of £100M or so over the years - early days, sales of £10k each, a dozen a year. When I left, I was selling as many £5M three year contracts each year with the same core two points. I don’t say this to brag, just to underscore that these aren’t scale-limited factors, and that as a founder, this is a pretty solid strategy - particularly if you’re selling to other founders.

The hardest hurdle was filling in the RFPs - always different, always asking the wrong questions. All that worked there was putting in the hours.


I just started a B2B software startup and my cofounder and I are looking for all the sales advice/mentorship we can get. Is there any chance we could talk to you sometime? My contact info is in my profile.


I convinced myself to start a B2B business[1] by telling myself that I wouldn't need to do this. I'm pretty sure I was wrong.

https://millenniumsoftwaredesign.com/


See this? "BRINGING LOW COST, FLEXIBILITY, AND FREEDOM TO EDA"

Put it in the location and font size of the Millenium Software Design above it.

I had to read the whole page before I could figure out what you sold. And I knew what EDA was beforehand. Still had to figure out if what I understood as EDA was the same thing you sold.


Thank you for the feedback!


You probably will. But I wrote the post so that people don't feel like becoming a sales person is this impossibly hard thing to do...


I've always cast a wide net when thinking conceptually about what "sales" is, especially when I was a founder and de-facto lead salesman for years. For the longest I considered sales to be just another flavor of persuasion, and at it's very best it's almost pedagogical.

However now, I think I'd rather just not be in business than do sales. That's really just a recognition that sales is an absolutely necessary part of all businesses, and how terrible I personally find it.


What made you change your mind to view it as so horrible?


I haven't sat and gotten deeply introspective about it, but when I think about all the trips and dinners and conferences etc I went to in order to build relationships to get a same, it feels deeply icky that the root of those relationships was a desire for a financial transaction.

I think we actually did as well as we did, in part because being rooted in a transaction felt so wrong that I actually tried to build relationships with the people I was trying to sell to, in a way that wasn't purely transactional. I'm actually still friendly with some of those people who bought from us today.


Did you believe the cost/benefit was in the purchasers favor? Or were you cynical about the solution/value of solution?

I’m a purchaser of enterprise software. This is something I try to gauge from the sales rep. There’s a lot of risk in buying software that doesn’t actually solve the problems you face and you typically don’t find this out until well into integration.


Yes, we had an amazing product and we could stand on firm conversion/engagement numbers - fundamentally it was a marketing/experience product for retailers. For reference I was the Founder/CEO and we were a computer vision company with mobile AR products for retailers.


>I’m a purchaser of enterprise software.

Hi - Can I add you to my Linkedin Professional Network?

But in all seriousness, does this mean you are part of the procurement department? I would love to see some posts/thoughts on how someone in this position approach procurement of enterprise software.


This was published in April 2020, but I'm guessing it wasn't written in the last month:

> Spend as much time in person with your prospects as possible. That means demos, as well as conferences, dinners, coffee, whatever you can. This will allow you to build trust, and learn a lot faster about your customer than doing calls or even video calls. Working out of one of their offices side by side is a great way to hear how they talk, what they care about, etc.


Or it was written assuming that people may read it in the future when this whole situation we are in (I hope) has blown over.

Also, Phil (original author), if you're reading these comments, hi!


Hey man!

Ya it was written to be more evergreen content...hoping that the world reverts to normal at some point.


Starting two B2B startups is easy and while there's lessons to be learned in failing, before reading your advice...one must ask/know if you financially succeeded in either via profit/exit? Sorry, the title isn't clear.


> Sorry, the title isn't clear.

If only the there was more to the title - like a link to an article that answers your question in literally the first paragraph.


We all evaluate if the click trough is worth it based on the title, and in this case looking for tips on success, not starting (the easiest part).




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