Reaching Your First Million in Revenue with Allison Pickens

INTRODUCTION: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, the co- founder and CEO of Bolster, and I'm happy to be here today with Allison Pickens. Allison is a solo GP investor in AI and SaaS startups. She's a board member at DBT Labs and before all of that, she was the COO at one of my favorite SaaS companies, Gainsight. So Allison, welcome to the Daily Bolster.

Allison Pickens: Thank you so much for having me, Matt.

Matt Blumberg: Yeah. So my question for you... You do a whole bunch of early stage investing now and focus on AI and SaaS as I mentioned. So you're there at the beginning when the company is trying to get its first million dollars in revenue, and I have always said the first million is the hardest. I would love to hear some of the fresh takes that you have seen or advised companies on paths to that first million.

Allison Pickens: Absolutely. Happy to chat about that. And I think it's important to talk about maybe some newer ideas because I think we've all seen an exhaustive amount of content on which sales rep is the right profile to pick and other ideas like that. But here are some hopefully new takes. So I think the first idea is to nail the right hires on the first try. I often see companies spinning when they get the first hire wrong. As a general framework, I would propose get the first hire right by identifying five companies that you can poach from. So in terms of coming up with that list, they should be similar to you, but three to five years ahead of you. The candidates that you're looking at should have been at the company when it was a seed stage or series A company and then stayed for two years after that. And I think those companies should also be similar to you in a few key respects. They should have a similar ACV and distribution of account sizes, similar buying behavior at the customer, so PLG versus top- down, the buyer coming from the customer- facing function versus R and D versus staff function. They should be similar to you in terms of how technical is the product and also how complex is the product, like are services required to get customers activated? So that's one, is poach people from-

Matt Blumberg: From the right places. So I love this. I'm going to have to use this for some of our searches at Bolster because this is something we say to clients all the time. What's number two?

Allison Pickens: All right, number two is take ownership of your messaging as the founder. I think often I see founders looking to hire that perfect product marketer because they're realizing that they as the founder are technical in nature and they need someone who can help them message things. I think the reality is the best founders take ownership over that messaging themselves. They have all the ideas in their head. They have more knowledge in their head about what the value prop of the solution is, why it should exist, than really anyone else. And so what I recommend is actually spending two hours every Sunday writing stuff down. Could turn into blog posts or internal company updates or things that you share with candidates when you're looking to sell them on your company, but bottom line is download your thinking, cover the value prop, the maturity curve for people to adopt your best practice... potential subject of a whole other podcast... and how you fit in relation to other key products in the tech stack. And I know we were looking to talk, Matt, about how to make founders scalable. I think crystallizing your messaging, downloading your brain is probably one of the most scalable things that you can do.

Matt Blumberg: Yeah, that is great advice. I recorded a podcast yesterday with Martina Lauchengco about product marketing. I don't know if you know Martina. I'm going to try to make sure this runs the day after hers because you just reinforced some stuff that she talked about, which was great. Okay, so get the first hire right, control the messaging and...?

Allison Pickens: Great. And then the third thing is to hire a generalist business person pretty early on. I know, Matt, you and I were talking before about how sometimes founders really early on say, oh, I think I need a COO.

Matt Blumberg: When there are like 10 people in the company.

Allison Pickens: Yeah. And that might be the sign of some other bigger problems, if we have in mind the same definition of COO. I think what you really need is someone who is an early stage entrepreneurial person. They might have come from another early stage startup, they might be an MBA, they might have come from a consulting firm, which sounds like a big company person, but actually there are a lot of first principles thinkers who work in these places. They could have been a BizOps function at another company where, again, they have to think for first principles. And you can deploy these folks to go solve some of your biggest problems in your go- to- market and other areas. I hired a number of folks like this in the early days at Gainsight. Barr Moses, who founded Monte Carlo, was one of them before she founded that company. inaudible was one of our early hires of this type. He went on later to become VP of Customer Success at LinkedIn. So these are people who can actually create massive leverage for you and they can scale a lot themselves. Some examples at other companies, inaudible, Jen Ong Vaughan at Assembled, Will Robins at Monte Carlo. And I would say put them on your biggest problems, and they'll help you get to that first one million.

Matt Blumberg: There is a lot of value in strong generalists early on, a hundred percent. So that is great advice. I love all three of those. You're right, they're not the first three things out of most people's mouths about the path to a million. But thank you for being here today and just great advice for founders.

Allison Pickens: Awesome. Thanks, Matt.