You’re asking the wrong question …

Written by Tyler Kastelberg

September 5, 2021

Happy Labor Day Weekend!

For most of the United States, Labor Day marks the end of summer. However, in San Francisco, Labor Day represents the end of our foggy season and the start of our Indian summer. Fun Fact – our warmest days of the year are typically in October.

Before we get into the meat … welcome to all the new subscribers! If this email was forwarded to you (and you like it), subscribe here.

Now for the meat …

How do I grow with sales and marketing in my startup?

This is a question that I received from two friends this week: one who launched a wine-industry startup earlier this year and the other who is considering launching a software concept.

It’s a fair question. Growth is one of the biggest things that investors look for when considering an investment in an early-stage business. Public companies trade at wild multiples when fast growth is expected. There are even conferences dedicated to 10X’ing your growth.

Moreover, I love talking about sales and marketing strategies. Owned media, SEO, inbound vs outbound sales, etc. – they all get my creative juices flowing.

However, it’s the wrong question.

Sales and marketing without a product that solves a problem that a lot of people have (and value) is akin to starting a dumpster fire with cash. The flames might grow quickly, but they’ll burn out when the cash is gone.

One note … creating a solution to a problem that a lot of people have and care about is commonly called product-market fit. However, this term is soooo misused that I’m going to try to avoid it for the remainder of this email. If you want more info on it, Y-Combinator has a good talk on product-market fit.

Better questions to ask before worrying about sales, marketing, and growth … with responses based on my experience starting Bullpen.

1) What problem am I solving, and who am I solving it for?

Before I started Bullpen, I noticed that there are a ton of real estate investors, developers, capital markets teams, and brokers that are too small to hire a full-time, in-house team (Initial Target Market). However, they still had a ton of work to do, which left the Principals doing it all (Problem). 

2) Do my target customers like my product and keep using it?

We launched Bullpen as a software similar to Upwork, where employers could post jobs and freelancers could apply for work. However, the majority of our customers didn’t like it. The price competition pushed the best freelancers off the platform, and employers weren’t happy with the massive amounts of lesser qualified applicants.

We totally scrapped the “DIY” platform functionality early in 2021 and pivoted to a sales-assisted hiring process. Employers tell our talent managers about the role they need filled, and our talent managers bring them a solid candidate within 48 hours. Employers loved it, and freelancers like that their rates aren’t crushed.

PS – The above pivot was a really hard decision for me as an entrepreneur. I fell into the trap of comparing myself to those who run software-only companies, and their success. It wasn’t until I swallowed my pride and hired a sales team that I realized I LOVE running a business that people want to use. Software/automation should be a last resort – not the goal (unless you’re building an AI business, then ignore that last sentence).

3) Are my unit economics good?

At Bullpen, we modeled what we thought our revenue would look like before we launched the sales-assisted hiring program. However, we didn’t know for sure until we received a few quarters of operating data. Surprise of the century – our model was a bit more optimistic than our actuals.

Nonetheless, after two-quarters of operating data, we’re confident that our pivot made sense. The numbers 100% work and we’ve been able to go “upstream” to work with bigger customers where margins are wider.

📚 Resource –> I’ve found the free content at on unit economics to be really helpful. Once you’re confident that your unit economics are good, they also have good content on creating a sales funnel. Warning – they have a very aggressive sales funnel on their site. If that typically turns you off, then just look past it and head straight to the content.

Note – If your unit economics aren’t good, but you have a solution that customers really like, you might consider more seriously if your solution would be better solved using custom software. At Bullpen, we use a web application to power the freelancer and contract management sides of our service – it wouldn’t be economic to do it differently.

That’s all for this week. I hope you found it helpful as you think about your different business ideas. I’m planning to write about our evolving sales and marketing strategies at Bullpen next week … let me know if you’d rather see something different!

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