Why did you join the Bowery Capital Revenue Council?
My passion in life is to build legendary companies--the rare ones that transcend their industry and their era by making a massive impact on how people live and work. I was initially drawn to the Bowery team as they see the world through a similarly bold lens, investing in the next generation software companies and founders who are re-inventing the entire stack in their respective industries. More importantly, I loved how Bowery's approach goes far beyond writing a check, deeply surrounding founders with a broad range of operating support, thought partnership, and resources from day 1.
How has the sales landscape for seed-stage startups changed in the last five years?
The go-to-market landscape has changed massively over recent years. The great news for entrepreneurs is that it's easier now to start a company than ever. With hardware, infrastructure, and core tools & services so readily available and usable out of the box, the availability of capital, and collaboration across decentralized teams more seamless than ever before (and pandemic-accelerated), the traditional laws of startup physics have bent so far in ways we couldn't imagine even a few short years ago. A founder can now quickly spool up a company anywhere, pulling talent from anywhere on the planet, and selling to customers/users pretty much everywhere--we've moved from checkers to 3D chess in a very short amount of time. The impact on GTM: founders are now competing for customers and talent globally from day 1. As scary as that sounds, it's also an opportunity to rethink the traditional playbooks and instead approach GTM strategy from a first principles lens. I'm convinced the companies that do this well will be the ones who win the 3D chess game in their respective industries.
What are some indicators of a healthy sales operation?
Building a healthy GTM machine starts with a focus on building the fundamental model well, and then measuring it closely with you scale up. Understanding what problem we're solving (use case, pain addressed, impact driven), for whom (the buyer and user, types of companies, industries, segments, regions), and how we will go about reaching those people (the narrative, the growth channels, whether we leverage PLG, inside/field sales, partners). As you answer those questions, you can start to build a pilot version of your GTM machine to test it. And remember: you can only manage what you can measure. At its core, the efficiency of your sales process is measured through pipeline created, conversion to signed customers, conversion of signed customers to launched, adoption rates, and retention/expansion rates. And if you're leveraging a sales-driven model, it's important to track the per-rep productivity of each of the roles involved. A healthy GTM means building a baseline-repeatable business that is (or at least has line of sight to being) economically viable, from which you can start to measure, optimize, and scale.
What are the most common roadblocks you’ve helped startups overcome at the early stage?
For early stage startups, a common roadblocks are often most fundamental questions. What is the problem we solve? Who do we solve it for? How do we reach and convert those people/companies? The alignment across product and GTM teams is critical in the early stages to finding where we can get to product-market fit, how to build a stronger product market fit in that initial ICP, and how to expand the ICP to grow. Tactically, this might look like spending time together to identify which segments or verticals to focus the initial GTM on, mapping out a hypothetical sales process to trial, or building a compelling narrative and messaging to reach target buyers.
What one piece of advice would you share with a founder looking to scale revenue at the seed stage?
I think of building a startup and particularly the GTM a lot like when I learned the scientific method in grade school: hypothesize, test, measure, analyze, and then tweak & test again. Invest the time up front to decide what markets and people to go after and how to go after them--not doing so will inhibit how quickly you'll learn and grow. It's so important to measure how we're doing so we can form a baseline of performance from which to optimize. Review the metrics and qualitative feedback from your customers regularly to draw insights on what's happening and root causes. Optimize and scale as you find success. Going fast is the name of the game, though resist the temptation to push from a test to large scale too quickly before having built a commensurately high level of conviction--the faster you're trying to scale, the more critical it is to be rigorous in your measurement/metrics.