Our Work-Bench NYC Enterprise Operators Retreat is one of our most anticipated events of the year. Why? We bring together 150+ operators from across Sales, Product, Marketing, Engineering, Customer Success, and more to get the lowdown on what’s been challenging and their strategies to triumph. This year, we were laser focused on the make-or-break phase of building from zero to one.

Our first speaker of the day was Dylan Fox, Founder and CEO of speech AI model AssemblyAI. He walked us through his journey applying for Y Combinator (past the application deadline nonetheless) to the tactical takeaways he’s learned now running a company with $115M in fundraising, 100+ employees, and 5000+ customers. 

As some quick background, the idea for AssemblyAI came about as the first class of voice-controlled intelligent assistants, like the Amazon Echo, hit the market in 2015. At that time, most products in the space were either built for the consumer or large-scale enterprises, with limited options for developers looking for APIs that would help them build their own products and capabilities with voice data. So Dylan built AssemblyAI to fill that gap.

Dylan’s Fundraising Advice

1. Focus on building, not talking to investors. Dylan recommends picking a date to kick start fundraising and be very structured about how you're going to run the fundraising process from that point on. Given “you can't network your way into a Term Sheet,” in the earliest days, it's important to focus on building your product and making tangible progress to show investors vs. over indexing on networking with investors. 
2. Articulate what you’re building clearly. Dylan sees a lot of Seed fundraising decks that clearly explain the market, but generally lack one critical element: a description of what the actual product is and does. Y Combinator’s application is designed specifically to get founders to articulate this messaging clearly. So, he recommends even if you're not going to apply to Y Combinator, to look at their application questions as a forcing function to describe what you're building, fluff free. 
3. Create urgency with a compelling “why now” event. Dylan doesn’t believe it's effective to head into fundraising meetings with the simple narrative of “I need cash and here is information about my company.” Investors want to be dazzled with creativity, imagination, potential, and opportunity. To meet that demand, try to be specific on why they should invest, but more importantly, why they should invest now. Why is this specific moment in time important? Did you just sign up a slew of customers? Did you just reach product-market fit? Are you seeing a big increase in top of funnel? 
4. Be super targeted in your outreach. Dylan used CrunchBase to identify ~100 investors who had put money into companies that had similarities to AssemblyAI in terms of a sector (AI / infrastructure) and go-to-market (competing against big tech) in the last two years. This provides a positive signal that those funds are writing checks and have a thesis that could match your company. From there, he found every possible inroad intro possible to those investors. 
5. Think about the hard questions in advance. Before heading into any fundraising meeting, write down all the possible questions investors could ask as well as the answers to each. This will allow you to walk into that pitch room confident and thoughtful. 

Dylan’s Advice on Scaling to 100 Employees

1. Take time to define your company values/operating principles early on. Having this information at the ready will be a competitive advantage to talent scouting out different companies. 
2. Take time to define your company strategy early on. Write it down and show it to new hires. This document will become a key artifact that new hires can quickly read to ramp up on the company and your point of view on the market. While this document may be frequently updated (especially in a dynamic market like AI), it will save you tons of time regurgitating information. 
3. Always be grooming your company operating cadence as your org grows (OKRs, All Hands, etc). While department meetings are critical and likely the first thing to make it on the calendar, remember to schedule cross-functional meetings to get a better sense of how the company is operating as a whole. 
4. Leaders you hire are super important – you won’t always get it right! While it's tempting to recruit executive leaders from some of the world’s biggest tech companies (think Google, Meta, etc.), they often don’t have the hustle and startup experience needed to lead at this earlier stage. Make sure each hire has experience around your current stage - these are the people most well-equipped to handle the challenges that will be thrown at you as you scale.‍
5. Invest in GTM before you need it. Most early hires will be builders (developers, engineers, product) to get the company product off the ground. Oftentimes marketing is put on the backburner in the earliest days, however, it's nearly impossible to scale to $25M+ in ARR with no marketing and on word-of-mouth alone. So make sure to get your marketing function set up before you need it, so they can hit the ground running when it’s time.

If you’re an early-stage enterprise founder or operator — connect with us directly to chat about anything GTM or check out our events page to stay in the loop on all things happening in the Work-Bench community.