Ten minutes into our first industry conference, I realized almost every cold email I’d sent in the last month was wrong.
We’re a startup entering workers’ compensation insurance, and last week we set up our booth at CCWC in Anaheim: two founders, a stack of brochures printed the night before, and a putting green to lure people in. We made a ton of mistakes. Here are the lessons, so you can show up better prepared than we did.
Sell, sell, sell
We are entering the workers’ compensation insurance market, and were still in the phase of doing user interviews to find the most painful problem our target users face.
Inspired by the book The Mom Test, I led most of my initial outreach to prospects with a research question: I told the prospect that I’m writing a report on XY and asked them to participate in exchange for access to this report once it’s done.
The instinct is roughly correct. At the start of a conversation with a potential buyer you should definitely focus on understanding what problems matter most to them.
But people come to a conference to buy, so you should actually try to sell to them, don’t be ashamed of that.
Unsurprisingly, the research approach did not work. Enterprise buyers already have packed schedules, and participating in “research” is not what they flew in for.
The same executives who ignored my research emails answered within hours when we changed the message to the actual problem we solve: “we can decrease your exposure by closing claims 10 times faster.” Lead with the pitch.
Write like an actual human
Early in our outreach journey we used LLMs to generate the messages we sent to prospects. Nothing wrong with that in principle, but make sure whatever you send actually sounds like a human.
Later I went back and looked at some of the emails I had sent. Honestly, if I received something like that, I would never bother to respond. It sounded so obviously AI-generated.
My approach now: I handwrite the email in my own style and keep it short (LLMs somehow love to be long-winded). I still use LLMs to personalize some parts of it, but the agent only sends it out after I proofread it and give my thumbs up.
This approach is obviously slower, but the response rate is much higher. In combination of leading with the pitch the rate went from 0% (you read that right) to 5%.
Set up meetings before the conference
We had a booth, but foot traffic is hit or miss.
A conference rarely contains only your ICP. Most attendees are in the industry, but adjacent to the people you sell to.
And the people with buying power rarely look at the stands. They are way too busy with the meetings they came for.
By far the best conversations we had were in the meetings we set up before the conference. Every single one converted into a follow-up call, booked then and there.
The math is simple: a pre-booked meeting converted at 100%, a booth conversation converted at maybe one in ten. So set up as many meetings as possible before you arrive.
Bother people
Workers’ comp is an extremely relationship-driven industry, so it’s hard to enter without knowing the right people. Our way around this: bother as many people as possible.
Be shameless. Chat people up. Don’t feel awkward if some conversations go nowhere. As a startup it’s all about survival, and getting these first customers is quite literally life or death for your company. I went into overdrive pulling people off the aisle and onto our booth. Yes, some people are introverted and this is not easy for everyone, but try to step out of your comfort zone.
Try to squeeze as much as possible out of the networking events around the conference. Most conferences have after-hours events. Talk with people and ask them where they’re going. Chances are they’ll invite you along, and if not, and the event seems big enough, there’s usually a way to sneak in. This is the one thing we got right from the start.
Keep failing
The main advantage a startup has over larger organizations is the speed of learning. And the single most effective way of learning is by figuring out what does not work, rather than finding the one perfect way of doing things from the start.
Every lesson above came from getting it wrong first and then working out why. So just get out there and make mistakes.
The Result
We walked away with over 50 leads and a handful of deeply networked people who might become advisors down the line. But the real return was the playbook for conference number two:
- Book as many meetings as we can before we land. The floor is a bonus, not the plan.
- Lead every message with the problem we solve, never with “research.”
- Handwrite every first touch. The LLM helps, but a human hits send.
- Network as much as possible, get into every event you can find.
If you’re prepping for your first industry conference, DM me and I’ll share the pre-conference outreach template we ended up with. And if you’re curious what we’re building, check out veltha.ai↗.