The CRM market has been disrupted twice — once by Salesforce, once by HubSpot. As key members of the last team to successfully disrupt this space, we came back together to do it again. But we didn’t announce it until a full year after we closed on our first round. And when we did announce our seed round, we generated 4,000+ waitlist signups in the first 72 hours, and the momentum has continued for months following the announcement. Here's what we learned along the way.
Background
Christopher and I had worked together before, bringing HubSpot CRM and Sales Hub to market, so we knew we could build something important and lasting together. We started Day.ai in May 2023. When we saw what would be now possible to build with AI, we knew it was time to run it back.
In our first six months, we experimented constantly. Christopher explored what LLMs could do, while I talked to everyone I could find about potential use cases. Once I'd exhausted my immediate network, I moved to referrals, then to friends of friends of friends. Each conversation refined our understanding of what we needed to build.
We raised our seed round in June 2023. And then we waited a full year before announcing it. That wasn't procrastination. And it wasn’t exactly a plan. But it was what felt right at every step, and we learned a ton throughout the process of getting ready to go public with the company and fundraising announcement.
When to Announce
We announced our funding exactly 12 months after we raised. Most people don't realize you can announce your funding round whenever you want. You certainly don’t have to do it right away. We closed our funding in June 2023 and announced it in June 2024. We looked at the announcement purely as a way to drive demand and build credibility - not as a way to celebrate an internal milestone.
It seemed like the right time. I was running out of people to talk to through referrals alone, and we had built enough of the product to make good on the promises we were about to make.
I wasn’t ready to start up cold outreach yet. We didn’t have enough reps with companies that we had no connection to. Getting those reps in and validating that we had an idea that strangers would be attracted to and willing to spend money on was priority number one.
So we defined our MVP launch feature set, aligned on our positioning, set a date, and worked backwards from there. We first sat down to plan the launch and announcement in March, and executed it on June 20th.
If we had immediately announced after fundraising, we would have wasted a great opportunity to attract the right type of people to our product when we needed their input most. We tried to time it so that we’d gone as far as we could go before we needed the momentum we'd create with a seed announcement.
The best launches and fundraising announcements are intentional, tell a compelling story, and result in your company being able to take advantage of the demand you generate in the way that matters most right now. I think of every opportunity like this like a “chip” we get to spend - And I want to make sure we spend it wisely.
Since we wanted to wait, we knew we had to keep everything quiet to preserve the newsworthiness of what we were going to say. This was pretty challenging at times. Once your story breaks, journalists aren’t going to touch it. So we didn’t talk about it — with anyone — until we were good and ready to tell the world.
Where to Announce
Our guiding principle for this announcement was to keep it right-sized. It needed to accurately represent who and what we were today, while still being extremely clear about the scale of our ambition. Some approaches we considered felt too grandiose — or too limited — and we'd feel a kind of visceral discomfort. It just wouldn’t sit right. We learned to trust those gut feelings, and wait until we found the move and the method that felt right for us.
We considered things like Product Hunt, but ultimately decided it wasn't for us. Launching with a waitlist on Product Hunt felt like a recipe for negative feedback.
Our “constraints” were that we were launching a product that we intended to onboard new teams 1:1 to via waitlist, and was very expensive to run. So we needed to be very judicious about who we let in, and do a lot of high-touch onboarding with early users to make sure we were learning and iterating fast.
In the end we decided on a simple, focused approach. We just wanted to:
- Get the best possible press coverage we could get. The goal was an article in TechCrunch to help build credibility and get reach
- Activate our supporter base on social media, specifically LinkedIn and X
- Ensure that anyone who came into contact with our launch would clearly understand our ambition, and notice the level of craft that we aspire to
In short, we prized doing less things extremely well. And that meant keeping our standards incredibly high.
How to Announce
We decided to focus on the following assets for our announcement:
- A one-page website that positioned the product against “Legacy CRMs”
- A blog post announcing the fundraising, that told a story about how we got here and what we raised the money to build
- Social posts from each team member, sharing the announcement from each person’s perspective
- Short descriptions of “What is Day.ai” to use on social profiles
- A lead form with a kickback email for waitlist signups
On launch day, we wanted all traffic flowing to our own site — where we could control the narrative and capture interest directly. The blog post and website had to work together perfectly, and everything needed to link back to Day.ai. We didn’t just want attention, we wanted to convert it into real signups and engagement.
We spent hours debating every aspect of both the website and blog post — how to talk about our past experiences, how to talk about the product, how to describe its current state and future promise. Each team member prepared their own social posts, telling the story from their own perspective, while maintaining the core message we’d decided on as a team. No lazy copy.
The CTA had to thread a difficult needle. We decided on a "Get Early Access" waitlist approach with a kickback email with some additional context. We wanted to set the expectation that onboarding would be done 1:1, and that we’d be prioritizing access based on who the product was the best fit for. I’d go through the list personally and send invites from there.
At one point, we debated putting my calendar link on the website — but then we realized we had no idea what to expect in terms of traffic or interest.
An investor of ours strongly advised against using my calendar link as the CTA. And she was right - Had we gone with that approach I would have been flooded for months with a ton of unqualified conversations.
Doing Things That Don't Scale
The core assets listed above would have made for a decent launch if we threw them together quickly, but what really made it successful was the work we put into doing things that don’t scale.
The Dogged Pursuit of PR
The first two TechCrunch journalists we pitched declined us. They didn’t give much feedback on why. We thought we had an exciting story to tell, and here were these industry experts essentially telling us we just weren’t newsworthy.
But we persisted, and eventually connected with someone at TechCrunch who saw the potential of what we had to say. But press coverage isn’t the same thing as user interest. PR is about credibility and distribution, not a reflection of how much actual prospects will like your idea.
Regardless, securing the TechCrunch article was a boost for the team, serves as credibility for Day.ai, and helped us get a lot of reach and momentum on our announcement day.
Personal Investor Outreach
I set up one-on-one calls with every single investor — we had about 6 firms and several angels to work with. I previewed with them everything that would go live when we announced and directly asked each of them what they could do to help us have a great day.
Their responses varied. One offered to write a post about why she invested. Dannie Herzberg at Sequoia wrote a deeply thoughtful post (customary for the investment lead to do). Others committed to giving us general social support. But just having these conversations at all meant our investors knew what was coming — and they were all happy to help amplify our message on announcement day in unique and valuable ways.
LP Activation Strategy
Stage 2 Capital had invested under their Catalyst program, giving us access to about 300 LPs who were sales leaders or RevOps professionals. We knew we wanted to reach out and activate them if we could. Stage 2 generously offered to send an email to these LPs on our behalf.
I created a “how to help us have a big launch” guide for LPs. A lot of them took us up on it and helped share the news. This was one of the more impactful things we did. These investors were eager to participate and to amplify the message of what a big day this was — for us and for them.
Authentic Customer Testimonials
I messaged each of our customers privately in Slack about the upcoming launch. This time, I deliberately avoided giving them any pre-written copy. I just asked them to write truthfully about their experience working with us, whether that focused on the product, our team, or their personal interactions with me.
Having real customers describe their genuine experience in their own words gave us strong social proof that was far more powerful than anything we could have scripted.
On The Day
For the launch day itself, we had a few key guidelines that helped us manage the day:
- We needed to have all of our assets prepared in advance. There would be no content creation happening on launch day — everything needed to be written, approved, and ready to go. Launch day is for responding and engaging, not creating.
- We were ready to start early, but knew we had to wait for the TechCrunch article to publish before releasing our own content. That article going live — at 9 am EST — was our signal to move. I prepared a “to execute in order” list of posts and emails to send ahead of time.
- We blocked off the entire day for engagement. We responded quickly to every comment, replied to every message, and kept the conversation going. Speed of response matters to social algorithms, and it shows that there are real humans behind the company who care.
- We knew we wouldn’t be clocking out early. We stayed online and responding until activity naturally slowed down.
Results
In the first 72 hours after announcing, we generated 4,000+ waitlist signups. We created momentum that's still going today, and built a pipeline that’s helped us onboard hundreds of teams (with thousands more still on the waitlist) that we’ve been able to build and iterate with.
8 months later, we're still getting consistent signups, without doing much other intentional marketing. We see regular inbound from target customers, strong word-of-mouth momentum, and have established a clear position in the market conversation, getting featured consistently on market maps and industry analyses.
What Worked Well
I attribute our successful launch to a few key decisions:
Staying Right-Sized
We constantly calibrated our plans to match our reality, avoiding over-promising, while still being extremely aggressive and clear about the scale of our ambition. Keeping this calibration top of mind helped us make and stick to decisions that felt authentic, not forced.
Quality over Convenience
We put major effort into our blog post and marketing materials. We debated every word, every angle, every message. This attention to detail came through in the final product — and reflected the care we take in building our product and team.
Activating Our Network
The one-on-one calls with investors, LPs, and customers created a powerful wave of authentic support. By taking the time to personally enroll each potential supporter, we generated exponentially more impact than if we'd simply sent a mass email asking for help.
What We Could Have Done Better
Despite the success of our announcement, I see at least two areas where we could have improved:
Nurturing Our Waitlist
We didn't have a well-developed plan for engaging the waitlist after launch. It's a tough balance - how do you keep people interested without giving them access right away? How often should you communicate? What should you tell them, when they’re still basically waiting to see what you’ve got?
This continues to be hard - keeping people engaged requires thoughtful and consistent communication. We’re getting better at this now. We could have planned it better from the start.
Maintaining Early Momentum
We could have built more off the momentum of the launch with more follow-up content. We could have written about the results of the campaign, shared metrics and learnings, or created additional materials that built on the initial interest.
When we eventually did share results, those posts performed exceptionally well. People were interested in the outcomes, but we missed the opportunity to capitalize on that interest immediately after launch. I’ll say it: I was more focused on onboarding the next cohort of users than continuing the momentum on the marketing side.
Resources That Made a Difference
Several partners were instrumental in our success.
The Sequoia Arc program pushed us to be bold with our positioning — both in terms of our scale of ambition (make it bigger) and to offer something that wasn't just better, but different. The team was very helpful in coaching us through the pursuit of PR, and gave excellent feedback on everything we shared along the way.
Underscore VC’s seed round announcement playbook gave us a helpful framework for thinking through our own launch. Their playbook was the most comprehensive that I came across.
Inspired Capital asked their partner PR firm to help distribute our announcement to a bunch of other publications and newsletters directly after our TechCrunch story went live, which yielded us some additional coverage and helped us get more exposure, without needing to navigate that ecosystem. This was a direct result of speaking with them 1:1 ahead of launching vs just sending them a note and asking them to like and share.
Mike Troiano, a Boston-based marketer and early-stage VC, played a crucial role in helping Christopher and me align on our approach. There were points we rigorously debated, like how we should position the product. Mike listened to both perspectives and helped us find the right middle path, showing us how our different viewpoints could be reconciled without either of us giving too much away. Mike also was a great sparring partner on copywriting, when I was early on and finding my own confidence with writing about our work.
Final Reflections
A year later, we're still getting waitlist signups from people who come across the assets generated for our seed announcement. I think that’s a good sign we did something right.
What I've learned is that successful launches aren't about following a formula or checking boxes. It’s about making intentional decisions that feel right for you. It’s about putting in hard — sometimes unscalable — work to create authentic connections with the people who play a role in your launch. And it’s about telling a story that resonates with the people you're trying to reach.
The right approach isn't necessarily the one with the most channels or the flashiest gimmicks. It's the one that honestly reflects who you are, where you’re at in your growth, and what your value proposition is to the people who matter most.
For us, that meant waiting until we were ready to capitalize on the momentum an announcement would generate, being transparent about where we were, and activating our network in a way that felt deeply personal rather than transactional.