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Chargebee interview with our CEO: Launching trumpet, & life at Hotjar

Chargebee sat down with our CEO Rory Sadler to discuss the launch of trumpet, life at Hotjar and more

Relay by Chargebee
June 26, 2023
February 24, 2024
Chargebee sat down with our CEO Rory Sadler to discuss the launch of trumpet, life at Hotjar and more
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About Chargebee

Chargebee is the leading subscription billing software powering end-to-end recurring billing, subscription management & auto invoicing for 4,500+ SaaS businesses. Follow them on LinkedIn.

Chargebee sat down with our CEO to discuss interviewing 200 Prospects (and as many end users), Building a quality/quantity waitlist, and invaluable lessons from Hotjar.

In the following exchange, trumpet’s 2 co-founder and CEO, Rory Sadler, illustrates the importance of thorough — even talking to end users — pre-product research despite solving for a long-witnessed, personal pain.

He also highlights their methodical approach to building (and learning the most from) their waitlist, lists the tools that allow trumpet to place customer voice front and center, and affectingly recounts lessons from the uniquely scrappy yet massively impactful ways of Hotjar.

Beginning with a personal itch
Really committing to early-stage research
A quality/quantity waitlist
Prioritizing the waitlist along ICP lines
Gathering attention in a crowded space
trumpet’s always-on customer delight stack
What Rory took away from his time at Hotjar

Beginning with a personal itch

The trumpet journey definitely began as a personal itch.

Having spent 7 years in B2B SaaS, building and leading teams, and having sold across SMBs, mid-market, and enterprise, I’d experienced first-hand the frustrations that buyers went through during demos.

The customer champions had such a painful, overwhelming time communicating information to wider stakeholders when I wasn’t in the room guiding them. So I started putting together and sharing these Notion pages/Google Drive links to help ease the process flow for them.

Soon, others on my team started asking, “can you build those for me?”

I was able to do it for the enterprise clients because they warranted more time owing to the potential deal value, but I wanted to be able to do it for all clients; why shouldn’t everyone have access to organized information that aids their buying efforts?

That was trumpet’s lightbulb moment.

We were solving a personal pain point (all the 3 co-founders had sold a lot of software) from the start. Even today, the entire team uses trumpet, day in, day out. Which is great, as we can be power users ourselves and always have a sense of what needs fixing.

But we didn’t want to presume, on behalf of our potential customers, what they wanted.

Really committing to early-stage research

Before we decided to go full time with trumpet we interviewed 200 salespeople and 200 end buyers to make sure we weren’t crazy.

The interviews were very detailed with 20-30 questions. At first we leveraged our close networks and soon started speaking with complete strangers, because people who know you somehow will probably give you the answers you most want to hear.

This was such an important step.

If you’re going to go on a 5/7/8-year journey towards building something, that investment of research in the beginning is worth every single minute you put into it.

You could rush into something because you think you’ve got this brilliant idea. Start building it. And then you hear crickets.

That’s why you need to double down on research. To make sure that the journey that you’re about to embark on is meaningful. And that you’re going to impact people’s lives because especially in this current climate you need to be focusing on:

— reducing risks
— reducing costs
— increasing revenue

In the last few years, we’ve had a lot of nice-to-haves and now the thing you’re building has got to be essential. Then, you want people to tell you something’s rubbish and why they think it’s rubbish.

They’re likely not saying the entire idea doesn’t work for them. Perhaps there’s some value proposition that you’ve miscommunicated or certain features/benefits/ROI that they haven’t quite understood.

Hearing honest and candid pre-product feedback shaped our early (the first 6-12 months) roadmap and go-to-market approach, helped us prioritize better, and grasp where we could add the most value.

And we learned so much about our assumptions.

For instance, with trumpet, we allow people to create microsites — an online hub, a portal, a dealroom, or a workspace, whatever one might call it — where buyers and sellers can collaborate.

On hearing that concept, some people asked: “Do buyers actually want to buy this way?”

“What if they just want to stick with email, jump on calls for demos, and don’t want to work on a collaborative digital space? If I’m selling to a CFO at a large global bank, there’s no chance they’d want to do that. They’re too busy to use a new tool.

That was refreshing to hear as most people until then had been super excited about trumpet.

There was definitely an education piece here. Like, if you go back to the early 2000s when Docusign was founded, e-signatures sounded crazy, you had to do pen and paper. Nobody trusted doing things digitally. Then, suddenly, everyone did.

Although, we couldn’t say, with 100% certainty, that the c-suite at enterprise businesses wanted to collaborate digitally, we knew that COVID had accelerated adoption of digital tools at these places.

Plus we knew that some of our customers would be selling into similar-sized companies.

Just having the awareness that we’d have to account for and address this buying behavior differently, prepared us for objections on our first sales calls and even for our investor conversations where the topic always came up.

A quality/quantity waitlist

We knew that it was going to take at least 6 months to build the V1 of trumpet’s MVP. We didn’t want to sit back and be a stealth startup on LinkedIn. There’s plenty of them.

In those 6 months, we saw an opportunity to build some FOMO, some intrigue before our launch. Because we were starting from nothing. Had no following across platforms. We had to turn heads, make people wonder, “what is this?” and get them interested in learning more.

A waitlist seemed perfectly suited for doing just that.

We began with a simple landing page.

The goals that we decided on weren’t so much around quantity (the no. of people we could get on the waitlist) but around quality. We wanted to make sure we were getting in front of the right kind of prospects and partners.

We had a nice little initial spike when we released this page, thanks to the great networks that my 2 co-founders had. From thereon, we were big believers in being present wherever our community was. For us, as we sold to salespeople, that place was LinkedIn.

So I committed to share, every day, learnings and experiences from my albeit small time (~6 years) in SaaS. Everything. The highs and the lows I’d had. Tricks, insights, and stories. Which started to compound.

We’d occasionally dip into trumpet as well and share teasers, screenshots, product updates, and whys behind what we were building.

Enough that some people grew desperate for access to trumpet. More and more of them were telling us, “this sounds awesome, what can I do to get my hands on it?”

That’s when we released a referral program.

And I didn’t necessarily know that was going to work. I’m not the biggest referrer of new tools myself. But it’s incredible how many people supported us. Around 18% of the 4,000 companies that signed up on the waitlist came through referrals.

Plus we didn’t sleep on the waitlist.

We sent out a weekly email with the latest sales insights, tools, and analysis that was most relevant for the seed, series A/B/C types of companies that were signing up.

Not content that HubSpot wrote about 5 years ago but fresh perspectives for teams that were just beginning to build their go-to-market motions.

At the same time, we also compiled a list of over 300 sales tools across lead generation, CRMs, podcasts as well. That ancillary offering went mini-viral, accidentally, and was shared in different sales communities all over LinkedIn. Which also drove waitlist sign-ups.

So there were a few of these things going on. We were pretty strategic with some of them, but some just happened naturally, and honestly, went better than planned.

Overall, the waitlist definitely accelerated our pace of learning.

We knew what kinds of roles and companies we were attracting based on our value proposition. We even changed our messaging 2-3 times before launch and it was interesting to note how that reflected on the kinds of companies that were then attracted.

Prioritizing the waitlist along ICP lines

In terms of categorizing the waitlist along ICP lines, our approach was typical:

  1. The region where they were based. Because we knew that the product wouldn’t be localized from day 1 and we’d only be able to target English-speaking parts, some of EMEA and most of North America.
  2. The company size, 3) the role of the person signing up, and 4) their industry as well. B2B software companies were our sweet spot. Agencies, we weren’t too sure of back then. Today, though, there’s lots of agencies using trumpet.

Scoring based on these broad classifications helped us prioritize who we gave early access to.

For example, we didn’t share instant access with some high-ICP scoring, big companies that we hoped would eventually become a customer, because the early product wasn’t everything it is today. We knew some of these companies would have high expectations.

It was easy to get excited (“let’s get them onboard!”) when the CRO of X enterprise subscribed to the waitlist, but we knew it would be risky.

That’s why we started with smaller teams where users had more time to give us feedback. And we could deliver immediate value compared to someone that needed a tool that had SSO, a fully-fledged Salesforce integration, and so on.

Gathering attention in a crowded space

With content, in particular, what helped us was starting from scratch.

As it’s easy to look at other people’s posts and think, “how do I write that.” There’s a lot of people that tell you, “join this course and learn how to become a LinkedIn creator and stuff like that.”

Having never posted on LinkedIn before, I thought I’d end up doing what others were doing. We had to have our own fresh voice and not just join the noise. Especially so as trumpet’s brand is about standing out.

Our focused subject was: selling in the modern day. Which was based on the idea that buyer behavior has changed, if you think of the next generation of buyers, they’re all glued to their phones, they don’t want to be on face-to-face calls.

There’s going to be a lot more digital collaboration.

We call it Buyer Enablement.

We also knew that hammering a solution-first message of “buyer enablement, buyer enablement” wouldn’t work. People will get bored quickly. So what we’ve tried bringing attention to is the problem and what’s changing.

That what has worked for the last 5/10/20 years might not continue working the same way.

How did we decide on what to publish?

I think this is the most beautiful thing about early-stage startups. You have so much freedom, you can just try and test new things. Overthinking what is our content strategy, what are we trying to achieve, and what success looks like, would have been a waste of time.

During those days, just taking action was the best thing.

Consistency was the best thing second to that.

It’s much like creating a sales playbook in the 1st year of a startup. That just doesn’t make sense. Because: Your customer changes every single week. Your ACV changes every single week. Your product changes every single week.

Any plan gets instantly outdated as soon as you make it.

We knew that we wanted to publish all sorts of ideas and formats within the umbrella of a problem statement, and ensure that we were consistently posting across LinkedIn communities and other channels.

The resulting compound effect, fortunately, paid off.

trumpet’s always-on customer delight stack

We’ve continued obsessing over customers as we’ve grown.

The following tools have been key in doing that.

First is Intercom. The 90% startup discount. In-app product tour. Chat functionality. We can even do emails through it.

We’ve set up automated emails based on activity or events and if someone hasn’t used trumpet in 7 days, they get a brief note:

“Rory here, a co-founder at trumpet, I want to understand why you haven’t been using us, here’s my Calendly.”

That’s the next tool.

My Calendly is everywhere. Emails. Intercom chat. Inside the app. My calendar is for our customers. Any time of the day. Doesn’t matter what size they’re at.

Because all the early adopters have taken a risk. They made a bet. They’ve taken time out of their busy lives to explore trumpet. The least I and the team can do is to understand what they love and what they don’t love. What can we do to make things 100x better?

Sometimes people think that a 10-person/50-person isn’t worth their time. They say, “let’s focus on the big logos instead.”

We’ve found that that’s a mistake.

As it’s the small teams (this was the case at Hotjar as well) that’ll become your best evangelists, they’d champion you through and through, refer you organically, without you ever asking.

It’s incredible who we’ve been introduced to from some of our smallest (even the one-man band) users. I’d say, never underestimate the power of your early users, irrespective of their size.

The next essential tool is 1. An in-app product roadmap and feature request solution. It’s been invaluable to us because it has given our users an in-app voice.

They can say what’s missing, what integrations they’d like to see, and then get notified when something was being reviewed/built or when something went live.

That kind of access makes it almost as if customers are building trumpet together with us. And it’s been the case since day 1. We’d never stop doing this.

Another product that enables us to extend this collaborative experience of the trumpet roadmap is Slack Connect. We have a bunch of Slack Connect channels for early customers.

They can always use Intercom for support. But Slack gives them direct access to me, our tech team, our head of CS, and other folks. They can ask questions, share detailed feedback, and get our thoughts and feedback on a pod they’ve built with trumpet.

Our approach to listening to customers is like an octopus.

We’ve got legs everywhere.

What Rory took away from his time at Hotjar

Hotjar was an incredible company to work for.

I learned so much there in a short period of time.

David Darmanin, the founder, was the reason I had joined.

I was obsessed with the world of tech.

And reading about Hotjar, the needle in the haystack, that was a bootstrapped market leader up against competitors that had raised 100s of millions. I thought, “this guy knows how to build a company, I need to go and see how he does it.”

And it was an invaluable experience. I learned a ton.

One of the things that I took to trumpet was how important culture is. If you’re going to build a true business and you want people to champion your product, they need to love where they work.

It doesn’t mean they need to love heatmaps and analytics. I don’t expect everyone that joins trumpet to love sales software or microsites. But if they love where they work and who they work with, we’ll fly.

The other important thing I learned was making data-based decisions and prioritizing ruthlessly. At Hotjar, being self-funded, we didn’t just throw money at problems. We worked to understand the root cause of a problem.

“How can we solve this with our existing team and existing toolset?”

Hotjar remained scrappy, even at the large size when I left.

We’re building a business in the same sense as well.

Not something that just burns VC money, gets the coveted unicorn status, and remains pretty messy and ugly behind the scenes.

That’s why we’re still a lean team. Only 17 of us. Working with a hell of a lot of customers. Always super, super busy. Because, again, from what I saw at Hotjar, you can’t just throw money at problems.

And then they were always transparent about the business and how it was doing. Making the entire team feel involved in the growth. We’ve been intentional about it as well, in getting people to realize that there’s a future ahead which we get to shape together.

You have to be vulnerable and honest. I have a good idea of what trumpet is today, what it’s going to become, but I don’t want to dictate that. I want our team, our customers, our advisors, our partners, to help build trumpet together.

Unlike Hotjar, we went down the VC route as we knew people needed trumpet yesterday, we knew we had to go quicker. I respect every founder that builds a bootstrapped business.

I envy them to some degree.

But we also realized that trumpet needed to be on the VC path. We, fortunately, have incredible investors who have a lot of conviction for what we’re building. We believe it’s the right support to aim for global growth.