How We Grew From $5m to $10m ARR

A lot of the same, and a few new tricks.

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It’s nearly impossible to summarize so many years’ worth of work into a short post, but good heavens we’re gonna try.

To hit our first $1m in annual recurring revenue (ARR) at Text Request, we used:

  • Outbound calling to our ideal customer

  • Outbound email to the same

  • Blogging and SEO to create inbound opportunities

You can see how we made those work here. We also made a ton of mistakes during that time, including:

  • Going to market without a core buyer (no product-market fit)

  • Over-spending on events

  • Trying to force partner marketing without good partners

To grow from $1m to $5m, we used:

  • PR in niche markets

  • Google search ads for buying-intent keywords

  • Online reviews on key platforms

  • A completely new website, rebuilt from the ground up

  • Customer referrals, as often as we could get ‘em

And 3 things that didn’t work in this phase were:

  • Outsourcing BDRs for cold calling

  • Retargeting ads and display ads

  • Submitting bids to requests for proposals (RFPs)

And now let’s talk about what worked on our way from $5m to $10m.

We had to keep everything running that was already working, though there were ebbs and flows to how well each continued to work (market shifts, and all). Then we added these 3 things on top, and saw it all getting better faster.

1. We built a brand (on purpose).

Brand and culture are the two things you create in a tech company without writing a single line of code.

Leading up to $5m, we knew we needed to be more intentional about our reputation, how we looked, and how we talked to customers.

First, we contracted a brand messaging agency (thanks, NewKind) to coach us through redefining our messaging. We analyzed competitors, synthesized our brand story, and created highly defined buyer personas. We honed core pillars for our brand, a tone of voice, and company descriptions.

It took 4 months, with several of our key employees. It was a ton of work, but also the basis for all the marketing we’ve done since.

Next, we began rolling out our new messaging across our online profiles. We completely rebuilt our website—again—every word, page, and picture. Visually, our branding changed significantly, and even our logo got a refresh (thank heavens).

It was still a work in progress—a brand is never done being built—and it still took time to prove its worth. But in time this brand (and the consistency around it) became valuable, helping us to better attract and serve our ideal customers.

2. Partnerships became significant.

It would be tough to look at our partnerships on the whole in this period and say, “That was a success.” And yet, you can’t deny how impactful the revenue from partnerships has been.

As with most things in a growing company, the successes make up for the failures and then some. The outlier success here was partnering with one of our upstream providers, Twilio.

They’d acquired our #1 competitor Zipwhip, decided to shut down Zipwhip’s software, and wanted to keep those customers still, in a way, using Twilio’s services. So we:

  • Partnered to help those customers have a soft landing with a similar service

  • Made sure any transfers from Zipwhip would still be sending texts through Twilio’s network

  • Built a “migration tool” integration so Zipwhip customers could transfer their data to Text Request with just one click and a few minutes

  • And put a full go-to-market motion around Zipwhip customers who were going to need a new platform

It worked beautifully. Over the lifetime of this partnership, we earned ~3,500 new accounts at a fraction of our standard cost to acquire. The first bit of that helped us power past the $10m mark.

In a way it was pure luck. In another, it was the culmination of a decade of good work and a great team coming together to take advantage of a massive opportunity.

Separate from this, we had some partnerships that looked more like enterprise sales, where other software companies began using our API. We had enough affiliates for that to be a regular source of new accounts, and a handful of agencies who’d managed texting for their clients.

We also built a decent number of integrations with key industry platforms (like HubSpot and Quickbooks) that either brought us referrals from their marketplace or helped us win deals because we could integrate with tech they already used.

Aside from Zipwhip, so single relationships was a catalyst for growth, but taken together they made an impact.

3. Formalized account expansion.

We’d always wanted customers to upgrade and add new features. We’d always tried to get one department or location that was using Text Request to champion us for the whole company. We’d nearly always had workflows and processes for it, too.

But this was the stage where we had a full strategy for expanding accounts, a team of people to do it well, tools to help them, and were intentionally measuring progress.

Personal training and outreach helped, new features brought new value, relationships with brand champions helped us reach more departments and locations, and we added in some small-but-effective prompts to tell customers when it was good to consider upgrading.

At the same time, we had a more effective strategy for minimizing cancellations (churn), that included improved support and proactive credit card expiration flows.

The combo of improving our expansion efforts and our cancellation prevention meant that revenue was growing each month, even if we didn’t earn any new customers. Thankfully we did both.

After implementing these 3 new initiatives on top of what was already working, all we needed was a bit of time, and we got to $10m ARR.

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