Onwards and Upwards — Rocketrip Story Pt. 1

Michael B. Gilroy
Jul 5, 2016 · 5 min read

Back in August of 2014 I met with Dan Ruch of Rocketrip for the very first time. For those unfamiliar, Rocketrip provides an enterprise SaaS solution for businesses that incentivizes employees to save money while traveling for work. At the time, Rocketrip made money on each transaction — for example, if an employee saved $500 on a business trip, the company (RT customer) would get $200, the employee would get $250 and Rocketrip would take $50. Five minutes into the conversation I remember saying to Dan; “I’ve never heard of a company with a solution that aligns incentives for every single person in the value chain. You don’t even need a sales force, this stuff sells itself”. Dan already knew incentives aligned of course, but there was still a herculean effort ahead of them to scale the business. While it’s true that every single person in the value chain is incentivized to use the software, Rocketrip was providing a brand new solution to the market — no one had ever tried this before. Two or three board meetings in it became clear that educating the market wouldn’t be a nominal task.

Being first in a brand new market is a double edged sword. On one hand, a first mover advantage can sometimes be enough to steal a market, while on the other, there’s a significant amount of time and money that are spent educating uninformed buyers. As a lean startup, Rocketrip knew this wouldn’t be easy, but looking back there are two things that they did extraordinarily well here.


The first is content marketing. For an early stage company, there is simply no excuse for not creating content, this is not rocket science. Not everyone is a great writer, but I’m willing to bet that every early stage company has at least one person capable of writing. Rocketrip has put out on average 12.5 blog pieces per quarter since January of 2015 when the team was less than 20 (no excuses!). They made the rather mundane topic of business travel fun with posts like this, and this (two things to note respectively; 1. They didn’t pay for infographics to be made, they repurposed from other research (read: didn’t increase burn)! 2. Tom Brady is a cheater). In a world where publication walls have been beaten down and everyone has a voice, there’s no excuse for a lack of content that tells your company’s story.

For all of you content marketing skeptics out there, the Rocketrip data doesn’t lie. The team did a study of the results from November 2015 to May 2016, and here is what they found.

— Share of total inbound leads from organic search increased from 24% to 42%. Meanwhile, leads from paid search decreased from 42% to 21%. In other words, by increasing organic discovery of Rocketrip, they could shift away from more expensive acquisition channels

— Leads from content marketing are qualified at a higher rate than other channels. The share of qualified inbound leads from organic search increased, from 28% to 42%. That’s a larger share than any other inbound channel (i.e. paid search, press, event marketing)

— Inbound channels (primarily search) accounted for an increasing share of late stage opportunities — from just over 25% of opportunities in Nov ‘15 to 34% by May ‘16. Put differently, the share of opportunities originating from unpaid inbound channels increased by almost 10%

— Unpaid inbound channels originated 26% of the total deals closed! The realized share of closed deals associated with these unpaid inbound channels increased slightly less than 5%, though the top of funnel opportunities have not yet matured through the sales cycle (check back in 3 mos, this # will be higher!)

Rocketrip was able to increase the number of leads at the top of the funnel, for less money while also increasing conversions — win, win situation. While a bit more difficult to quantify, the effort also led to Dan getting a weekly column in Inc. Which led to cool things happening, such as the CDO of McDonalds tweeting about it.

Fun Fact: Charlie Schaub, the Rocketrip Marketing Associate writing most of this content, learned about the company when a college acquaintance crashed on his couch while on a business trip to LA. Charlie learned that he was being paid to stay there instead of in a hotel and he liked the idea so much that he moved to NYC to join the team.


The second thing Rocketrip did was to be maniacal about customer evangelization. Your early customers are your very best sales reps, and they’re free. When you’re a startup selling enterprise software early customers don’t buy because you’re great at sales or have nice hair (sorry, Dan), they buy because they NEED your product, otherwise they’d never take the risk on a startup. It is your job to discover, nurture and capture that enthusiasm.

Rocketrip started Twitter wars with power users of their platform, further contributing to an already awesome culture at Opower. A nice byproduct is the additional engagement with the Rocketrip platform, of course. In addition to tweeting, the Rocketrip team hosted joint breakfasts and dinners, featured one of their employees on their blog, and invited them to participate in PR opportunities. Customer evangelization is undoubtedly difficult to quantify, but few can argue against it. In Rocketrip’s case, it has led to the very best marketing you can ever ask for (here, here and here). It has also led to testimonials, which are much better than customer reference calls (though they were supplied with their fair share of those as well!).


While Charlie and team were busy activating the sales funnel, Dan was iterating on the business model. Most customers were incredibly happy, but we noticed an uptick in churn, and engagement was varying more than we would have liked.

This is part 1 of the Rocketrip story. In my next post I’ll be going deep on their approach to addressing the churn and engagement issues. Dan made the incredibly difficult decision to shift the revenue model from transactional to SaaS, something that has yielded unbelievable results for the business, and customers.

The Rocketrip team has built something that is truly unique. We’re incredibly lucky to be partnered with this group of entrepreneurs who take pride in doing things the right way.

Michael B. Gilroy

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Canaan Partners VC — U.C. Berkeley California Bear — SF Bay Area Native