Last week, our company announced our Series A investment from world-class investors Lee Fixel of Addition and Mo Koyfman of Shine Capital. This marks a milestone for us as a company, and subsequently a great opportunity for the growth of both our team and our product. 

A fundraise is a snapshot of a moment in time, but the work we do in the background to prepare for growth and scale has truly been ongoing and continuous. Even before I joined Rose Rocket (over a year ago), building a world-class engineering organization had been an important goal for the team. Today, the added investment means even more opportunities to push that vision forward, and I’m excited to take the opportunity to formally introduce myself and talk about the future of Rose Rocket Engineering. 

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Hi 👋🏽, I’m Ian. I’m the VP of Engineering at Rose Rocket. 

A bit about me - My background has been vastly in consumer technology, with a previous focus on payments and financial software. Some highlights of my career so far include being the 7th engineering hire at Airbnb, where I eventually went on to lead upwards of a quarter of Airbnb’s Engineering team. At Airbnb, I spearheaded their Payments, Business Travel, and Monetization Engineering divisions. I was fortunate enough to witness and experience what it was like to grow a company 100x on every metric, from customers to usage to valuation, and many of my philosophies around what a world-class engineering organization and culture look like are deeply inspired by this experience. 

When it was time to put down some roots, we relocated to my home in Toronto where both my wife and my family reside, and I was incredibly excited to build world-class engineering teams right here in Canada. I joined consumer rewards leader Drop, and helped build their Engineering org and data strategy for almost three years. While at Drop, I led mobile product development in the loyalty space combined with applied machine learning solutions to surface recommendations and key insights for millions of users.

So what drew me to Rose Rocket? 

Whenever I am considering a next play, I always develop a rubric of values and factors that are important to me. This rubric includes founder & leadership alignment, market opportunity, and growth potential, among other factors, to keep me on track when making a big career decision. Assessing startups is not new to me by any means – I actively angel invest in companies and looking out for huge potential is something that is exciting and familiar to me. Rose Rocket came up on top across the board, amongst a few of the top software companies in Canada. There are many reasons why they stood out, but here were my top three:

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‍Founders with deep domain and tech expertise: 

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When I found out that the Rose Rocket founders have years of experience in trucking and the freight-tech space, this was interesting to me. Founders with deep industry expertise have an edge when it comes to growing a company because they have unique and novel insights when it comes to product innovation. In fact, the founders previously started a logistics company, called FR8nex, upon which they gathered key insights to take on a new approach with Rose Rocket. That paired with the fact that they were YC alums gave me a well-rounded picture of leaders who knew the pressures of startups and the needs of their customers in the vertical.

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An industry ripe for disruption: 

Throughout COVID-19, trucking has been in the limelight more than ever, but this foundational sector of our economy has been operating in the background for decades. With millions of trucking companies in North America, there is a true opportunity to build high-quality, cloud-native trucking software that pairs trucking logistics with a consumer-first experience. Everyone loves Airbnb and Instagram, but can that consumer experience be translated to trucking users? With my background in consumer products, I was truly excited to think of a future where our trucking customers can have access to software that feels like every other app they use on the internet. Also, with my background in payments and fin-tech, I was excited to lead an inherently complex product in logistics ripe for automation, simplification, and network effects from the ground up.

Cultural alignment around building high performance teams: 

This one’s an interesting one, because every tech startup will preach that they are looking to build a great culture with top talent – it is a given in the tech space. With Rose Rocket, I felt a sense of values alignment not only with the founding team, but with other engineering leaders I’ve met during my interviewing process. I am honored to say that over a year in, and I can still vouch for the high-quality teams we have built here, from the level of intelligence to how much each team member cares about our executional velocity, product quality, and customer focus. 

So what’s next?

As I’ve mentioned before, a funding round is only a snapshot of the bigger picture. At Rose Rocket, we’ve been building solid foundations for our Engineering team, and we’re excited to scale this as we grow our product offerings and customer base. Here are a few themes for Engineering growth for the foreseeable future:

More investments into product-outcome & foundational teams:

Rose Rocket Engineering teams are defined around outcomes. Having product-outcome teams is a way to ensure that engineering efforts are tied to the outcomes of our customers and business, and not just the outputs of our team members. This structure also allows greater ability to move resources to teams that need it, which ultimately allows engineers to get familiar with different parts of the codebase while adding speed and quality to our releases. 

Currently, our product-outcome teams include:

• Growth: Helping customers discover, onboard, adopt, and succeed on Rose Rocket faster.
• Network: Making connections between the different parties involved in the transport process - drivers, partner carriers, internal teams, and customers - work more effectively together. 
• Workflows: Ensuring the product has features that are needed in the day-to-day operations of a trucking back-office.
• Mobile: Creating workflows for drivers on iOS and Android and, in the future, enabling more workflows for different parties.
• Ecosystems: Building connections with other software that trucking companies use to allow them to choose the pieces of software that are best for their business.
• PSX (Product & Service Excellence): Delivering excellence in Rose Rocket’s products and services, in partnership with Customer Experience, to generate cost savings, efficiency, and customization.‍
• R&D (Research & Development): Developing emerging tech and unlocking new opportunities for the trucking industry.

Foundational teams are the backbone of Rose Rocket Engineering, and they work to make sure our developers are working effectively, and that our customers are getting the highest quality experience with Rose Rocket. These teams create a great amount of leverage and efficiency for other teams. They include:

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• Data: Getting increasingly sophisticated about how we structure and think about data, including building a data warehouse to help benchmark performance to bring more insights to our customers. 
• Infrastructure: Ensuring that the right tools, developer experience, security, and building blocks are in place for our team and customers to thrive at Rose Rocket.

We’re leveraging the momentum of a growth period to add team members to those areas of the business in order to be able to move even faster. 

More focus on pairing enterprise-grade software with consumer experiences:

We’ve heard from customers, that sometimes their newly hired employees would take weeks to months to be productive because the learning curve of their TMS is too steep. This unfortunately, is not a new experience for our industry. There is a huge opportunity in trucking to build a powerful piece of software, that people actually like using. While Rose Rocket is already ahead of the curve when it comes to how user friendly it is, there’s always room for improvement.

On the surface it looks cosmetic - we’re updating the product to make it look nicer and feel more intuitive. However, it really has a massive impact on our customers and their businesses. This is an industry where the tech is mostly bought by the owners and managers of trucking companies, without much thought for how the end-user - their dispatchers, CSRs, bookkeepers - would use it. The existing way of life makes onboarding challenging, creates delays in adopting software, and ultimately causes friction in an environment that is already hectic every day. 

There’s a big opportunity to democratize trucking software for companies of all sizes, and it all starts with the end-user, since the software is only useful if widely adopted. We’re heavily investing in making Rose Rocket even easier to use, to every role at a trucking company. Behind the scenes, we build using a modern software stack: Golang, React, Redux, Kubernetes, Terraform, CircleCI, and more.

More investment in data as a company: 

Having access to quality data helps us make decisions better, both for our entire company and for our customers. As mentioned above, we’re building a data warehouse to help customers benchmark performance in order to bring more insights. 

However, we’re also investing in data education across all departments. This means empowering the company to better understand usage behaviors to intelligently serve our market. Internally, our modern data stack will enable us to make more quantitative decisions, measure progress, and ultimately, launch us towards faster growth.

We’ve grown a nimble Data team to accelerate platform intelligence. They enable the validation of hypotheses and the creation of actionable feedback loops within the platform. The future of experimentation, benchmarking, and machine learning-powered features will all be enabled through our investments. There are real customer needs for optical character recognition (OCR) and other applied techniques to streamline workflows. Behind the scenes, we build using a modern data stack: Snowflake, Looker, Airflow, PostgreSQL, Heap, and more.

More focus on quality and speed, without burnout:

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Having been through the growth stages of both Airbnb and Drop, one thing is clear: high quality, high speed, and high growth don’t always go hand-in-hand with sustainable growth. Actually, they almost never do. We’re a people first company which means we also pay close attention to individual burnout.

As a company, we care a great deal about the code we push, since our software is vital to the operations of a trucking office. When anything goes wrong (and even with our best intentions, sometimes things do go wrong), the impact is felt by our customers. This is both a blessing and a curse – as an engineer, it’s amazing to build software that people actually use every day, and as an employee, there’s a lot resting on our team’s shoulders every time we make an update. 

This, paired with the fact that we prioritize shipping fast, means that often our team can get overworked. It’s an unfortunate side effect of a high-growth startup. This is also why burnout is so prevalent in our sector. 

As we head into a different stage of our company, we’re going to invest in how to grow fast while not overloading the team, which means additional focus on workload management, test automation, structural changes around release schedules, investments in pipelining for talent, and more. I’ve learned that being an investor makes me a better operator and vice versa. In fact, the technical investment mindset is precisely what I aim to instill in every Rose Rocket Engineering member so that there is a constant stream of efforts that yield high value.

This theme of sustainable growth doesn’t factor away high growth, it just keeps in mind that we’re humans working with other humans, and we need to be mindful around the programs, processes, and expectations we have for one another as we grow a company. 

In summary...

Kudos for reaching the end! I promise it’s close. 

My final note is this:

Additional funding is amazing, but we’re not reinventing the wheel overnight. We’ve made foundational investments to scale Engineering and we’re going to keep doing what we’ve been doing this whole time. Just at a faster pace, with higher stakes. 

We believe we have a great shot at making trucking more collaborative, between every user and every party in the transport process. If this resonates with you, we’re hiring across many departments at Rose Rocket and we’re excited to hear from you! Learn more about Rose Rocket careers.

Thanks for your time, 

Ian Logan

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