CTO Sessions: Aaron Rankin, Sprout Social

Name: Aaron Rankin

Company: Sprout Social

Job title: Co-founder & CTO

Date started current role: April 2010

Location: Chicago, USA

Aaron Rankin is CTO and co-founder of Sprout Social, an industry-leading provider of cloud-based social media management software. He leads the company’s technology strategy and oversees all of its engineering efforts. Rankin has astutely built the team’s tech culture around simplicity, scrappiness and common sense. Prior to co-founding Sprout, Rankin held various leadership and solution development positions at Endeca Technologies. His work on information discovery systems and big data in these roles led a natural progression into emerging technologies, particularly social media. Rankin began his career working for IBM's CIO solving strategic IT problems after graduating from Carnegie Mellon University.

What was your first job? I started delivering newspapers when I was 11, but at 14 I was developing marketing landing webpages for a dot-com startup. The company was an ecommerce retailer named Spree.com and if they’d succeeded they might be Amazon today. Funny story—I saw the job listing in the newspaper I delivered. By that age I’d taught myself HTML, CSS and Javascript from books, so I quickly typed up a cover letter and resume using MS Word and mailed it off. I was shocked to be called in, and only when my mother dropped me off did they realise my age!

Did you always want to work in IT? Yes! Ever since getting my first computer (a 1980 IBM XT, that I received in 1993) I’ve been hooked. I grew up in a working class neighbourhood and so a “good” job was learning a  trade, and a “great” job was in medicine or law, which was a far-fetched dream for most. I didn’t get exposure to much else until the computer opened my eyes to software development and IT.

What was your education? Do you hold any certifications? What are they? For undergraduate, I studied Information Systems and Computer Science at Carnegie Mellon. It was very theoretical, so I rounded my studies with the software engineering practice of the IS curriculum. I also layered in a professional Masters of Info Systems Management in parallel to my senior year of undergrad. This was like a technical MBA that covered broad business subjects, practical security and privacy topics, telecommunications, and operations research.

Explain your career path. Did you take any detours? If so, discuss. After my Spree.com gig, I spent my high school years working on Windows and Linux administration and Visual Basic ASP development for eCal. They were building something like Google Calendar, but selling it as SaaS (before it was called that). Those experiences, and a college internship with IBM Extreme Blue convinced me I wanted to focus on software development. 

After graduating, I found myself on a different track. The best job offer I received was working on IT security policy and strategy for IBM’s CIO. There I wrote lots of PowerPoints and no code, and ultimately I was miserable. 

So I followed a friend into a high growth startup named Endeca. They were similar to a proprietary, on-prem Elasticsearch. My gig there was centred around serious software development, but more to support strategic sales and business development opportunities rather than building shippable products. Those experiences were hugely formative. I was exposed to a diverse set of industries and high value business problems. Each project was almost like founding a new product and proving its value. Endeca was a fertile place for budding entrepreneurs and it was that experience that gave me the confidence and conviction to found Sprout Social.

What type of CTO are you? I see myself as an organic, from-first-principles leader. The way I pursue the role is to start by assessing what the company and team need from me. This is constantly in flux. Every year our company grows and evolves, and what it needs from this role changes. This means I’m continuously learning and adapting.

At this stage, I see my role as providing structure and resources, and helping teams to make good decisions on behalf of the business—then getting out of the way. In my work, I've had the most success and satisfaction when given responsibility and autonomy in exchange for accountability. With this in mind, I strive to build teams who understand their objectives and are resourced and empowered to get things done.

Which emerging technology are you most excited about the prospect of? This might be a boring answer, but I’m fired up about the power of managed Cloud services. Operating technology at scale in production is hard and resource intensive. Unless you are a Cloud provider, it’s not your core competency. The more you leverage the power of managed services, the stronger the fabric of your products. This enables your teams to focus on adding unique customer value. It warms my soul when we aren’t having to reinvent production grade databases and instead can focus on building our products and supporting our engineers’ unique needs.

Are there any technologies which you think are overhyped? Why? AI/ML, and sorry if that’s the clichéd answer. It’s a really interesting, powerful set of techniques that literally, if invisibly, affect our lives everyday. But real value is only being created by a narrow set of massive firms supported with the biggest data sets and most skilled practitioners. For the rest of us mortals, AI is mostly marketing snake oil and engineer catnip.

What is one unique initiative that you’ve employed over the last 12 months that you’re really proud of? What we do is such a team effort that I can’t take credit or pick one. We have about 30 healthy, hungry teams who are constantly shipping powerful customer-facing products. Whether they are refining our internal systems and tools to give their peers superpowers, or are rethinking our codebases and architecture to unlock the next level of products and experiences, every one of us plays a big part.

Are you leading a digital transformation? If so, does it emphasise customer experience and revenue growth or operational efficiency? If both, how do you balance the two? As a product/tech company, Sprout has always been digitally native/literate. So in the spirit of the question, we aren’t digitally transforming so much as constantly evolving. 

But if I answer from a different angle, we are transforming our product development model to scale our team towards a multi-product, multi-modality future. This is catalysed by the need for continued revenue growth, but that’s not what’s top of mind for me or the team at large. We’re squarely focused on maintaining excellent customer experiences while really ratcheting up operational efficiency.

What is the biggest issue that you’re helping customers with at the moment? Their own digital transformations. We all know consumers are shifting from physical stores to online, or from legacy tech like phone and email, to newer channels like social media and messaging. Sprout Social empowers brands to meet customers where they are and build deep relationships in these new forums. As these channels gain prominence, Sprout is helping our customers to bridge these new customer records and the associated intelligence with the rest of the stacks their businesses operate on. Legacy IT and business processes have not yet caught up to the era of social media.

How do you align your technology use to meet business goals? Having grown up as a tech startup we still embrace cycles of frenetic expansion followed by rational consolidation. This means our teams and departments have a lot of autonomy to experiment and solve their own problems most effectively. Over time, we find company-wide patterns that lead to standardising technologies to improve cross-company collaboration and operational efficiency. 

Do you have any trouble matching product/service strategy with tech strategy? I generally want to say no. When it comes to third-party choices our teams are excellent at evaluating build/buy and making smart decisions. Where we struggle is with “build” decisions that don’t fit our organisational structure. As we grow larger, we are hitting a number of these Conway’s Law scenarios—where your architecture resembles your organisation—even to a fault. We’re learning to be intentional about first identifying the ideal strategy or architecture, and then aligning our organisation to build it correctly.

What makes an effective tech strategy? Technology is a business enabler so effective tech strategy must be in service to optimising business outcomes on all levels. Strategy is not an outcome or artifact, but rather an approach. I think of it as a compass for making the best tech decisions on behalf of the business. Great strategy empowers a technologist or team to make choices that are both in service of their objectives and overall business success.

What predictions do you have for the role of the CTO in the future? It will encompass more and mean less. What a CTO is or does will broaden to support new needs, but in turn, the role will become more general; less about being a great practitioner of something specific. As this happens we’ll see more specialisation among the CTO’s leadership team.

What has been your greatest career achievement? I can’t be more proud of how Sprout Social has grown to make a positive impact in the world. From the testimonials of what we mean to our customers, to the example our culture sets in the corporate world, to the craftsmanship we’ve cultivated among our team and alumni. I won’t take credit—it has been a 12-year-long team effort—but having been a part of it, having taken the risk at the beginning that catalysed it into being, and having worked to guide it culturally, this will be hard to top!

Looking back with 20:20 hindsight, what would you have done differently? I continued to code too long into our company’s history. Almost as a badge of honour, I proudly coded well into my fifth year as CTO, largely under the false belief that it was the best way to apply that time. Looking back, I recognise that my attention would have been better spent nurturing our team.