I have been fortunate to witness first hand and be part of a hypergrowth story. I joined Hootsuite as one of three initial salespeople at a time when the company was bootstrapped and had no revenue to speak of. The product was already getting significant traction with a freemium model in place and a lot of customer love. Our job was to help launch a paid Enterprise version of the product. Fast forward to a few short years later and we were crossing the $150M ARR mark with Enterprise representing the bulk of the revenue.
During my time there I went from being an Account Executive working with some of our biggest customers, to leading several teams before heading up our North America East region (one of our largest) and an office in Toronto. When I look back at my roles and responsibilities there is a clear pattern – they were consistently about building out new growth engines: helping figure out our Enterprise Go-To-Market post Product/Market fit, building our first team focused on Mid-Market accounts and working alongside new leaders to fine tune our Inbound process, building a Large Accounts team and helping fine tune our Outbound process, building out new vertically-focused Strategic Account teams which ended up becoming some of the largest revenue segments and finally building a new office and region from the ground up in a new city with all the revenue, people and cross-functional responsibilities a de facto General Manager role requires.
I say all this not to brag but to humbly highlight my journey and ponder on how incredibly grateful I am for the learnings along the way. I had a first row seat to what was happening both on the front lines and in the boardroom. I worked with a world class team and got introduced to sales leaders and entrepreneurs from other hypergrowth startups in the Bay Area, New York, Boston, London and other places to connect and compare notes.
When I joined Hootsuite I didn’t come from a traditional Sales background – my background is technical. I remember how hard it was to learn about Sales and Go-to-Market while operating at a company that moved at a hundred miles per hour. It truly felt like figuring out how to build a plane while flying it. This was especially true in the context in which we were operating at the time: the Internet and Social Media were starting to completely transform the way buyers research, evaluate and buy products and services. More than ever before, delighting customers and helping them make the right choices was critical. There were very few playbooks out there on how to build Go-To-Market teams and old school sales methodologies (many of which are still followed blindly) were quickly becoming inadequate. Luckily we had a fantastic CRO early on who knew his stuff and I worked with a number of great Sales, Marketing, Customer Success and Product leaders along the way who taught me invaluable lessons.
Even so, my technical mind made me question and challenge everything – especially when it came to conventional Sales and Marketing notions and sometimes to the dismay of my managers and colleagues. I approached every methodology, strategy or process with a healthy dose of skepticism, ran experiments to validate them in our context, thought about the math, looked for patterns, built frameworks and tried new things. Thankfully my experiments mostly lead to consistent quota attainment! but while we clearly did a lot of things right as a Go-To-Market team, we probably made just as many mistakes along the way. The wins and failures both provided invaluable lessons that I would like to pay forward and share here.
While Hootsuite was the start, it was just the beginning of a journey that I intend to experience many times over as a revenue leader, entrepreneur, advisor and investor. Enterprise SaaS is witnessing another major shift in market context with the advent of PLG, AI and the digital-first world. Just as the Internet and Social Media have before, it is inevitable this will change Buyer/Vendor relationships and how each side go about running their business. More experiments will be necessary, more frameworks and Go-To-Market and mathematical models will be needed and I for one am excited about what this means for the future of Entrepreneurship and the Sales profession.
Thank you for joining me on this journey.