Taking the Leap into Venture Capital

In October, I joined the Bay Area investment team at OMERS Ventures, where I’ll be focused on B2B SaaS. I’m excited to be challenged, to learn, and to have a ton of fun along the way.

I’ve always been addicted to learning and problem solving. I’m naturally drawn to the broken glass. For my career, that has manifested itself with BizOps roles and tackling problems of growth and scale. Outside of work, I’ve been climbing for two decades and am hooked on the sport’s combination of mental and physical challenges.

While working at Zenefits, Intercom, and Slack, I’ve met a chorus of smart, driven people and I began angel investing on the side. I’ve also always spent time taking a macro view and coming up with my own perspectives on business, technology, and the future of work.

After 3 years at Slack and with the Salesforce integration in full swing, I began to think about my next play and moving into a full-time early stage investing role at OMERS Ventures ticked a lot of boxes.

Building the future of work

I’m truly excited for the future of work and what we’ll see develop within B2B SaaS. There are already so many challenges on the path to building a great company and culture. Software continues to make inroads in letting leaders focus on what truly matters when building businesses.

After a career spent playing an active role in the internal operations, processes, and technology development at companies like Zenefits, Intercom, Slack, and Salesforce, it is so obvious to me that there’s an incredible opportunity for innovative technology to make an impact. Businesses are consistently evaluating software that might save them 10% more time or give them additional insights. After being the buyer, evaluator, and user for countless software solutions at several different stops, I know it’s a mixed bag when it comes to the existing “best of breed” technology.

At each of those stops, I’ve been part of a team that has built things custom from the ground up to solve business needs when we wish we could’ve just bought something. At Slack, as we grew the sales & success team from 250 to 500 to 750 to 1,500, we consistently needed to uplevel the ways we operated, planned, and delivered. At Zenefits, when we quickly went from 80 employees to 1,600 in less than 2 years, that brought a host of challenges and we needed to constantly reinvent the ways that we worked within teams and across teams. As we built custom tools and processes, the results were often a mixed bag of quality, effectiveness, and adoption. If given the opportunity, I (and many others) would much rather buy than build if possible.

Here are a few areas that get me fired up along with a few companies trying to solve each space:

• Organizational Design, Coverage Model, and Headcount Planning: At organizations big and small, this is built on an army of analysts and spreadsheets. This might be the most important part of annual planning but it’s cobbled together with sweat and spreadsheets. Every year, headcount is the biggest investment decision for each leader, but the process by which we plan for it is broken. How can you even tell the difference between scenario A and B when they are just different sets of hundreds of rows in a spreadsheet? Examples: TheOrg, Trace, and ChartHop.
• Sales & CS Forecasting: More so than AI and machine learning, sales & customer success leaders want frictionless bottoms up forecasting with accountability at each level of management that naturally slide into their weekly forecasting cadence.
• Product lead growth (PLG): I’m excited to see innovation towards PLG-centric CRMs. At every company I worked at, we built custom internal tools to store and centralize product data and then painstakingly integrated that with Salesforce to arm our go-to-market (GTM) teams. Examples: Endgame and Pocus.
• Sales Productivity: There’s massive room for improvement for arming teams with content and deliverables for prospects and customers, or automating the tail end of those interactions. Examples: Cast.app.
• Data and Business Intelligence: The best teams and leaders are data driven and we need to bring data and insights to where people work and operate. At the same time, the reporting functionality within Salesforce and other “best of breed” systems is broken. Moreover, as teams work quickly to make data accessible, they need to implement documentation, governance, and tools to manage data sprawl. Companies like Continual, Datafold, and Transform.

In the world of B2B SaaS, I’m a true believer that competition doesn’t kill and that there’s room for multiple players. Software is a massive market, which is why beyond the metrics, and the hockey stick growth charts, it’s the team that truly matters. I am looking for founders that are passionate, smart, and able to articulate their space to a broad audience. Can they recruit top talent and paint a 5–10 year vision? Do I believe in their future worldview and can I add value along that journey? Do they have attention to detail and a focus on execution? Are they self-aware and open to change?

Bottomline, I’m excited to apply my operator background, GTM learnings, and PLG expertise towards investing and supporting companies. I know how to stand up GTM teams and operations for all segments of the market, both in the early innings and how to scale effectively during a company’s growth stage. I can also help steer you towards self-serve and PLG models that can then in turn feed your enterprise sales machines. And if I can’t help you, I will find someone in my network that can.

If you are building in the space and think we should talk, reach out. I will always make sure that your time spent in conversation with us is worth it from your side — because I know first hand how important that time is! You can find me at @justindouyang or jouyang@omersventures.com