Year In Review - 2021

2021 was an incredible year to be investing in technology companies.

The level of interest and capital available in 2021 increased as a result of the vast set of opportunities in SaaS and Cloud technology against a backdrop of accelerated Cloud adoption. The pandemic highlighted a number of trends causing many industries and sectors to prioritize their digital transformation. Businesses are accelerating their transition to online and the cloud, as their customers expect seamless, delightful and efficient experiences. Fortunately, a set of new, easy to use, secure solutions that can launch quickly are now available and proven. When you add in the intelligent, proactive features that AI can layer onto these solutions, you see agile businesses and their technology providers experience tremendous growth.

We were fortunate to anticipate a number of these trends and make some previous B2B Cloud investments that saw their businesses grow and benefit from the accelerating move to the cloud. 

The number of quality companies we saw this year also led us to have our busiest and most active year of investing. 

As we look ahead, we intend to continue with our thesis of backing the most ambitious entrepreneurs building category leading B2B companies, from Seed to Series B, in Canada, the US and Israel.

We are excited to continue the momentum into 2022, and have some exciting announcements coming about incredible founders with which we’ve partnered.

Portfolio Highlights

Our portfolio collectively raised $500M in follow-on capital this past year, including Ada’s $160M Series C led by Spark Capital, and Drata’s Seed, Series A, and Series B, all happening within ten months. We were fortunate to work with and invest in Drata’s Seed financing in January, and continued to invest as part of the $25M Series A led by GGV and the $100M Series B led by ICONIQ at a $1B valuation.

The growth, execution and velocity of both the Ada and Drata teams continue to impress and pave the way for their dominance in AI-powered chatbots and Security and Compliance. 

Spatial also made a splash with $25M in fresh funding to fuel their focus on the Metaverse, as did TopHat with their $72M Series D.

360 Insights continued to expand organically and augment their offerings with their  acquisition of CR Worldwide and Channel Maven, expanding their blue chip client base and augmenting their management team through these acquisitions.

CallRail acquired PhoneWagon, and welcomed a new CEO, Marc Ginsberg. It has been an incredible journey and a pleasure working with Andy Powell as he transitions to advisor and board member, after nearly a decade of leading CallRail as CEO. 

CrowdRiff made major recent additions to its management team, including adding a new VP Product, VP Marketing, VP Engineering, and VP People. More news coming on this in 2022.

Seegrid expanded their product offerings with the release of the Palion Tow Tractor, featuring enhanced path and surroundings comprehension, extended field of view and short clearance height


Our journey with three portfolio companies came to an end this year, as SNYK acquired Manifold, Optimizely acquired Zaius, and Audax Private Equity acquired a majority investment in FlashPoint Intelligence. We’d like to congratulate the Manifold, Zaius, and FlashPoint teams on exciting and meaningful runs as independent companies.

New Investments

Alongside the exits came a set of new companies in the Leaders Fund portfolio.

For 2021, in addition to follow-on investments in existing portfolio companies,  we led investment rounds into three stealth companies in three sectors: Construction Tech, Machine Learning Op (ML Ops), and Enterprise Tax Software. We’re excited to announce all three and share more details in early 2022.

As we mentioned in last year’s Year in Review, ecommerce was a big focus for us in 2021, yielding our largest investment to date, where we led the $35M Series B in Threekit, a Visual Commerce company bringing AR/VR and 3D shopping experiences to ecommerce. 

We also participated in Upscribe’s $4M Seed round led by Uncork to fuel their mission to enable Shopify stores to offer subscriptions for their D2C products, serving customers like Athletic Greens and Four Sigmatic.

What’s ahead

In 2022, we will continue to back world-class SaaS founders across Canada, US and Israel solving mission critical problems for businesses.

Within B2B SaaS, we expect to focus on Cloud Infrastructure, Compliance, Machine Learning Ops (ML Ops), and Construction Tech , as the shift to the cloud is still in the early innings.

We are also excited to continue backing founders in our two backyards: Toronto/Canada and Atlanta. As our portfolio companies, Ada (Toronto-based), 360 Insights (Whitby-based), and CallRail (Atlanta-based) have demonstrated, Canada & Atlanta are excellent places to build world class technology companies.

Final Thoughts

While the world has changed immensely in 2021, what has remained consistent is the resilience and determination of founders building in this rapidly changing landscape. 

We are excited for this upcoming year and the new founders we will meet and have the opportunity to partner with in the next 12 months. 

Until then,

The Leaders Fund Team

Published on
December 22, 2021
Thought Leadership
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