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Latest news and insights from the Canvas Ventures team



November 2022

Now Is the Time to Be Opportunistic

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The next ten years are a building opportunity like we haven’t seen in a long time.

I came into venture right after the 2008 crash. I saw the opportunity. The crash hindered the market, and everything froze. If you look back at the patterns of this industry, everything is cyclical.

While marketers should certainly cut expensive unnecessary spending, the smartest ones out there know that now is the time to test, learn, and grow. Channel by channel, you should already know the optimal price you want to pay; if your favorite channels haven’t dropped to your number yet, take a beat, because they might tomorrow and you’ll be well-positioned to snap up inventory at the right cost. Also, try negotiating with advertisers on channels you have been wanting to test but have been too expensive. Finally, if you have a channel that’s working, but you don’t love what you’re paying for it, you should definitely try renegotiating, as your competitors are likely pulling spending.

Having lived through three market cycles, I have put all of these strategies into action myself. At NextCard in 1999 and 2000, instead of turning off advertising altogether, we waited until the prices dropped and then bought advertising spots for half the price while everyone else’s ad spend remained frozen. The very same thing happened in 2008. 

I recently asked our GTM Council members for their best advice on how to be opportunistic today. 

Interested in participating in events about Go-to-Market hosted by Canvas? Let us know here.


Go back to your customers and ask them three key questions.

Ashley Blackmon led Zillow’s growth marketing strategy between 2011 and 2018. She built a 60-person department from the ground up, and created & launched the marketing team for Zillow's Premier Agent product, driving over 45% of new monthly revenue. Over Ashley’s tenure, the Zillow business grew from $30M to over $1.3B in revenue. Ashley is currently the CMO at Restream, a live-streaming company, where she has doubled subscriber conversions in the last six months.

“Under ‘normal’ circumstances, most people are short on time and attention; in stressful macro environments (like a recession), decision fatigue can prevent people from taking action. It’s more important than ever to understand who your customers are and the benefit you provide for them. Here are a few key questions I always ask:

  • What problem are you trying to solve? This will help you not just identify the problem the person is trying to solve, but also the desired outcome, in their own words. 
  • Walk me through the steps you usually take to solve the problem. This can often lead you to someone’s process or sequence of actions to solve a problem. 
  • What is most challenging about solving this problem? This can lead you to identify areas that you can optimize along the user journey.


Refresh your story to be especially timely; focus on how you're helping, not what your product does.

Matt McAllister has built brand and growth teams at three companies pre-acquisition. Matt was the fifth hire at Mobile Tech RX driving a product-led growth engine that produced 98% of ARR in 16 months. And in the past year and a half at Yelp for Restaurants, Matt has doubled marketing-sourced revenue. 

“The first must-do is story refresh. You've likely done a ton of work nailing your narrative and value props, but your audience's mindset changes when the economy does. It's time to double down on customer support-focused marketing, referral loops, and PR. The brands that move the fastest to help before selling are the most likely to maintain growth rates. In the early days of COVID, we at Yelp made the call to cut fees earlier than competitors. It kept churn to a minimum and gave us a story to use through sales and marketing channels to keep new customer acquisition steady.” 


Get laser-focused on the audience segment that has the most significant potential.

Andrea Collins has 20 years of experience as a DTC marketer with expertise in fintech and insurtech. She was the first marketing hire at Hippo creating & leading a marketing strategy that scaled the company's sales 4x and expanded the company's footprint from 0-65% over 4 years before taking the company public in 2021. Previously she was one of the first 15 employees at PolicyGenius, the first D2C insurance marketplace where she developed a content-driven marketing model that drove 3x organic traffic during her tenure that accounted for +25% of the company's sales each quarter. She is now CMO at Canvas portfolio company, Flyhomes

“Now is the time to start looking for a critical market or segment to find your opportunities for success. When we hit a slowdown at PolicyGenius in late 2015, we started looking for the segment bringing in profit the fastest. It turned out to be moms for our most profitable insurance lines, the person leading finances for their families. It allowed us to find and develop a profitable business out of an individual market. We were then able to intelligently grow starting from there instead of just reflexively cutting everything.”


As others take their foot off the gas, have several tricks up your sleeve.

Nick Fairbairn served as CMO of Canvas portfolio company Gabi and led the team through the 2021 Experian acquisition after scaling 500% in less than two years. Previously VP of Marketing and Director of Acquisition at Dollar Shave Club, Nick delivered a 300% increase in revenue before the company’s $1B acquisition. Nick is also a former Executive-in-Residence at Canvas.

“I love a bear market because it creates a force for responsible growth and innovation. I grew up in the ad agency world. In the ‘08 crash, everyone’s first instinct was to slash budgets. My advice? Spend on it but be thoughtful. Revising guidance is okay but shouldn’t be the first instinct. Don’t miss an opportunity by acting short-sighted. Slashing short-term targets might make your midterm targets that much bigger. Be nimble, creative, and resourceful to find the growth but keep your team and leadership grounded in reality, as growth hacking can only go so far. And truly, you need to assume everything will change and have flexible options ready to go.”


Incentivize your best customers to stay loyal—and bring others along with them.

Declan Schweitzer was one of the first growth hires at pioneering early-stage companies Headspace, Bird, and Albert. Declan built Albert’s growth team and added 300,000 paying customers through paid marketing channels in 18 months. At Bird, he increased 1st purchase CVR by 19% and purchases per user by 18%. Declan also managed multi-channel growth marketing campaigns at Headspace, adding more than 350,000 subscribers between 2015 and 2018. He currently leads Rain’s growth organization. 

“When consumers are more cost-conscious, they need extra incentives like a referral to convert to paying customers. A referral program's inherent social proofing and incentive mechanism go a long way. Lifecycle communications are essential and low-cost tactics [Push, SMS, In-app, Email]. A well-timed message to a user can be the difference between a conversion and not if you effectively understand what a user is asking you for and respond appropriately. Think of each user event in your database as a signal from the user about what they want. Once you know what a user is asking you for (i.e., what events they are triggering), you can figure out the correct response and deliver it via CRM channels.”


Figure out just how much you can get out of your winning channel.

Jamie Young Perlman has held a number of roles over the past 20 years, including business development roles at Dropbox, Box, and Slideshare. In 2008, at SlideShare, Jamie helped the company land on its revenue model, bringing in its first seven figures in ad revenue. As Box’s 61st employee, Jamie grew strategic partnerships from $0 to deliver a double-digit percentage of company ARR. He currently leads the business development function at Dropbox.

“People and companies still spend money, even in recessions. They're just being more thoughtful about whether they really need to make that particular expenditure. If the need is real, your solution is good, and you can insert your product into the consideration set at the right time, then the macroeconomic environment matters less. So it's doubly important to ensure that your solution is mission-critical and that it is promoted in a relevant setting, at the time of need. My teams start with a strong data-based hypothesis that leads us to believe a particular motion or channel will yield results. Then we work methodically to prove or disprove that hypothesis until we land on a winning approach that can be scaled. Having conviction up-front in the hypothesis allows us to continue to chip away at a particular opportunity despite challenges or setbacks. While this approach is relevant in any market, it's particularly relevant in a bear market where resources are tight, and you can't afford to misspend them, but you still need to learn and grow.” 


When exploring a new channel, give yourself the right amount of time to understand if it’s working. Don’t cut bait too fast!

Patrick Moran is a consumer marketing leader out of Houzz and Spotify. At Houzz, Patrick created paid media, lifecycle marketing, martech, and analytics teams across the company’s consumer and eCommerce verticals. Between 2017 and 2018, when Spotify went public, Patrick played a key role in increasing Spotify's MAU from 160M to 207M, or a 30% YoY growth rate globally, by developing the company's growth plan, which informed investments and objectives in acquisition and lifecycle marketing.

“There are two paths to consider on the paid media front when faced with slowing or declining acquisition challenges. The first is to continue optimizing existing channels. The second is to expand to other channels. Most companies will default to the second without truly considering the cost-benefits of doing so. Continuing to focus on existing channels is usually not that much of a drain on existing resources. If companies choose to invest in additional channels, they should do so knowing that there is a cost to learn, and it usually takes more than a few weeks to get a decent enough read on whether to invest further in those channels. This is why a lot of companies are investing in other forms of distribution like PLG, organic acquisition, and community building to address CAC. ”


Don’t overlook “free” activities that help you retain and build market share.

Coley Czarnecki was one of the first PMMs at Uber and served as the first product marketer on grocery delivery, which has since grown into a multi-billion dollar business. Today, she leads marketing for Uber One - Uber's global membership program across Uber and Uber Eats. 

“People oftentimes aren’t considering their owned channels—they are “free” and often allow for fast experimentation. Outbound channels, like push and email, or modular product surfaces, like in-app messaging, are top of mind.”

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