A Marketing Leader's Guide

Driving Growth With Smart Bets

Outline of chapters


Looking the Storm in the Eye

To put it mildly, the current economic situation is strange. Faced with a storm shaped by unprecedented conditions, pundits are hard-pressed to predict what will happen next.

In past recessions and crises, macroeconomists and experts forecasted outcomes with confidence. But now, the Federal Reserve has its hands tied—they should be increasing interest rates more, but they can’t because it creates too much systemic risk across the financial sector.

Metaphorically speaking, they’ve lost control of the rudder. Interest rates are at the mercy of capital markets and government spending. And with an election on the horizon, politicians are unlikely to cut spending and rein in inflation any time soon.

So, though the length and severity of the current storm is unpredictable, one thing's for sure: We’re in for a rocky ride.

If you're a marketing leader in the tech industry, this is hardly news. With interest rates through the roof, growth valuations have taken a hard hit leading to budget cuts, hiring freezes, mass layoffs and widespread alarm. Given these circumstances, you’d be forgiven for feeling a little grim.

But all is not lost. While the tech industry is recalibrating, many classic sectors, like consumer packaged goods (CPG), retail and insurance, are still experiencing growth. In addition to looking to these sectors for expansion opportunities, it’s time tech giants took a page from traditional business playbooks and moved to a model centered on sustainable growth, managing costs and profitability.

The key word here: Sustainable. As Hanna Larsson, a GTM Advisor and Fractional Revenue Leader, explains: The era of mythical unicorns and growth at all costs is at an end. In this new age, companies should consider the humble camel as a model for growth; able to adapt, survive and thrive in even the harshest climates.

How to thrive in even the harshest climates

Like today’s macroeconomic storm, the desert can be harsh and unpredictable. But if you’re a camel, you have mechanisms to protect yourself against calamities, survive without sustenance and thrive against all odds.

So, how do you become a camel? How do you build a long-term, healthy organization that’s able to shift with the market, remain agile and grow even stronger through adversity? These are some of the questions we’ll strive to answer from a marketing and design perspective in the chapters to come.

In other words, consider this your guide to antifragile marketing.

In his seminal work, Antifragile, Nassim Nicholas Taleb, explains, “Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.” He goes on to urge his readers to use randomness, uncertainty and chaos, not hide from it.

Similarly, we’ll make a case for leaning into today’s market and continuing to place smart, calculated bets on growth.

Now, this may seem to oppose our earlier point around sustainability and cost management. But in fact, it’s complementary—part of placing “smart” bets is balancing where to reduce costs versus where to invest in growth. Though the knee-jerk reaction may be to cut costs across the board, there needs to be a balance. You can’t cut your way to a positive outcome.

On the contrary, history has shown us over and over again companies that invest in growth in uncertain times come out on top. Deloitte’s Global Marketing Trends Report for 2023 highlights this fact stating, “Investing in marketing during a downturn could contribute to future growth.”

But do the people agree? We surveyed almost 300 marketing and design professionals at mid-market to enterprise-sized companies and asked, “Do you believe companies that invest in growth in turbulent times have an advantage over their competition?”

Think of it this way: While your competition is cutting back, you can fill the gaps.

As Meghan Keaney Anderson, VP of Marketing at Jasper, explains, “If you have capacity to invest in growth during turbulent times, it can set you up well for the other side. Turbulent times typically mean uneven times. Look for the industries and customer groups for which growth hasn’t slowed and invest heavier in those segments. If you can, also make brand investments as turbulent times can mean less competition for attention and your brand dollars go farther.”

But we’re getting ahead of ourselves! We’ll unpack this advice further a little later on. Suffice to say, there’s a lot to be learned from SaaS leaders with a strategic investment mindset, like Jasper, Zapier and Figma—to name just a few.

Let’s start by taking a look at how a few companies have not only weathered past recessions and the present SaaS slump, but continued to grow and get stronger throughout it all. That is, what makes them antifragile. Need a pick-me-up before diving in? Watch the video below for some inspiration.

Beyond the tech industry, there are countless more examples of brands finding the light through the gaps in the clouds. From toy titans like LEGO to insurance giants like Progressive, companies with investment mindsets, tenacious teams and creative cultures can and have come through many an economic slump stronger than ever.

As Sam Jacobs, CEO at Pavilion, put it, “If you’ve got some moxy, if you’ve got some interesting marketing ideas, now is a time you can build a powerful and authentic brand that zigs while your competition zags.”

Which brings us to the question of the hour, “How?”

It all starts with building a resilient organization…

Chapter 1

Building a Resilient Crew

There’s an old Norwegian proverb that goes, “The ancients were no fools.” Though not a perfect translation, the meaning of this proverb transcends cultural boundaries.

And in response to today’s volatile technology industry, we expect to see this wisdom in action. Leaders will look to traditional business practices and mindsets that were popular 10, 20 years ago. Not only will the focus shift to sustainability, but resilient organizations will roll up their sleeves and do more with less.

The right organization design and culture is the foundation to be able to accomplish more with less resources, and ultimately, react to the market in an agile way.

In other words, resilience starts from within and goes hand in hand with agility. Both of these qualities are essential for organizations to adapt, innovate and look for long-term opportunities in the face of uncertain markets and unstable times. As the Baldrige Criteria for performance excellence explains:

“Success in today’s ever-changing, globally competitive environment demands agility and organizational resilience. Agility requires a capacity for rapid change and for flex­ibility in operations. Organizational resilience is the ability to anticipate, prepare for, and recover from disasters, emergencies, and other disruptions.”

So, let’s dig into how to build resilience and agility on an organizational level. Note, while any business leader can get value from the insights to follow, we’ve geared them towards our specialty: Marketing and design teams.

The building blocks of resilient marketing and design organizations

As we’ve touched on, resilience and agility start with your organization design and culture. Build these characteristics into your team, and you’ll be able to overcome just about anything the market (or the world) throws at you.

Gaurav Agarwal, Chief Growth Officer at ClickUp, put it this way, “Strong winds make good sailors. Times like these bring people together and create great teams. In the end, having the most capital does not guarantee success. The truth is, the team with the most hustle and grit will come out on top.”

So, how can you build grit and antifragility into your marketing and creative teams? Watch the video below for some quick tips or read on for a deeper dive into the structure and culture of resilient organizations, based on interviews with experts, the latest research and our own experience.

What goes into a resilient organizational structure?

The actual structure of your marketing and design organizations will depend on your product, company and go-to-market strategy. So, rather than tell you whether your teams should be centralized, embedded or hybrid, we’ll focus on a few key insights designed to help you foster resilience and agility. Plus, structure isn't everything...

In fact, how well your teams align and collaborate is more important for driving results than any single organizational structure.

Case in point: In a recent report, McKinsey & Company found more collaborative creative teams drove higher business performance, but organizational structure didn’t affect how well design teams collaborated cross-functionally.

What did contribute to success?

Greater exposure or “surface area” of designers across the business and keeping the function flexible. To accomplish this, McKinsey found many business and design leaders organized, “designers to operate primarily within their cross-functional project or product team while retaining a secondary alignment to design leadership and a broader design community.”

In plain English, designers were part of both project-based teams and the overall creative organization. Whether you’re running a creative or marketing team, the same concept can apply. For marketing teams, the equivalent would be a distributed production model where marketers own projects or channels while maintaining alignment to leadership.

As Lauren Sudworth, Head of Brand and Content at PhotoRoom, explains, “I firmly believe that distributed production leads to greater ownership and better results. Teams that know a channel like the back of their hand are going to produce better creative.”

At Superside, we’ve implemented this concept using an organizational framework we call “AstroPods.” Basically, AstroPods are agile, cross-functional squads dedicated to specific problem areas. Each pod consists of a leader, a project manager (PM), a creative lead and supporting team members. For example, we have an Ad Creative AstroPod led by our Director of Growth Marketing, with support from our Marketing PMO and Director of Brand and Marketing Creative.

The beauty of this model is that each pod aligns back to overall team goals, making both marketers and creatives accountable for results and creating an environment where everyone is moving in the same direction. Not only does this setup breed better results, it means leaders don’t need to keep restructuring their organization.

Why? Because regardless of whether your design organization is centralized or decentralized, hybrid or agile, this pod model can work. It allows marketing and creative departments to contribute resources to projects as needed—all while building trust business-wide and exposing team members to different skill sets, knowledge and expertise.

This last point is especially pertinent. In their survey, McKinsey highlighted how crucial it is for designers to understand the business beyond the creative department. Specifically, designers at top-performing companies were “up to 10 percent more likely to have expertise beyond design.”

Of course, this finding lines up with the importance of cross-functional collaboration for business performance. But it also highlights how design performs best when it’s a strategic function—a team of trusted advisors that understand business goals and contribute to decision-making.

To become strategic partners, your design team needs two things: Space and trust. A team that’s constantly over capacity won’t have the headspace or the time to contribute at the strategy layer. To solve this problem, Zapier’s creative team uses strong prioritization and a strategic creative partner to handle overflow.

“We leverage self-management tools like our Prioritization Framework which Design Managers and ICs use to measure the impact of active projects against the overall effort required to meet team goals. We use this as a guide to help us decide on and prioritize tasks by urgency and importance, sorting out less urgent and important tasks which we either delegate or if necessary, say no to.”

Aaron Poe
Aaron PoeHead of Creative at Zapier Brand Studio

Throughout McKinsey’s research, establishing trust and empowering designers to contribute to decision-making was also a central theme. One Chief Design Officer (CDO) summed it up in a quote from an executive at his company, “We used to tell the designers what to do, now they’re showing us what is possible—and it’s so much better.”

Now, it might be more accurate to say creative teams as service centers is the “old old way” of doing things. For many organizations, moving to a model where the creative department is a strategic partner is an ongoing transformation. You might be at a stage where part of your team operates as order-takers while some parts can lead.

Regardless of where you are right now, the key is to recognize the value of aligning creative teams with concrete objectives, which empowers them to participate in strategic conversations.

Again, the same can be said for marketers. Marketing teams perform best when they collaborate cross-functionally, have a deep understanding of business objectives and can make decisions locally. After all, the more decisions team members can make, the faster your organization can move at scale. In a recent podcast episode, Dave Gerhardt, founder of Exit Five shared his thoughts on moving fast at scale:


To sum things up, rather than obsess over hierarchies or matrices, ask yourself the following questions when organizing your teams:

Quick tip

How to gauge org structure effectiveness

Ask yourself, how much “surface area” does my marketing or design team cover?How well does my marketing or design team collaborate cross-functionally?
How aligned is my team to departmental and business goals? How empowered are team members to contribute to decision-making?

What type of culture fosters resilience?

Culture is a loaded term, so we’ll start by unpacking it. In the context of resilience, we’re using the term “culture” to refer to a mindset—a lens that will allow your team to shift with the market and be nimble. At its core, a resilient culture embraces change, instead of bracing against it.

As Jim Collins points out in his book, Built to Last: Successful Habits of Visionary Companies, “Deep restlessness is far more important and powerful than simple ambition or raw intelligence. It is the foundation of resilience and self motivation.”

Never has this been more true than in the current market. In an environment that’s shifting by the day, the willingness to adapt to new realities, shift strategies and make smart bets, will determine who sinks and who swims. Like a child building up an immune system through exposure to germs at school, companies who take on a healthy amount of risk will emerge stronger on the other side.


So, what characteristics support this type of resilient, adaptable mentality? Though not an exhaustive list, here are some of the values we foster at Superside that have helped us stay agile and resilient at scale.

  • Versatility and scrappiness. Organizations no longer have the luxury of just throwing a body at a problem. In this new reality, the more versatile and scrappy your people are, the more resilient your organization will be. By looking to people with diverse skill sets—ones who like to roll up their sleeves and solve problems—you’ll be able to accomplish a lot more with limited resources.
  • Agility and speed to market. When disaster strikes, new technologies emerge or the world simply changes, organizations who are agile enough to adapt have a much better chance at survival. Hand in hand with agility, the ability to respond swiftly in these situations can determine whether an organization thrives, survives or dies out. Simply put, it’s safer to move fast than to move slow.
  • Local decision-making. Beyond allowing organizations to move faster, local-decision making puts the power in the hands of the people who are closest to the problem. Often, this leads to better decision-making, rather than comprises by committee or top-down edicts. Plus, teams that make their own decisions take more ownership, leading to more accountability, or as they say, “skin in the game.”
  • Experimentation mindset. In a rapidly changing world, companies simply can’t afford to not experiment. The way we consume information, interact with brands and complete simple tasks is changing. Why then, would your strategies stay the same? In brief, embracing an experimentation mindset, pushing boundaries and learning from missteps, is the only way to stay relevant… let alone get ahead.
  • Creativity (or boundless curiosity). Creativity is at the epicenter of a resilient mentality. Not to be confused with the ability to come up with ideas on demand, we think of creativity as boundless curiosity. On the deepest level, creative individuals are persistently curious. They like to ask why, solve problems and take risks. It all ties back to deep restlessness, and yes, the bottom line…
The relationship between creativity and business performance

Though it may be hard to define, a wealth of research shows creativity is tied to business performance. Most recently, in their annual Global Marketing Trends Report, Deloitte found 90% of high-growth brands agreed with creative values, while only 33-42% of their negative growth peers held the same values. Specifically, those values were:

  • Fostering creative ideas
  • Encouraging risk-taking
  • Promoting creative collaboration

According to our research, most marketers and designers do believe, “Creative ideas are essential for long-term success.” When asked how strongly they agreed with this statement on a scale of one to five, 88.3% of respondents rated it a four or higher, with 58.3% giving it a four and 30% choosing an enthusiastic five.

Tall ship and bubbles

“Creative ideas are essential for long-term success”

On a scale of one to five, 88.3% of respondents gave this statement a four or a five.

The takeaway? It might feel safe to stick with well worn playbooks, copy competitors or draw within the lines of a brand book, but as Dmitry Shamis, VP of Brand and Creative at SEVENROOMS, put it, “Where’s the growth? If you're not thinking about the next big swing then you're only focused on surviving. If you're just surviving then you're not thriving.”

A note for leaders on culture in turbulent times

We’ve been beating the adaptability drum pretty hard here! But there’s an important distinction to be drawn for leaders: Your strategies should change, but your core values should stay as consistent as possible.

Though it may be tempting to turn over every stone in the search for solutions, stick to your foundational values. As sailors say when bearing down to fight through a storm, hold fast. In the long run, you’ll save your ship from capsizing.

Chapter 2

Recalibrating Your Compass

In an unstable economy, it can feel like the sun is rising in the west and setting in the east. Facts become fluid. Things just don’t work the same way they always did before.

So, though you may have charted a course forward in the past, the facts have changed. The poles reversed. Growth is no longer a land grab. Between dwindling demand and limited resources, leaders need to recalibrate their compass and make sure every bet counts.

As we’ve seen, a resilient organization will embrace these changes. For marketing leaders, that starts with re-accessing your unique business situation. There are several factors to consider when laying down new plans. But for starters, the most basic question to answer is, “What’s your appetite for risk?”

If your company is well capitalized, you’re still seeing growth, your revenue per employee is decent and your net dollar retention (NDR) isn’t tanking, you may have more appetite for risk. On the other hand, if you’re under capitalized, the opposite may be true.

If you’re unsure what type of risk is appropriate, you’re not alone. It’s a tough market to gauge. That’s why instead of trying to predict the way the winds will blow, we recommend looking within…

Key metrics to reassess in this market

Is your marketing organization sustainable? Possibly, but bear in mind with interest rates through the roof, ROI requirements are much higher than they used to be. That means, it’s not enough for a program to simply yield positive ROI anymore. Depending on capitalization, your programs might need to drive an annual return of 10 to 15 percent or more to be viable.

So, first things first, make sure you have visibility into the revenue metrics and overall unit economics of your company, including how each function contributes.

In a big business, this is easy to lose track of… but that doesn’t mean you’re off the hook. If you’re in a revenue function, understanding these metrics should be ground zero for any plans or programs.

To that end, there are 101 metrics we could talk about, and you probably track 99 of them. Of the metrics you track, many will ladder up to or feature in your OKRs or goal-setting framework. But before setting a single goal, you should know your North Star Metric(s)—the one or two top-line metrics your whole company can rally around. The metrics that really represent the health of your business.

Of course, your North Star Metric(s) will depend on your GTM strategy. We'll take a closer look at GTM motions and how they tie in to goals a little later on. But first, here are some real examples of North Star Metrics from 10 growth-stage tech companies to help you hone in on the right constellation for your strategy, courtesy of investor and former Airbnb product lead Lenny Ratchitsy.

To explore more examples of North Star Metrics, check out Ratchitsy's article on the topic.

Once your North Star is set, it becomes much easier to identify which levers to pull to make a real business impact. For example, if your North Star is revenue growth, you might plan programs to optimize net dollar retention (NDR). On the other hand, if you’re interested in growth efficiency, you might focus on improving payback period.

By the way, both of these metrics are especially pertinent in today’s macroeconomic climate. Watch the video below if you’re unfamiliar with them! Or, keep reading for a discussion of a few key B2B and B2C metrics, given today’s need for more sustainable business models paired with higher ROI requirements.

Examples of B2B & B2C metrics

Payback period

Payback period is almost like a measure of sustainability. If it takes you ages to pay off the cost of acquiring a customer, your growth engine lacks efficiency and may not be sustainable. On the flip side, the shorter your payback period, the better your growth outlook and capital efficiency.

Of course, what constitutes a “short” or “long” payback period will vary depending what industry you’re in. For SaaS companies specifically, a recent report found businesses with an annual recurring revenue of $50M or more had a median payback period of 16 months.

Now, you might think the lower the payback period the better. Technically this is true, but the reality in the current market is that many deals are stuck, stalled or taking longer to come through due to increased scrutiny of spend across the board.

So, if you’re a well-capitalized business, it might make sense to accept longer payback periods right now. That way, you can continue making the growth investments you need to ensure you’re not losing too much momentum in the long run. (And maybe even grab market share while you’re at it!)

Net dollar retention (NDR)

If payback period is a measure of sustainability, net dollar retention (NDR) is like a measure of resilience. The higher your NDR, the more secure your business position. By taking into account churn, contraction and expansion, this metric gives you a holistic view of customer retention and a glimpse into what the future may hold.

For example, if your NDR is over 100%, your business will likely continue to grow even if you don’t acquire any new customers. If your NDR is below 100%, your bucket is leaky and unless acquisition overcompensates for churn, your business will shrink. In other words, your position is precarious.

You can see how this metric would be especially important to pay attention to when times get tough. If your customers are cutting costs and your platform is getting pruned, recalculating your NDR can sound the alarm. If you’re only tracking MRR, you could easily miss a trend like this, depending on how many new customers you’re bringing in.

Wondering what a “good” NDR looks like? Based on a review of 40 SaaS businesses, 109% is the median and 120%+ gets a gold star.

Quality of revenue

Another factor to consider when it comes to resilience? The quality of revenue you’re bringing in. Just like not every lead is made equal, not all revenue is made equal. If the use case fit isn’t there, a customer may churn before you’ve even had a chance to recoup the cost of acquisition.

So, make sure you’re keeping an eye on what goes on in the closed / won column as well. What “quality revenue” entails will vary by business, but we think of it as:

  • Revenue that’s recurring.
  • Revenue from a contract with an annual or greater commitment.
  • Revenue from a growable or expandable segment: Not just more seats or usage, but the potential for increased share of wallet through new products or services.
  • Revenue from a strong use-case fit: Leading to better stickiness and high NDR.
  • Revenue from a company with a clear champion: Most of us have decision-makers who are “bought in” but having a champion is a game-changer!
Rule of 40

In the time of the unicorn, growth trumped all other metrics. But with the move towards a more sustainable, camel-like mentality, looking at efficiency has become just as important. That’s why we’re highlighting the rule of 40—a metric that combines the concepts of growth and efficiency by looking at a company’s growth rate plus its profit margin.

If this number is higher than 40, a company is in good standing. Though it’s possible to hit 40+ with negative profit margins, it’s unlikely. In these instances, a company would have to be growing a massive amount—at a rate of 60%, 90% or even 100%—to counter-balance losses.

Basically, this rule will show you at what cost growth is being achieved. In an environment where profitability is more important than ever, the rule of 40 can show you how you’re tracking, and whether you need to focus on becoming more efficient, in addition to pursuing further growth.

Return on ad spend (RoAS)

When times get tough, advertising budgets often get slashed. This presents a unique opportunity for brands willing to play a more long-term game. By paying attention to trends in RoAS across channels and platforms, you can identify where there’s less competition and optimize your campaigns accordingly.

As our Director of Demand Generation, Miles DePaul explains, “If OOH or TV was too expensive last year, perhaps the changing market landscape presents an opportunity to experiment with new channels and find previously untapped positive ROI channels.”

So, though it’s tempting to cut ad spend in a downturn—after all, it just takes a few clicks to reduce campaign budgets—consider doing the opposite. By looking for opportunities to scale your paid campaigns and experiment with new channels, you may be able to grab market share at reduced cost, while ensuring your company doesn’t lose too much momentum in the long run.

What a “good” RoAS looks like will depend on your profit margins, business model and overall goals, but a 4:1 ratio (four dollars in revenue for every one dollar spent) is often cited as a benchmark for this metric.

Customer acquisition cost (CAC)

On a less granular level, keeping track of how much time and money you’re spending on acquiring customers across your programs is equally important. And in a difficult market, it becomes even more important to track CAC. There are two reasons for this…

First, being able to tie actions back to revenue is crucial in times when every marketing program is under extra scrutiny. Second, this metric will invariably rise as a result of fewer consumers having pocket money to spend on new products—and if your CAC is getting out of control, you need to be able to sound the alarm and take action.

Our Director of Growth Marketing, Andres Levinton, suggests focusing on another metric in addition to CAC, “Obviously, you want to mix up your marketing efforts in an attempt to decrease CAC, but an increase in CAC can also be combated by dedicated effort to improve lifetime value (LTV). A longer LTV gives you more room to invest in acquisition.”

Again, this metric will vary wildly by industry and product, but one report found the average CAC for SaaS companies ranges between $274 and $1280.

Quick tip

How to reduce CAC

Marketing and design are some of the finest tools for driving down customer acquisition costs.The more a prospect sees you, the more familiar they become with your brand, the less money needs to be spent bringing them onboard.
Having a repository of strong brand assets is how many creative marketing teams bring down their CAC.When creative is abundant and available to distribute across a multitude of channels, it’s easier and less expensive to move the needle.

How to approach planning and budgeting in this market

Let’s get real: Budgets are educated guesses. Even the most carefully laid plans may need to change depending on live inputs and events.

“Budget, forecasts and plans are educated guesses. The fluidity comes with knowing your outcomes and responsibilities. Then, together as a team, look at your results month over month, quarter by quarter and if it’s working, pour more in. If it’s not, what do we need to learn to continue to be iterative and drive the right momentum?”

Tara Robertson,
Tara Robertson,CMO at Bitly

The quick takeaway here: Planning and budgeting needs to be a core activity that happens multiple times a year. And as we’ve covered, understanding your company’s appetite for risk and performance across the full funnel is key for making informed decisions.

But how do you actually go about planning a budget? You might jump around or skip steps, but here’s a step-by-step process and some quick tips from three marketing powerhouses to help you put together a plan:

How to plan a marketing budget

Step 1: Build your forecast model

Here’s where the “educated guess” comes into play. Once you have a rough revenue target from your board, the first step is to build a forecast model to see if it’s achievable within your organization’s current reality. If you’re in B2B, start by asking yourself where your leads and pipeline come from. For B2C, you might simply ask where your customers come from.

Using historical data, calculate the average performance of each source, taking into account projected growth or shrinkage. Again, if you’re in B2B, you’ll likely want to break down conversion rates from demos to opportunities and opportunities to new customers. For B2C, your forecast might include conversion to purchase, or for subscription products, you might look at conversion from freemium to paid. Suffice to say, everyone’s forecasting spreadsheet will look a little different, but the core premise is the same: You’re mapping out how much revenue you can expect to bring in from all your initiatives.

Step 2: Break down your cohorts

Depending on your product and market, you might have multiple cohorts. For example, at Superside, we segment our data by company size. Knowing that our best-fit, stickiest customers are mid-market to enterprise-sized companies, we pay close attention to demo volume and conversion rates for these segments.

If you’re in B2C, your segments might look a little different. Instead of company size, you might be interested in analyzing demographic or persona-based cohorts. Regardless of the specifics, segmenting by cohort in your forecasting model can help you identify which initiatives bring in the highest value customers and prioritize your strategies accordingly.

Step 3: Analyze your pipeline

Just like breaking down your cohorts, analyzing your pipeline sources can help you identify the most effective strategies. As Ashley Lewin, Sr. Director of Research and IP at Refine Labs, explains, "Pipeline Source Analysis is taking all the sources, following them through the funnel, documenting the various sales metrics, and getting a snapshot of how they all perform." To give a general example, a B2B company might break down their inbound pipe by lead generation, events and paid advertising. Within their outbound bucket, they might look at cold outbound, partners and ABM.

By following each of these sources through the funnel and documenting sales metrics, like total opportunities, win-rate, average account value and average sales cycle, you can identify which channels are worth investing in. For instance, after taking a look at closed won revenue vs. ad CAC for your lead generation channel, you might find it’s actually unprofitable. The same concept can apply for B2C, but instead of metrics like win rates, you might focus on average order value, repeat customers and LTV.

Step 4: Fill the delta

Once your forecast model is complete and you have an estimate of the MRR or revenue you can expect from all your marketing channels, you can assess how close this gets you to your targets. Chances are, your existing initiatives won’t get you all the way to where you want to be. If that’s the case, it’s time to problem solve. How will you fill the delta?

This is where your cohort and pipeline analyses will come in handy. Based on this data, it should be clear where to focus your energy. But in all likelihood, optimizing or scaling existing programs won’t be enough to hit ambitious targets. Cue the experiments and moonshots. More on this in just a sec.

Step 5: Measure and iterate

Remember how we said planning isn’t a one and done activity? Just like a captain will recalculate a ship’s trajectory multiple times over the course of a voyage, a marketing leader should keep a close eye on indicators, trends and results month over month.

If you’re starting to trend behind in any areas, think about what you can do to catch up. How can you iterate and continue to drive the right momentum? Or, if the water is flowing easily in areas, think about pouring more effort in. At the end of the day, it’s all about managing momentum by knowing when to double down vs. when to cut your losses.

3 tips to guide your planning

1. Consider all the layers of the cake

Every marketing strategy has layers. Starting with your company’s targets and strategy, layer in your core programs until you get to experiments and brand new initiatives. A comprehensive plan is one where all the layers work together.

“All the layers of the cake need to work together. The layers aren’t prescriptive, they’re intended to be what’s right for your business. But you need all these different layers to have a comprehensive plan. It starts with table stakes then layer in those things that may be more experimental.”

Kim Losey,
Kim Losey,CMO at Rapid Robotics Inc.

In other words, once you’ve shored up the essentials, you can add in experiments and moonshots. This top layer is where the delta is filled. Your core programs will only get you within X of your goals—to get the rest of the way, you’ll need to place some smart bets.

2. Use the rule of three

But how many new bets should you be placing? A simple framework for thinking about experiments is to use the rule of three. Try and cap your new bets at three per quarter, otherwise your team risks being pulled in too many directions.

“We use a rule of three. There are never more than three, typically one, big priorities per quarter that are new bets. We’ve got our focus and we’re also not trying to chase in too many different directions. And for anything with a non-predictable metric, we’ll have a learning goal, so if we achieved it, awesome. If we didn’t, that’s cool because we’re learning. It gives us the space to fail forward.”

Tara Robertson,
Tara Robertson,CMO at Bitly

The fact of the matter is, we’re all doing table stakes work. To stand out in the digital world, you have to place big bets. Even if 99% don’t work, that one percent is a huge win. And by setting a learning goal for each bet, you’re moving forward no matter the outcome.

3. Make room for the transformative

Even if you can only do one instead of three, never cut out big bets completely. Often, in tough economic times, experiments and moonshots are the first projects to get pruned. But you can’t just do the dependable things and expect to move the needle.

“My big buckets are really concrete, measurable things like paid ad spend, lead generation activities, events, things where I know if I do X, Y will happen. But you can’t only rely on the dependable, arithmetic math equation. You need to make bigger bets, make room for stuff that is potentially transformative.”

Meghan Keaney Anderson,
Meghan Keaney Anderson,VP of Marketing at Jasper

Of course, this puts a whole lot of pressure on choosing the right bets for your business, especially if you only have a couple cards to play per quarter...

So, the next question becomes what is a smart bet given the current economic climate?

We don’t have all the answers, but we can share our observations to help you chart a course forward in a world that’s being spun in new directions.

Chapter 3

Charting a Course Forward

With true north established, your course should be a lot more clear. Still, there are a million possible directions you can take depending on your unique business model and go-to-market (GTM) strategy.

But broadly speaking, in this market, the optimal strategy may be to:

  • Reduce unnecessary overhead
  • Increase efficiency and optimize ROI on marketing spend
  • Continue to invest in growth programs with positive ROI

When it comes to optimizing ROI, there are two levers you can pull: Profitability and efficiency. For many companies, efficiency hasn’t been a priority in recent years. But with the current market, that’s changing. Now, reducing costs and increasing gross margin is a key lever for companies whose valuations have dropped as a result of interest rates. (And any company looking to use its resources more wisely, for that matter.)

On the other hand, people have always been trigger happy when it comes to the profitability lever. But in the past, they pulled it by pushing higher prices towards customers. With increased price sensitivity, this is no longer a good option. Instead, companies should pull this lever by growing customer lifetime value.

Watch the clip below for a quick explanation of these levers and how to pull them:


A key takeaway here: Growth isn’t just about net new business. It’s time for marketing teams to focus more on existing customers and growing lifetime value. With demand down, budgets gone and doors closed, it makes sense to re-concentrate some of your efforts towards nurturing, growing and expanding existing relationships.

As Alexandra Watts, an award-winning growth marketer at Figma, explains, “Growth marketing isn't just about net new business, it's also how we nurture and focus on existing clients by developing strategies that build loyalty, trust, collaboration and continued investment. Investing in this aspect of growth during these times is key.”

At this point, you might be wondering which marketing programs can help you accomplish these goals. What levers can you pull to build long-term customer loyalty and value? How can you actually increase efficiency? All great questions, but first thing’s first, make sure you’re clear on your GTM strategy…

Outlining your GTM strategy

If you’re in the $100M+ club, you're undoubtedly eking out pipeline from a multitude of GTM motions. By GTM motion, we’re referring to how you market and sell to specific segments. Within this motion, you may have different GTM types—that is, methods of bringing your products and services to a segment.

For example, at Superside we leverage several GTM types, including:

Given our Creative-as-a-Service (CaaS) offering and GTM approach, it makes sense for us to invest in content marketing and demand generation activities. But if you’re in a more niche market, you may want to focus more on outbound instead of wasting energy on casting a wide net, which will likely lead to high customer acquisition costs.

Suffice to say, it really depends on your business. Just make sure you have your GTM approach figured out before prioritizing marketing programs and activities.

All set? Great. Let’s talk smart bets!

5 smart bets to consider for your brand

When we refer to “smart bets,” we mean doing your homework before pursuing a strategy. Leveraging available data, looking at historical examples of success and estimating ROI—these are all good ways to add a little intelligence to your gamble.

We’ll go over our exact framework for making smart bets in the next chapter. But first, we wanted to acknowledge that prioritizing marketing strategies can often feel like playing a game of bingo. Try the game below and see if you can win:

Did you hit bingo? Then you’re already covering a lot of ground!

That said, there may be more ground worth exploring or areas where you should double down. So, we asked our audience what smart bets they think marketing and design teams should be making in these times. Though not necessarily for everyone, three strategies trended above the rest:

Wales and a tall ship in space

What smart bets are marketing and design teams making right now?

Out of 290 respondents, almost 50% think pursuing the following three strategies is a smart bet.

Leveraging co-marketing, influencer and creative partnerships
50.7 %
Leveraging co-marketing, influencer and creative partnerships
Repurposing content across channels in an agile manner
49.7 %
Repurposing content across channels in an agile manner
Launching a brand community to connect with their audience
49 %
Launching a brand community to connect with their audience

In addition to these strategies, building a powerful brand (37.6%) and adopting AI into workflows (33.8%) figured prominently on the list of activities marketing and designers believe in. Tellingly, leveraging creator partnerships also earned a spot in Deloitte’s Global Marketing Trends Report. Watch the video below for a quick look at these five strategies or keep reading for a deeper dive.

1. Leveraging co-marketing, influencer and creator partnerships to unlock growth

As Deloitte put it, “We are living in an era of cocreation.” Gone are the days of creative isolationism. From design teams collaborating in real time on Figma boards to content teams partnering with subject matter experts (SMEs) to deliver real value, creation has become a collective pursuit.

Taking this concept a step further, more and more brands are collaborating on content beyond the four walls of their organization. In fact, Deloitte’s survey predicts twice as many brands will use creator partnerships this year. By creator partnerships, we’re referring to enlisting external creators or influencers to produce content that feels more authentic and resonant.

James Carbary, Founder of Sweet Fish Media, explained the difference between a creative and a creator best:

He also highlights several brands in the tech space that are already pursuing this strategy: Clari, Airmeet and Lavender. Clari is a revenue platform. Airmeet, an event platform. And Lavender, an AI email assistant. The point being, regardless of what your product is, creator partnerships may be worth exploring.

Here at Superside, we’re also planning to scale this strategy, having seen success partnering with influencers like Harry Dry, Liz Willits and Dave Gerhardt. The flip side to this coin is teaming up with brands and customers to produce events and content, like this guide or our recent Ignite Summit.

In a nutshell, getting your audience’s attention is harder than ever right now. Partnerships can help by amplifying your reach and infusing your content with real value and authenticity. Plus, co-creating—bringing in fresh perspectives, ideas and experiences—is a surefire way to ignite creativity, which as we’ve seen, fuels success.

2. Embracing an agile approach to repurposing content

Our Head of Content and Community, Cassandra King, has a theory: The bigger your company gets, the harder it is to repurpose content effectively. The one person content team must by necessity repurpose, repurpose, repurpose. But as a team grows and roles get more specialized, that machine often breaks down in favor of new, new, new.

It’s a capacity thing. And it’s a collaboration thing. But with a little conscientiousness, it’s not a necessary thing. Whether you work for an enterprise or a mid-market company, your brand can benefit from making better use of its existing content. There’s no need to overcomplicate the process either. With a simple playbook, you can repurpose content like a nimble startup and use your resources to the fullest.

Jess Cook, Head of Content at LASSO, shared a super simple framework for repurposing a blog post across social channels:

For more details on this strategy, check out Cook’s podcast episode, One Blog Post Four Ways: Channel Specific Repurposing. The key phrase to note here is “channel specific.” If you’re not creating platform native content, don’t bother.

You might’ve been able to get away with reposting the exact same content across all your social channels ten, even five years ago. But with the level of noise on social platforms these days, algorithms incentivising posts that keep readers on platforms and, let’s be honest, the difficulty of getting heard as a brand, not an individual to begin with, this approach simply doesn’t cut it anymore.

So, by all means, repurpose! If you’re looking for ways to increase efficiency and use resources wisely in these times, this is a simple, actionable place to start. Just remember, native content is now queen.

3. Launching a brand community to develop stronger ties with your audience

This bet comes with a disclaimer: Not every brand needs or will benefit from a community. In fact, in the current environment, it may make more sense to focus on “community initiatives” rather than launching a dedicated community, which is a high-lift commitment. That said, there are companies that will absolutely benefit from this bet.

Anderson recommends being brutally honest with yourself about whether interest in a community exists. Before launching Jasper’s community, she recounts spotting signals that indicated interest in a dedicated space to discuss their tool. “We saw people publicly sharing their amazement with the tool. That was a good signal we were ready for a community,” Anderson says. It was also an indication of what kind of community Jasper should build: A community of platform vs. a community of practice.

As you can see, a community of platform is centered around your product. For Jasper, there was a real interest in discussing and exploring how to use their tool. On the other hand, a community of practice is more of a social group. The product plays a minor role and discussions center around strategies and tactics.

Of course, this is a binary view of how communities work. Most brand communities will fall somewhere on a spectrum of platform to practice. But to set the right goals, it’s helpful to understand where you might fall on that spectrum. For instance, if you fall closer to platform, community-driven activations would be a good metric. For practice, you’d want to look at community growth and engagement.

All this to say, community can absolutely be a moat for growth. By facilitating interactions and encouraging knowledge sharing, this strategy can help you turn your audience into advocates. And advocacy is how real people buy. But before you jump in with both feet, make sure you ask yourself, “Are there people who want to be educated about this? Or, is there a social need?”

4. Building a powerful, authentic brand to support long-term growth

In some schools of thought, brand is a dirty word. But the truth is, without the foundation of a solid brand, all your other efforts will fall flat. Though not a quick play, building your brand pays off in the long run when your company sticks in the public consciousness and your customer acquisition costs go way down.

You can shrug it off as a solid product, clever budgeting or excellent operations, but it’s so much more than that. As Aaron Poe, Head of Creative for Zapier’s Brand Studio, puts it, “Good brands have customers. Great brands have fans.” And fans help brands expand.

Of course, brand is notoriously hard to measure. Brian Button, Creative Director of Brand Marketing at Instacart, offers a solution: Don’t overthink it. “The biggest metric for me is, how does it make me feel? Does it excite me? Does it make me nervous? Does it make me fall out of my chair? If that’s the case, then we’re on to something.”

If you can make someone fall out of a chair, well, you’ve made an impression. Your brand is likely to stick in their minds, not slip away like a dream within a minute of waking. And though it may feel prudent to be conservative in times like these, pushing boundaries is the better move to combat dwindling demand.

Plus, as Anderson mentioned, with less competition for attention and lower costs, your brand dollars can go a long way right now. In other words, it’s a great time to scale paid advertising, run that brand commercial or buy out that billboard. But answer this question about the creative first: Does it make you feel something?

5. Adopting AI into marketing and creative workflows to increase efficiency

AI can 50X your speed and 10X your output. Just kidding. Stats like these are meaningless to marketers and designers on the ground trying to figure out how to actually use this technology in their workflows. But one thing’s for sure, everyone should be trying.

The mandate of the hour is to do more with less. Be more efficient. Move faster. Adopting AI is a natural response to these demands. The question is, how can marketers and designers make the best use of this technology? Our Director of Brand and Marketing Creative, Piotr Smietana, shared a pertinent example for this guide.

Smietana had a challenge: He needed to brief a visual of a lighthouse floating in space, surrounded by old-timey galleons and fantastical whales. In a pre-AI era, he would’ve spent hours, days even designing mockups for his team. With AI, he tried a few prompts, pointed out the parts he liked and saved himself hours of time. Though AI couldn't capture Superside's distinct brand and illustration style, it provided a solid starting point.

“AI becomes my private creative sparring partner. I can just bounce ideas and take a piece of that or a piece of this,” says Smietana. Similarly, our Director of Growth Marketing, Andres Levinton, finds AI useful for ad copy ideation. He explained the technology might not spit out the perfect headline, but it will give you bits and pieces to use as starting points or spark new ideas.

At the end of the day, there’s always going to be the next big thing. Right now, it’s AI and a looming recession. Smietana urges leaders to become more resilient and use this opportunity to revisit frameworks or processes that were established a long time ago. Future proofing your team means getting ahead of trends, especially useful ones like AI.

Honorable mentions
  • Taking advantage of less competition and scaling paid advertising (31.2%)
  • Doubling down on channels with longevity like organic and YouTube (30.6%)
  • Implementing innovative technology like AR and VR (20.3%)

We could go on. Talk about organic and video. Augmented reality (AR) and 3D design. The truth is, one, none or all of these bets could make sense for your brand. Which ones? The following framework will give you a map to follow as you set your course.

Chapter 4

Mapping Smart Bets for Your Brand

Before we get into our map for making smart bets in these turbulent times, let’s talk about another popular map: The marketing funnel. Now, we all know the funnel isn’t literal. It’s simply a framework to help us plan marketing activities and programs.

These days, it’s a given the buyer journey is non-linear. In fact, it always has been. It’s just walled gardens and privacy regulations have made it even harder to understand. But the point is buyers jump ahead, jump back, ghost and get onboard in perplexing patterns.

So, how do you decide which marketing activities and programs to invest in? And how do you adjust over time?

This might be the hardest question to answer in marketing and it connects to an even larger problem we like to call: THE BIG UNKNOWN.

That is, how much of your audience is “in-market” vs. “out-of-market.” It’s difficult to estimate the size of these groups, which leads to marketing teams not knowing how to balance their efforts between demand capture vs. demand creation. What a conundrum.

Of course, you can make assumptions based on the jobs to be done (JTBD) of your buyer personas or whether your company is in a well-understood, saturated or brand new space. For example, in a saturated space, you might focus on demand capture activities, like bottom-of-funnel advertising or content for buyer-intent keywords.

But at the end of the day, your carefully planned marketing programs may still feel like a whole lot of hunches and guesswork. (Bingo, anyone?)

So, this guesswork needs to be paired with a solid numerical framework that makes marketing into a calculated experiment, instead of a series of missteps. A framework for placing your bets based on an understanding of your company’s momentum, appetite for risk and the potential impact of your decisions.

A framework for making smart bets

There are many frameworks for “placing bets” in marketing, like Data, Insight, Belief, Bet (DIBB) or Impact, Ease, Confidence (ICE). Though they’re certainly useful, these frameworks are tactical in nature. They don’t take into account the bigger picture: A company’s position, including the appropriate level of risk, ROI and overall impact a program needs to deliver to be worthwhile given that position.

This is where the REI framework comes into play.

Provided you understand your company’s goals, GTM strategy and market position, you can apply this simple framework to quickly gauge whether a bet is worth placing. For example, if my North Star Metric is revenue growth and expansion within organizations is the main input lever I want to focus on to affect this metric given slowed demand and sky high CAC, then a smart bet might be to focus on my account-based marketing (ABM) motion and upselling to existing enterprise accounts.

So, I have a smart bet in mind. At the same time, given the shift around preference for uncertainty and the cost of capital, I know any programs I run need to yield a positive ROI of 15% or more to be viable. I’m ready to apply the REI framework:

Risk: Is it a slam dunk, experiment or moonshot?

A slam dunk is a growth bet you can take to the bank. Either from historical context or market proof, you know this type of program will yield results with a high degree of certainty. For instance, if I know my ABM channel converts at a high 40% rate and the average increase in annual contract value (ACV) from upselling to enterprise accounts is $60,000, I can postulate my expansion focused bet will be a slam dunk.

On the other hand, if you have little to no historical context and market proof is mixed, indirect or non-existent, you might consider a bet an experiment. With experiments, you need to be more comfortable taking on risk. If our example was an experiment, I wouldn’t be guaranteed to see results, but the potential for a 15% ROI or higher would be there. This is where momentum and appetite for risk need to be factored in. If your company’s seeing decent growth, it may be appropriate to run more experiments. If momentum is at a standstill, you might focus on slam dunks to get the flywheel turning again.

A moonshot is a long-term bet with the potential for outsized impact. Think Nvidia’s bet on accelerated computing and deep learning. It took over a decade to see the fruits of this gamble, but now, Nvidia is on the brink of being a trillion dollar business. With a moonshot, you may not see results for years, decades even. But when you do, your company will rise to brand new heights. The potential ROI isn’t 15% or higher. It’s more like 150% or higher.

Efficiency: What’s the projected ROI?

This is the numerical part of the framework. Depending on whether you have historical context, your projection may be more or less certain. Hence the terminology “slam dunk, experiment or moonshot.” But regardless of the type of bet you’re placing, you need to make a quick assessment of the potential ROI.

To keep things simple, let’s say I have plans to go after 10 enterprise accounts for expansion. Based on the historical conversion rate of 40% and ACV of $60,000, the potential return is $240,000. Taking into account $200,000 in investments, this bet would yield a healthy 20% ROI.

Impact: What’s the potential impact?

Finally, based on the projected ROI, you can label the potential impact of your bet. To keep things simple, we think of impact as low, medium or high. For instance, my ROI requirement was 15% or more, so with a 20% projected ROI, the potential impact of my bet is high.

  • Low: The ROI falls below requirements
  • Medium: The ROI meets requirements
  • High: The ROI exceeds requirements

On the importance of experimentation

Given the example we just ran through, you might think focusing on slam dunks would be a no-brainer. But the thing is, slam dunks aren’t necessarily efficient and the ROI may not be amazing. Though we used a bet that made sense right now, we could’ve given an example, like outbound sales—a strategy that’s historically a slam dunk, but that may not be efficient, especially in this market. In other words, this type of bet will have an impact, but likely not a massive one.

That’s why, if you have the resources, you should never cut out the “big” bets—the experiments and the moonshots—completely. This is especially true for companies at scale. As a mid-market or enterprise business, if you’re not pushing beyond your fully-developed strategies, then you’re stuck chasing tiny returns. As Kieran Flanagan, the CMO at Zapier, put it, “Most teams at scale get too comfy in the 'iterate-to-nothing' zone.”

Another reason to continue experimenting? Differentiation. As a whole, marketing and creative has become too mimetic. But the best marketers do things their own way, marrying best practices and playbooks with original thinking and experiments.

“I don’t think as marketers we can afford to not experiment, especially in the market right now. The world has changed and it’s never been harder to capture people’s attention. So, if you’re doing the table stakes, go-to-market execution, you’re not standing out.”

Tara Robertson,
Tara Robertson,CMO at Bitly

How to experiment is a whole topic in and of itself. From velocity of learning to fuel-pipe fit, we could write a whole playbook on the topic. (If fact, we intend to!) But in the meantime, here are a three quick tips to help you get the most out of your experiments:

3 quick tips to fuel your experiments

1. Set learning goals

It goes without saying, you should set clear goals for any experiment. But this can be tricky when an idea is brand new and you have no historical data. In these instances, Robertson suggests setting a learning goal—what are you hoping to achieve? Is the outcome aligned to acquisition? Brand?

Defining the outcome will ensure you get something out of every experiment—whether it’s a success or a learning to make the next experiment a success.


2. Measure velocity of learning

The faster you can adjust and learn from your experiments, the faster you can identify the right conditions for a positive outcome. So, in addition to setting learning goals, consider the velocity of learning.

How long does it take for you to iterate on an experiment? Do you have a system in place to track leading indicators and capitalize on insights? If you focus on velocity of learning over revenue, it frees you to give experiments a real shot, instead of trying things halfway and retreating when they don’t pan out.


3. Consider fuel-pipe fit

If you’re not obsessing over fuel-pipe fit, now’s the time to start. Similar to product-market fit, fuel-pipe fit refers to how well your content or offer (the fuel) fits in a specific channel (the pipe). Often, the problem might not be the content or the channel, but rather how they fit together.

That’s why, before giving up on any experiment, you should ask yourself questions like, “Does the fuel need to be adjusted for this particular pipe?” or “Is it possible the fuel would work better if it was distributed via a different pipe?”


At the end of the day, the big magic trick in marketing is balancing experimentation and proven programs.

And remember, don't give up too soon or without a thorough analysis. Perseverance can often be the difference between a win and a loss. As Carilu Dietrich, a hypergrowth advisor, put it, "Perseverance is a hallmark of success—the most successful CMOs I know have had some duds and some home runs. What they have in common is perseverance to take another at-bat. The more at-bats, the more chance of hitting a home run."

All the concepts we’ve talked about so far will play into what balance of experiments or "bets" makes sense for your brand. So, we put together a cheat sheet to help you think through everything from your business position and North Star Metric(s), to your GTM strategy and next big bets.


Finding Your Way to Safe Harbor

A downturn, a slump, a leveling out…

Whatever you want to call it, times have been tough lately. Whether the storm breaks tomorrow or six months from now, we hope this guide equipped you with tools to take the tiller and guide your ship to safe harbor.

Though there’s no one path companies can take to come out of this economy safely, there are universal characteristics of resilient, antifragile teams, including:

  • Restlessness—Never content to settle for the status quo, the restless organization embraces change and thrives on uncertainty.
  • Agility—Empowered to make decisions and collaborate cross-functionally, agile teams shift with the market and move fast at scale.
  • Creativity—Rather than just surviving, creative organizations thrive by pushing boundaries, looking for new opportunities and innovating not mimicking.

If you have these values down, you’ve won half the battle. The other half is deciding what strategies make sense for your unique business. So go ahead, fill out our Smart Bets Framework for yourself and place your chits. May the odds be ever in your favor. 😉

Smart bets giveaway

Complete the following steps for a chance to win a smart bets gift box!

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