Q&A with Wheels Up Collective Co-Founder, Amy Winner

Building a startup can be a thrilling pursuit. You get the unique chance to be “the next big thing” in a given space. But with all the effort that goes into becoming an industry pioneer, developing a marketing strategy can quickly fall to the wayside. A real shame, since a well-executed marketing plan can work wonders to drive revenue and establish your business as a permanent player in the game.



I recently sat down with our co-founder, Amy Winner, to chat about what it takes for a startup to establish a successful marketing plan. With 24 years of growth marketing strategy experience, she had some valuable insight to share. Here are the highlights of our conversation:


Why do startups struggle with marketing strategy development?


This will likely be an unpopular answer, but it’s because marketing is expensive and it takes a long time. Early stage companies have fought hard to bootstrap their way into existence, and sticker shock is real – even with the scrappiest of marketing programs. I’d argue that most companies dipping their toe into marketing for the first time underspend and end up not doing enough to realize any value from the investment.


If you’re an early stage business and just getting started, avoid checking the marketing box by hiring a junior marketer to tackle regularly scheduled activities like social media, newsletters, email blasts, and blog posts. These channels are tempting to focus on because they are “free.” But they aren’t. They take time and attention, and the kicker is that no one will even see the content shared there since you don’t yet have an established audience following you.


While we are by no means advocating that you start setting money on fire, investors gave you that money to grow the company. So spend it! Find yourself someone who is strategic and clever and can have C-suite conversations. Start with your highest level business goal, and work backward to create a bespoke marketing strategy that fits the needs of your company now. Don’t stick marketing in a corner and expect it to run on autopilot. Check in, keep formulating hypotheses about the business, test what you can, and change course quickly and opportunistically. But like anything in life worth doing, it’s going to take time, energy, and money to make it work.


What is the most common marketing strategy mistake startups make?


The biggest snag we hit with clients is an expectation that you can drive quality leads right out of the gate. Frequently in discovery, we hear “we need qualified leads, now.” By definition, our startup clients are creating a totally new solution or technology – frequently to address a problem the market doesn’t know it has or even realizes is possible to solve. So it’s really hard to go from “I didn’t know anything like this existed” to “I want to have a serious sales conversation right now” with just one marketing program.


The sales funnel is hard to outsmart. Prospects need to go through the buyer’s journey, and it’s really hard to skip steps. Think about when you first found out about the iPhone, Bitcoin, or Tesla – you’ll always have a small group of early adopters, but by and large, disruptive products and solutions take a good amount of education before the majority of the market is ready to embrace them. For better or worse, it takes time to learn the audience and find the right series of touchpoints to build a qualified lead; you need to think about your first marketing strategy through this lens.


What 3 characteristics make a strong marketing strategy?


  1. Strong marketing strategies are tied to high-level business goals - and I’m not talking about a vague nod, either. It needs to be very clear how your strategy is going to impact whatever metric it is the C-suite is prioritizing. This is the best way to ensure that marketing programs aren’t labeled as “nice to haves” and are instead valued as driving the business forward.

  2. A strong marketing strategy also builds in a research component to run in the background. One of the biggest opportunities most often missed by marketing organizations is that pretty much any marketing endeavor can double as market research. If you build your strategies with the questions you’d like to answer in mind, you’re guaranteed to find value in the program. Plus, working cross-functionally with other teams like sales or product ensures that you understand what’s important to them, and can opportunistically use your marketing tool belt to help them be successful.

  3. Lastly, strong marketing strategies are rooted in customer empathy. It’s so easy to forget that the “Bs” in B2B are people. Successful companies are solving problems. Make sure that your marketing team has off-the-charts customer empathy when it comes to the problems you’re solving. This will drive marketing that’s resonant and builds an army of champions within your customer base.


What is the biggest misconception when it comes to marketing for startups?


That they are too early to start thinking about marketing. You certainly don’t need a full blown marketing organization when you’re early stage, but I would argue that the sooner you shift from a product-led mindset to a customer-led mindset, the faster your organization is going to grow. Too often, companies are building really cool technology without knowing what its use case is going to be. The old adage “it’s worth whatever someone will pay for it” rings true here; if there’s no product market fit, then it’s not worth anything.


Dedicating early stage intellectual bandwidth to “marketing” includes things like market research, ideal customer profiling, product packaging, and thought leadership (and frequently, category creation). These elements help you hone in on what’s important to the audience, and where the sweet spot is to win in your total addressable market (TAM). The sooner you figure that out, the better.


What is something you didn’t expect about marketing that you learned over the course of your career?


My favorite thing about marketing is the opportunity to work with every single part of the business. Companies used to be so siloed, and marketers were left out of big conversations because by and large, their work was not measurable. But with the proliferation of better measurement technology, marketing can support every functional area of a company. It can queue up highly qualified leads and accelerate sales. It can uncover market trends and research that informs product development, pricing, and packaging. It can tell the story of a company’s culture, helping HR find great new teammates. It can raise leadership’s profile, opening doors to all sorts of opportunities. And it can give the finance team the valuable data it needs to model budgets and forecasts that are based on data, not hunches. If you’re not thinking about your marketing organization this way, you’re leaving massive value on the table.


If you could go back in time to the beginning of your career and give yourself one piece of advice about what it takes to have a successful marketing career, what would it be?


Don’t get too attached. Especially in the startup world, things change on a dime. You can be 95% of the way through a big project, and the CEO can announce a major pivot. It’s so, so easy early in your career to take this really personally and let it get you down.


Learning to be adaptable and resilient sounds cliche, but is so important if you’re going to make it as a startup marketer. Take a quick breath and regroup when the wave of change hits, then get to work figuring out what can be salvaged, learned, and reused from the work you’ve done. While good marketers put their soul into their work, it’s not personal – and that’s why you get a paycheck.


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