Wheels Up Collective’s Amy Winner On How To Lead A Successful Marketing Management Team
It should go without saying that effective marketing management can make or break a company's success. To understand the best ways to lead a successful Marketing Management team, we asked CMOs and other leaders in the marketing space to share tips, stories and insights from their experiences. As a part of this series, we had the pleasure of interviewing Amy Winner.
Thank you so much for doing this with us! To begin, can you share a bit of your backstory and how you got started in your career?
I grew up on a family dairy farm in NJ, and if there’s one thing I know to be true about dairy farmers, it’s that they know hard work. While the cows weren’t my personal career aspiration, I’d like to think I did learn how to hustle. Out of college, I cut my teeth in NYC as a media planner at the 6th largest ad agency in the world, followed by a handful of inhouse marketing jobs for high-growth companies including 12 years in Seattle startup tech. Looking back, the common theme through every role I had was that we were always working through some sort of change: recessions, launching products into new categories, the real estate market implosion. The startup world has been a great fit for me since I like turning change or challenge into opportunity with the right marketing strategy.
When COVID-19 hit in the early spring of 2020, my Wheels Up Collective co-founder and I happened to both be coming off stints at large companies that just sort of left bad tastes in our mouths because of culture misalignments. We both felt a sense of obligation to build a place where the culture empowered and inspired each team member to do the best work of their career, all while living a full personal life. We founded Wheels Up Collective with this vision of delivering high-quality results while supporting each other and living fulfilling personal lives. Building it has been the hardest thing I’ve ever done (which is saying a lot because I used to coach teenage girls in the sport of crew!) but it’s something that I’m super proud of and excited to continue to grow.
What are three strengths, skills, or characteristics that helped you to reach this place in your career? How can others actively build these areas within themselves?
1. Figure out what motivates people. This is important from the most junior to the most senior people on your team, to your prospects and customers, to influencers and partners and the media. Understanding what each person you work with needs is the key to becoming someone that everyone wants to work with. Many times, this is an exercise in messaging and positioning, and it changes not only from person to person but sometimes from day to day. The work you have done or the value you can offer doesn’t change, but the way you massage it into something that makes ears perk up does.
It’s very easy to get caught up in our own narrative. You’ve got to keep thinking about it from the other side of the conversation. No matter who you are working with, they are always thinking, “Yeah? So? What’s in it for me?” Delivering intel that sets people up to be successful (whatever that looks like) turns you into a super valuable resource.
2. Learn how to balance caring deeply about your work with accepting when others disagree with you. We call this the “agency dance” on my team. We chose our teammates because they are wildly passionate about their work (and damn good at it, too!). But as an agency, there are lots of times when our clients pick a different visual direction, or go with language that wasn’t our favorite. Sometimes they listen to our recommendations and still go in a completely different direction. And that’s okay! It is a skill that you have to intentionally develop to be able to come to work every day refreshed and energized to deliver stellar work, even when your stakeholders disagree. Finding consensus sometimes requires detaching yourself from your strong-held opinions and finding the best solution together. It’s not always easy.
3. Create a ritual for separating work life from personal life. When I lived in Seattle, I used to take the water taxi to work. It was an 8-minute boat ride across a beautiful harbor followed by a 15 minute walk. On the way to work, I got a jumpstart on my email inbox. On the way home, I sat on the top deck of the ferry with my phone shut off and breathed in the beautiful view. It sounds silly, but I still start my day sifting through emails and I have a mini-meditation/breathing exercise I do at the end of each working period. They talk about “work/life integration” now. Your phone is always on and it’s become acceptable to Slack and text colleagues after hours. Sure, there are times when it’s appropriate. But in order for me to come to work ready to be creative and engaged, I need to shut that part of my brain off regularly and consistently.
What specific backgrounds, qualities, or credentials do you look for when hiring for management and senior positions?
I am a big fan of hiring all-around athletes. I want team members – especially leaders – who are agile, flexible, competitive, and work hard. You can’t teach someone how to have the right attitude, but you can teach them how to build a content strategy or stand up a new HubSpot instance.
Hiring fatigue is a real thing. You have to figure out your own system for quickly filtering out the people who just plain aren’t qualified. After that initial pass, I typically go straight to a quick call. I can learn more about a candidate through a 10-minute phone call than I can by spending twice the time reading a resume, looking through work history, and googling the candidate. I actually don’t even look at the resume during that first call. I like to get them talking, and listen without much preconceived bias.
My favorite question is: “tell me about the projects you’re most proud of.” Usually (hopefully) they are excited about this work and confident in what they achieved and happy to talk about it. My follow-up question is: “now that it’s done, what would you have done differently?” These two questions alone usually tell me if I have a Rockstar, Superstar, or dud. (Rockstar and Superstar are from the Radical Candor book and if you haven’t read it, are two very different, yet both very valuable, personality types.) Do they think big? Are they able to admit what they did wrong? Are they super detail-oriented?
To this day, two of my all-time best hires were 1) a customer marketing manager who had no marketing experience but had worked as a nanny of twin toddlers, and 2) an events manager who had never been to a trade show but had worked in community health advocacy. In both cases, I had to fight hard with leadership to get them hired because they didn't fit the job description. They ended up being stellar employees because they were able to connect with the stakeholders they ultimately served in incredibly effective ways. As their manager, it was my responsibility to develop them in these roles and make sure they had the technical know-how to be successful.
When it comes to managing large teams, WFH, and different time zones, how do you prioritize communication and collaboration to ensure a cohesive marketing strategy?
Transparency. It’s cliche but true. Our calendars and work queues are all shared. We have a hierarchy of communication tools - if it’s urgent, call or text. If it’s something that needs an answer quickly, Slack DM. If it’s a broad question that needs attention in the next hour or two, Slack channel. Otherwise, email. We also have an Asana instance that some might argue is over-engineered (by someone, I mean me). But it’s not for me, it’s for the team and it’s as granular as they need to keep projects on time.
Frequently the opposite is the bigger problem - over communicating. Context switching absolutely kills productivity, so we all block time on our calendars for heads-down work. We try to batch questions so we’re not constantly pinging each other. And we try to calibrate communication based on urgency. As an agency, we sometimes find it hard to balance communication with our clients, particularly our larger engagements where we are in their Slack or Teams instance. With clients, we have clear SLAs around communication turnaround and work delivery. Nine times out of ten just being on the same page makes collaboration smooth and keeps everyone on the same page.
How do you stay on top of the latest trends, technologies, and AI to ensure your team is implementing the most effective marketing strategies?
I think it’s super easy to get intoxicated by the latest bells and whistles. In our world of squishy vision, tight timelines, and even tighter budgets, we recommend that most of our startup clients stick to basics. There’s a lot you can do with Google Analytics and a spreadsheet. Many times, new tools and tech require extensive onboarding and setup and are super sticky by design, making it painful to switch. Most of the time, our clients don’t really know what they’re going to need long term. The last thing they want is to waste time on setup only to be stuck with an expensive tech solution that’s a bad fit.
That said, I am an avid podcast listener (on 2x speed of course!) and love listening to stories about technology and entrepreneurs. We also have some pretty amazing tech clients; staying on top of their competitive environments is largely how I end up hearing about industry trends and new tech.
In an industry that is often focused on data and metrics, how do you balance the importance of quantitative data with the qualitative insights and instincts needed for success?
We actually did a webinar on this very topic called “Trust Your Gut: Why Your Business Hunches Matter.” It was a super interesting conversation with an intuition coach about how and when to tune into your own instincts to back up the hard data that you have. She talked about paying attention to the unconscious cues you are constantly sending yourself – like if you’re saying “should” a lot, it usually means you’re following an external norm that you don’t necessarily agree with. And body language – if you find yourself leaning forward into a conversation with someone, you’re usually onto something. Alternatively, if you are sitting back with your arms crossed, it’s sometimes a cue that your gut is saying this is wrong. Once you start paying attention to these quirks, it’s remarkable how spot on they usually are.
Particularly as you advance in your career, your intuition develops. It’s like an unconscious voice rooted in your own experience and expertise. It’s funny, we joke that as women we’d never get into a car with someone we just met if they gave us a bad vibe, but we are quick to brush off vibes about work decisions. I’m certainly not suggesting that all decisions come from your gut, but a healthy consideration of big data, thick data (a term coined by tech ethnographer Tricia Wang to represent the qualitative, contextual data), and your own marketing intuition usually delivers decisions that land well with the intended audience.
In my day-to-day life, staying as close as possible to the customer helps with this. I have metrics and data from trusted sources, and our own intel about customers gleaned from conversations, research, and market trends. Add in my gut that’s fueled by 25 years in marketing, and I think I’m usually able to get pretty close to the right answer.
What tips do you have to motivate and inspire your team to consistently meet and exceed their goals?
I like to think about this as a venn diagram of:
- What they are good at
- What they enjoy doing
- What the organization needs
If you can make sure that at least 50% of each of your team member’s time is spent working in that sweet spot (and you hired great people to start), then you usually have high-performing teams that are self-fueled and motivated. This takes great management to A) understand what your people are good at and what they aspire to do, and B) load balance amongst your team resources to get it all done. I think that anchoring development conversations in these three venn diagram categories helps your people understand that you care about their happiness, but also that they will sometimes be stuck doing work that they don’t necessarily love without it leading to burnout.
How do you handle underperforming team members?
Treat them like people you genuinely care about and find out what’s really going on. Is it a personal issue? A knowledge gap? A lack of motivation? Or was it a mismatched hire and there’s no way they are going to be successful? Work together to find a solution – whether that’s better support or moving on to a new role. Usually, a healthy dose of humanity has a much better resolution rate than a PIP.
What would you say is the most valuable marketing software in your tech stack?
Google Meet. Maybe I’m old school, but I like to look someone in the eye when we are talking, and as a distributed-by-design org, we need video conferencing. I like to see my teammates so we build authentic, personal connections. I like to be able to read clients as we’re making decisions or they are delivering feedback. And I need to see prospects to get a good gut read on whether they are the kind of people who will work well with our team.
A fun practical tip - I’m sure Zoom and Teams have similar functionality, but Google Meet makes it easy to record meetings and produce transcripts. Then we use Chat GPT to turn those transcripts into meeting notes and to-do lists, which frees up our project managers on calls so they can be more engaged in the conversation and less distracted taking notes.
Based on your experience, what are the five things you need to lead a successful marketing management team?
1. Managers Need to Manage
After spending a decade in tech, I moved back across the country to my hometown to help my mom after my dad passed away in an accident. South Jersey isn’t exactly a hot spot for startup tech, so I ended up working at a very large, privately/family-held, $1B+ company. It could not have been more different than what I was used to. The leadership style, the corporate culture, the employee profile - it was all almost the opposite. They sent me to a full day of psychological analysis and cognitive/IQ testing to see if I’d be a good fit for a leadership role, and thought I’d fit in perfectly. TL/DR: I did not.
There were a lot of very happy people in this organization, and many productive teams packed with lifers. But what was so surprising and jarring to me was the culture of manager-envy. Everyone wanted to be promoted to be a manager, not because they aspired to help develop talent or produce a high-functioning team, or they wanted more strategic responsibility. The company had a comp structure that was packed with perks reserved for manager + levels. They were very committed to promoting from within, so mediocre managers led mediocre teams that promoted from within to produce more mediocre managers. I remember one specific 1:1 I had with one of my younger direct reports where we talked about her career trajectory and aspirations. “I just want to be a manager!” she said with stars in her eyes. When I asked her what about being a manager she was most excited about, she said she didn’t know, she just wanted to be eligible to go on the year-end trip for managers.
We forget that when we cross over from individual contributor to manager/director/leadership, we (in part) hold our team’s livelihood in our hands. We have the ability to make coming to work every day something they look forward to, or something that jeopardizes their mental health. Can they afford the mortgage on the bigger house? How much time can they spend with their family? We are so defined by our professional lives, and the leadership of a company can have such a profound impact. I think about that when I sit down (remotely now) to start each day with our team at Wheels Up. I’m not suggesting that I’m always doing it right, but I am saying that being in a leadership role needs to be taken seriously. It’s not just a pay bump, it’s taking responsibility for and accountability to your team in a very different way. It’s your job to set them on a trajectory that’s going to fuel their career growth. It’s not enough to just hire great people; you have to focus on ongoing talent development.
2. Make sales easy.
At the end of the day, a marketing team’s #1 job is to drive sales. My experience is predominantly in sales-led B2B organizations, and while our company may ultimately be selling to other companies, my marketing team’s customer is our sales organization. Marketing exists to make their job easier. My job is to deliver prospects who are fully qualified and ready for a contract. The less time our sellers spend with (ultimately successful) prospects, the better. Calibrating on this tenet ensures that my team is all following the same North Star.
Sometimes this is easy because the product or service is a knockout and sells itself, or you have just super stellar sellers who close all day long. Sometimes it’s harder. (Particularly if there’s not a great culture of sales and marketing collaboration at the company to begin with.) But that kind of doesn’t matter – it’s your job to do everything in your power to make sales easy.
We were in an annual planning workshop with a client that was having a soft year. Their sales organization was almost entirely new hires, and they weren’t closing very many deals. The sales organization blamed marketing for delivering junk leads. The marketing team blamed sales for not doing their job. Leadership just wanted the revenue issue fixed. This theme of finger pointing came up a few times throughout the two-day workshop, and our team kept bringing up sales support as a recurring missing component to the marketing programs we were fleshing out.
Exacerbated, one of the marketing managers asked: “how long do we need to keep spoon feeding the sales team?” My equally exacerbated response was: “UNTIL THEY HIT THE NUMBER.”
I may have been too sharp in my reply, but I stand by the sentiment. It’s marketing’s job to make sales successful. It doesn’t matter how thought-provoking your leadership is, how well attended your webinars are, or how many thousands of likes your last Instagram post got if no one buys whatever it is you're selling. Patting yourself on the back for those metrics in the absence of successful sales is blindly following vanity metrics. You may be producing fantastic marketing, but it’s not doing its job, which is to drive sales.
3. Get marketing out of the red and into the black.
Historically, and notoriously, marketing has been a huge red number on the company’s budget. Your CFO has preconceived notions about the value the marketing organization holds because of your typically disproportionate department budget. Historically, the lack of attribution data has made it difficult to tie marketing dollars to actual revenue, forcing your CFO to throw their hands up in the air and watch as you light money on fire. CFOs hate this. As a marketing leader, you must get ahead of this. Otherwise marketing will always be on the chopping block when money is tight. And the bummer of that is that stunting good marketing will most likely stunt the company’s growth.
Luckily, we live in a time with tremendous data. You have the opportunity to align with your financial team and build your reporting to support and inform the KPIs they are tracking at a high organizational level. You can aspire to build predictable campaign models that deliver demand on time and at scale. You can be a partner to DevOps, helping with capacity planning, pipeline analysis, and headcount decisions. You can make responsible program decisions because you’re able to measure true ROI at a campaign level. You can cherry-pick marketing initiatives because you know which are profitable and which are just pretty marketing. You can do it. It’s not easy, but building a strong relationship with the CFO will get you working with them instead of against them.
4. Have plans A-E, but be ready to throw them all out the window and roll with it. Preparation is mostly a ritual, your experience is really the most important.
I ran the first-ever customer conference for a startup with little to no leadership direction. The CMO told the CEO we were having one that calendar year, then put it on my personal goals worksheet. Surprise!
My team spent the better part of a year planning the event. There were so so so many wins that first year - selling out, great speakers, (mostly smooth) operations. There were so so many laughs – trying to talk Customs into releasing our custom LEGO swag at 2:00 AM the first day of the event. Some not-so-fun surprises – the Airbnb we lived in for the 2 weeks leading up to the event was infested with mice. And some absolute heartbreaks – meeting a new colleague in the bathroom while she was miscarrying. But it all worked out because at the end of the day, you can be uber-prepared, and end up throwing literally everything out the window and winging it. Have confidence in your chops. You can do it.
5. Do not become the marketing help desk.
The CEO wants to change the background image on a slide in their pitch deck and needs new stock art. One of the product managers was hoping you could just help them with a new screen mockup real fast. Customer Success is launching a new project management tool and they need the logo resized to fit the header. HR is planning the annual picnic and needs help ordering t-shirts, and oh by the way, designing them too. These are just a few of the requests I’ve personally received over the years as someone in senior marketing leadership.
I’d like to think that my expertise can be better focused on something more important than resizing a logo, but to that CS VP, that was the most important thing marketing could do for her that day. This was particularly disappointing because there was a ton marketing could have done to help her launch her new PM tool to the customer base. But she didn’t think of marketing as a strategic partner that could help her programs be more successful. She thought of us as someone who had Photoshop and could resize a logo.
Falling into the trap of becoming a marketing help desk is dangerous for three reasons:
- Marketing help desk culture is very difficult culture to change. Once the company sees you that way, it’s so hard to get them to open their eyes to the possibility of you as a strategic partner.
- It’s going to be really hard to move from the red to the black, not only because you won’t be able to spend time on impactful programs that drive revenue, but also because headcount is expensive and you won’t be doing work that’s valuable enough to justify the overhead.
- You will drown in low-level tasks, constantly context switching, trying to read people’s minds, and doing low-value work. This will drive your team crazy, they’ll feel undervalued, it will be difficult to provide professional growth opportunities, and you’ll ultimately deal with high team turnover.
So how do you avoid this? In short, building cross-functional value. Understand how your work can complement and assist other departments. Marketing holds tremendous value by owning customer intel and relationships. Work with your senior leadership to align marketing programs, KPIs, and budget to high-level business goals so they see the value in what you are working on. And practice what you preach! Marketing teams need to market themselves sometimes. Share the work you’re doing with the rest of the organization through lunch-and-learns or guest speaking appearances at other teams’ planning meetings. Make sure marketing has a standard time slot in every sales kickoff and QBR. Lastly, keep your marketing queue visible, and when someone comes to you with a help-desk type marketing request, you can have a serious conversation about priorities and decide together if their request really does outweigh the other work you have in motion.
Lastly, if you could inspire a movement that would bring a great amount of good to the most people, what would that be?
Echoing one of my earlier comments, I’d love to see managers do a better job genuinely caring for their people. Caring about their happiness, their career path, and their personal development. With so many professionals dealing with burnout, anxiety, depression, and apathy, I believe better managers could change the culture of work dramatically, improving the quality of life for our teams and their families.
How can our readers best continue to follow your work online?
People can find me on LinkedIn or follow my business, Wheels Up Collective, on Twitter, Facebook, Instagram, and LinkedIn. I also regularly contribute to the Wheels Up’s blog.
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