14 Leadership Insights from Wander CMO Kyle Tibbitts

We chatted with our CMO Kyle Tibbitts about his 14 years in high-impact leadership roles at high-growth startups. 

Kyle has made a career of building marketing machines from the ground up at companies like Opendoor (where he was the second marketing hire) and HotelTonight (acquired by Airbnb). Kyle also invests in early-stage startups with a specialty in advising founders in marketing via his fund  Paradox Capital.

Kyle and family in their travels

Here are 14 insights Kyle shared with me during our conversation:

#1: Focus your role based on the impact

“From a business standpoint, the thing that matters the most is the impact. What did you deliver to the business? Not, “ I work all these hours or I worked really hard. You reach a point very quickly in any role where what’s being measured is the output, not the input.”

“The more you think that way, the more you'll spend time on the right things or thinking through the right strategies, and pouring your energy into really what's going to drive a difference, versus just having your energy spread out across a bunch of different things, some of which may not matter.” - K

#2: “Soft Skills” do not mean “Lesser Skills” 

“Something that is under-discussed is emotional intelligence. You hear it called “soft skills” instead of “hard skills”, and can be interpreted as saying that somehow they're lesser, or they're maybe not as important. I think that's really, really wrong.

I think that whether it's empathy, gratitude, giving recognition, or just taking the time to know who you're working with on a more personal level, that stuff matters because startups are really hard. You're going to hit points that are really difficult. And the only way you're going to stay together in the trenches battling to make the company successful is if there's more holding you together that just works.” - K

#3: Gather ideas and insights from the bottom-up

“You want every single person in the company or who touches your product to be generating ideas. Good ideas can and will come from anywhere. It doesn't matter if it's someone that's not even an employee of the company –  a contractor that cleans our homes can have an idea about how to do something more efficiently that's brilliant, and that when propagated across the whole platform, is really, really impactful.

Part of how you encourage people to bring those ideas forward is you need a culture where that's normal and people see other people doing it. You also see a lot of transparency, right? Because if people understand and see the problems, and feel empowered to speak up about them.” - K

#4 Merge and clarify ideas with the top-down vision

“When ideas get generated from the bottom-up, you want to merge and align them with top-down leadership. Not necessarily because top-down ideas are better, but it's really important in a startup that leaders in the company have a really clear vision for where the company is going. You always want to be talking at the leadership level about that vision, editing that vision, taking in new information, and adjusting it. Part of the job for any great team manager or leader is to take bottom-up inputs into the ideation process and merge it with top-down overall strategy and vision to align on the ideas that matter most.” - K

#5 The biggest secret of hiring is compatibility 

“We talk a lot in Silicon Valley and in tech generally about  ‘culture fit’, but as John Andrew says: what you're actually looking for is really ‘compatibility’.

Put into practice, compatibility has two parts: Part one is compatibility for the role – skills required to do the job and do the job successfully, and gauging someone’s ability to figure out stuff that maybe they don't know.

Part two is compatibility with others in the team – where you recruit the type of people you can see working with for five years, ten years, twenty years, and where you’re on the same wavelength in terms of emotional intelligence versus just the raw intellectual horsepower.” - K

#6 Successful startup teams have a mix of experience levels

“You ultimately want a team with different levels of experience. It's bad if everybody's too experienced and it's bad if everybody's not experienced. You want a really healthy combination of both and a high amount of hunger across all experience levels.” - K

#7 Startups that win hire for slope vs. y-intercept

“You're looking for someone that's got potential to really scale. So, maybe they haven't worked at that many companies yet, maybe they didn't go to some fancy college, maybe they didn't go to college at all. But if you can tease out in the interview process they've got incredible potential with some raw talent, that is a really great startup hire.

Startups have limited resources compared to massive corporations, so you can't necessarily compete on salary. You want to look for folks that are kind of undervalued by the market or more specifically have potential that the market doesn’t necessarily see. When you hire someone like this and they are succeeding, you give them more and more responsibility, you give them promotions. There's really no limit in the startup where someone can go, because startups are not based on seniority or hierarchy but much more based upon impact.” - K 

#8 Handle the inevitable setbacks with transparency

“Setbacks are inevitable because building a startup is incredibly hard. In a sense, all a startup is a seemingly never-ending series of problems to solve. Some of those efforts will go well and some won’t. 

I think honesty is a really important thing within the company. If things aren't going well either across the board or in a specific area of the business, it's much better to be honest about it and shine a spotlight on it than pretend it's not happening. When leaders pretend a problem isn't there but everyone can see it, they lose tons of credibility and it breaks down trust as an organization.

I've seen it first-hand where everyone knows something's broken but it's not being addressed and it's infinitely better to address it head-on. In fact, the team will often be relieved, because everyone is occupying the same shared reality. Once everyone can see a problem, the entire team can put effort behind fixing it.

#9 Hard times build important bonds

“Some of this probably is revisionist history or a trick our minds play on us to make us more resilient – but some of my very best memories working in startups were actually the hard times. It’s the difficult challenges you pushed through. It’s the brick walls you broke down together.

At Opendoor, I remember a time when some of our core markets weren't growing fast enough and we were heading into a key fundraise. It was a huge problem for the company – maybe even an existential problem. The whole team came together in “a war room” and we literally worked from there for weeks. We threw a  bunch of ideas against the wall, shipped a bunch of experiments, and tried to figure out how to turn things around. And it worked. We turned things around. It wasn't easy, but we did it, and I actually look back on those times with incredible fondness. So, it’s great to know even during a setback or a challenge, on the other side of that challenge is very likely a large opportunity if you can push through it.

Resilience is really important in a startup. It might even be the number 1 thing.” - K

#10 Define your values early and reference them constantly

“For each company, the set of values required to be successful can be entirely different, but their importance is universal. I think it’s important to start defining values very early – in fact, the founding team should at least be discussing them if not putting pen to paper. For values to become real, they have to be lived. That not only means everyone in the company knows what they are, but they hear them repeated and referenced all the time. That’s the only way they can truly take root. In many cases you’ll have a few values that come very naturally because of the personalities in the organization – maybe a “bias towards action” or something like that. In other cases, values may be more aspirational, something you are striving towards – that could be something like “every dollar counts.” -K

#11 A “great culture” is when company values are truly exemplified

“For a lot of businesses, the values are just words on a wall that don't really mean anything. What some don’t realize, is the values live within the individual people on your team. A company’s values and culture are probably the most difficult ‘product’ (and I use the term ‘product’ in quotes) that the company builds, because it's the thing that delivers all the value in the future – whether that’s a product or a process or people that join. And it’s the thing that once ruined is basically impossible to repair.” -K

#12: Lead from the front

“When Peter Thiel was leading PayPal, he had this idea that the best person at X, whether that's engineering or marketing or ops, should lead the team. It's a bit of an extreme opinion, because naturally, as you spend more time leading and managing, it's harder to keep certain skills sharp. But, I think the overall point is true: the best way to lead people is not to tell them what to do or to shout strategy from the Ivory Tower of your leadership role, but to actually show them, to embody the values, to embody the things you want to see. I don't care what my role is or how senior it is from a leadership standpoint. I want to be leading by building and getting my hands dirty.” - K 

#13: Over-communicate in a “remote” environment

“I love remote work but like anything else there are trade-offs. One difficulty is that the importance of communication – not only externally, but internally –  is much higher. Writing becomes a very important superpower in the remote context, whereas maybe speaking and socializing are more important in an office. Updates in Slack channels around progress, wins, blockers, shoutouts, etc. are important not just for getting the work done, but for building team momentum, spreading learnings across the organization, and bringing people together.”

#14: Most importantly, be humble

“I think humble leadership is the best type of leadership. Humility is strength, not weakness. It doesn't matter how experienced or talented or smart you are, there's an infinite universe of things that you know nothing about. The further I go in my career, the more I realize how little I know and how much I can learn from others.”

That's a wrap!

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