You’ve never met a marketer like Kevin Marasco. His path to CMO at Zenefits embodies his passion for learning – a B2B software platform, automating HR, payroll, benefits, and scheduling for small and mid-size businesses.
For the past 20 years, Kevin’s focus has been sales and marketing, specifically the go-to-market side, in leadership roles at various high-growth public and private B2B SaaS firms. With 10 capital raises, an S1 process, and 12 M&A deals behind him, you might say he’s done it all.
What his résumé doesn't show: more failures than wins, by his own count.
“As I look back on my career, I think I’ve had more failures than successes. But that’s okay, because I consider failure, learning.”
Most success stories skip the failed bets that made them possible.
As an ultramarathon runner, a former competitive surfer, and…professional rock musician (who toured and opened for Blink 182), Kevin’s drive to embrace adversity and learn new things – even if it means failing sometimes – never ends.
"There's going to be adversity. There's going to be challenges.... The important thing is to embrace the learnings."
He now shares career advice and what he's figured out on The First 100 Days podcast.
Career advice: pick the right job opportunities
Picking the right opportunity is critical to a successful career. But when evaluating job offers, it’s easy to get caught up in title, compensation, and perks, especially in the startup world. Kevin warns against short-term thinking.
"Do your due diligence to improve your odds, and think like an investor."
Many of the same principles apply: talk to customers, competitors, the board, the management team.
Startups may appear promising, but the failure rate is high so you need to evaluate as if you're making a serious investment. Because it is.
Assess the DNA of the company:
Culture, the team, the leadership team
Sales and marketing team (if you're on the go-to-market side)
Competitive landscape (what does that look like? How is that going to evolve?)
Have a really good 360-degree view of the business:
Who are the investors?
What stage are they at?
What does success look like for them?
What's their timeline?
What's their track record in history?
Really understand the makeup of the board
It's in a venture world or private equity world
All of those things can have a big impact on the path of the company.
"Analyze the ability of your strengths to add value."
The skills, strengths, and experience you bring can profoundly impact your financial and commercial success – if they align with the company’s objectives.
Start with good self-awareness:
Where can you come in and add value?
What are your strengths and what could they be?
Then map that to the needs of the company and how that aligns to what you think the trajectory of the opportunity will be.
Evaluate the opportunity on a personal level. Ask yourself:
What am I trying to do? Am I trying to build career equity?
What does success look like for me?
What does that path look like?
And then how well does this opportunity fit into that vision I have for my own career?
Can I come in and help move this along in a positive way that's going to be a fun and enjoyable experience for everybody?
Set aside title, perks, paycheck size, and team size when making your decision. Find an opportunity to learn something new and exciting, and then go for it.
Excel in your first 100 days
“You need to come in and add value in that first 100 days,” says Kevin. “100 days is a lot of time. Facebook was built in two weeks."
“The 'first 100 days' starts before your day 1."
You want to listen to your new team and take time before committing to a decision. But you should be doing homework and formulate hypotheses around:
the category
competitors and the dynamics
what customers think
their perception of value in the category
go-to-market motion
ideal customer profile
marketing channels and strategies
data and metrics
So that when you're coming in the first 100 days, you can immediately add more value in every conversation you have.
Learn from failure
For Kevin, there is no failure if you’re learning from your mistakes. Failure is learning and failure precedes success.
Running ultras, competing in surf, touring with a band — he's applied the same logic across all of it: embrace the hard thing, learn from it, repeat.
“Challenges will always be present. What matters is how you deal with them.”
As an ultra-runner, Kevin knows all about resilience. Running teaches him persistence and pain accompanies every goal.
“You just need to start. It's one mile at a time, one step at a time and you just put one foot in front of the next."
“You're going to go through crazy highs and crazy lows. The highs will be euphoric. The lows will be like, I can't step another foot forward. Just like in business challenges. Good quarter, bad quarter. But it's how you build on the highs and then also work through and grind through the lows, the adversities.”
Advice for startups
One of the easiest traps to fall into when you’re starting is trying to do too many things or having too wide a service area.
"Don’t get distracted. Prioritize your resources and time."
Keep a fluid perspective because the market is constantly changing. Most importantly focus on your customer needs, as they will guide your decisions better than anything else.
When it comes to creating your own category or joining an existing category, the approach varies for each startup. A category is something all startups should think about and take a position on, but before moving forward, you need to **determine if it makes sense. ****
“Know what you’re getting into and what [creating a new category] requires to be successful…because it does take time and capital commitment."
Ask yourself:
What does the competitive dynamic look like?
Where are we at in our stage of growth and where are we going?
What do we think that path looks like?
Could we be better off breaking off a piece of the category to create a new category?
Is it a paradigm shift?
Is this creating something entirely new?
You can go it alone and own the category, but you’ll need a strategy that depends on where you are, and the capital to back it up.
A later entrant with greater resources can come along and claim the category position. You just want to be mindful of those things and kind of think about the timing.
Live in balance
We closed by asking Kevin about balance — because every high-performance operator eventually has to answer that question.
"Having some level of balance in Zen, in your life, can help. For me, my way to do that is running, meditation, and trying to eat fairly healthy. It keeps you balanced and keeps your head level to where you can deal with adversity and continuous change.”
“Mental balance is an essential tool to deal with adversity and continuous change."
Markets shift. Teams change. The operators who handle that well tend to be the ones who've built in a way to stay level — whatever that looks like for them.
Tune in to The First 100 Days for the full interview with Kevin Marasco.
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