Graphic of people pole-vaulting to get to a flag
Graphic of people pole-vaulting to get to a flag

You’ve never met a marketer like Kevin Marasco. His passion for learning is embodied in his path to CMO at Zenefits – 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.  

But there’s a deeper story under the surface of his notable career. What you don’t see is the failures, adversity, and setbacks he overcame along the way.

“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.”

It’s easy to get blinded by the headlines of huge success stories, but often what’s missing are the failures, the behind-the-scenes stories you never hear about.

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."

Today, this self-professed “accidental marketer” shares candid advice and lessons learned on The First 100 Days podcast

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?

Finally, don't worry about the title, perks, the size of your paycheck, or the size of your team. 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 from your new team and don't want to jump to a decision immediately. 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.

His diverse accomplishments in business, athletics, and music exemplify a growth mindset, resilience, and willingness to move beyond comfort zones.  

“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 no goal is reached without pain. 

“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, it’s not a one size fits all scenario. 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.

There are also cases where it's not necessarily the first that owns the category; someone with more resources can come along and steal your position. You just want to be mindful of those things and kind of think about the timing.

Live in balance

Trinity’s interview with Kevin focused mainly on work, but at the end of the day, health and mental well-being matter most. So, we ended with a reminder to live in balance to succeed in this ultra-marathon called “life.”

"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."

We live in a world of chaos. “I mean, just look at the year that was 2020, change after change, after change.”  But if you're able to be fluid, adapt to change, keep a level head, and make smart decisions, you learn to enjoy life one day at a time.

Tune in to The First 100 Days for the full interview with Kevin Marasco. 

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