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It’s not every day that you find a successful person so willing to openly discuss their mistakes, so that you can avoid them.

Ben Rogers, CMO at Travala, who recently joined me on the Sales Engagement Podcast, is one of those rare finds. 

In this episode we discuss:

  • What to expect when transitioning from a corporate role into your own startup
  • Which advice not to take and what to replace it with instead
  • How Ben fosters a growth culture at Travala
  • The mistakes that Ben made and how you can avoid them

Let’s get going, shall we?


What to expect while transitioning from corporate to startups

Ben’s story is so relatable: he wasn’t enjoying corporate life and took the plunge, starting a few of his own businesses. He is candid from the first moment of our conversation, emphasizing how unprepared he was for that change.

The greatest differences between corporate and startups revolve around time and money. When you’re in a corporate environment, you get a steady paycheck and you spend almost all your time on what your job specification calls for.

In startup life, your money is the company’s money and you’re trying to fill every skill gap by yourself, especially during the early days. Socially, you’ll also notice that the people around you change: you lose a lot of the people you knew in your corporate life, but you do get to meet more people along the way.


Which advice not to take and what to replace it with instead

Hindsight is 20/20 vision, as affirmed by Ben. He’s one of very few people I’ve spoken with who outright states that he shouldn’t have used some of the resources that he leaned on.

Here’s some of the advice that tends to float around startup founder circles:

  • Attend a devoted startup event or program
  • Attend networking events
  • Watch specific videos
  • Read particular books
  • Find a mentor
  • Grow your team

Ben admits that if he had the choice to do it over, he would have gone for far less of these things and made simpler decisions.


How Ben fosters a growth culture at Travala

Everything revolves around the simplest, clearest goal: make more money while spending less.

Ben has replaced the word ‘marketing’ with ‘growth’ intentionally. He doesn’t waste time by pulling people into meetings too often, and all of his professional check-ins relate directly to the core goal.

His second core principle is to come up with ideas that can be executed. So often, teams get caught up with their heads in the clouds, dreaming of possibilities, forgetting to plant their feet firmly on the ground and walk the walk.

Ben regularly reflects on the team’s shared ability to execute towards ideas, and everyone’s attitude toward developing the necessary skills for those journeys. By removing bureaucracy he accelerates the path from ideation to learning and success, creating a healthy growth culture.


The mistakes Ben made and how you can avoid them

Mistake #1: Hiring cheap

Ben regrets not bringing in the right experts early enough. He took on green candidates who didn’t have sufficient expertise or experience to draw on to deliver the appropriate operational pace.


Mistake #2: Working on assumptions

Not everyone has the same goals and ambitions as the startup founder. Ben learned this the hard way. He hired people on the assumption that people were aligned with his vision and personal definition of success.


Mistake #3: Not firing people

Learn from Ben’s experience. He didn’t let go of people who were struggling to perform, and it affected both the business culture and performance. It takes a long time to undo the kind of damage that can be caused by the wrong employee-employer fit.


Mistake #4: Not talking to people

This is especially the case in customer relations. Looking back, Ben would rely less on ads and social media and put more effort into having genuine conversations with people, understanding their needs and delivering the product to meet those.


Mistake #5: Ignoring the power of observation

When Ben first joined Travala, he jumped in and rattled bushes very quickly despite stating his intention to observe the current status quo for a month. He recommends taking your first month in a new organization to really observe things and get familiar with your context.


Ben adds some closing advice to always change and freshen up the questions that you ask, being mindful not to lead your respondents.

Check out these resources we mentioned during the podcast:

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, Spotify, or our website.

Listening on a desktop & can’t see the links? Just search for Sales Engagement in your favorite podcast player.

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