Michael Coscetta graduated from Harvard in 2003, and has already held powerful Executive positions in four different companies over his relatively short business career. Starting with the Cutco/Vector Marketing sales organization where he began as a student, Michael advanced to the position of Division Manager, responsible for the entire NYC Metro and surrounding areas. He later worked as the VP of Sales & Marketing for Structured Web, then moved to San Francisco to join Square, where he advanced as far as becoming the Global Head of Sales, responsible for growing the sales and business development organization from 40 to 200+ people across 5 major countries, accounting for $1 billion in annual revenue.

Now, he’s back in NYC serving as the Chief Sales & Strategy Officer for Compass, a company which is striving to revolutionize the real estate sales industry throughout the US and the world. An extremely talented and highly intelligent leader, Michael is considered to be among the most successful and accomplished Cutco/Vector alumni.



Q: Why don’t you start off by telling us how you got started with Cutco/ Vector?

  • I had 2 jobs that both fell through and I got a letter in the mail so I went in for the interview and I didn’t know anything about selling but I was willing to learn.

Q: What were some of your lessons from your early experiences that you feel you’ve been utilizing until this day?

  • As a BioChem major at Harvard I was a relatively introverted, nerdy kid working with Cutco/ Vector, the extravert was pulled out of me and I realized I could sell.
  • Sales became very formulaic to me and I realized it can be taught to anyone.
  • Learning how to sell was more than learning how to sell a product, it was about how to have better control. Training your mind primarily.

Q: What are some memorable experiences from your Cutco/ Vector career?

  • Being so young and learning how to hire and train so many people (300 people during my summer as a 19 year old).

Q: Why did you decide to stay with Cutco/ Vector when you graduated from Harvard?

  • I really wanted to own my own business and most of my friends were working just to make money and I wanted to do something that I could learn and grow in.
  • I liked the idea of having a franchise-like model that Vector has which includes a proven system and a support team in place to ensure you’ll succeed.

Q: I’ve noticed that you’ve advanced so quickly in the industries you’ve pursued once you left Cutco/ Vector… Were there some skills you gained or experiences you had in leadership as a manager that have enabled you to move up more quickly?

  • Think in scale. Don’t just solve a problem for the one situation in front of you, solve that problem for the next 20 scenarios that are likely to come up in the future.
  • The art of influence. Help people set their goals and believe in them and then show them how to achieve their goal.
  • Always go back to teaching people why. Why is this important?  Why do you want to do this?  Why you think this will work/ not work?
  • Being able to manage large groups of people. Speaking in front of a group of people and learning how to influence them to want to do more.

Q: You left Vector in 2013 and eventually ended up working at Square.  What did you do in between and how did you end up working at Square?

  • I traveled for 8 months and then finally started searching for work. I worked at Structured Web and after 3 years there I was recruited by Square.  I eventually became responsible for global sales.

Q: Tell us more about the role that you had at Square and some of the successes you experienced there.

  • We went from a team with 10’s of people to hundreds of people in our department. Our team helped to 10X Square’s revenue and our department was responsible for half of the company’s sales.

Q: In the course of your time at Square you got to work with Jack Dorsey, the CEO of Square and Twitter … he’s one of the most prominent business leaders today.  I think it would be awesome for our listeners to be able to gain a bit of an insight into what it was like working with someone like him.  What were some of his strengths?  What can you teach us in relation to working with Jack?

  • I think he will go down as one of the top innovators in the 21st century.
  • He lives in the future. One thing I always took away from Jack is, “don’t live in the present because today is done.  You have to live 5 years from now, or 3 years from now, or 50 years from now.  Really stress-test your brain in this way to really think about what’s possible.
  • Jack is also a master of clarity and transparency. Also, no one is too senior or too junior to make a decision if it’s the right one. This allows people to put their brains to work.  Your opinion matters because if you assume you hire smart people and you know your people are there for a reason, they probably know about the day-to-day or the details of something a lot better than someone more senior.

Q: Let’s talk about where you are now, Compass.  Tell us why you left Square and what do you see happening at Compass.

  • It was a few things:
    • I wanted to go back to New York because my friends and family are there.
    • Another thing is that I wanted to have was an opportunity to move up to a C-level job and at Square that didn’t look likely for a while.’
    • The Real Estate world where Compass operates is the largest asset class in the world.
    • The world I come from merges sales and technology.

Q: Tell us about influencing people over the long-term through a certain path to success.  What are some of the attributes and qualities that you feel go into that?

  • See, Follow and Share. People should be seeing you setting a positive example, then they follow in your footsteps, then other people see them and it begins to establish a culture, and then you share the goals you have and the things you want to accomplish and you share the things you’re learning and that’s how you multiply your influence.

Q: There are a lot of young entrepreneurial-minded people who will be listening to this podcast, what advice would you give to people who want to accelerate their career the same way you did?

  • You can always do more than you assume you can do.
    • If someone offered you $1 Million would you be able to get it done?
  • Don’t screw up. People make bad decisions that can really make things hard to achieve later on in life.
  • Surround yourself with people moving in the direction you want to move.
  • Spend most of your day challenging yourself.

Q: As you look ahead in your career and in your life, how do you aspire to change people’s lives through your work or through your influence?

  • I love to teach!
  • One of my eventual goals is to be a CEO of a growing tech company and eventually take them through the process of going public.


  • There’s an important connection between achieving small goals and being able to achieve the much larger aspirations that we have in life. Start by setting out to achieve small goals and then gradually up-level your objectives and achievements.
  • There’s a true art to influence. See, Follow, Share.  People should be seeing you setting a positive example, then they follow in your footsteps, then other people see them and it begins to establish a culture, and then you share the goals you have and the things you want to accomplish and you share the things you’re learning and that’s how you multiply your influence.
  • Living in the future and being able to create a greater level of vision for what’s possible in your life and the world.
  • Being a master of clarity and transparency.
  • Having zero ego and encouraging open communication and feedback and creating a culture where people around you feel like their opinion really matters.
  • Remember that you can always do more than you might think you can right now. Build your belief.
  • Don’t screw up by making bad decisions. Make good decisions moving you in the direction you want to go and steadily and surely and in that process over 5 or 10 or 15 years you can advance very quickly in your life.


  • Fast Start- a contest new Cutco reps get for their first 10 days on the job.
  • DVM (Division Manager)- a Cutco/ Vector manager who runs a team of District and Branch Managers as well as their own “Pilot Office.”
  • Pilot Sales Manager- right hand to the Division Manager. Responsible for day to day operations in the Pilot office.
  • Branch Manager- a Vector/ Cutco manager, often a college student, who runs a sales office during the summer months.
  • District Manager- a Cutco/ Vector office/ manager that runs a year-round office full time.
  • Silver Cup- The trophy award to the #1 rep/ manager in a given competitive category.


Show Notes for this episode provided by Carlo Cipollina.

To learn more and get access to all episodes, visit our podcast page!


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