Lessons From Top Execs: Ben Braverman (Chief Customer Officer at Flexport) | Village Global’s Venture Stories with Erik Torenberg and Adam Gelman

Key Takeaways

  • The path to becoming an executive is never linear
  • Ben Braverman’s most important accomplishments for the first 12 months at Flexport:
    • Selling a lot
    • Figuring out what their product should be
    • Defining the early playbook for other sellers
  • Ben learned more from interviewing people than from any other path
    • He compiled the knowledge of 100+ VPs of Sales, VPs of Marketing, and CRO’s
  • They always keep an eye out for curious people; that is Flexport’s secret
    • Curious people are great sellers
  • List construction – the most important thing for your sales machine
    • Figure out a way to automate list construction, automate the majority of enrichment
  • Flexport is a highly outbound motivated business
    • 1.3 billion of Flexport’s last year revenue, 90% of those dollars started with an outbound e-mail or call
  • “One of the things we forget in sales is that the way to give people skin in the game is not always to give them a bunch of cash, it’s to give them a way to earn ownership of the business.”Ben Braverman
    • In the case of Flexport, people who have been adequately compensated in terms of equity have always stayed and made decisions that were in the best interest of the company
  • One of Ben’s favorite business experimentation’s at Flexport:
    • Finding a way to incentivize sales leaders to care more about team ramping and less about hitting a short term goal
  • There is no way to get real mentorship from someone other than to work for them
    • Useful conversations and wisdom sharing are nice, but you learn the best when you work for them

Intro

  • “So much of what it means to be human and a sales leader is not knowing the right thing to do.”Ben Braverman
  • Ben Braverman (@braveben) is Chief Customer Officer at Flexport, after serving as Chief Revenue Officer for 6 years during the company’s hyper growth period
    • He joins the Village Global’s Venture Stories podcast to discuss his experience at Flexport, how to build a good sales machine, and share his thoughts on marketing and forming early SDR teams
    • Host: Erik Torenberg (@eriktorenberg)
    • Guest co-host: Adam Gelman (@Adam_Gelman)

The Evolution of Flexport and Ben Braverman

  • The path to becoming an executive is never linear
    • For Ben, the beginning was very traditional – he sold a lot of things
    • “At every level of the game, you are trying to move as much product into the customer’s hand as humanly possible, and delight them in the process.”Ben Braverman
  • Ben’s most important accomplishments for the first 12 months at Flexport:
    • Selling a lot
    • Figuring out what their product should be
    • Defining the early playbook for other sellers
  • They brought a lot of special people who were supper aligned with the mission and the idea that Flexport could be one of the most important companies in the world
    • Together, they figured out the needs of their target customers, and how they want to be spoken to
    • They wrote it all down and built a code of conduct, a company ethos
    • The foundation they laid down in the first 18 months helped them get ahead faster

Deep Learning Interviews

  • Ben learned more from interviewing people than from any other path
    • He interviewed 100+ VP of Sales and CRO’s because they were under constant pressure to continue executing well and they needed help
    • They interviewed constantly; “I was low ego enough, to tell some of these people ‘I don’t know what I’m doing’, because I’ve never seen a company at this scale or growing this fast. I need you to tell me what you would do in this context.'”Ben Braverman
  • He asked them how they do their job, the playbooks they put in place, experiments they pushed, etc.
    • Writing all of that down, you ultimately get better at doing the job yourself
    • He compiled the knowledge of 100+ VPs of Sales, VPs of Marketing, and CRO’s
  • General Interview Guidelines
    • They always keep an eye out for curious people; that is Flexport’s secret
    • Curious people are great sellers
    • People who display interest in the company’s business and the industry as a whole are people who are more likely to succeed
    • Typically, these types of people have a lot of genuine questions about how the puzzle fits together (e.g. why the company and the opportunity exist)
  • How to evaluate what makes a great CRO at interviews?
    • Ben never hired one, but he believes a CRO must complement the CEO, and the stage they are currently in
    • CRO is a conduit to the market for both CEO and engineering organization

Advising Company Founders

  • When to hire for experience, when to hire for slope?
    • It depends on the needs of the founder: 
      • Is the founder a capable seller? 
      • Does their sale necessitate founder-led sales?
  • A lot of companies sell products that are too big or complicated or at a high point of entry
  • Before you have a brand, if you are going to have a founder-led sale go to market in the first 12 months
  • You have to be careful about the people you bring in and when
    • “It may be that you are better off bringing in someone that is going to be a Robin to your Batman vs someone who wants to own a big machine and who feels like they need to rewrite the playbook.” Ben Braverman
    • Figure out where you (as a founder) are in the company’s life cycle and what type of person would complement you best

How to Build and Scale Sales Machine 

  • List construction – the most important thing for your sales machine
    • Figure out a way to automate list construction, automate the majority of enrichment
    • Your data set should grow every month and you should try to refine your ideal customer and automatically assign them
  • Flexport is a highly outbound motivated business
    • 1.3 billion of Flexport’s last year revenue, 90% of those dollars started with an outbound e-mail or call
    • List construction is the foundation for everything else you are going to build in the company
    • Getting better at building a list ☛ list gets bigger ☛ you get better at assigning the right leads to your representatives ☛ positive momentum
  • SDR’s get the list initially, working through it and trying to generate the meeting for the full cycle of salespeople
    • “If you are an SDR and you can automate the job, it’s called marketing” Ben Braverman
  • Every SDR candidate at Flexport:
    • Their job is to generate 8-12 of the highest quality opportunities 
    • They give them a dedicated list of a hundred and set a helpful constraint:
    • They can only generate an opportunity (set a meeting for a full cycle sales rep) or they fail
    • It’s a very creative role, “…your job is to look at this list and think about the best fits for the company and how to get them to know who you are and be curious to take a meeting.” – Ben Braverman

Quick-Start Guide to Equity Compensation

  • “One of the things we forget in sales is that the way to give people skin in the game is not always to give them a bunch of cash, it’s to give them a way to earn ownership of the business.”Ben Braverman
    • In the case of Flexport, people who have been adequately compensated in terms of equity have always stayed and made decisions that were in the best interest of the company
  • One of Ben’s favorite business experimentation’s at Flexport:
    • Finding a way to incentivize sales leaders to care more about team ramping and less about hitting a short term goal
  • Key statements they tell to their sales leaders:
    • Your goal is a roll-up of your team’s goal 
      • E.g. If you have 8 people on the team and you are the 9th as a leader, your total goal is 9x quota
      • You (sales leader) plus your sales team is the total capacity the company should have
    • We don’t care how you hit the goal (it can be any arrangement of your team generating the revenue number they assign to you, or you can do it on your own)
      • But, there is a catch, for every person on your team whose performance exceeds the threshold that they set, you get a significant portion of equity
    • This was the main way how their sales leaders could earn a good part of the equity
  • With the combination of short term and long term goals they would get a lot of money and a part of the equity

Composition of a Revenue Team

  • Sales operations are something you should invest in early on; Ben and his team did not and regret it
    • One of Ben’s weaknesses was always general organization
  • There is going to be more and more models of sales leadership where you have a CRO and a sales COO
    • Someone that is responsible for all the tooling, analytics, preparing an update for the board, making sure the pipeline data is regularly updated, etc.
  • If you are a sales leader who is not good at these things, you need to have a partner who can do it

Team Evolution During Hypergrowth

  • The number 1 evolution that happened at Flexport
    • In the beginning, they had zero success at hiring out of the industry, and people who came from the industry were miserable
    • It was a bad fit in both directions, but today a huge % of their leadership team are people that have come from other parts of the traditional “legacy” freight forwarding industry
  • In the early days of the business, it was tough for the “legacy” type people to come in
    • You can’t afford to have people that are going to point out everything that is wrong with your startup
    • Recruiting senior leaders from the industry in their early days would’ve been a mistake
    • You need to have some of the naive enthusiasm at the beginning, but over time the ratio changes dramatically

Ben’s Advice on Mentorship

  • There is no way to get real mentorship from someone other than to work for them
    • Useful conversations and wisdom sharing are nice, but you learn the best when you work for them
    • It’s a special position to be in; when you are there to execute against their vision and they know more about the world than you do
  • Go work for someone who is a full degree further in life than you are, and listen a lot
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